LBF18304HP04: Difference between revisions

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


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|LipidBank=DFA8065
|LipidBank=DFA8065
|LipidMaps=LMFA01040049
|LipidMaps=LMFA01040049
|SysName=Methyl-10,16-Dihydroperoxy-8,12,14-Octadecatrienoate
|SysName=Methyl-10,16-dihydroperoxy- (trans-8,cis-12,trans-14) -octadecatrienoic acid
|Common Name=&&Methyl-10,16-Dihydroperoxy-8,12,14-Octadecatrienoate&&
|Common Name=&&Methyl-10,16-dihydroperoxy- (8E,12Z,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=468[M]; 439[M-CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 349[439-HOTMS]; 271[SMTO=CHCH=CH(CH2)6COOCH3]; 197[M-271]; CI-MS(110): m/e=339[M+H-H20]; 323[M-OOH]; 305[323-H2O]; 199[CHOCH=CH(CH2)6COOCH3+H]
|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=468[M]; 439[M-CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 349[439-HOTMS]; 271[SMTO=CHCH=CH(CH2)6COOCH3]; 197[M-271]; CI-MS(110): m/e=339[M+H-H20]; 323[M-OOH]; 305[323-H2O]; 199[CHOCH=CH(CH2)6COOCH3+H]
|UV Spectra=Conjugated diene: <FONT FACE="Symbol">l</FONT>max=232nm[[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=232nm[[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: 3700-3140cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[bonded], 3520-3510cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[free]; conjugated cis,trans diene: 985-979cm<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,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]
|IR Spectra=OOH group: 3700-3140cm^{-1}[bonded], 3520-3510cm^{-1}[free]; conjugated cis,trans diene: 985-979cm^{-1}, 953-935cm^{-1}; isolated trans unsaturation: 968-960cm^{-1}[[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,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]: C2: 2.31ppm; C7, 11, 17: 2.08ppm; C8, 9, 12, 13, 15: 5.25-6.25ppm; C10, 16: 4.34ppm; C14: 6.55ppm; C18: 0.93ppm; OOH: 8.04ppm[[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,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]: C2: 2.31ppm; C7, 11, 17: 2.08ppm; C8, 9, 12, 13, 15: 5.25-6.25ppm; C10, 16: 4.34ppm; C14: 6.55ppm; C18: 0.93ppm; OOH: 8.04ppm[[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]
|Source=It is produced from 10- 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 09:44, 29 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8065
LipidMaps LMFA01040049
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18304HP04
Methyl-10,16-dihydroperoxy- (8E,12Z,14E) -octadecatrienoic acid
LBF18304HP04.png
Structural Information
Methyl-10,16-dihydroperoxy- (trans-8,cis-12,trans-14) -octadecatrienoic acid
  • Methyl-10,16-dihydroperoxy- (8E,12Z,14E) -octadecatrienoic acid
Formula C19H32O6
Exact Mass 356.219888756
Average Mass 356.45378
SMILES COC(=O)CCCCCCC=CC(OO)CC=CC=CC(CC)OO
Physicochemical Information
It is produced from 10- 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=468[M]; 439[M-CH2CH3]; 437[M-OCH3]; 378[M-HOTMS]; 349[439-HOTMS]; 271[SMTO=CHCH=CH(CH2)6COOCH3]; 197[M-271]; CI-MS(110): m/e=339[M+H-H20]; 323[M-OOH]; 305[323-H2O]; 199[CHOCH=CH(CH2)6COOCH3+H]
UV Spectra Conjugated diene: λ max=232nm Neff_WE et al.
IR Spectra OOH group: 3700-3140cm-1[bonded], 3520-3510cm-1[free]; conjugated cis,trans diene: 985-979cm-1, 953-935cm-1; isolated trans unsaturation: 968-960cm-1 Neff_WE et al.
NMR Spectra 1H-NMR Neff_WE et al.: C2: 2.31ppm; C7, 11, 17: 2.08ppm; C8, 9, 12, 13, 15: 5.25-6.25ppm; C10, 16: 4.34ppm; C14: 6.55ppm; C18: 0.93ppm; OOH: 8.04ppm Neff_WE et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18304HP04 See above. Frankel_EN 1984
n.a. LBF18304HP04 See above. Fujimoto_K et al. 1984
n.a. LBF18304HP04 See above. Neff_WE et al. 1984
n.a. LBF18304HP04 See above. Neff_WE et al. 1982


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