LBF18304HP03: Difference between revisions

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|Common Name=&&Methyl-13,16-Dihydroperoxy-9,11,14-Octadecatrienoate&&
|Common Name=&&Methyl-13,16-Dihydroperoxy-9,11,14-Octadecatrienoate&&
|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}}]]: m/e=453[M-CH3]; 439[M -CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 143[(CH2)6C00CH3], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(102) m/e=443[M-OCH3]; 315[SMTO=CH(CH2)11COOCH3]
|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}}]]: m/e=453[M-CH3]; 439[M -CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 143[(CH2)6C00CH3], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(102) m/e=443[M-OCH3]; 315[SMTO=CH(CH2)11COOCH3]
|UV Spectra=Conjugated diene: lambdamax=233-235nm[[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 diene: lambda max=233-235nm[[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 cis, trans diene: 988-979cm^- ^1 , 953-935cm^- ^1 ; isolated trans unsaturation: 968-960cm^- ^1 [[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 cis, trans diene: 988-979cm^- ^1 , 953-935cm^- ^1 ; isolated trans unsaturation: 968-960cm^- ^1 [[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=^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: 2.3ppm; C8, 17: 1.8-2.2ppm; C9, 10, 11, 12, 14, 15: 5.26-6.28ppm, C13, 16: 4.40-4.42ppm; C18: 1.02ppm; OOH: 8.07ppm
|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: 2.3ppm; C8, 17: 1.8-2.2ppm; C9, 10, 11, 12, 14, 15: 5.26-6.28ppm, C13, 16: 4.40-4.42ppm; C18: 1.02ppm; OOH: 8.07ppm

Revision as of 14:00, 19 February 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8062
LipidMaps LMFA01040046
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18304HP03
Methyl-13,16-Dihydroperoxy-9,11,14-Octadecatrienoate
LBF18304HP03.png
Structural Information
Methyl-13,16-Dihydroperoxy-9,11,14-Octadecatrienoate
  • Methyl-13,16-Dihydroperoxy-9,11,14-Octadecatrienoate
Formula C19H32O6
Exact Mass 356.219888756
Average Mass 356.45378
SMILES COC(=O)CCCCCCCC=CC=CC(OO)C=CC(CC)OO
Physicochemical Information
It is produced from a 16-hydroperoxy isomer during autooxidation of linoleate Frankel_EN Frankel_EN Neff_WE et al.. It is produced from 13- 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.: m/e=453[M-CH3]; 439[M -CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 143[(CH2)6C00CH3], GC-EI-MS(after reduction, hydrogenation and TMS-derivatization)(102) m/e=443[M-OCH3]; 315[SMTO=CH(CH2)11COOCH3]
UV Spectra Conjugated diene: λ max=233-235nm 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 cis, trans diene: 988-979cm-1, 953-935cm-1; isolated trans unsaturation: 968-960cm-1 Neff_WE et al. Neff_WE et al.
NMR Spectra 1H-NMR Neff_WE et al. Neff_WE et al.: C2: 2.3ppm; C8, 17: 1.8-2.2ppm; C9, 10, 11, 12, 14, 15: 5.26-6.28ppm, C13, 16: 4.40-4.42ppm; C18: 1.02ppm; OOH: 8.07ppm
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18304HP03 See above. Frankel_EN 1983
n.a. LBF18304HP03 See above. Frankel_EN 1984
n.a. LBF18304HP03 See above. Fujimoto_K et al. 1984
n.a. LBF18304HP03 See above. Neff_WE et al. 1981
n.a. LBF18304HP03 See above. Neff_WE et al. 1982


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