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|LipidBank=DFA8046
|LipidBank=DFA8046
|LipidMaps=LMFA01060071
|LipidMaps=LMFA01060071
|SysName=9-Oxo-10,12-Octadecadienoic Acid/9-Oxo-10,12-Octadecadienoate
|SysName=9-Oxo-10,12-octadecadienoic acid
|Common Name=&&9-Oxo-10,12-Octadecadienoic Acid&&9-Oxo-10,12-Octadecadienoate&&
|Common Name=&&9-KODE&&
|Mass Spectra=GC-EI-MS(after methanolysis and hydrogenation)[[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:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]][[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}}]][[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]]: m/e=308[M], 277[M-OCH3], 237[M-(CH2)4CH3], 185[C(O)(CH2)6COOCH3], 166[CH3(CH2)4-CH=CH-CH=CH-C(OH)=CH2; Maclafferty transposition] 151[M-(CH2)7COOCH3]GC-EI-MS(TMS)[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]: m/e=366[M], 341[M-CH3], 295[ [M-(CH2)4CH3], 276[M-HOTMS]
|Mass Spectra=GC-EI-MS(after methanolysis and hydrogenation)[[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:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]][[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}}]][[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]]: m/e=308[M], 277[M-OCH3], 237[M-(CH2)4CH3], 185[C(O)(CH2)6COOCH3], 166[CH3(CH2)4-CH=CH-CH=CH-C(OH)=CH2; Maclafferty transposition] 151[M-(CH2)7COOCH3]GC-EI-MS(TMS)[[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]: m/e=366[M], 341[M-CH3], 295[ [M-(CH2)4CH3], 276[M-HOTMS]
|UV Spectra=<FONT FACE="Symbol">l</FONT> MeOH /max=277-278nm(<FONT FACE="Symbol">e</FONT>=20300),<FONT FACE="Symbol">l</FONT>max=267nm(cyclohexane)[[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:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]
|UV Spectra= lambda  MeOH /max=277-278nm( epsilon =20300), lambda max=267nm(cyclohexane)[[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:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]
|IR Spectra=Trans, trans unsaturations(strong absorption at 1000-990cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), trans,cis unsaturations(960-955cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>), unsaturated ketone(1695-1600cm<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}}]][[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]][[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]]
|IR Spectra=Trans, trans unsaturations(strong absorption at 1000-990cm^{-1}), trans,cis unsaturations(960-955cm^{-1}), unsaturated ketone(1695-1600cm^{-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}}]][[Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847|{{RelationTable/GetFirstAuthor|Reference:Streckert_G:Stan_HJ:,Lipids,1975,10,847}}]][[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:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]][[Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Nelson_EC:Tjarks_LW:England_RE:,Chem. Phys. Lipids,1984,35,87}}]]
|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}}]][[Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]: C8(2.54ppm), C10, 12, 13(6.06-6.21ppm), C11(7.02-7.51ppm), C14(2.20-2.23ppm)
|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}}]][[Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613|{{RelationTable/GetFirstAuthor|Reference:Sessa_DJ:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1977,12,613}}]]: C8(2.54ppm), C10, 12, 13(6.06-6.21ppm), C11(7.02-7.51ppm), C14(2.20-2.23ppm)
|Source=A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[trans, trans; or trans, cis][[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]. A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)[[Reference:Yamamoto_Y:Saeki_N:Haga_S:Niki_E:_Kamiya_Y:,Bull. Chem. Soc. Jpn.,1984,57,3177|{{RelationTable/GetFirstAuthor|Reference:Yamamoto_Y:Saeki_N:Haga_S:Niki_E:_Kamiya_Y:,Bull. Chem. Soc. Jpn.,1984,57,3177}}]].
|Source=A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[trans, trans; or trans, cis][[Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Kleiman_R:Weisleder_D:,Lipids,1974,9,696}}]]. A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II)[[Reference:Yamamoto_Y:Saeki_N:Haga_S:Niki_E:_Kamiya_Y:,Bull. Chem. Soc. Jpn.,1984,57,3177|{{RelationTable/GetFirstAuthor|Reference:Yamamoto_Y:Saeki_N:Haga_S:Niki_E:_Kamiya_Y:,Bull. Chem. Soc. Jpn.,1984,57,3177}}]].
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=
|Metabolism=
|Biological Activity=It showed a slightly lower toxicity than linoleate monohydroxyperoxide<!--8045-->[[Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21|{{RelationTable/GetFirstAuthor|Reference:Fujimoto_K:,Fragrance J. (in Japanese),1986,76,21}}]].
}}
{{MassbankSpectra|
UT000271
UT000272
UT000273
UT000274
UT000275
UT000276
UT000277
UT000278
UT000279
}}
}}


{{Lipid/Footer}}
{{Lipid/Footer}}

Latest revision as of 00:00, 17 January 2014

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Upper classes: LB LBF



9-KODE
LBF18206OX01.png
Structural Information
9-Oxo-10,12-octadecadienoic acid
  • 9-KODE
Formula C18H30O3
Exact Mass 294.21949482599996
Average Mass 294.429
SMILES CCCCCC=CC=CC(=O)CCCCCCCC(O)=O
Physicochemical Information
A degradation product of hydroperoxylinoleate in the presence of Fe(III)-cystein[trans, trans; or trans, cis] Gardner_HW et al.. A degradation product of hydroperoxymethyllinoleate in the presence of di-t-butyl diperoxyoxalate or Co(II) Yamamoto_Y et al..
It showed a slightly lower toxicity than linoleate monohydroxyperoxide Fujimoto_K .
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis and hydrogenation) SchieberlePet al. Sessa_DJ et al. Frankel_EN et al. Gardner_HW et al.: m/e=308[M], 277[M-OCH3], 237[M-(CH2)4CH3], 185[C(O)(CH2)6COOCH3], 166[CH3(CH2)4-CH=CH-CH=CH-C(OH)=CH2; Maclafferty transposition] 151[M-(CH2)7COOCH3]GC-EI-MS(TMS) Gardner_HW et al.: m/e=366[M], 341[M-CH3], 295[ [M-(CH2)4CH3], 276[M-HOTMS]
UV Spectra λ MeOH /max=277-278nm( ε =20300), λ max=267nm(cyclohexane) Gardner_HW et al. StreckertGet al. SchieberlePet al. Sessa_DJ et al.
IR Spectra Trans, trans unsaturations(strong absorption at 1000-990cm-1), trans,cis unsaturations(960-955cm-1), unsaturated ketone(1695-1600cm-1) Gardner_HW et al. StreckertGet al. SchieberlePet al. Sessa_DJ et al. Gardner_HW et al.
NMR Spectra 1H-NMR Gardner_HW et al. Sessa_DJ et al.: C8(2.54ppm), C10, 12, 13(6.06-6.21ppm), C11(7.02-7.51ppm), C14(2.20-2.23ppm)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18206OX01 See above. Frankel_EN et al. 1977
n.a. LBF18206OX01 See above. Fujimoto_K 1986
n.a. LBF18206OX01 See above. Gardner_HW et al. 1974
n.a. LBF18206OX01 See above. Gardner_HW et al. 1984
n.a. LBF18206OX01 See above. Schieberle_P et al. 1979
n.a. LBF18206OX01 See above. Sessa_DJ et al. 1977
n.a. LBF18206OX01 See above. Streckert_G et al. 1975
n.a. LBF18206OX01 See above. Yamamoto_Y et al. 1984
n.a. LBF18206OX01 See above. Yamamoto_Y et al. 1984