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|LipidBank=DFA8016
|LipidBank=DFA8016
|LipidMaps=LMFA01070005
|LipidMaps=LMFA01070005
|SysName=9,10-Epoxy-13-Oxo-11-Octadecenoic Acid
|SysName=9,10-Epoxy-13-oxo-11-octadecenoic acid
|Common Name=&&9,10-Epoxy-13-Oxo-11-Octadecenoic Acid&&
|Common Name=&&9,10-Epoxy-13-oxo-11-octadecenoic acid&&
|Mass Spectra=GC-EI-MS(after methanolysis and trimethylsilylation )[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]], GC-EIMS(after BF3-MeOH treatment and trimethylsilylation)(075/072): m/e=428[M], 413[M-CH3], 259[SMTO=CH(CH2)7- COOCH3], 242[CH3OCH-CH=CH-C(OTMS)(CH2)4CH3]
|Mass Spectra=GC-EI-MS(after methanolysis and trimethylsilylation )[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]], GC-EIMS(after BF3-MeOH treatment and trimethylsilylation)(075/072): m/e=428[M], 413[M-CH3], 259[SMTO=CH(CH2)7- COOCH3], 242[CH3OCH-CH=CH-C(OTMS)(CH2)4CH3]
|UV Spectra=<FONT FACE="Symbol">l</FONT> ether/max=229-230nm; <FONT FACE="Symbol">e</FONT>=16500 (<FONT FACE="Symbol">a</FONT>,<FONT FACE="Symbol">b</FONT>-unsaturated carbonyl)[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]][[Reference:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448|{{RelationTable/GetFirstAuthor|Reference:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448}}]]
|UV Spectra= lambda  ether/max=229-230nm; epsilon =16500 ( alpha , beta -unsaturated carbonyl)[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]][[Reference:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448|{{RelationTable/GetFirstAuthor|Reference:Schieberle_P:Tsoukalas_B:Grosch_W:,Z. Lebensm. Unters. Forsch.,1979,168,448}}]]
|IR Spectra=Methyl ester: trans monoene(973cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), trans epoxide(885cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), cis epoxide(825 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), conjugated carbonyl(1700, 1680, and 1635cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>)[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]
|IR Spectra=Methyl ester: trans monoene(973cm^{-1}), trans epoxide(885cm^{-1}), cis epoxide(825 cm^{-1}), conjugated carbonyl(1700, 1680, and 1635cm^{-1})[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]: C9(2.9ppm;trans epoxide), C10(3.20ppm; trans epoxide), C9(3.14ppm; cis-epoxide),C10(3.47ppm; cis epoxide), C11(6.57-6.63ppm), C12(6.34-6.36ppm), C14(2.52ppm), J9-10=2Hz(trans epoxide), J9-10=4Hz(cis epoxide), J11-12=16Hz(trans olefin)
|NMR Spectra=^1 H-NMR[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]: C9(2.9ppm;trans epoxide), C10(3.20ppm; trans epoxide), C9(3.14ppm; cis-epoxide),C10(3.47ppm; cis epoxide), C11(6.57-6.63ppm), C12(6.34-6.36ppm), C14(2.52ppm), J9-10=2Hz(trans epoxide), J9-10=4Hz(cis epoxide), J11-12=16Hz(trans olefin)
|Source=A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the epoxide ring: trans or cis, the double bond: trans][[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]][[Reference:Gardner_HW:Kleiman_R:,Biochim. Biophys. Acta,1981,665,113|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:,Biochim. Biophys. Acta,1981,665,113}}]];>. A minor reactive product between linoleate and soy bean extracts[[Reference:Gardner_HW:Kleiman_R:,Lipids,1977,12,941|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:,Lipids,1977,12,941}}]];>.
|Source=A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the epoxide ring: trans or cis, the double bond: trans][[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]][[Reference:Gardner_HW:Kleiman_R:,Biochim. Biophys. Acta,1981,665,113|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:,Biochim. Biophys. Acta,1981,665,113}}]]. A minor reactive product between linoleate and soy bean extracts[[Reference:Gardner_HW:Kleiman_R:,Lipids,1977,12,941|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:,Lipids,1977,12,941}}]].
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=
|Metabolism=

Latest revision as of 06:00, 15 April 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8016
LipidMaps LMFA01070005
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18107EO02
9,10-Epoxy-13-oxo-11-octadecenoic acid
Structural Information
9,10-Epoxy-13-oxo-11-octadecenoic acid
  • 9,10-Epoxy-13-oxo-11-octadecenoic acid
Formula C18H30O4
Exact Mass 310.21440944799997
Average Mass 310.4284
SMILES C(C(C=CC(=O)CCCCC)1)(CCCCCCCC(O)=O)O1
Physicochemical Information
A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[the epoxide ring: trans or cis, the double bond: trans] Gardner_HW et al. Gardner_HW et al.. A minor reactive product between linoleate and soy bean extracts Gardner_HW et al..
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis and trimethylsilylation ) Gardner_HW et al., GC-EIMS(after BF3-MeOH treatment and trimethylsilylation)(075/072): m/e=428[M], 413[M-CH3], 259[SMTO=CH(CH2)7- COOCH3], 242[CH3OCH-CH=CH-C(OTMS)(CH2)4CH3]
UV Spectra λ ether/max=229-230nm; ε =16500 ( α , β -unsaturated carbonyl) Gardner_HW et al. SchieberlePet al.
IR Spectra Methyl ester: trans monoene(973cm-1), trans epoxide(885cm-1), cis epoxide(825 cm-1), conjugated carbonyl(1700, 1680, and 1635cm-1) Gardner_HW et al.
NMR Spectra 1H-NMR Gardner_HW et al.: C9(2.9ppm;trans epoxide), C10(3.20ppm; trans epoxide), C9(3.14ppm; cis-epoxide),C10(3.47ppm; cis epoxide), C11(6.57-6.63ppm), C12(6.34-6.36ppm), C14(2.52ppm), J9-10=2Hz(trans epoxide), J9-10=4Hz(cis epoxide), J11-12=16Hz(trans olefin)
Other Spectra
Chromatograms
[hide]Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18107EO02 See above. Gardner_HW et al. 1981
n.a. LBF18107EO02 See above. Gardner_HW et al. 1974
n.a. LBF18107EO02 See above. Schieberle_P et al. 1979


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