LBF18302HP01: Difference between revisions

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|LipidBank=DFA8055
|LipidBank=DFA8055
|LipidMaps=LMFA01040039
|LipidMaps=LMFA01040039
|SysName=Methyl-15-Hydroperoxy-9,12,16-Octadecatrienoate
|SysName=Methyl-15-hydroperoxy- (cis-9,cis-12,trans-16) -octadecatrienoic acid
|Common Name=&&Methyl-15-Hydroperoxy-9,12,16-Octadecatrienoate&&
|Common Name=&&Methyl-15-hydroperoxy- (9Z,12Z,16E) -octadecatrienoic acid&&
|Mass Spectra=EI-MS(Me-ester; after reduction and hydrogenation)[[Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100}}]]: m/e=271[O=CH(CH2)13C(=OH)OCH3]; 242[CH2(CH2)12C(=OH)OCH3]; 239[O=CH(CH2)13C=O]; GC-EI-MS(Me-ester; after reduction and hydroganation)[[Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234}}]]: m/e=143[SMTO=CH-CH=CH-CH3]
|Mass Spectra=EI-MS(Me-ester; after reduction and hydrogenation)[[Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:,J. Am. Oil Chem. Soc.,1977,54,100}}]]: m/e=271[O=CH(CH2)13C(=OH)OCH3]; 242[CH2(CH2)12C(=OH)OCH3]; 239[O=CH(CH2)13C=O]; GC-EI-MS(Me-ester; after reduction and hydrogenation)[[Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234|{{RelationTable/GetFirstAuthor|Reference:Terao_J:Matsushita_S:,J. Am. Oil Chem. Soc.,1977,54,234}}]]: m/e=143[SMTO=CH-CH=CH-CH3]
|Source=Oxidation of linoleate by singlet oxygen[[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]].
|Source=Oxidation of linoleate by singlet oxygen<!--8022--><!--8023-->[[Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1980,19,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1983,22,1}}]][[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]]<!--8027--><!--8030-->.
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=
|Metabolism=
|Biological Activity=Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously.[[Reference:Logani_MK:Davies_RE:,Lipids,1980,15,485|{{RelationTable/GetFirstAuthor|Reference:Logani_MK:Davies_RE:,Lipids,1980,15,485}}]]<!--8044--><!--8045-->[[Reference:Sevanian_A:Hochstein_P:,Annu. Rev. Nutr.,1985,5,365|{{RelationTable/GetFirstAuthor|Reference:Sevanian_A:Hochstein_P:,Annu. Rev. Nutr.,1985,5,365}}]][[Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21|{{RelationTable/GetFirstAuthor|Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21}}]]<!--8048--><!--8049-->. It reacts with DNA in the presence of Fe ions and ascorbic acid[[Reference:Fujimoto_K:Neff_WE:Frankel_EN:,Biochim. Biophys. Acta,1984,795,100|{{RelationTable/GetFirstAuthor|Reference:Fujimoto_K:Neff_WE:Frankel_EN:,Biochim. Biophys. Acta,1984,795,100}}]].
|Note=Isomerization of hydroperoxides: Positional isomers at 9, 10, 12, 13, 15 and 16 and their geometric isomers of cis, cis, trans- or cis, trans, trans are formed. The proportion of 9-, 16- isomers is higher than that of 12-, 13- isomers.
}}
}}


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{{Lipid/Footer}}

Latest revision as of 10:42, 29 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8055
LipidMaps LMFA01040039
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18302HP01
Methyl-15-hydroperoxy- (9Z,12Z,16E) -octadecatrienoic acid
LBF18302HP01.png
Structural Information
Methyl-15-hydroperoxy- (cis-9,cis-12,trans-16) -octadecatrienoic acid
  • Methyl-15-hydroperoxy- (9Z,12Z,16E) -octadecatrienoic acid
Formula C19H32O4
Exact Mass 324.23005951199997
Average Mass 324.45498
SMILES CC=CC(OO)CC=CCC=CCCCCCCCC(=O)OC
Physicochemical Information
Oxidation of linoleate by singlet oxygen Frankel_EN Frankel_EN Frankel_EN .
Pysiological damages are induced by these hydroperoxides which are incorporated into bodies or synthesized endogenously. Logani_MK et al. Sevanian_A et al. Fujimoto_K . It reacts with DNA in the presence of Fe ions and ascorbic acid Fujimoto_K et al..
Isomerization of hydroperoxides: Positional isomers at 9, 10, 12, 13, 15 and 16 and their geometric isomers of cis, cis, trans- or cis, trans, trans are formed. The proportion of 9-, 16- isomers is higher than that of 12-, 13- isomers.
Spectral Information
Mass Spectra EI-MS(Me-ester; after reduction and hydrogenation) Chan_HWS : m/e=271[O=CH(CH2)13C(=OH)OCH3]; 242[CH2(CH2)12C(=OH)OCH3]; 239[O=CH(CH2)13C=O]; GC-EI-MS(Me-ester; after reduction and hydrogenation) TeraoJet al.: m/e=143[SMTO=CH-CH=CH-CH3]
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18302HP01 See above. Chan_HWS 1977
n.a. LBF18302HP01 See above. Frankel_EN 1980
n.a. LBF18302HP01 See above. Frankel_EN 1983
n.a. LBF18302HP01 See above. Frankel_EN 1984
n.a. LBF18302HP01 See above. Fujimoto_K 1986
n.a. LBF18302HP01 See above. Fujimoto_K et al. 1984
n.a. LBF18302HP01 See above. Logani_MK et al. 1980
n.a. LBF18302HP01 See above. Sevanian_A et al. 1985
n.a. LBF18302HP01 See above. Terao_J et al. 1977


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