LBF18108HP01: Difference between revisions

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|IR Spectra=Isorated trans unsaturation(970cm^{-1}), trans epoxide(885cm^{-1}), OOH(3600 AND 3430cm^{-1}) [[Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246}}]]
|IR Spectra=Isorated trans unsaturation(970cm^{-1}), trans epoxide(885cm^{-1}), OOH(3600 AND 3430cm^{-1}) [[Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246}}]]
|NMR Spectra=^1 H-NMR(methyl ester)[[Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246}}]]: C9(4.33ppm), C10(5.85ppm), C11(5.47ppm), C12(3.11ppm), C13(2.84ppm) J10-11=16Hz(trans olefin), J12-13=2Hz(trans epoxide)
|NMR Spectra=^1 H-NMR(methyl ester)[[Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246}}]]: C9(4.33ppm), C10(5.85ppm), C11(5.47ppm), C12(3.11ppm), C13(2.84ppm) J10-11=16Hz(trans olefin), J12-13=2Hz(trans epoxide)
|Source=Major reactive products between 13-hydroperoxylinoleate (or linoleate) and soy bean extracts(pH=6.9)[[Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246}}]]. Copper-catalyzed degradation products of linoleate methylhydroperoxide[[Reference:Wu_GS:Stein_RA:Mead_JF:,Lipids.,1977,12,971|{{RelationTable/GetFirstAuthor|Reference:Wu_GS:Stein_RA:Mead_JF:,Lipids.,1977,12,971}}]]. Production mechanism [[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]]<!--8030-->[[Reference:Gardner_HW:,J. Agric. Food Chem.,1975,23,129|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:,J. Agric. Food Chem.,1975,23,129}}]]<!--8074-->.
|Source=Major reactive products between 13-hydroperoxylinoleate (or linoleate) and soy bean extracts(pH=6.9)[[Reference:Gardner_HW:Weisleder_D:Kleiman_R:,Lipids,1978,13,246|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:Weisleder_D:Kleiman_R,Lipids,1978,13,246}}]]. Copper-catalyzed degradation products of linoleate methylhydroperoxide[[Reference:Wu_GS:Stein_RA:Mead_JF:,Lipids,1977,12,971|{{RelationTable/GetFirstAuthor|Reference:Wu_GS:Stein_RA:Mead_JF:,Lipids,1977,12,971}}]]. Production mechanism [[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]]<!--8030-->[[Reference:Gardner_HW:,J. Agric. Food Chem.,1975,23,129|{{RelationTable/GetFirstAuthor|Reference:Gardner_HW:,J. Agric. Food Chem.,1975,23,129}}]]<!--8074-->.
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=
|Metabolism=

Latest revision as of 08:31, 4 November 2010

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Upper classes: LB LBF



12,13-Epoxy-9-hydroperoxy-10-octadecenoic acid
LBF18108HP01.png
Structural Information
12,13-Epoxy-9-hydroperoxy-10-octadecenoic acid
  • 12,13-Epoxy-9-hydroperoxy-10-octadecenoic acid
Formula C18H32O5
Exact Mass 328.224974134
Average Mass 328.44368000000003
SMILES C(C(C=CC(OO)CCCCCCCC(O)=O)1)(CCCCC)O1
Physicochemical Information
Major reactive products between 13-hydroperoxylinoleate (or linoleate) and soy bean extracts(pH=6.9) Gardner_HW et al.. Copper-catalyzed degradation products of linoleate methylhydroperoxide Wu_GS et al.. Production mechanism Frankel_EN Gardner_HW .
It showed a slightly higher toxicity than linoleate monohydroxyperoxide. Fujimoto_K
Spectral Information
Mass Spectra GC-EI-MS(after methanolysis, reduction and trimethylsilylation) Gardner_HW et al. TokitaMet al.
UV Spectra
IR Spectra Isorated trans unsaturation(970cm-1), trans epoxide(885cm-1), OOH(3600 AND 3430cm-1) Gardner_HW et al.
NMR Spectra 1H-NMR(methyl ester) Gardner_HW et al.: C9(4.33ppm), C10(5.85ppm), C11(5.47ppm), C12(3.11ppm), C13(2.84ppm) J10-11=16Hz(trans olefin), J12-13=2Hz(trans epoxide)
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18108HP01 See above. Frankel_EN 1984
n.a. LBF18108HP01 See above. Fujimoto_K 1986
n.a. LBF18108HP01 See above. Gardner_HW 1975
n.a. LBF18108HP01 See above. Gardner_HW et al. 1978
n.a. LBF18108HP01 See above. Tokita_M et al. 1987
n.a. LBF18108HP01 See above. Wu_GS et al. 1977