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


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|LipidBank=DFA8059
|LipidBank=DFA8059
|LipidMaps=LMFA01040043
|LipidMaps=LMFA01040043
|SysName=Methyl-13,15-Epidioxy-12-Hydroperoxy-9,16-Octadecadienoate
|SysName=Methyl-13,15-epidioxy-12-hydroperoxy- (cis-9,trans-16) -octadecadienooic acid
|Common Name=&&Methyl-13,15-Epidioxy-12-Hydroperoxy-9,16-Octadecadienoate&&
|Common Name=&&Methyl-13,15-epidioxy-12-hydroperoxy- (9Z,16E) -octadecadienoate&&
|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]; 299[SMTO=CHCH2CH=CH(CH2)7COOCH3]; 113[M-299]; 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}}]]: m/e=457[M-CH3-HOTMS]
|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]; 299[SMTO=CHCH2CH=CH(CH2)7COOCH3]; 113[M-299]; 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}}]]: m/e=457[M-CH3-HOTMS]
|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[[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}}]]
|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=
|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 19:51, 29 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8059
LipidMaps LMFA01040043
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF18203HP03
Methyl-13,15-epidioxy-12-hydroperoxy- (9Z,16E) -octadecadienoate
Structural Information
Methyl-13,15-epidioxy-12-hydroperoxy- (cis-9,trans-16) -octadecadienooic acid
  • Methyl-13,15-epidioxy-12-hydroperoxy- (9Z,16E) -octadecadienoate
Formula C19H32O6
Exact Mass 356.219888756
Average Mass 356.45378
SMILES C(O1)(CC(C=CC)O1)C(OO)CC=CCCCCCCCC(=O)OC
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]; 299[SMTO=CHCH2CH=CH(CH2)7COOCH3]; 113[M-299]; GC-EI-MS(after reduction, hydrogenation and TMS-derivatization) Neff_WE et al.: m/e=457[M-CH3-HOTMS]
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 Neff_WE et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18203HP03 See above. Frankel_EN 1984
n.a. LBF18203HP03 See above. Fujimoto_K et al. 1984
n.a. LBF18203HP03 See above. Neff_WE et al. 1982


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