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|LipidBank=DFA8061
|LipidBank=DFA8061
|LipidMaps=LMFA01040045
|LipidMaps=LMFA01040045
|SysName=Methyl-9,16-Dihydroperoxy-10,12,14-Octadecatrienoate
|SysName=Methyl-9,16-dihydroperoxy-10,12,14-octadecatrienoic acid
|Common Name=&&Methyl-9,16-Dihydroperoxy-10,12,14-Octadecatrienoate&&
|Common Name=&&Methyl-9,16-dihydroperoxy-10,12,14-octadecatrienoic acid&&
|Mass Spectra=GC-EI-MS(after reduction and TMS-derivatization)[[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]], GC-EIMS(after reduction,hydrogenation and TBDMS-derivatization)[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]],CI-MS[[Reference:Frankel_EN:Neff_WE:Plattner_RD:,Lipids,1986,21,333|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Plattner_RD:,Lipids,1986,21,333}}]]
|Mass Spectra=GC-EI-MS(after reduction and TMS-derivatization)[[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]], GC-EIMS(after reduction,hydrogenation and TBDMS-derivatization)[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]],CI-MS[[Reference:Frankel_EN:Neff_WE:Plattner_RD:,Lipids,1986,21,333|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Plattner_RD:,Lipids,1986,21,333}}]]
|UV Spectra=Conjugated triene: <FONT FACE="Symbol">l</FONT>max=258-260, 268-269, 278-280nm[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]
|UV Spectra=Conjugated triene: lambda max=258-260, 268-269, 278-280nm[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]
|IR Spectra=OOH group: 3712-3140cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[bonded], 3530-3510cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[free]; olefinic protons: 3005cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>; conjugated trans, cis, trans triene: 960cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>; conjugated trans, trans, trans triene: 996-991cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]
|IR Spectra=OOH group: 3712-3140cm^{-1}[bonded], 3530-3510cm^{-1}[free]; olefinic protons: 3005cm^{-1}; conjugated trans, cis, trans triene: 960cm^{-1}; conjugated trans, trans, trans triene: 996-991cm^{-1}[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR[[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]: C2: 2.30-2.37ppm; C8,17: 1.50-1.85ppm; C9, 16: 4.34-4.42ppm; C10, 11, 12, 13, 14, 15: 5.25-6.90ppm; C18: 0.94-0.95ppm; OOH:7.70-7.94ppm
|NMR Spectra=^1 H-NMR[[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]: C2: 2.30-2.37ppm; C8,17: 1.50-1.85ppm; C9, 16: 4.34-4.42ppm; C10, 11, 12, 13, 14, 15: 5.25-6.90ppm; C18: 0.94-0.95ppm; OOH:7.70-7.94ppm
|Source=It is produced from 9- or 16-hydroperoxy isomer during autooxidation of linoleate[[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}}]][[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]];>. Oxidation of linoleate in presence of Fe(III)-ascorbic acid[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]];>. It is produced from 9- or 16-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen[[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]][[Reference:Neff_WE:Frankel_EN:,Lipids,1984,19,952|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:,Lipids,1984,19,952}}]];>.
|Source=It is produced from 9- or 16-hydroperoxy isomer during autooxidation of linoleate[[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}}]][[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]]. Oxidation of linoleate in presence of Fe(III)-ascorbic acid[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]]. It is produced from 9- or 16-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen[[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]][[Reference:Neff_WE:Frankel_EN:,Lipids,1984,19,952|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:,Lipids,1984,19,952}}]].
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=
|Metabolism=
|Biological Activity=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}}]].
}}
}}


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Latest revision as of 08:17, 26 May 2010

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Upper classes: LB LBF



Methyl-9,16-dihydroperoxy-10,12,14-octadecatrienoic acid
LBF18304HP02.png
Structural Information
Methyl-9,16-dihydroperoxy-10,12,14-octadecatrienoic acid
  • Methyl-9,16-dihydroperoxy-10,12,14-octadecatrienoic acid
Formula C19H32O6
Exact Mass 356.219888756
Average Mass 356.45378
SMILES COC(=O)CCCCCCCC(OO)C=CC=CC=CC(CC)OO
Physicochemical Information
It is produced from 9- or 16-hydroperoxy isomer during autooxidation of linoleate Frankel_EN Frankel_EN Toyoda_I et al. Neff_WE et al.. Oxidation of linoleate in presence of Fe(III)-ascorbic acid Toyoda_I et al.. It is produced from 9- or 16-hydroperoxy isomer during oxidation of linoleate by singlet-oxygen Frankel_EN Neff_WE et al. Neff_WE et al..
It reacts with DNA in the presence of Fe ions and ascorbic acid Fujimoto_K et al..
Spectral Information
Mass Spectra GC-EI-MS(after reduction and TMS-derivatization) Neff_WE et al., GC-EI-MS(after reduction, hydrogenation and TMS-derivatization) ToyodaIet al. Neff_WE et al., GC-EIMS(after reduction,hydrogenation and TBDMS-derivatization) ToyodaIet al.,CI-MS Frankel_EN et al.
UV Spectra Conjugated triene: λ max=258-260, 268-269, 278-280nm ToyodaIet al. Neff_WE et al. Neff_WE et al.
IR Spectra OOH group: 3712-3140cm-1[bonded], 3530-3510cm-1[free]; olefinic protons: 3005cm-1; conjugated trans, cis, trans triene: 960cm-1; conjugated trans, trans, trans triene: 996-991cm-1 ToyodaIet al. Neff_WE et al. Neff_WE et al.
NMR Spectra 1H-NMR Neff_WE et al. Neff_WE et al.: C2: 2.30-2.37ppm; C8,17: 1.50-1.85ppm; C9, 16: 4.34-4.42ppm; C10, 11, 12, 13, 14, 15: 5.25-6.90ppm; C18: 0.94-0.95ppm; OOH:7.70-7.94ppm
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18304HP02 See above. Frankel_EN 1983
n.a. LBF18304HP02 See above. Frankel_EN 1984
n.a. LBF18304HP02 See above. Frankel_EN et al. 1986
n.a. LBF18304HP02 See above. Fujimoto_K et al. 1984
n.a. LBF18304HP02 See above. Neff_WE et al. 1981
n.a. LBF18304HP02 See above. Neff_WE et al. 1982
n.a. LBF18304HP02 See above. Toyoda_I et al. 1982