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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
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|LipidBank=DFA8012
|LipidBank=DFA8012
|LipidMaps=LMFA01070004
|LipidMaps=LMFA01070004
|SysName=9,10-Epoxy-13-Hydroxy-11-Octadecenoic Acid/9,10-Epoxy-13-Hydroxy-11-Octadecenoate
|SysName=9,10-Epoxy-13-hydroxy-11-octadecenoic acid
|Mass Spectra=GC-EI-MS(after methanolysis and trimethylsilylation)<<8017/8056/8009/8012>>: m/e= 398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3]
|Common Name=&&9,10-Epoxy-13-hydroxy-11-octadecenoate&&
|UV Spectra=<FONT FACE="Symbol">l</FONT>=277 and 316nm(very weak absorption)<<8009>>
|Mass Spectra=GC-EI-MS(after methanolysis and trimethylsilylation)[[Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415}}]][[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}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908}}]]: m/e= 398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3]
|IR Spectra=Metyl ester<<8017/8056/8009>>: trans olefin(965-958cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), trans epoxide(890-874 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), cis epoxide(weak absorprion; 845 AND 830cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), free OH(3600cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>),bonded OH(3640-3380cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>)
|UV Spectra= lambda =277 and 316nm(very weak absorption)[[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(methyl ester)<<8017/8056/8009>>: C9(2.83ppm), C10(3.09-3.1ppm;trans epoxide), C11(5.45-5.53ppm), C12(5.93-5.95ppm), C13(3.9-4.2ppm), C12, 13(2.9-3.4ppm;cis epoxide), OH proton(3.6ppm), J11-12=15.6Hz(trans unsaturation), J9-10=2-2.2Hz(trans epoxide)
|IR Spectra=Metyl ester[[Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415}}]][[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}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]]: trans olefin(965-958cm^{-1}), trans epoxide(890-874 cm^{-1}), cis epoxide(weak absorprion; 845 AND 830cm^{-1}), free OH(3600cm^{-1}),bonded OH(3640-3380cm^{-1})
|NMR Spectra=^1 H-NMR(methyl ester)[[Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415}}]][[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}}]][[Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352|{{RelationTable/GetFirstAuthor|Reference:Graveland_A_:,J. Am. Oil Chem. Soc.,1970,47,352}}]]: C9(2.83ppm), C10(3.09-3.1ppm;trans epoxide), C11(5.45-5.53ppm), C12(5.93-5.95ppm), C13(3.9-4.2ppm), C12, 13(2.9-3.4ppm;cis epoxide), OH proton(3.6ppm), J11-12=15.6Hz(trans unsaturation), J9-10=2-2.2Hz(trans epoxide)
|Source=A degradation product of 13-hydroperoxymethyllinoleate[[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}}]][[Reference:Schieberle_P:Grosch_W:,Z. Lebensm. Unters. Forsch.,1981,173,192|{{RelationTable/GetFirstAuthor|Reference:Schieberle_P:Grosch_W:,Z. Lebensm. Unters. Forsch.,1981,173,192}}]]. A major compound generated by autooxidation of methyllinoleate[the epoxide ring and double bond show trans configuration][[Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Scholfield_CR:Wesleder_D:,Lipids,1978,13,415}}]][[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BP:Garwood_RF:Weedon_BC:,Lipids,1977,12,908}}]]. Oxidation of linoleic acid by wheat lipoxygenase[the epoxy ring shows cis configuration].
|Chemical Synthesis=
|Metabolism=
}}
}}
{{Lipid/Footer}}

Latest revision as of 21:00, 14 April 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8012
LipidMaps LMFA01070004
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18107EO01
9,10-Epoxy-13-hydroxy-11-octadecenoate
LBF18107EO01.png
Structural Information
9,10-Epoxy-13-hydroxy-11-octadecenoic acid
  • 9,10-Epoxy-13-hydroxy-11-octadecenoate
Formula C18H32O4
Exact Mass 312.23005951199997
Average Mass 312.44428
SMILES C(C(C=CC(O)CCCCC)1)(CCCCCCCC(O)=O)O1
Physicochemical Information
A degradation product of 13-hydroperoxymethyllinoleate Schieberle_P et al. Schieberle_P et al.. A major compound generated by autooxidation of methyllinoleate[the epoxide ring and double bond show trans configuration] Neff_WE et al. Frankel_EN et al.. Oxidation of linoleic acid by wheat lipoxygenase[the epoxy ring shows cis configuration].
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis and trimethylsilylation) Neff_WE et al. SchieberlePet al. Graveland_A_ Frankel_EN et al.: m/e= 398[M], 383[M-CH3], 367[M-OCH3], 327[M-(CH2)4CH3], 241[M-(CH2)7COOCH3]
UV Spectra λ =277 and 316nm(very weak absorption) Graveland_A_
IR Spectra Metyl ester Neff_WE et al. SchieberlePet al. Graveland_A_ : trans olefin(965-958cm-1), trans epoxide(890-874 cm-1), cis epoxide(weak absorprion; 845 AND 830cm-1), free OH(3600cm-1),bonded OH(3640-3380cm-1)
NMR Spectra 1H-NMR(methyl ester) Neff_WE et al. SchieberlePet al. Graveland_A_ : C9(2.83ppm), C10(3.09-3.1ppm;trans epoxide), C11(5.45-5.53ppm), C12(5.93-5.95ppm), C13(3.9-4.2ppm), C12, 13(2.9-3.4ppm;cis epoxide), OH proton(3.6ppm), J11-12=15.6Hz(trans unsaturation), J9-10=2-2.2Hz(trans epoxide)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18107EO01 See above. Graveland_A_ 1970
n.a. LBF18107EO01 See above. Neff_WE et al. 1978
n.a. LBF18107EO01 See above. Schieberle_P et al. 1979


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