LBF18203HP02: Difference between revisions

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|LipidBank=DFA8058
|LipidBank=DFA8058
|LipidMaps=LMFA01040042
|LipidMaps=LMFA01040042
|SysName=Methyl-10,12-Epidioxy-13-Hydroperoxy-8,15-Octadecadienoate
|SysName=Methyl-10,12-epidioxy-13-hydroperoxy- (trans-8,cis-15) -octadecadienoic acid
|Common Name=&&Methyl-10,12-Epidioxy-13-Hydroperoxy-8,15-Octadecadienoate&&
|Common Name=&&Methyl-10,12-epidioxy-13-hydroperoxy- (8E,15Z) -octadecatrienoic acid&&
|Mass Spectra=GC-EI-MS(after reduction(PH3P) 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=307[M-CH3- HOTMS]; 241[M-171]; 171[SMTO=CHCH2CH=CHCH2CH3], GC-EI-MS(after reduction, hydrogenation, 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}}]]
|Mass Spectra=GC-EI-MS(after reduction(PH3P) 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=307[M-CH3- HOTMS]; 241[M-171]; 171[SMTO=CHCH2CH=CHCH2CH3], GC-EI-MS(after reduction, hydrogenation, 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}}]]
|IR Spectra=OOH group: 3660-3150cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[bonded], 3520cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[free]; OLEFINIC PROTONS: 3020-3002cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>; isolated trans unsaturation: 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: 3660-3150cm^{-1}[bonded], 3520cm^{-1}[free]; OLEFINIC PROTONS: 3020-3002cm^{-1}; isolated trans unsaturation: 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(105): C17[terminal methyl group attached ton the vinyl group]: 1.78ppm [[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(105): C17[terminal methyl group attached ton the vinyl group]: 1.78ppm [[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=Photoenhancemant of linoleate peroxydation[Type II][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]];>. Production of 10-hydroperoxyradical by singlet-oxygen mediated oxydation of linolate via 1,3-cyclization[[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}}]];>.
|Source=Photoenhancemant of linoleate peroxydation[Type II][[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1982,17,780}}]]. Production of 10-hydroperoxyradical by singlet-oxygen mediated oxydation of linolate via 1,3-cyclization[[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}}]].
|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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{{Lipid/Footer}}

Latest revision as of 10:08, 29 October 2010

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Upper classes: LB LBF



Methyl-10,12-epidioxy-13-hydroperoxy- (8E,15Z) -octadecatrienoic acid
LBF18203HP02.png
Structural Information
Methyl-10,12-epidioxy-13-hydroperoxy- (trans-8,cis-15) -octadecadienoic acid
  • Methyl-10,12-epidioxy-13-hydroperoxy- (8E,15Z) -octadecatrienoic acid
Formula C19H32O6
Exact Mass 356.219888756
Average Mass 356.45378
SMILES C(O1)(CC(C=CCCCCCCC(=O)OC)O1)C(OO)CC=CCC
Physicochemical Information
Photoenhancemant of linoleate peroxydation[Type II] Neff_WE et al.. Production of 10-hydroperoxyradical by singlet-oxygen mediated oxydation of linolate via 1,3-cyclization Frankel_EN 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(PH3P) and TMS-derivatization) Neff_WE et al.: m/e=307[M-CH3- HOTMS]; 241[M-171]; 171[SMTO=CHCH2CH=CHCH2CH3], GC-EI-MS(after reduction, hydrogenation, and tms-derivatization) Neff_WE et al.
UV Spectra
IR Spectra OOH group: 3660-3150cm-1[bonded], 3520cm-1[free]; OLEFINIC PROTONS: 3020-3002cm-1; isolated trans unsaturation: 960cm-1 Neff_WE et al.
NMR Spectra 1H-NMR(105): C17[terminal methyl group attached ton the vinyl group]: 1.78ppm Neff_WE et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18203HP02 See above. Frankel_EN 1984
n.a. LBF18203HP02 See above. Fujimoto_K et al. 1984
n.a. LBF18203HP02 See above. Neff_WE et al. 1982