Hentriacontanonaene

Hentriacontanonaene
Names
	IUPAC name (3Z,6Z,9Z,12Z,15Z,19Z,22Z,25Z,28Z)-Hentriaconta-3,6,9,12,15,19,22,25,28-nonaene
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:209018;
ChemSpider	67168488;
PubChem CID	52922084;
CompTox Dashboard (EPA)	DTXSID401032410 ;
	InChI InChI=1S/C31H46/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29,31H,3-4,9-10,15-16,21-22,27-28,30H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29- Key: QBQCAYTWEQRERN-VHUCEKMMSA-N;
	SMILES CC\C=C/C\C=C/C\C=C/C\C=C/CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC;
Properties
Chemical formula	C31H46
Molar mass	418.709 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hentriacontanonaene is a long-chain polyunsaturated hydrocarbon produced by numerous gamma-proteobacteria primarily from the marine environment. Hentriacontanonaene was originally isolated from bacterial isolates from Antarctic sea ice cores.^[1] All isolated bacteria that produced hentriacontanonaene also produced the polyunsaturated fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).^[1]^[2] Given its polyunsaturated nature it has been proposed that this molecule is produced as part of a response to maintain optimal membrane fluidity.^[1]^[3]

^ ^a ^b ^c Nichols, David S.; Nichols, Peter D.; McMeekin, Tom A. (1995). "A new n-C31:9polyene hydrocarbon from Antarctic bacteria". FEMS Microbiology Letters. 125 (2–3): 281–285. doi:10.1111/j.1574-6968.1995.tb07369.x. ISSN 0378-1097.
^ Sugihara, Shinji; Hori, Ryuji; Nakanowatari, Hitomi; Takada, Yasuhiro; Yumoto, Isao; Morita, Naoki; Yano, Yutaka; Watanabe, Kazuo; Okuyama, Hidetoshi (2009). "Possible Biosynthetic Pathways for all cis-3,6,9,12,15,19,22,25,28-Hentriacontanonaene in Bacteria". Lipids. 45 (2): 167–177. doi:10.1007/s11745-009-3380-9. hdl:2115/43824. ISSN 0024-4201. PMID 20037794. S2CID 4036770.
^ Sukovich, D. J.; Seffernick, J. L.; Richman, J. E.; Hunt, K. A.; Gralnick, J. A.; Wackett, L. P. (2010). "Structure, Function, and Insights into the Biosynthesis of a Head-to-Head Hydrocarbon in Shewanella oneidensis Strain MR-1". Applied and Environmental Microbiology. 76 (12): 3842–3849. Bibcode:2010ApEnM..76.3842S. doi:10.1128/AEM.00433-10. ISSN 0099-2240. PMC 2893466. PMID 20418444.

[NicholsNichols1995-1] Nichols, David S.; Nichols, Peter D.; McMeekin, Tom A. (1995). "A new n-C31:9polyene hydrocarbon from Antarctic bacteria". FEMS Microbiology Letters. 125 (2–3): 281–285. doi:10.1111/j.1574-6968.1995.tb07369.x. ISSN 0378-1097.

[SugiharaHori2009-2] Sugihara, Shinji; Hori, Ryuji; Nakanowatari, Hitomi; Takada, Yasuhiro; Yumoto, Isao; Morita, Naoki; Yano, Yutaka; Watanabe, Kazuo; Okuyama, Hidetoshi (2009). "Possible Biosynthetic Pathways for all cis-3,6,9,12,15,19,22,25,28-Hentriacontanonaene in Bacteria". Lipids. 45 (2): 167–177. doi:10.1007/s11745-009-3380-9. hdl:2115/43824. ISSN 0024-4201. PMID 20037794. S2CID 4036770.

[SukovichSeffernick2010-3] Sukovich, D. J.; Seffernick, J. L.; Richman, J. E.; Hunt, K. A.; Gralnick, J. A.; Wackett, L. P. (2010). "Structure, Function, and Insights into the Biosynthesis of a Head-to-Head Hydrocarbon in Shewanella oneidensis Strain MR-1". Applied and Environmental Microbiology. 76 (12): 3842–3849. Bibcode:2010ApEnM..76.3842S. doi:10.1128/AEM.00433-10. ISSN 0099-2240. PMC 2893466. PMID 20418444.

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