LBF18303HP02: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}


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|LipidBank=DFA8051
|LipidBank=DFA8051
|LipidMaps=LMFA01040014
|LipidMaps=LMFA01040014
|SysName=12-Hydroperoxy-9,13,15-Octadecatrienoic Acid/12-Hydroperoxy-9,13,15-Octadecatrienoate
|SysName=12-Hydroperoxy-9,13,15-octadecatrienoic acid
|Mass Spectra=EI-MS(Me-ester; after reduction and hydrogenation)<<8020/8076>>: m/e=229[O=CH(CH2)10C(=OH)OCH3]; 200[CH2(CH2)9C(=OH)OCH3]; 197[O=CH(CH2)10C=O], GC-EI-MS(Me-ester; after reduction and TMS)<<8090/8077>>: m/e=380[M]; 365[M-CH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2-CH3]
|Common Name=&&12-Hydroperoxy-9,13,15-octadecatrienoic acid&&
|UV Spectra=(Me-ester;after reduction;in etoh)<<8076>>, cis, trans, cis isomer: <FONT FACE="Symbol">l</FONT>max=233nm , cis, trans, trans isomer: <FONT FACE="Symbol">l</FONT>max=232nm
|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}}]][[Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837}}]]: m/e=229[O=CH(CH2)10C(=OH)OCH3]; 200[CH2(CH2)9C(=OH)OCH3]; 197[O=CH(CH2)10C=O], GC-EI-MS(Me-ester; after reduction and TMS)[[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}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055}}]]: m/e=380[M]; 365[M-CH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2-CH3]
|IR Spectra=(Me-ester; after reduction)<<8076/8077>>, cis, trans,cis isomer: 990-983 and 951-945cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>; cis, trans, trans isomer: 992-983cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>, (Me-ester)<<8078>>, OOH group: 3400cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>
|UV Spectra=(Me-ester;after reduction;in ethanol)[[Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837}}]], cis, trans, cis isomer: lambda max=233nm , cis, trans, trans isomer: lambda max=232nm
|IR Spectra=(Me-ester; after reduction)[[Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Levett_G:,Lipids,1977,12,837}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055}}]], cis, trans,cis isomer: 990-983 and 951-945cm^{-1}; cis, trans, trans isomer: 992-983cm^{-1}, (Me-ester)[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]], OOH group: 3400cm^{-1}
|Source=Auto oxidation of linoleate<!--8029--><!--8022--><!--8023--><!--8021-->[[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-->[[Reference:Chan_HWS:Coxon_DT:Peers_KE:Price_KR:,Food Chemistry,1982,9,21|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Coxon_DT:Peers_KE:Price_KR:,Food Chemistry,1982,9,21}}]]. 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=
|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, 12, 13, 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.
}}
}}
{{Lipid/Footer}}

Latest revision as of 08:15, 26 May 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8051
LipidMaps LMFA01040014
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18303HP02
12-Hydroperoxy-9,13,15-octadecatrienoic acid
LBF18303HP02.png
Structural Information
12-Hydroperoxy-9,13,15-octadecatrienoic acid
  • 12-Hydroperoxy-9,13,15-octadecatrienoic acid
Formula C18H30O4
Exact Mass 310.21440944799997
Average Mass 310.4284
SMILES CCC=CC=CC(OO)CC=CCCCCCCCC(O)=O
Physicochemical Information
Auto oxidation of linoleate Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al.. 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, 12, 13, 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 Chan_HWS et al.: m/e=229[O=CH(CH2)10C(=OH)OCH3]; 200[CH2(CH2)9C(=OH)OCH3]; 197[O=CH(CH2)10C=O], GC-EI-MS(Me-ester; after reduction and TMS) TeraoJet al. Frankel_EN et al.: m/e=380[M]; 365[M-CH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2-CH3]
UV Spectra (Me-ester;after reduction;in ethanol) Chan_HWS et al., cis, trans, cis isomer: λ max=233nm , cis, trans, trans isomer: λ max=232nm
IR Spectra (Me-ester; after reduction) Chan_HWS et al. Frankel_EN et al., cis, trans,cis isomer: 990-983 and 951-945cm-1; cis, trans, trans isomer: 992-983cm-1, (Me-ester) ToyodaIet al., OOH group: 3400cm-1
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18303HP02 See above. Chan_HWS 1977
n.a. LBF18303HP02 See above. Chan_HWS et al. 1982
n.a. LBF18303HP02 See above. Chan_HWS et al. 1977
n.a. LBF18303HP02 See above. Frankel_EN 1980
n.a. LBF18303HP02 See above. Frankel_EN 1983
n.a. LBF18303HP02 See above. Frankel_EN 1984
n.a. LBF18303HP02 See above. Frankel_EN et al. 1977
n.a. LBF18303HP02 See above. Fujimoto_K 1986
n.a. LBF18303HP02 See above. Fujimoto_K et al. 1984
n.a. LBF18303HP02 See above. Logani_MK et al. 1980
n.a. LBF18303HP02 See above. Sevanian_A et al. 1985
n.a. LBF18303HP02 See above. Terao_J et al. 1977


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