Study on the chemical constituents of Desmarestia menziesii (Ochrophyta, Desmarestiales), an Antarctic seaweed

Study on the chemical constituents of Desmarestia menziesii (Ochrophyta, Desmarestiales), an Antarctic seaweed | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Study on the chemical constituents of Desmarestia menziesii (Ochrophyta, Desmarestiales), an Antarctic seaweed Isac José da Silva Filho, Erika Mattos Stein, Aline Paternostro Martins, and 4 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-6814752/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 30 Apr, 2026 Read the published version in Polar Biology → Version 1 posted 7 You are reading this latest preprint version Abstract This study investigated the chemical composition of the Antarctic brown macroalga Desmarestia menziesii , collected from Penguin and Livingston Islands. Sequential extractions using hexane, dichloromethane, ethyl acetate, and methanol were performed, followed by GC-MS, NMR, IR, and mass spectrometry analyses. The hexane extract revealed the presence of sterols such as fucosterol, isofucosterol, 24-ethylcholesta-5,24(25)-dienol, and stigmasta-5,24(28)-dien-3β-ol, in addition to saturated and unsaturated fatty acids. Environmental contaminants, including phthalates and siloxanes, were also detected, highlighting the alarming spread of anthropogenic pollution even in remote Antarctic environments. The ethyl acetate extract contained aromatic meroterpenoids with recognized antioxidant, antimicrobial, and cytotoxic activities. The methanolic extract was predominantly composed of mannitol (over 50%), a polyol with osmoregulatory, cryoprotective, and antioxidant properties. These findings expand the current knowledge of the chemodiversity of Antarctic macroalgae and highlight the biotechnological potential of the identified metabolites, with promising applications in pharmaceuticals, cosmetics, functional foods, and biopreservation. Antarctic macroalgae Secondary metabolites Antifreeze compounds Mannitol Marine sterols Bioactive compounds Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 Introduction All living organisms rely on a complex network of biochemical pathways to maintain homeostasis, growth, and reproduction. Primary metabolites—such as amino acids, nucleotides, lipids, carbohydrates, and pigments—are synthesized through highly conserved metabolic pathways assisted by enzymes with low catalytic promiscuity (O’Brien & Herschlag, 1999; Kazlauskas, 2005; Moghe & Last, 2015). These compounds are ubiquitous across taxa and are essential for energy production, structural integrity, and cellular regulation (Jimenez-Garcia et al., 2013). In addition to primary metabolism, organisms produce a wide variety of functional or secondary metabolites. These compounds are not directly involved in growth or reproduction but play crucial roles in ecological interactions and adaptation to environmental pressures, including defense against herbivores, protection from UV radiation, and tolerance to extreme temperatures (Pohnert et al., 2007 ; Mukherjee et al., 2015; Carrington et al., 2018 ;). Functional metabolites often exhibit antioxidant, antimicrobial, photoprotective, or antifreeze properties, enhancing resilience to abiotic and biotic challenges. The production of primary and functional metabolites by marine macroalgae is strongly influenced by environmental stressors such as salinity, light intensity, UV radiation, and temperature (Torres et al., 2022 ). In the Antarctic region, macroalgae are exposed to extreme conditions, including subzero temperatures, seasonal darkness or continuous daylight, and elevated ultraviolet radiation (Fraire-Velázquez & Balderas-Hernández, 2013 ; Freedman, 2016 ; Convey & Peck, 2019 ). These conditions have driven the evolution of unique biochemical adaptations, including the accumulation of polyunsaturated fatty acids to maintain membrane fluidity (Paternostro, 2013 ; Pasqualetti, 2015 ) and the synthesis of cryoprotective compounds like polyols (Rousvoal et al., 2011 ). Although antifreeze proteins are well documented in bacteria, diatoms, fish, and insects (Bayer-Giraldi et al., 2014 ; Kim et al., 2017 ), their presence has not yet been confirmed in macroalgae. Instead, these organisms likely rely on alternative mechanisms such as the accumulation of cryoprotective sugars and sugar alcohols like mannitol, as well as meroterpenoids and polyphenolic compounds. Despite the ecological relevance of Antarctic macroalgae, their chemical diversity remains underexplored relative to their tropical and temperate counterparts (Bernardi et al., 2016 ; Colepicolo et al., 2021). The genus Desmarestia (Ochrophyta, Desmarestiales) is among the most abundant and ecologically important brown algae in the Antarctic marine ecosystem. Prior studies have identified sulfated polysaccharides, phlorotannins, meroterpenoids, and sterols in related species (Rivera et al., 1990 ; Findlay & Patil, 1985 ; Davyt et al., 2016 ; Pereira et al., 2017 ). However, comprehensive chemical studies focused on Desmarestia menziesii are still lacking. This study aims to characterize the chemical composition of D. menziesii through sequential solvent extractions using hexane, dichloromethane, ethyl acetate, and methanol. The isolated compounds were analyzed by chromatographic and spectroscopic techniques (GC-MS, NMR, IR, and MS), with a focus on identifying bioactive metabolites. In addition, this research highlights the occurrence of plasticizers and siloxanes in the algal samples, raising concerns about anthropogenic contamination even in remote Antarctic ecosystems (Waller et al., 2017 ; González-Pleiter et al., 2020 ). Material and Methods Algal samples were collected from Penguin Island (62 ° 6'0 "S, 57 ° 56'0" W) in January 08, 2015 and from Livingston Island (62 ° 7'S, 60 ° 49'8''W) on January 12, 2016. Specimens were identified by two authors (N.S.Y. and A.P.M.) and a voucher specimen is deposited at the Maria Eneyda P. Kauffman Fidalgo Herbarium, at the Instituto de Botanica, São Paulo (number of deposit of copies: island Penguin SP 470436; Livingston Island SP 470437). The biomass was lyophilized, milled and then serially extracted with the following solvents: hexane (EH), dichloromethane (ED), ethyl acetate (EAE) and methanol (EME). The extracts were concentrated in vacuo at 40°C; the dried extracts were stored in hermetically sealed bottles. GC-MS analyses of hexane extract The first study was performed on a Gas Chromatography coupled to Mass Spectrometry GCMS-QP2010 Plus, Shimadzu, Japan interfaced to a scan from 50 to 1.000 m/z. detector. The capillary column (30 m x 0.25 mm x 0.25 µm film thickness) was ZBWax. The samples were injected in the split mode (split ratio of 80:1). The injector temperature was kept at 250°C. The interface temperature was held at 200°C. The column temperature was initially 50 ºC with a hold of 5 minutes then programmed to 250ºC at the rate of 5 ºC/min. The carrier gas was helium, having a constant flow rate of 1 ml/min, The samples were injected in the split mode (split ratio of 10:1), and the injection volume was 1 µl. Standard 70 eV EI spectra were recorded from 50 to 1000 m/z mass range. Identification of compounds was conducted using NIST database. The name, formula and molecular weight of the identified compounds were ascertained (Fig. 1 ). In the re-study of hexane extract by GC/MS, the column used was an HP - 5MS (5%-phenylmethylpolysiloxane, 30 m x 0,25 mm, 0,25 µm i.d.) however the chromatographic conditions were the same as in the previous analysis. Study on dichloromethane extract Dichloromethane extract (500 mg) was fractioned by column chromatographic over silica gel 60 (70–230 mesh ASTM) by gradient elution with n-hexane in ethyl acetate (AcOEt ) system (95:5 to 0:100, each 10 mL) and finally Methanol (MeOH) 100%. The 203 fractions collected were compared by TLC chromatography (silica gel 20 x 20 cm, 0,25 mm, Kieselgel 60GF254, E.Merck; derivatization with p-hydrobenzaldeyde) and the similar ones are pooled together. The pooled fractions column-chromatographic-V-53-68 (D-V-53-68) (94 mg) were applied to a silica gel 60 column eluted with an increasing linear gradient from 15 to 100% (v/v) methanol in ethyl acetate. 80 fractions were collected, also chromatographed by TLC on silica gel (derivatization with p-hydrobenzaldeyde) and t he similar fractions were pooled together. The combined fractions D- VI- 26–42 (3,8 mg) were injected into a CG/MS system for analysis. The GC/MS analysis was carried out with a Shimadzu (GCMS - QP2010 Plus, Kyoto) system. HP - 5MS column (5%-phenylmethylpolysiloxane, 30 m x 0,25 mm, diâm. int. 0,25) was used with a helium carrier gas at 1.0 mL/min. The injection was made in splitless and the injector temperature was 250°C. The oven initial temperature was 60 ° C, and then programmed to increase at a rate of 3°C per min until it reaches 260 ° C, and held for 40 min. The interface temperature was 240°C, mass spectra were taken at 70 eV and the mass range was from m.z 40 to 1000. The compound identification was performed by comparing the spectra with the NIST08, NIST08s, Wiley9 and Nist Mass Spectral Search Program from Nist/ Epa/ Nih Mass Spectral Library Version 2.0 and literature data. Studies on ethyl acetate extract The ethyl acetate extract (400 mg) was fractioned by chromatography column on sílica gel 60 (70–230 mesh ASTM). The column was eluted with a stepwise gradient of ethyl acetate (AcOEt ) e Methanol (MeOH) (95:5 to 0:100) and after being analyzed by TLC, the similar fractions were bulked together according to their TLC profile. The bulked fractions labeled D-I 91–154 were submitted to chromatographic purification on sílica gel 60 (70–230 mesh ASTM) column with isocratic elution by AcOEt / MeOH 99:1, (v/v). The eluted fractions were evaluated and pooled together according to TLC analysis. The pooled fractions D-II 27–51 were studied by 1 H Nuclear Magnetic Resonance Spectroscopy (NMR spectroscopy). About 320 mg of ethyl acetate extract were submitted to a TLC-DPPH guided frationation on preparative plates as stationary phase and mixture of ethyl acetate/ Methanol (99:1, v/v) as mobile phase. After development, the DPPH-positive region were removed from the plates and extracted with MeOH. This extract was submitted to a clean-up procedure on a sílica gel 60 column eluted with ethyl ether, AcOEt/MeOH 1%, AcOEt/MeOH 10% and MeOH 100%. The purified fractions were evaluated by TLC and pooled together according to their similarities. The pooled fractions DII- 9–12 and D-II 15–19, each one in this turn, were chromatographed on a Sephadex-LH-20 column (60 cm x 2 cm) eluted with AcOEt/MeOH 99:1 (v/v). After evaluation by TLC analyzes, from the first procedure, three groups of fractions were formed: D-III 1–25, D-III 33–39 and D-III 41–51 which were studied by 1 H and 13 C NMR spectroscopy. From the second procedure, the D-IV 1–31 e D-IV 32–47 fractions were bulked together and studied by 1 H NMR spectroscopy. Results and discussion Chemical studies of hexane and dichloromethane extracts The GC-MS analysis of the hexane extract revealed the presence of 104 (Fig. 1 ) compounds (listed in the attached Table 1 ), including hydrocarbons, esters, alcohols, fatty acids, as well as contaminants such as silicones (polysiloxanes) and phthalates. This is particularly concerning from an environmental perspective, given that the sampling site is located within a protected area (Ministério do Meio Ambiente, 2009 ; Marinha do Brasil, 2016 ) (table 2). Recent studies continue to report the widespread presence of such contaminants in marine environments, including remote regions, indicating long-range atmospheric transport and deposition of anthropogenic residues (Waller et al., 2017 ; González-Pleiter et al., 2020 ; Barletta et al., 2021 ; Bergmann et al., 2022 ; Li et al., 2023 ). Table 1 Substances (metabolites and pollutants) identified by CG-MS of hexane extract Nº *RT (min) *SI *KI Substance Molecular formula Molecular weight % Source Additional Information References Algae Vegetables and animals # Synthesis ## Synthesis 1 5,167 93 913,2 Ethane C 2 H 2 Cl 4 169,85 0,02% - - - - - - 2 13,267 3 15,975 90 1223,1 Oxiranecarboxaldehyde C 10 H 16 O 2 168,236 0,05% - - - - - - 4 17,983 89 1270,7 3,7-Dimethyl-2,6-Octadienal C 10 H 16 O 152,237 0,09% - - - - Manufacture of other chemical products Pubchem/ Physical Description from CAMEO Chemicals 5 20,15 93 1367 Nerolic acid C 10 H 16 O 2 168,236 0,15% - - - - - - 6 20,592 94 1398,9 Cyclohexasiloxane C 12 H 36 O 6 Si 6 444,924 0,16% - -- - Silicone residue 7 23,383 91 1499,1 Docosane (CAS) C 22 H 46 310,61 0,26% - Plants - Flavorful Used in organic systems for synthesis, calibration and temperature detection Kamenarska et al., 2006/ Pubchem/ Physical Description from CAMEO Chemicals 8 25,108 88 1542 4-Hexen-3-one (CAS) C 6 H 10 O 98,145 0,29% - - - Flavoring - Pubchem/ HMDB 9 27,442 93 1599,7 Tricosane C 23 H 48 324,637 0,35% - - - - - - 10 27,667 94 1605,5 Cycloheptasiloxane C 14 H 42 O 5 Si 6 458,995 0,37% - - - - Silicone residue - 11 27,85 88 1610,2 Pentadecanal C 15 H 30 O 226,404 0,38% - - - - - - 12 27,925 92 1612,2 Phenol, 2,4-bis(1,1-dimethylethyl)- (CAS) C 14 H 22 O 206,329 0,40% - - - - - -- 13 28,475 88 1626,4 Dihydroactinidiolide C 11 H 16 O 2 180,247 0,42% - - - - - - 14 29,867 85 1662,3 Glycine C 15 H 29 NO 3 271,401 0,46% - - - - - - 15 31,117 94 1694,6 1,2-Benzenedicarboxylic acid, C 12 H 14 O 4 222,24 0,49% - - - - Plasticizer / makes plastics more flexible Pubchem/ HMDB 16 31,317 92 1699,7 Heneicosane C 21 H 44 296,583 0,51% - - - - - - 17 34,133 88 1776 Cyclooctasiloxane C 16 H 48 O 8 Si 8 593,232 0,55% - - - - Silicone residue - 18 35,017 90 1799,9 Eicosane C 20 H 42 282,556 0,57% - - - - - - 19 35,933 91 1825,9 Octadecanoic acid C 19 H 38 O 2 298,511 0,64% - Plants - Anti-foaming agent and fermentation nutrients - Pubchem/ HMDB 20 37,333 93 1865,6 Tetradecanoic acid C 14 H 28 O 2 228,376 0,68% - Animal and vegetable fats Cosmetics Flavoring Soaps Pubchem/ MeSH HMDB 21 39,775 84 1936,7 Cyclononasiloxane C 18 H 54 O 9 Si 9 667,386 0,73% - - - - Silicone residue - 22 39,867 94 1939,4 Neophytadiene C 20 H 38 278,524 0,75% - - - - - - 23 40,058 84 1945,1 2-Pentadecanone, 6,10,14-trimethyl- C 18 H 36 O 268,485 0,77% - - - - - - 24 40,708 90 1964,5 3,7,11,15-Tetramethyl-2-hexadecen-1-ol C 20 H 40 O 296,531 0,81% - - - - - Nist web 25 40,825 96 1967,9 1,2-Benzenedicarboxylic acid C 16 H 22 O 4 278,348 1,04% - - - - Plasticizer - 26 42,5 88 2018,6 (E, E) -7,11,15-Trimethyl-3-methylene-hexadeca-1,6,10,14-tetraene C 20 H 32 272,476 0,90% - - - - - - 27 42,758 90 2026,7 Hexadecanoic acid C 17 H 34 O 2 270,457 0,93% - - - - - - 28 43,983 91 2064,8 Palmitic acid C 16 H 32 O 2 256,43 1,01% - Animal, vegetable and human fat - - - Pubchem/ Pharmacology from NCIt/ HMDB 29 44,825 81 2091 Eicosamethylcyclodecasiloxane C 20 H 60 O 10 Si 10 741,54 1,04% - - - - Silicone residue - 30 46,392 93 2121,3 Doconexent C 22 H 32 O 2 328,496 1,12% - Animal oil (fish) - - - Pubchem/ MeSH 31 47,242 82 2135,4 Di-isopentylphthalate C 18 H 26 O 4 306,402 1,14% - - - - Plasticizer - 32 48,183 88 2151,1 9-Octadecenoic acid (Z)- C 19 H 36 O 2 296,495 1,19% - - - - - - 33 49,008 87 2164,9 Methyl Octadecanoate C 19 H 38 O 2 298,511 1,23% - Plants - Anti-foaming agent and fermentation nutrients - HMDB 34 49,158 94 2167,4 9,12-Octadecadienoic acid (Z,Z)- C 18 H 32 O 2 280,452 1,25% - - - - 35 50,033 88 2181,9 Ascorbic acid 2,6-dihexadecanoate C 18 H 36 O 2 284,484 1,30% - Animal and vegetable fat - - - Pubchem/ Pharmacology from NCIt/ HMDB 36 52,758 90 2258,1 5,8,11,14-Eicosatetraenoic acid, methyl ester C 21 H 34 O 2 318,501 1,36% - Animal and human fat - - - Pubchem/ MeSH 37 53,975 94 2301,2 Arachidonic acid C 20 H 32 O 2 304,474 1,10% - Animal and human fat - - - Ahern et al., 1983/ Kim and Chojnacka, 2015/ Pubchem/ HMDB 38 55,192 83 2346 Benzyl butyl phthalate C 19 H 20 O 4 312,365 1,50% - - - Plasticizer Pubchem/ HMDB 39 56,65 89 2399,7 Hexanedioic acid, bis (2-ethylhexyl) ester (CAS) C 22 H 42 O 4 370,574 1,56% - - - Aditivo alimentar indireto decorrente do contato com polímeros e adesivos Plasticizer Pubchem/ HMDB 40 59,617 89 2513,9 Phosphine oxide C 18 H 15 OP 278,291 1,61% - - - - - - 41* 60,475 96 2547,8 1,2-Benzenedicarboxylic acid C 16 H 22 O 4 278,348 1,63% - - - - Plasticizer Pubchem/ HMDB 42 67,242 94 2826,5 2,6,10,14,18,22-Tetracosahexaene C 30 H 50 410,73 1,74% - Animal, vegetable and human fat - - - - 43 70,592 78 2948,9 Cholesteryl bromide C 27 H 45 Br 449,561 1,78% - - - - - - 44 77,108 93 3123,9 Vitamin E C 29 H 50 O 2 430,717 1,89% - Plants - - - - 45 85,858 87 - Stigmasta-5,24(28)-dien-3-ol, (3.beta.)- (CAS) C 29 H 48 O 412,702 1,90% - Plants - - - - Among the natural metabolites detected, four sterols were noteworthy: fucosterol, isofucosterol, 24-ethylcholesta-5,24(25)-dienol, and stigmasta-5,24(24)-dien-3-ol. These compounds are widely reported in brown algae, where they play structural roles in cellular membranes, as well as exhibiting potential bioactivities such as anti-inflammatory, antioxidant, and anticancer properties (Findlay & Patil, 1985 ; Kerr & Baker, 1991 ; Lopes et al., 2020 ; Moss et al., 2021 ). Fucosterol, in particular, is commonly found in species of the orders Fucales, Laminariales, and Desmarestiales, where it contributes to the regulation of membrane fluidity under cold and saline conditions, as observed in Antarctic algae (Mayer et al., 2013 ; Pereira et al., 2017 ; Silva et al., 2023 ). Recent studies have reinforced its pharmacological potential, highlighting neuroprotective, hypoglycemic, and anti-inflammatory effects (Jiang et al., 2023 ; Lee et al., 2022 ; Sathasivam et al., 2019 ). In addition to sterols, the presence of saturated and unsaturated fatty acids was significant, especially hexadecanoic acid (palmitic acid), oleic acid, and linoleic acid. These compounds are known to play essential roles in protection against oxidative stress and in chemical communication both within and between species (Guschina & Harwood, 2009 ; Wang et al., 2022 ). The detection of compounds such as phthalates and polydimethylsiloxanes raises serious environmental concerns and suggests diffuse contamination, corroborating recent findings that demonstrate the persistent presence of microplastics and their chemical derivatives even in minimally impacted marine ecosystems (Obbard et al., 2014 ; Lacerda et al., 2019 ; Pabortsava & Lampitt, 2020 ; Bergmann et al., 2022 ; Li et al., 2023 ). The GC-MS analysis of the dichloromethane extract, after chromatographic fractionation, confirmed the presence of major fractions composed of lipophilic metabolites, including phenolic derivatives and sterols. These findings are consistent with chemical profiles reported for brown macroalgae (Hakim & Patel, 2020 ; Moss et al., 2021 ; Kang et al., 2022 ). Although present in smaller quantities, these compounds are of high biotechnological interest due to their potential bioactive properties. Overall, the chemical profile obtained aligns with the literature describing brown macroalgae as rich sources of bioactive compounds, particularly sterols, terpenes, long-chain fatty acids, and polyphenols, with potential applications in the pharmaceutical, cosmetic, and functional food industries (Holdt & Kraan, 2011 ; Lopes et al., 2020 ; Moss et al., 2021 ). Aromatic Compounds in the Ethyl Acetate Extract Fractions obtained from the ethyl acetate extract of Desmarestia menziesii showed fluorescence under UV light, indicating the presence of aromatic compounds (Fig. 2 ). Nuclear Magnetic Resonance (NMR) analysis revealed signals consistent with meroterpenoids, a class of hybrid molecules derived from terpenoid and polyketide biosynthetic pathways (Fig. 3 ). These compounds are widely distributed in brown algae and are associated with various biological functions (Davyt et al., 2016 ; Blunt et al., 2018 ; Hakim & Patel, 2020 ). Meroterpenoids are known for their antioxidant, antimicrobial, and cytotoxic properties, contributing to the defense mechanisms of algae against microbial colonization and herbivory (Numata et al., 1991 ; Blunt et al., 2018 ; Hakim & Patel, 2020 ). Recent studies have reinforced that brown algae produce a broad diversity of bioactive meroterpenoids, including phlorotannins and other aromatic secondary metabolites, which play critical roles in ecological interactions and stress tolerance (Hakim & Patel, 2020 ; Nazir et al., 2021 ). Furthermore, phenolic compounds commonly found in brown algae, such as phlorotannins, are responsible for UV protection and oxidative stress mitigation, particularly in polar and intertidal environments (Bayer-Giraldi et al., 2014 ; Cotas et al., 2020 ; Nazir et al., 2021 ). These compounds absorb harmful UV radiation and neutralize reactive oxygen species (ROS), enhancing algal survival in extreme habitats. From a biotechnological perspective, the antioxidant, antimicrobial, and anti-inflammatory activities of these aromatic compounds make them promising candidates for applications in cosmeceuticals, nutraceuticals, and pharmaceuticals (Rivera et al., 1990 ; Davyt et al., 2016 ; Nazir et al., 2021 ). Their bioactivities are being increasingly explored for human health applications, especially due to their radical scavenging, anti-aging, and anti-tumoral properties (Numata et al., 1991 ; Blunt et al., 2018 ; Nazir et al., 2021 ). Isolation and Characterization of Mannitol A colorless crystalline compound (17.5523 g) was isolated from the methanolic extract (33.4516 g) of D. menziesii , representing approximately 52% of the total extract. The crystals were thoroughly washed with heptane and subjected to spectrometric and spectroscopic analyses. The infrared (IR) spectrum (Fig. 4 ) displays characteristic absorption bands corresponding to hydroxyl (O-H) groups and C-H stretching from methylene (CH₂) and methine (CH) groups. The complete vibrational assignments are presented in Table 3 . Based on this analysis, the compound is composed of a chain of sp³ carbons bearing multiple hydroxyl groups. Table 2 Contaminants identified from the Hexane extract by GC-MS Nº *RT (min) *IS *IK Substance Molecular formula Molecular weight % Source Additional Information References Algae Vegetables and animals # Synthesis # # Synthesis 1 60,475 96 2547,8 1,2-Benzenedicarboxylic acid C 16 H 22 O 4 278,348 26% - - - - Plasticizer Pubchem/ HMDB 2 56,65 89 2399,7 Hexanedioic acid, bis (2-ethylhexyl) ester (CAS) C 22 H 42 O 4 370,574 5% - - - Indirect food additive due to contact with polymers and adhesives Plasticizer Pubchem/ HMDB 3 55,192 83 2346 Benzyl butyl phthalate C 19 H 20 O 4 312,365 1% - - - Plasticizer Pubchem/ HMDB 4 47,242 82 2135,4 Di-isopentylphthalate C 18 H 26 O 4 306,402 1% - - - - Plasticizer - 5 44,825 81 2091 Eicosamethylcyclodecasiloxane C 20 H 60 O 10 Si 10 741,54 3% - - - - Silicone residue - 6 40,825 96 1967,9 1,2-Benzenedicarboxylic acid C 16 H 22 O 4 278,348 21% - - - - Plasticizer - 7 39,775 84 1936,7 Cyclononasiloxane C 18 H 54 O 9 Si 9 667,386 4% - - - - Silicone residue - 8 34,133 88 1776 Cyclooctasiloxane C 16 H 48 O 8 Si 8 593,232 5% - - - - Silicone residue - 9 31,117 94 1694,6 1,2-Benzenedicarboxylic acid, C 12 H 14 O 4 222,24 6% - - - - Plasticizer / makes plastics more flexible Pubchem/ HMDB 10 27,667 94 1605,5 Cycloheptasiloxane C 14 H 42 O 5 Si 6 458,995 13% - - - - Silicone residue - 11 20,592 94 1398,9 Cyclohexasiloxane C 12 H 36 O 6 Si 6 444,924 12% - -- - Silicone residue 12 13,267 90 1157,2 Cyclopentasiloxane C 10 H 30 O 5 Si 5 370,77 2% - - Cosmetics and skin emollient - Silicone residue Pubchem/ DrugBank *N - Number/ RT - retention time (minutes) / SI - similarity index / D - database / KI - Kovats index / % - percentage # Synthesis - Special care products / ## Synthesis - Food additives Table 3. Assignment for IR characteristic bands of functional groups and of the bands of the crystalized compound Stretch Absorption cm − 1 Strain Absorption cm − 1 Observed Absorption cm − 1 C-H of alkanes 2.962–2.853 ∼ 1.340 2.935; 2.340 C-H 2 1.484–1.445 722 1.453; 702 O-H (in association) 3.400–3.200 ∼ 1.050 3.250; 1.089* C-O 1.350–1.260 ∼ 1.050 1.340; 1.029* The values 1.340 and 1.029 can be interchangeable *Dyer, 1965. The ^1H NMR spectrum (Fig. 5 ) reveals four distinct groups of signals related to hydrogens bonded to sp³ carbons attached to hydroxyl groups: two double doublets at δH 3.56 (J = 16, 6 Hz) and δH 3.78 (J = 14, 3.4 Hz); a doublet of double doublets at δH 3.66 (J = 16.7, 3 Hz); and a doublet at δH 3.69 (J = 9 Hz). The ^13C NMR spectrum (Fig. 6 ) shows three signals at δ 63.18, 69.0, and 70.7 ppm, which are indicative of carbons bonded to hydroxyl groups. The HSQC spectrum (Fig. 7 ) confirms that the molecule consists of one methylene (-CH₂OH) group and two methine (-CHOH) groups. The molecular structure suggests that the methylene group is located at one end of the chain, adjacent to a methine group, which in turn is connected to another methine group. This arrangement is only possible if the molecule is symmetric. The mass spectrum (Fig. 8 ) displays a molecular ion peak at m/z 183.172, consistent with the molecular formula C₆H₁₄O₆, which corresponds to mannitol (Hagiwara et al., 2005 ; Moreira, 2009 ), with an exact molecular weight of 183.0861. The peak at m/z 205.0678 corresponds to the sodium adduct (M + Na)+, while the fragment peaks at m/z 165.0756, 147.0645, 129.0545, and 111.0441 are attributed to successive losses of water molecules (Δm = 18) (Fig. 9 ). Mannitol is a polyol known for its remarkable physicochemical properties. It exists in multiple crystalline forms—up to seven, as described by Pitkinen et al. ( 1993 )—some of which spontaneously form upon cooling from the melt (162 ± 2°C). These polymorphs have been characterized using Raman and infrared spectroscopy (Ye & Byron, 2008 ). Mannitol can also form hydrates (Yu et al., 1999 ) and exhibits a low freezing point of -117°C (Gunasekara et al., 2014). Functional Roles in Brown Algae Osmoregulation and Cryoprotection Mannitol plays a crucial physiological role in brown algae, functioning as an osmotic regulator that allows the organism to withstand fluctuating salinity and desiccation, typical of intertidal and polar environments. It also serves as a cryoprotectant by minimizing ice formation during freeze-thaw cycles, thereby enhancing cell survival in cold habitats (Robinson, 2001 ; Groisillier et al., 2014 ; Hakim & Patel, 2020 ). This cryoprotective function arises from mannitol’s ability to form hydrogen bonds with water molecules, preventing ice crystal nucleation and growth. The spatial arrangement of hydroxyl groups, with oxygen-oxygen distances of approximately 4.2 to 4.5 Å, is key to this antifreeze activity (Baruch et al., 2008 ). Additionally, ice-binding proteins (IBPs) in marine algae work synergistically with polyols like mannitol to further inhibit ice recrystallization (Bayer-Giraldi et al., 2014 ; Bar Dolev et al., 2016 ). These mechanisms are particularly critical for macroalgae from Antarctic environments, where repeated freeze-thaw cycles and osmotic stress are persistent challenges (Mayer et al., 2013 ; Bar Dolev et al., 2016 ). In this study, over 50% of the methanolic extract was composed of mannitol, underscoring its significant physiological role. Antioxidant and Metabolic Functions Beyond its role in osmoregulation and cryoprotection, mannitol functions as a primary carbon and energy reservoir in brown algae. It accumulates during photosynthesis and is mobilized under stress conditions such as low light, darkness, or environmental fluctuations (Groisillier et al., 2014 ; Hakim & Patel, 2020 ). Mannitol also exhibits potent antioxidant activity by scavenging reactive oxygen species (ROS), which are generated in response to stressors like high UV radiation, temperature extremes, and oxidative damage (Rousvoal et al., 2011 ; Mayer et al., 2013 ; Hakim & Patel, 2020 ). Biotechnological Applications The high abundance of mannitol in D. menziesii highlights its significant potential for biotechnological and industrial applications. In the pharmaceutical industry, mannitol is widely used as an osmotic diuretic, excipient, and component of various medical formulations. It also serves as a low-calorie sweetener in the food industry and as a stabilizer in cosmetic products. In biotechnology, its cryoprotective, osmoprotective, and antioxidant properties are exploited in biopreservation and the development of sustainable, eco-friendly products (Groisillier et al., 2014 ; Hakim & Patel, 2020 ; Nazir et al., 2022). Recent research emphasizes the sustainable extraction of mannitol from macroalgae as a renewable alternative to synthetic production, contributing to greener industrial processes (Nazir et al., 2022) Conclusion The chemical characterization of Desmarestia menziesii revealed a significant diversity of bioactive metabolites, including sterols, fatty acids, meroterpenoids, and the polyol mannitol. These compounds play essential roles in the alga's adaptation to extreme Antarctic conditions, providing protection against freezing, osmotic stress, UV radiation, and oxidative damage. The high concentration of mannitol confirms its critical physiological function as a cryoprotectant and antioxidant. Beyond ecological and physiological significance, these metabolites exhibit substantial biotechnological potential, particularly for applications in pharmaceutical, cosmetic, and food industries, as well as in biopreservation and the development of sustainable products. On the other hand, the detection of organic pollutants such as phthalates and siloxanes in samples from remote Antarctic regions underscores the alarming global spread of plastic pollution, reinforcing the urgent need for global actions to mitigate environmental impacts. This study provides valuable insights into the bioprospecting and conservation of Antarctic marine resources while strengthening the scientific basis for future developments in marine biotechnology. Declarations Funding Declaration This work was developed with funding from the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPQ, Brazil), project: 134529/2016-2. Author Contribution EMS and APM contributed to the structuring of the article.ANG and LRC contributed to the writing, structure and review.PCN and NSY contributed to the material, infrastructure, assistance and technical support. Acknowledgments The authors wish to thank Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPQ, Brazil) for the scholarship awarded to the first author. References Andrady AL (2011) Microplastics in the marine environment. Mar Pollut Bull 62(8):1596–1605. https://doi.org/10.1016/j.marpolbul.2011.05.030 Bar Dolev M, Braslavsky I, Davies PL (2016) Ice-binding proteins and their function. Annu Rev Biochem 85:515–542. https://doi.org/10.1146/annurev-biochem-060815-014710 Barreneche C, Gil A, Sheth F, Fernández AI, Cabeza LF (2013) Effect of D-mannitol polymorphism in its thermal energy storage capacity when it is used as PCM. 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Cite Share Download PDF Status: Published Journal Publication published 30 Apr, 2026 Read the published version in Polar Biology → Version 1 posted Editorial decision: Revision requested 10 Jan, 2026 Reviews received at journal 16 Jul, 2025 Reviewers agreed at journal 27 Jun, 2025 Reviewers invited by journal 18 Jun, 2025 Editor assigned by journal 18 Jun, 2025 Submission checks completed at journal 09 Jun, 2025 First submitted to journal 03 Jun, 2025 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-6814752","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":473233777,"identity":"4057f242-3d8d-4c52-934e-f1bdfa779bb8","order_by":0,"name":"Isac José da Silva Filho","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAAzklEQVRIiWNgGAWjYBACNjDJw8DPD6ITCkjQIjmzAaTFgATbJDccAFHEaOHjP/zwA4NMnYTx+dWJHx4YMMjzix0g4DCJNGMJBp7DEmY33m6WADrMcObsBEJaGMyAfjlQZ3bj7AaQlgSD24S08B//BtQCdNiMs5t/EKeFIQdkC7OEAX/vNiJtkcgplkgA+kXiBu82iwQDCcJ+ke8/vvHDx546Cf7+s5tv/qiwkeeXJqAFDBJ7gIQEWKUEEcrB4AcQ8x8gVvUoGAWjYBSMNAAAfpY7s85YHPAAAAAASUVORK5CYII=","orcid":"","institution":"Universidade Federal do ABC","correspondingAuthor":true,"prefix":"","firstName":"Isac","middleName":"José da Silva","lastName":"Filho","suffix":""},{"id":473233779,"identity":"579bdf63-4618-4995-9dd0-e338d4e6edce","order_by":1,"name":"Erika Mattos Stein","email":"","orcid":"","institution":"Universidade de São Paulo","correspondingAuthor":false,"prefix":"","firstName":"Erika","middleName":"Mattos","lastName":"Stein","suffix":""},{"id":473233780,"identity":"577d3e0d-f650-4a26-bf57-dfc68e756eff","order_by":2,"name":"Aline Paternostro Martins","email":"","orcid":"","institution":"James Cook University","correspondingAuthor":false,"prefix":"","firstName":"Aline","middleName":"Paternostro","lastName":"Martins","suffix":""},{"id":473233781,"identity":"0c2f6c11-673e-4d04-84ea-b5c43784ae56","order_by":3,"name":"Angelica Nunes Garcia","email":"","orcid":"","institution":"Instituto de Pesquisas Ambientais","correspondingAuthor":false,"prefix":"","firstName":"Angelica","middleName":"Nunes","lastName":"Garcia","suffix":""},{"id":473233782,"identity":"e5b3acc9-d9c7-4b34-abca-efd28ead3525","order_by":4,"name":"Pio Colepicolo Neto","email":"","orcid":"","institution":"Universidade de São Paulo","correspondingAuthor":false,"prefix":"","firstName":"Pio","middleName":"Colepicolo","lastName":"Neto","suffix":""},{"id":473233783,"identity":"54947e4a-4064-49fe-8bc0-3c76a910767e","order_by":5,"name":"Nair Sumie Yokoya","email":"","orcid":"","institution":"Instituto de Pesquisas Ambientais","correspondingAuthor":false,"prefix":"","firstName":"Nair","middleName":"Sumie","lastName":"Yokoya","suffix":""},{"id":473233784,"identity":"fc1d653f-faed-4d6f-9957-957e4063e7c1","order_by":6,"name":"Luciana Retz de Carvalho","email":"","orcid":"","institution":"Instituto de Pesquisas Ambientais","correspondingAuthor":false,"prefix":"","firstName":"Luciana","middleName":"Retz","lastName":"de Carvalho","suffix":""}],"badges":[],"createdAt":"2025-06-03 22:53:14","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-6814752/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-6814752/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1007/s00300-026-03478-x","type":"published","date":"2026-04-30T15:58:11+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":85030469,"identity":"fd4d608b-97a9-4404-be12-d0fc1e007f7e","added_by":"auto","created_at":"2025-06-20 07:13:36","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":50668,"visible":true,"origin":"","legend":"\u003cp\u003eChromatogram obtained from the hexagonal extract of \u003cem\u003eD. menziesii\u003c/em\u003e, by GC / MS, in column ZBWax\u003c/p\u003e","description":"","filename":"image1.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/b4620e53e7d0fb3235720c57.png"},{"id":85029582,"identity":"a13b882c-7baa-451b-928a-db6eaf34b2c9","added_by":"auto","created_at":"2025-06-20 07:05:36","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":463481,"visible":true,"origin":"","legend":"\u003cp\u003eChromatograms of fractions D-IV 1-31 and 32-47, developed with a mobile phase - AcOEt / MeOH 99: 1 v / v, observed under ultraviolet light at wavelengths 254 nm and 366 nm\u003c/p\u003e","description":"","filename":"image2.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/4af19709fbc49bbc210fa62a.png"},{"id":85030465,"identity":"53aab27d-eb91-4cb7-ac05-4ecdead700a4","added_by":"auto","created_at":"2025-06-20 07:13:36","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":19350,"visible":true,"origin":"","legend":"\u003cp\u003e\u003csup\u003e1 \u003c/sup\u003eH-NMR (superimposed) spectra of fractions D-IV 1-31 and D-IV 32-47 (500 MHz, CDCl 3)\u003c/p\u003e","description":"","filename":"image3.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/4e653c4b6ab8c641a74e335a.png"},{"id":85031426,"identity":"c59c2257-cb80-4033-94cf-73572b2a1d35","added_by":"auto","created_at":"2025-06-20 07:29:36","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":18703,"visible":true,"origin":"","legend":"\u003cp\u003eInfrared spectrum of the crystalized compound\u003c/p\u003e","description":"","filename":"image4.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/49172b712a429e4cc5facbfa.png"},{"id":85030789,"identity":"28c35713-9738-40c3-842d-4204e678ddcc","added_by":"auto","created_at":"2025-06-20 07:21:36","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":24312,"visible":true,"origin":"","legend":"\u003cp\u003e\u003csup\u003e1\u003c/sup\u003eH RMN spectrum of the crystal (500 MHz, solvent D\u003csub\u003e2\u003c/sub\u003eO)\u003c/p\u003e","description":"","filename":"image5.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/65ac7fc0612d02e3a887a960.png"},{"id":85029594,"identity":"a1366114-575f-4fd3-8d00-8df7cb109787","added_by":"auto","created_at":"2025-06-20 07:05:36","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":10452,"visible":true,"origin":"","legend":"\u003cp\u003e\u003csup\u003e13\u003c/sup\u003eC NMR spectrum of crystallized compound (125 MHz, solvente D\u003csub\u003e2\u003c/sub\u003eO)\u003c/p\u003e","description":"","filename":"image6.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/4612a3d409d5ece24f4f1f64.png"},{"id":85030471,"identity":"62e8332e-697e-47fd-b626-5843a4695c3c","added_by":"auto","created_at":"2025-06-20 07:13:36","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":40209,"visible":true,"origin":"","legend":"\u003cp\u003eHSQC spectrum of the crystallized substance\u003c/p\u003e","description":"","filename":"image7.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/c43dbec47f1402dd6275ffb2.png"},{"id":85029590,"identity":"ac98bb53-9696-4a46-b905-f24bd41e6824","added_by":"auto","created_at":"2025-06-20 07:05:36","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":35241,"visible":true,"origin":"","legend":"\u003cp\u003eMass spectrum of the crystallized substance\u003c/p\u003e","description":"","filename":"image8.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/6068488c06d8fa6325888305.png"},{"id":85030474,"identity":"8887b05f-fdbd-44e0-b140-dde2e0a3a11f","added_by":"auto","created_at":"2025-06-20 07:13:36","extension":"png","order_by":9,"title":"Figure 9","display":"","copyAsset":false,"role":"figure","size":10206,"visible":true,"origin":"","legend":"\u003cp\u003eMannitol structure\u003c/p\u003e","description":"","filename":"image9.png","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/391ed9afa9263d3bb5fcf3f2.png"},{"id":108440275,"identity":"c8086046-a23e-44c9-a061-6dd96cd4586f","added_by":"auto","created_at":"2026-05-04 16:35:25","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":1401594,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-6814752/v1/66aaf03e-a000-4e34-b8b3-e07dc5fc0eb0.pdf"}],"financialInterests":"No competing interests reported.","formattedTitle":"Study on the chemical constituents of Desmarestia menziesii (Ochrophyta, Desmarestiales), an Antarctic seaweed","fulltext":[{"header":"Introduction","content":"\u003cp\u003eAll living organisms rely on a complex network of biochemical pathways to maintain homeostasis, growth, and reproduction. Primary metabolites\u0026mdash;such as amino acids, nucleotides, lipids, carbohydrates, and pigments\u0026mdash;are synthesized through highly conserved metabolic pathways assisted by enzymes with low catalytic promiscuity (O\u0026rsquo;Brien \u0026amp; Herschlag, 1999; Kazlauskas, 2005; Moghe \u0026amp; Last, 2015). These compounds are ubiquitous across taxa and are essential for energy production, structural integrity, and cellular regulation (Jimenez-Garcia et al., 2013).\u003c/p\u003e \u003cp\u003eIn addition to primary metabolism, organisms produce a wide variety of functional or secondary metabolites. These compounds are not directly involved in growth or reproduction but play crucial roles in ecological interactions and adaptation to environmental pressures, including defense against herbivores, protection from UV radiation, and tolerance to extreme temperatures (Pohnert et al., \u003cspan citationid=\"CR51\" class=\"CitationRef\"\u003e2007\u003c/span\u003e; Mukherjee et al., 2015; Carrington et al., \u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e2018\u003c/span\u003e;). Functional metabolites often exhibit antioxidant, antimicrobial, photoprotective, or antifreeze properties, enhancing resilience to abiotic and biotic challenges.\u003c/p\u003e \u003cp\u003eThe production of primary and functional metabolites by marine macroalgae is strongly influenced by environmental stressors such as salinity, light intensity, UV radiation, and temperature (Torres et al., \u003cspan citationid=\"CR59\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). In the Antarctic region, macroalgae are exposed to extreme conditions, including subzero temperatures, seasonal darkness or continuous daylight, and elevated ultraviolet radiation (Fraire-Vel\u0026aacute;zquez \u0026amp; Balderas-Hern\u0026aacute;ndez, \u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e2013\u003c/span\u003e; Freedman, \u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e2016\u003c/span\u003e; Convey \u0026amp; Peck, \u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e2019\u003c/span\u003e). These conditions have driven the evolution of unique biochemical adaptations, including the accumulation of polyunsaturated fatty acids to maintain membrane fluidity (Paternostro, \u003cspan citationid=\"CR47\" class=\"CitationRef\"\u003e2013\u003c/span\u003e; Pasqualetti, \u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e2015\u003c/span\u003e) and the synthesis of cryoprotective compounds like polyols (Rousvoal et al., \u003cspan citationid=\"CR55\" class=\"CitationRef\"\u003e2011\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eAlthough antifreeze proteins are well documented in bacteria, diatoms, fish, and insects (Bayer-Giraldi et al., \u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e2014\u003c/span\u003e; Kim et al., \u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e2017\u003c/span\u003e), their presence has not yet been confirmed in macroalgae. Instead, these organisms likely rely on alternative mechanisms such as the accumulation of cryoprotective sugars and sugar alcohols like mannitol, as well as meroterpenoids and polyphenolic compounds.\u003c/p\u003e \u003cp\u003eDespite the ecological relevance of Antarctic macroalgae, their chemical diversity remains underexplored relative to their tropical and temperate counterparts (Bernardi et al., \u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e2016\u003c/span\u003e; Colepicolo et al., 2021). The genus \u003cem\u003eDesmarestia\u003c/em\u003e (Ochrophyta, Desmarestiales) is among the most abundant and ecologically important brown algae in the Antarctic marine ecosystem. Prior studies have identified sulfated polysaccharides, phlorotannins, meroterpenoids, and sterols in related species (Rivera et al., \u003cspan citationid=\"CR52\" class=\"CitationRef\"\u003e1990\u003c/span\u003e; Findlay \u0026amp; Patil, \u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e1985\u003c/span\u003e; Davyt et al., \u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e2016\u003c/span\u003e; Pereira et al., \u003cspan citationid=\"CR49\" class=\"CitationRef\"\u003e2017\u003c/span\u003e). However, comprehensive chemical studies focused on \u003cem\u003eDesmarestia menziesii\u003c/em\u003e are still lacking.\u003c/p\u003e \u003cp\u003eThis study aims to characterize the chemical composition of \u003cem\u003eD. menziesii\u003c/em\u003e through sequential solvent extractions using hexane, dichloromethane, ethyl acetate, and methanol. The isolated compounds were analyzed by chromatographic and spectroscopic techniques (GC-MS, NMR, IR, and MS), with a focus on identifying bioactive metabolites. In addition, this research highlights the occurrence of plasticizers and siloxanes in the algal samples, raising concerns about anthropogenic contamination even in remote Antarctic ecosystems (Waller et al., \u003cspan citationid=\"CR60\" class=\"CitationRef\"\u003e2017\u003c/span\u003e; Gonz\u0026aacute;lez-Pleiter et al., \u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e2020\u003c/span\u003e).\u003c/p\u003e"},{"header":"Material and Methods","content":"\u003cp\u003eAlgal samples were collected from Penguin Island (62 \u0026deg; 6'0 \"S, 57 \u0026deg; 56'0\" W) in January 08, 2015 and from Livingston Island (62 \u0026deg; 7'S, 60 \u0026deg; 49'8''W) on January 12, 2016. Specimens were identified by two authors (N.S.Y. and A.P.M.) and a voucher specimen is deposited at the Maria Eneyda P. Kauffman Fidalgo Herbarium, at the Instituto de Botanica, S\u0026atilde;o Paulo (number of deposit of copies: island Penguin SP 470436; Livingston Island SP 470437).\u003c/p\u003e \u003cp\u003eThe biomass was lyophilized, milled and then serially extracted with the following solvents: hexane (EH), dichloromethane (ED), ethyl acetate (EAE) and methanol (EME). The extracts were concentrated in vacuo at 40\u0026deg;C; the dried extracts were stored in hermetically sealed bottles.\u003c/p\u003e \u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003eGC-MS analyses of hexane extract\u003c/h2\u003e \u003cp\u003eThe first study was performed on a Gas Chromatography coupled to Mass Spectrometry GCMS-QP2010 Plus, Shimadzu, Japan interfaced to a scan from 50 to 1.000 m/z. detector. The capillary column (30 m x 0.25 mm x 0.25 \u0026micro;m film thickness) was ZBWax. The samples were injected in the split mode (split ratio of 80:1). The injector temperature was kept at 250\u0026deg;C. The interface temperature was held at 200\u0026deg;C. The column temperature was initially 50 \u0026ordm;C with a hold of 5 minutes then programmed to 250\u0026ordm;C at the rate of 5 \u0026ordm;C/min. The carrier gas was helium, having a constant flow rate of 1 ml/min, The samples were injected in the split mode (split ratio of 10:1), and the injection volume was 1 \u0026micro;l. Standard 70 eV EI spectra were recorded from 50 to 1000 m/z mass range. Identification of compounds was conducted using NIST database. The name, formula and molecular weight of the identified compounds were ascertained (Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eIn the re-study of hexane extract by GC/MS, the column used was an HP\u003cem\u003e-\u003c/em\u003e5MS (5%-phenylmethylpolysiloxane, 30 m x 0,25 mm, 0,25 \u0026micro;m i.d.) however the chromatographic conditions were the same as in the previous analysis.\u003c/p\u003e \u003c/div\u003e\n\u003ch3\u003eStudy on dichloromethane extract\u003c/h3\u003e\n\u003cp\u003eDichloromethane extract (500 mg) was fractioned by column chromatographic over silica gel 60 (70\u0026ndash;230 mesh ASTM) by gradient elution with n-hexane in ethyl acetate (AcOEt ) system (95:5 to 0:100, each 10 mL) and finally Methanol (MeOH) 100%. The 203 fractions collected were compared by TLC chromatography (silica gel 20 x 20 cm, 0,25 mm, Kieselgel 60GF254, E.Merck; derivatization with p-hydrobenzaldeyde) and the similar ones are pooled together. \u003cem\u003eThe pooled fractions\u003c/em\u003e column-chromatographic-V-53-68 (D-V-53-68) (94 mg) were applied to a silica gel 60 column eluted with an increasing linear gradient from 15 to 100% (v/v) methanol in ethyl acetate. 80 fractions were collected, also chromatographed by TLC on silica gel (derivatization with p-hydrobenzaldeyde) and t\u003cem\u003ehe similar fractions were pooled\u003c/em\u003e together. The combined fractions D- VI- 26\u0026ndash;42 (3,8 mg) were injected into a CG/MS system for analysis.\u003c/p\u003e \u003cp\u003eThe GC/MS analysis was carried out with a Shimadzu (GCMS\u003cem\u003e-\u003c/em\u003eQP2010 Plus, Kyoto) system. HP\u003cem\u003e-\u003c/em\u003e5MS column (5%-phenylmethylpolysiloxane, 30 m x 0,25 mm, di\u0026acirc;m. int. 0,25) was used with a helium carrier gas at 1.0 mL/min. The injection was made in splitless and the injector temperature was 250\u0026deg;C. The oven initial temperature was 60 \u0026deg; C, and then programmed to increase at a rate of 3\u0026deg;C per min until it reaches 260 \u0026deg; C, and held for 40 min. The interface temperature was 240\u0026deg;C, mass spectra were taken at 70 eV and the mass range was from m.z 40 to 1000. The compound identification was performed by comparing the spectra with the NIST08, NIST08s, Wiley9 and Nist Mass Spectral Search Program from Nist/ Epa/ Nih Mass Spectral Library Version 2.0 and literature data.\u003c/p\u003e\n\u003ch3\u003eStudies on ethyl acetate extract\u003c/h3\u003e\n\u003cp\u003eThe ethyl acetate extract (400 mg) was fractioned by chromatography column on s\u0026iacute;lica gel 60 (70\u0026ndash;230 mesh ASTM). The column was eluted with a stepwise gradient of ethyl acetate (AcOEt ) e Methanol (MeOH) (95:5 to 0:100) and after being analyzed by TLC, the similar fractions were bulked together according to their TLC profile. The bulked fractions labeled D-I 91\u0026ndash;154 were submitted to chromatographic purification on s\u0026iacute;lica gel 60 (70\u0026ndash;230 mesh ASTM) column with isocratic elution by AcOEt / MeOH 99:1, (v/v). The eluted fractions were evaluated and pooled together according to TLC analysis. The pooled fractions D-II 27\u0026ndash;51 were studied by \u003csup\u003e1\u003c/sup\u003eH Nuclear Magnetic Resonance Spectroscopy (NMR spectroscopy).\u003c/p\u003e \u003cp\u003eAbout 320 mg of ethyl acetate extract were submitted to a TLC-DPPH guided frationation on preparative plates as stationary phase and mixture of ethyl acetate/ Methanol (99:1, v/v) as mobile phase. After development, the DPPH-positive region were removed from the plates and extracted with MeOH. This extract was submitted to a clean-up procedure on a s\u0026iacute;lica gel 60 column eluted with ethyl ether, AcOEt/MeOH 1%, AcOEt/MeOH 10% and MeOH 100%. The purified fractions were evaluated by TLC and pooled together according to their similarities. The pooled fractions DII- 9\u0026ndash;12 and D-II 15\u0026ndash;19, each one in this turn, were chromatographed on a Sephadex-LH-20 column (60 cm x 2 cm) eluted with AcOEt/MeOH 99:1 (v/v). After evaluation by TLC analyzes, from the first procedure, three groups of fractions were formed: D-III 1\u0026ndash;25, D-III 33\u0026ndash;39 and D-III 41\u0026ndash;51 which were studied by \u003csup\u003e1\u003c/sup\u003eH and \u003csup\u003e13\u003c/sup\u003eC NMR spectroscopy. From the second procedure, the D-IV 1\u0026ndash;31 e D-IV 32\u0026ndash;47 fractions were bulked together and studied by \u003csup\u003e1\u003c/sup\u003eH NMR spectroscopy.\u003c/p\u003e"},{"header":"Results and discussion","content":"\u003cdiv id=\"Sec7\" class=\"Section2\"\u003e\n \u003ch2\u003eChemical studies of hexane and dichloromethane extracts\u003c/h2\u003e\n \u003cp\u003eThe GC-MS analysis of the hexane extract revealed the presence of 104 (Fig. \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e) compounds (listed in the attached Table \u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e), including hydrocarbons, esters, alcohols, fatty acids, as well as contaminants such as silicones (polysiloxanes) and phthalates. This is particularly concerning from an environmental perspective, given that the sampling site is located within a protected area (Minist\u0026eacute;rio do Meio Ambiente, \u003cspan class=\"CitationRef\"\u003e2009\u003c/span\u003e; Marinha do Brasil, \u003cspan class=\"CitationRef\"\u003e2016\u003c/span\u003e) (table 2). Recent studies continue to report the widespread presence of such contaminants in marine environments, including remote regions, indicating long-range atmospheric transport and deposition of anthropogenic residues (Waller et al., \u003cspan class=\"CitationRef\"\u003e2017\u003c/span\u003e; Gonz\u0026aacute;lez-Pleiter et al., \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Barletta et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e; Bergmann et al., \u003cspan class=\"CitationRef\"\u003e2022\u003c/span\u003e; Li et al., \u003cspan class=\"CitationRef\"\u003e2023\u003c/span\u003e).\u003c/p\u003e\n \u003cdiv class=\"gridtable\"\u003e\n \u003ctable id=\"Tab1\" border=\"1\"\u003e\n \u003ccaption\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eSubstances (metabolites and pollutants) identified by CG-MS of hexane extract\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eN\u0026ordm;\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e*RT (min)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e*SI\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e*KI\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eSubstance\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eMolecular formula\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eMolecular weight\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e%\u003c/p\u003e\n \u003c/th\u003e\n \u003cth colspan=\"4\" align=\"left\"\u003e\n \u003cp\u003eSource\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eAdditional Information\u003c/p\u003e\n \u003c/th\u003e\n \u003cth rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eReferences\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eAlgae\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eVegetables and animals\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e# Synthesis\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003e## Synthesis\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e5,167\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e913,2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEthane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e2\u003c/sub\u003eH\u003csub\u003e2\u003c/sub\u003eCl\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e169,85\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,02%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e13,267\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"12\" align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e15,975\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1223,1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOxiranecarboxaldehyde\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e168,236\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,05%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e17,983\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e89\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1270,7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3,7-Dimethyl-2,6-Octadienal\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e152,237\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,09%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eManufacture of other chemical products\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ Physical Description from CAMEO Chemicals\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e20,15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1367\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNerolic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e168,236\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,15%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e20,592\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1398,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCyclohexasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e6\u003c/sub\u003eSi\u003csub\u003e6\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e444,924\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,16%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e--\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e23,383\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1499,1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDocosane (CAS)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e46\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e310,61\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,26%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlants\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eFlavorful\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eUsed in organic systems for synthesis, calibration and temperature detection\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKamenarska et al., 2006/ Pubchem/ Physical Description from CAMEO Chemicals\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e25,108\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1542\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4-Hexen-3-one (CAS)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e10\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e98,145\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,29%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eFlavoring\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e27,442\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1599,7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eTricosane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e48\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e324,637\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,35%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e27,667\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1605,5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCycloheptasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e42\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003eSi\u003csub\u003e6\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e458,995\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,37%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e27,85\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1610,2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePentadecanal\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e226,404\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,38%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e27,925\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e92\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1612,2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePhenol, 2,4-bis(1,1-dimethylethyl)- (CAS)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e206,329\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,40%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e--\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e28,475\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1626,4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDihydroactinidiolide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e11\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e180,247\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,42%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e29,867\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e85\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1662,3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eGlycine\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e29\u003c/sub\u003eNO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e271,401\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,46%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e31,117\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1694,6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,2-Benzenedicarboxylic acid,\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e222,24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,49%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer / makes plastics more flexible\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e16\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e31,317\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e92\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1699,7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eHeneicosane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e44\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e296,583\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,51%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e17\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e34,133\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1776\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCyclooctasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e48\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003eSi\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e593,232\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,55%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e18\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e35,017\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1799,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEicosane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e42\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e282,556\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,57%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e19\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e35,933\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1825,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eOctadecanoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e298,511\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,64%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlants\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eAnti-foaming agent and fermentation nutrients\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e20\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"char\"\u003e\n \u003cp\u003e37,333\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"char\"\u003e\n \u003cp\u003e93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e1865,6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eTetradecanoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e228,376\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e0,68%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eAnimal and vegetable fats\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eCosmetics\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eFlavoring\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eSoaps\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ MeSH\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eHMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e21\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e39,775\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e84\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1936,7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCyclononasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e54\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003eSi\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e667,386\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,73%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e22\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e39,867\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1939,4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNeophytadiene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e278,524\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,75%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e23\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e40,058\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e84\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1945,1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2-Pentadecanone, 6,10,14-trimethyl-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e268,485\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,77%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e40,708\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1964,5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3,7,11,15-Tetramethyl-2-hexadecen-1-ol\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e40\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e296,531\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,81%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNist web\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e25\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e40,825\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1967,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,2-Benzenedicarboxylic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e278,348\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,04%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e26\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e42,5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2018,6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e(E, E) -7,11,15-Trimethyl-3-methylene-hexadeca-1,6,10,14-tetraene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e272,476\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,90%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e27\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e42,758\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2026,7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eHexadecanoic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e270,457\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e0,93%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e28\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"char\"\u003e\n \u003cp\u003e43,983\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"char\"\u003e\n \u003cp\u003e91\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e2064,8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003ePalmitic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e256,43\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e1,01%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eAnimal, vegetable and human fat\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ Pharmacology from NCIt/\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eHMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e29\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e44,825\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e81\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2091\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEicosamethylcyclodecasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e60\u003c/sub\u003eO\u003csub\u003e10\u003c/sub\u003eSi\u003csub\u003e10\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e741,54\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,04%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e46,392\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2121,3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDoconexent\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e328,496\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,12%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eAnimal oil (fish)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ MeSH\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e31\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e47,242\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e82\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2135,4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDi-isopentylphthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e306,402\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,14%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e32\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e48,183\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2151,1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9-Octadecenoic acid (Z)-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e296,495\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,19%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e33\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e49,008\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e87\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2164,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eMethyl Octadecanoate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e298,511\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,23%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlants\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eAnti-foaming agent and fermentation nutrients\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eHMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e34\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e49,158\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2167,4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9,12-Octadecadienoic acid (Z,Z)-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e280,452\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,25%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e35\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"char\"\u003e\n \u003cp\u003e50,033\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"char\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e2181,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eAscorbic acid 2,6-dihexadecanoate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e284,484\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e1,30%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003eAnimal and vegetable fat\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ Pharmacology from NCIt/\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eHMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e36\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e52,758\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2258,1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5,8,11,14-Eicosatetraenoic acid, methyl ester\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e318,501\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,36%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eAnimal and human fat\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ MeSH\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e37\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e53,975\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2301,2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eArachidonic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e304,474\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,10%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eAnimal and human fat\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eAhern et al., 1983/ Kim and Chojnacka, 2015/ Pubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e38\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e55,192\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e83\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2346\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBenzyl butyl phthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e312,365\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,50%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e39\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e56,65\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e89\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2399,7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eHexanedioic acid, bis (2-ethylhexyl) ester (CAS)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e42\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e370,574\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,56%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eAditivo alimentar indireto decorrente do contato com pol\u0026iacute;meros e adesivos\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e40\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e59,617\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e89\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2513,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePhosphine oxide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eOP\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e278,291\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,61%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e41*\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e60,475\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2547,8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,2-Benzenedicarboxylic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e278,348\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,63%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e42\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e67,242\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2826,5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2,6,10,14,18,22-Tetracosahexaene\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e30\u003c/sub\u003eH\u003csub\u003e50\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e410,73\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,74%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eAnimal, vegetable and human fat\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e43\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e70,592\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e78\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2948,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCholesteryl bromide\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e45\u003c/sub\u003eBr\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e449,561\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,78%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e44\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e77,108\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e93\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3123,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eVitamin E\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e29\u003c/sub\u003eH\u003csub\u003e50\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e430,717\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,89%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlants\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e45\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e85,858\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"char\"\u003e\n \u003cp\u003e87\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eStigmasta-5,24(28)-dien-3-ol, (3.beta.)- (CAS)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e29\u003c/sub\u003eH\u003csub\u003e48\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e412,702\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,90%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlants\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n \u003c/div\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003cp\u003eAmong the natural metabolites detected, four sterols were noteworthy: fucosterol, isofucosterol, 24-ethylcholesta-5,24(25)-dienol, and stigmasta-5,24(24)-dien-3-ol. These compounds are widely reported in brown algae, where they play structural roles in cellular membranes, as well as exhibiting potential bioactivities such as anti-inflammatory, antioxidant, and anticancer properties (Findlay \u0026amp; Patil, \u003cspan class=\"CitationRef\"\u003e1985\u003c/span\u003e; Kerr \u0026amp; Baker, \u003cspan class=\"CitationRef\"\u003e1991\u003c/span\u003e; Lopes et al., \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Moss et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eFucosterol, in particular, is commonly found in species of the orders Fucales, Laminariales, and Desmarestiales, where it contributes to the regulation of membrane fluidity under cold and saline conditions, as observed in Antarctic algae (Mayer et al., \u003cspan class=\"CitationRef\"\u003e2013\u003c/span\u003e; Pereira et al., \u003cspan class=\"CitationRef\"\u003e2017\u003c/span\u003e; Silva et al., \u003cspan class=\"CitationRef\"\u003e2023\u003c/span\u003e). Recent studies have reinforced its pharmacological potential, highlighting neuroprotective, hypoglycemic, and anti-inflammatory effects (Jiang et al., \u003cspan class=\"CitationRef\"\u003e2023\u003c/span\u003e; Lee et al., \u003cspan class=\"CitationRef\"\u003e2022\u003c/span\u003e; Sathasivam et al., \u003cspan class=\"CitationRef\"\u003e2019\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eIn addition to sterols, the presence of saturated and unsaturated fatty acids was significant, especially hexadecanoic acid (palmitic acid), oleic acid, and linoleic acid. These compounds are known to play essential roles in protection against oxidative stress and in chemical communication both within and between species (Guschina \u0026amp; Harwood, \u003cspan class=\"CitationRef\"\u003e2009\u003c/span\u003e; Wang et al., \u003cspan class=\"CitationRef\"\u003e2022\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eThe detection of compounds such as phthalates and polydimethylsiloxanes raises serious environmental concerns and suggests diffuse contamination, corroborating recent findings that demonstrate the persistent presence of microplastics and their chemical derivatives even in minimally impacted marine ecosystems (Obbard et al., \u003cspan class=\"CitationRef\"\u003e2014\u003c/span\u003e; Lacerda et al., \u003cspan class=\"CitationRef\"\u003e2019\u003c/span\u003e; Pabortsava \u0026amp; Lampitt, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Bergmann et al., \u003cspan class=\"CitationRef\"\u003e2022\u003c/span\u003e; Li et al., \u003cspan class=\"CitationRef\"\u003e2023\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eThe GC-MS analysis of the dichloromethane extract, after chromatographic fractionation, confirmed the presence of major fractions composed of lipophilic metabolites, including phenolic derivatives and sterols. These findings are consistent with chemical profiles reported for brown macroalgae (Hakim \u0026amp; Patel, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Moss et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e; Kang et al., \u003cspan class=\"CitationRef\"\u003e2022\u003c/span\u003e). Although present in smaller quantities, these compounds are of high biotechnological interest due to their potential bioactive properties.\u003c/p\u003e\n \u003cp\u003eOverall, the chemical profile obtained aligns with the literature describing brown macroalgae as rich sources of bioactive compounds, particularly sterols, terpenes, long-chain fatty acids, and polyphenols, with potential applications in the pharmaceutical, cosmetic, and functional food industries (Holdt \u0026amp; Kraan, \u003cspan class=\"CitationRef\"\u003e2011\u003c/span\u003e; Lopes et al., \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Moss et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e).\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec8\" class=\"Section2\"\u003e\n \u003ch2\u003eAromatic Compounds in the Ethyl Acetate Extract\u003c/h2\u003e\n \u003cp\u003eFractions obtained from the ethyl acetate extract of \u003cem\u003eDesmarestia menziesii\u003c/em\u003e showed fluorescence under UV light, indicating the presence of aromatic compounds (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e). Nuclear Magnetic Resonance (NMR) analysis revealed signals consistent with meroterpenoids, a class of hybrid molecules derived from terpenoid and polyketide biosynthetic pathways (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e). These compounds are widely distributed in brown algae and are associated with various biological functions (Davyt et al., \u003cspan class=\"CitationRef\"\u003e2016\u003c/span\u003e; Blunt et al., \u003cspan class=\"CitationRef\"\u003e2018\u003c/span\u003e; Hakim \u0026amp; Patel, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003cp\u003eMeroterpenoids are known for their antioxidant, antimicrobial, and cytotoxic properties, contributing to the defense mechanisms of algae against microbial colonization and herbivory (Numata et al., \u003cspan class=\"CitationRef\"\u003e1991\u003c/span\u003e; Blunt et al., \u003cspan class=\"CitationRef\"\u003e2018\u003c/span\u003e; Hakim \u0026amp; Patel, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e). Recent studies have reinforced that brown algae produce a broad diversity of bioactive meroterpenoids, including phlorotannins and other aromatic secondary metabolites, which play critical roles in ecological interactions and stress tolerance (Hakim \u0026amp; Patel, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Nazir et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eFurthermore, phenolic compounds commonly found in brown algae, such as phlorotannins, are responsible for UV protection and oxidative stress mitigation, particularly in polar and intertidal environments (Bayer-Giraldi et al., \u003cspan class=\"CitationRef\"\u003e2014\u003c/span\u003e; Cotas et al., \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Nazir et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e). These compounds absorb harmful UV radiation and neutralize reactive oxygen species (ROS), enhancing algal survival in extreme habitats.\u003c/p\u003e\n \u003cp\u003eFrom a biotechnological perspective, the antioxidant, antimicrobial, and anti-inflammatory activities of these aromatic compounds make them promising candidates for applications in cosmeceuticals, nutraceuticals, and pharmaceuticals (Rivera et al., \u003cspan class=\"CitationRef\"\u003e1990\u003c/span\u003e; Davyt et al., \u003cspan class=\"CitationRef\"\u003e2016\u003c/span\u003e; Nazir et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e). Their bioactivities are being increasingly explored for human health applications, especially due to their radical scavenging, anti-aging, and anti-tumoral properties (Numata et al., \u003cspan class=\"CitationRef\"\u003e1991\u003c/span\u003e; Blunt et al., \u003cspan class=\"CitationRef\"\u003e2018\u003c/span\u003e; Nazir et al., \u003cspan class=\"CitationRef\"\u003e2021\u003c/span\u003e).\u003c/p\u003e\n\u003c/div\u003e\n\u003ch3\u003eIsolation and Characterization of Mannitol\u003c/h3\u003e\n\u003cp\u003eA colorless crystalline compound (17.5523 g) was isolated from the methanolic extract (33.4516 g) of \u003cem\u003eD. menziesii\u003c/em\u003e, representing approximately 52% of the total extract. The crystals were thoroughly washed with heptane and subjected to spectrometric and spectroscopic analyses.\u003c/p\u003e\n\u003cp\u003eThe infrared (IR) spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e) displays characteristic absorption bands corresponding to hydroxyl (O-H) groups and C-H stretching from methylene (CH₂) and methine (CH) groups. The complete vibrational assignments are presented in Table\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e. Based on this analysis, the compound is composed of a chain of sp\u0026sup3; carbons bearing multiple hydroxyl groups.\u003c/p\u003e\n\u003cdiv class=\"gridtable\"\u003e\n \u003cdiv class=\"colspec\" align=\"left\"\u003e\u0026nbsp;\u003c/div\u003e\n \u003ctable id=\"Tab2\" border=\"1\"\u003e\n \u003ccaption\u003e\n \u003cdiv class=\"CaptionNumber\"\u003eTable\u0026nbsp;2\u003c/div\u003e\n \u003cdiv class=\"CaptionContent\"\u003e\n \u003cp\u003eContaminants identified from the Hexane extract by GC-MS\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eN\u0026ordm;\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e*RT (min)\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e*IS\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e*IK\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eSubstance\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMolecular formula\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eMolecular weight\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e%\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"4\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eSource\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eAdditional Information\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" rowspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eReferences\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eAlgae\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003eVegetables and animals\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e# Synthesis\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u003cstrong\u003e# # Synthesis\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e60,475\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2547,8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,2-Benzenedicarboxylic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e278,348\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e26%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e56,65\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e89\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2399,7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eHexanedioic acid, bis (2-ethylhexyl) ester (CAS)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e42\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e370,574\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eIndirect food additive due to contact with polymers and adhesives\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e55,192\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e83\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2346\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eBenzyl butyl phthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e312,365\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e47,242\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e82\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2135,4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDi-isopentylphthalate\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e306,402\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e44,825\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e81\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2091\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEicosamethylcyclodecasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e60\u003c/sub\u003eO\u003csub\u003e10\u003c/sub\u003eSi\u003csub\u003e10\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e741,54\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e40,825\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e96\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1967,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,2-Benzenedicarboxylic acid\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e278,348\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e21%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e39,775\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e84\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1936,7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCyclononasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e54\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003eSi\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e667,386\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e34,133\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e88\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1776\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCyclooctasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e48\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003eSi\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e593,232\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e31,117\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1694,6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1,2-Benzenedicarboxylic acid,\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e222,24\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePlasticizer / makes plastics more flexible\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003ePubchem/ HMDB\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e27,667\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1605,5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCycloheptasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e42\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003eSi\u003csub\u003e6\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e458,995\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e13%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e20,592\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1398,9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCyclohexasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e6\u003c/sub\u003eSi\u003csub\u003e6\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e444,924\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e--\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"2\" align=\"left\"\u003e\n \u003cp\u003e12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e13,267\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1157,2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCyclopentasiloxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003eSi\u003csub\u003e5\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e370,77\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2%\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCosmetics and skin emollient\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eSilicone residue\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\n \u003cp\u003ePubchem/ DrugBank\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"14\" align=\"left\"\u003e\n \u003cp\u003e*N - Number/ RT - retention time (minutes) / SI - similarity index / D - database / KI - Kovats index / % - percentage\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"14\" align=\"left\"\u003e\n \u003cp\u003e# Synthesis - Special care products / ## Synthesis - Food additives\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd colspan=\"3\" align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n\u003c/div\u003e\n\u003cdiv class=\"gridtable\"\u003e\n \u003cdiv class=\"colspec\" align=\"left\"\u003e\u0026nbsp;\u003c/div\u003e\n \u003cdiv class=\"colspec\" align=\"left\"\u003e\u0026nbsp;\u003c/div\u003e\n \u003cdiv class=\"colspec\" align=\"left\"\u003e\u0026nbsp;\u003cstrong\u003eTable 3.\u0026nbsp;\u003c/strong\u003eAssignment for IR characteristic bands of functional groups and of the bands of the crystalized compound\u0026nbsp;\u003c/div\u003e\n \u003cdiv class=\"colspec\" align=\"left\"\u003e\u0026nbsp;\u003c/div\u003e\n \u003ctable id=\"Taba\" border=\"1\"\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\u0026nbsp;\u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eStretch Absorption\u003c/p\u003e\n \u003cp\u003ecm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eStrain Absorption\u003c/p\u003e\n \u003cp\u003ecm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eObserved Absorption\u003c/p\u003e\n \u003cp\u003ecm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC-H of alkanes\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.962\u0026ndash;2.853\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u0026sim; 1.340\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2.935; 2.340\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC-H\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.484\u0026ndash;1.445\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e722\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.453; 702\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eO-H (in association)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3.400\u0026ndash;3.200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u0026sim; 1.050\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3.250; 1.089*\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eC-O\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.350\u0026ndash;1.260\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e\u0026sim; 1.050\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1.340; 1.029*\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"4\" align=\"left\"\u003e\n \u003cp\u003eThe values 1.340 and 1.029 can be interchangeable *Dyer, 1965.\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n\u003c/div\u003e\n\u003cp\u003eThe ^1H NMR spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003e) reveals four distinct groups of signals related to hydrogens bonded to sp\u0026sup3; carbons attached to hydroxyl groups: two double doublets at \u0026delta;H 3.56 (J\u0026thinsp;=\u0026thinsp;16, 6 Hz) and \u0026delta;H 3.78 (J\u0026thinsp;=\u0026thinsp;14, 3.4 Hz); a doublet of double doublets at \u0026delta;H 3.66 (J\u0026thinsp;=\u0026thinsp;16.7, 3 Hz); and a doublet at \u0026delta;H 3.69 (J\u0026thinsp;=\u0026thinsp;9 Hz).\u003c/p\u003e\n\u003cp\u003eThe ^13C NMR spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003e) shows three signals at \u0026delta; 63.18, 69.0, and 70.7 ppm, which are indicative of carbons bonded to hydroxyl groups. The HSQC spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e7\u003c/span\u003e) confirms that the molecule consists of one methylene (-CH₂OH) group and two methine (-CHOH) groups. The molecular structure suggests that the methylene group is located at one end of the chain, adjacent to a methine group, which in turn is connected to another methine group. This arrangement is only possible if the molecule is symmetric.\u003c/p\u003e\n\u003cp\u003eThe mass spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e8\u003c/span\u003e) displays a molecular ion peak at m/z 183.172, consistent with the molecular formula C₆H₁₄O₆, which corresponds to mannitol (Hagiwara et al., \u003cspan class=\"CitationRef\"\u003e2005\u003c/span\u003e; Moreira, \u003cspan class=\"CitationRef\"\u003e2009\u003c/span\u003e), with an exact molecular weight of 183.0861. The peak at m/z 205.0678 corresponds to the sodium adduct (M\u0026thinsp;+\u0026thinsp;Na)+, while the fragment peaks at m/z 165.0756, 147.0645, 129.0545, and 111.0441 are attributed to successive losses of water molecules (\u0026Delta;m\u0026thinsp;=\u0026thinsp;18) (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e9\u003c/span\u003e).\u003c/p\u003e\n\u003cp\u003eMannitol is a polyol known for its remarkable physicochemical properties. It exists in multiple crystalline forms\u0026mdash;up to seven, as described by Pitkinen et al. (\u003cspan class=\"CitationRef\"\u003e1993\u003c/span\u003e)\u0026mdash;some of which spontaneously form upon cooling from the melt (162\u0026thinsp;\u0026plusmn;\u0026thinsp;2\u0026deg;C). These polymorphs have been characterized using Raman and infrared spectroscopy (Ye \u0026amp; Byron, \u003cspan class=\"CitationRef\"\u003e2008\u003c/span\u003e). Mannitol can also form hydrates (Yu et al., \u003cspan class=\"CitationRef\"\u003e1999\u003c/span\u003e) and exhibits a low freezing point of -117\u0026deg;C (Gunasekara et al., 2014).\u003c/p\u003e\n\u003ch3\u003eFunctional Roles in Brown Algae\u003c/h3\u003e\n\u003cdiv id=\"Sec11\" class=\"Section2\"\u003e\n \u003ch2\u003eOsmoregulation and Cryoprotection\u003c/h2\u003e\n \u003cp\u003eMannitol plays a crucial physiological role in brown algae, functioning as an osmotic regulator that allows the organism to withstand fluctuating salinity and desiccation, typical of intertidal and polar environments. It also serves as a cryoprotectant by minimizing ice formation during freeze-thaw cycles, thereby enhancing cell survival in cold habitats (Robinson, \u003cspan class=\"CitationRef\"\u003e2001\u003c/span\u003e; Groisillier et al., \u003cspan class=\"CitationRef\"\u003e2014\u003c/span\u003e; Hakim \u0026amp; Patel, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eThis cryoprotective function arises from mannitol\u0026rsquo;s ability to form hydrogen bonds with water molecules, preventing ice crystal nucleation and growth. The spatial arrangement of hydroxyl groups, with oxygen-oxygen distances of approximately 4.2 to 4.5 \u0026Aring;, is key to this antifreeze activity (Baruch et al., \u003cspan class=\"CitationRef\"\u003e2008\u003c/span\u003e). Additionally, ice-binding proteins (IBPs) in marine algae work synergistically with polyols like mannitol to further inhibit ice recrystallization (Bayer-Giraldi et al., \u003cspan class=\"CitationRef\"\u003e2014\u003c/span\u003e; Bar Dolev et al., \u003cspan class=\"CitationRef\"\u003e2016\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eThese mechanisms are particularly critical for macroalgae from Antarctic environments, where repeated freeze-thaw cycles and osmotic stress are persistent challenges (Mayer et al., \u003cspan class=\"CitationRef\"\u003e2013\u003c/span\u003e; Bar Dolev et al., \u003cspan class=\"CitationRef\"\u003e2016\u003c/span\u003e). In this study, over 50% of the methanolic extract was composed of mannitol, underscoring its significant physiological role.\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec12\" class=\"Section2\"\u003e\n \u003ch2\u003eAntioxidant and Metabolic Functions\u003c/h2\u003e\n \u003cp\u003eBeyond its role in osmoregulation and cryoprotection, mannitol functions as a primary carbon and energy reservoir in brown algae. It accumulates during photosynthesis and is mobilized under stress conditions such as low light, darkness, or environmental fluctuations (Groisillier et al., \u003cspan class=\"CitationRef\"\u003e2014\u003c/span\u003e; Hakim \u0026amp; Patel, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e).\u003c/p\u003e\n \u003cp\u003eMannitol also exhibits potent antioxidant activity by scavenging reactive oxygen species (ROS), which are generated in response to stressors like high UV radiation, temperature extremes, and oxidative damage (Rousvoal et al., \u003cspan class=\"CitationRef\"\u003e2011\u003c/span\u003e; Mayer et al., \u003cspan class=\"CitationRef\"\u003e2013\u003c/span\u003e; Hakim \u0026amp; Patel, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e).\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv id=\"Sec13\" class=\"Section2\"\u003e\n \u003ch2\u003eBiotechnological Applications\u003c/h2\u003e\n \u003cp\u003eThe high abundance of mannitol in \u003cem\u003eD. menziesii\u003c/em\u003e highlights its significant potential for biotechnological and industrial applications. In the pharmaceutical industry, mannitol is widely used as an osmotic diuretic, excipient, and component of various medical formulations. It also serves as a low-calorie sweetener in the food industry and as a stabilizer in cosmetic products.\u003c/p\u003e\n \u003cp\u003eIn biotechnology, its cryoprotective, osmoprotective, and antioxidant properties are exploited in biopreservation and the development of sustainable, eco-friendly products (Groisillier et al., \u003cspan class=\"CitationRef\"\u003e2014\u003c/span\u003e; Hakim \u0026amp; Patel, \u003cspan class=\"CitationRef\"\u003e2020\u003c/span\u003e; Nazir et al., 2022). Recent research emphasizes the sustainable extraction of mannitol from macroalgae as a renewable alternative to synthetic production, contributing to greener industrial processes (Nazir et al., 2022)\u003c/p\u003e\n\u003c/div\u003e"},{"header":"Conclusion","content":"\u003cp\u003eThe chemical characterization of \u003cem\u003eDesmarestia menziesii\u003c/em\u003e revealed a significant diversity of bioactive metabolites, including sterols, fatty acids, meroterpenoids, and the polyol mannitol. These compounds play essential roles in the alga's adaptation to extreme Antarctic conditions, providing protection against freezing, osmotic stress, UV radiation, and oxidative damage. The high concentration of mannitol confirms its critical physiological function as a cryoprotectant and antioxidant. Beyond ecological and physiological significance, these metabolites exhibit substantial biotechnological potential, particularly for applications in pharmaceutical, cosmetic, and food industries, as well as in biopreservation and the development of sustainable products. On the other hand, the detection of organic pollutants such as phthalates and siloxanes in samples from remote Antarctic regions underscores the alarming global spread of plastic pollution, reinforcing the urgent need for global actions to mitigate environmental impacts. This study provides valuable insights into the bioprospecting and conservation of Antarctic marine resources while strengthening the scientific basis for future developments in marine biotechnology.\u003c/p\u003e "},{"header":"Declarations","content":"\u003cp\u003e \u003cb\u003eFunding Declaration\u003c/b\u003e \u003c/p\u003e \u003cp\u003eThis work was developed with funding from the Conselho Nacional de Desenvolvimento Cient\u0026iacute;fico e Tecnol\u0026oacute;gico (CNPQ, Brazil), project: 134529/2016-2.\u003c/p\u003e\u003ch2\u003eAuthor Contribution\u003c/h2\u003e\u003cp\u003eEMS and APM contributed to the structuring of the article.ANG and LRC contributed to the writing, structure and review.PCN and NSY contributed to the material, infrastructure, assistance and technical support.\u003c/p\u003e\u003ch2\u003eAcknowledgments\u003c/h2\u003e \u003cp\u003eThe authors wish to thank Conselho Nacional de Desenvolvimento Cient\u0026iacute;fico e Tecnol\u0026oacute;gico (CNPQ, Brazil) for the scholarship awarded to the first author.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eAndrady AL (2011) Microplastics in the marine environment. 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J Pharm Sci 88(2):196\u0026ndash;198\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"polar-biology","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"pobi","sideBox":"Learn more about [Polar Biology](http://link.springer.com/journal/300)","snPcode":"300","submissionUrl":"https://submission.nature.com/new-submission/300/3","title":"Polar Biology","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Antarctic macroalgae, Secondary metabolites, Antifreeze compounds, Mannitol, Marine sterols, Bioactive compounds","lastPublishedDoi":"10.21203/rs.3.rs-6814752/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-6814752/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThis study investigated the chemical composition of the Antarctic brown macroalga \u003cem\u003eDesmarestia menziesii\u003c/em\u003e, collected from Penguin and Livingston Islands. Sequential extractions using hexane, dichloromethane, ethyl acetate, and methanol were performed, followed by GC-MS, NMR, IR, and mass spectrometry analyses. The hexane extract revealed the presence of sterols such as fucosterol, isofucosterol, 24-ethylcholesta-5,24(25)-dienol, and stigmasta-5,24(28)-dien-3β-ol, in addition to saturated and unsaturated fatty acids. Environmental contaminants, including phthalates and siloxanes, were also detected, highlighting the alarming spread of anthropogenic pollution even in remote Antarctic environments. The ethyl acetate extract contained aromatic meroterpenoids with recognized antioxidant, antimicrobial, and cytotoxic activities. The methanolic extract was predominantly composed of mannitol (over 50%), a polyol with osmoregulatory, cryoprotective, and antioxidant properties. These findings expand the current knowledge of the chemodiversity of Antarctic macroalgae and highlight the biotechnological potential of the identified metabolites, with promising applications in pharmaceuticals, cosmetics, functional foods, and biopreservation.\u003c/p\u003e","manuscriptTitle":"Study on the chemical constituents of Desmarestia menziesii (Ochrophyta, Desmarestiales), an Antarctic seaweed","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-06-20 07:05:31","doi":"10.21203/rs.3.rs-6814752/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2026-01-10T16:41:00+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-07-16T11:21:01+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"199906430136190608480464834904533420673","date":"2025-06-27T11:33:59+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-06-18T07:23:12+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-06-18T07:19:19+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-06-09T09:08:43+00:00","index":"","fulltext":""},{"type":"submitted","content":"Polar Biology","date":"2025-06-03T22:45:47+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"polar-biology","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"pobi","sideBox":"Learn more about [Polar Biology](http://link.springer.com/journal/300)","snPcode":"300","submissionUrl":"https://submission.nature.com/new-submission/300/3","title":"Polar Biology","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"8d565a5a-8e82-4589-99c2-3af7c3e4838e","owner":[],"postedDate":"June 20th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2026-05-04T16:35:17+00:00","versionOfRecord":{"articleIdentity":"rs-6814752","link":"https://doi.org/10.1007/s00300-026-03478-x","journal":{"identity":"polar-biology","isVorOnly":false,"title":"Polar Biology"},"publishedOn":"2026-04-30 15:58:11","publishedOnDateReadable":"April 30th, 2026"},"versionCreatedAt":"2025-06-20 07:05:31","video":"","vorDoi":"10.1007/s00300-026-03478-x","vorDoiUrl":"https://doi.org/10.1007/s00300-026-03478-x","workflowStages":[]},"version":"v1","identity":"rs-6814752","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-6814752","identity":"rs-6814752","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}