LBF18304HP03: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}


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|LipidBank=DFA8062
|LipidBank=DFA8062
|LipidMaps=LMFA01040046
|LipidMaps=LMFA01040046
|SysName=Methyl-13,16-Dihydroperoxy-9,11,14-Octadecatrienoate
|SysName=Methyl-13,16-dihydroperoxy- (cis-9,trans-11,trans-14) -octadecatrienoic acid
|Common Name=&&Methyl-13,16-Dihydroperoxy-9,11,14-Octadecatrienoate&&
|Common Name=&&Methyl-13,16-dihydroperoxy- (9Z,11E,14E) -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}}]]: 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: <FONT FACE="Symbol">l</FONT>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}}]]
|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<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 cis, trans diene: 988-979cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>, 953-935cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>; isolated trans unsaturation: 968-960cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[[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=<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: 2.3ppm; 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
|Source=It is produced from a 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:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]]. It is produced from 13- 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=
|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}}]].
}}
}}
{{Lipid/Footer}}

Latest revision as of 10:30, 29 October 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- (9Z,11E,14E) -octadecatrienoic acid
LBF18304HP03.png
Structural Information
Methyl-13,16-dihydroperoxy- (cis-9,trans-11,trans-14) -octadecatrienoic acid
  • Methyl-13,16-dihydroperoxy- (9Z,11E,14E) -octadecatrienoic acid
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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