LBF18203HP01: Difference between revisions

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


{{Metabolite
{{Metabolite
|LipidBank=DFA8056
|LipidBank=DFA8056
|LipidMaps=LMFA01040040
|LipidMaps=LMFA01040040
|SysName=Methyl-10,12-Epidioxy-9-Hydroperoxy-13,15-Octadecadienoate
|SysName=Methyl-10,12-epidioxy-9-hydroperoxy-13,15-octadecadienoic acid
|Common Name=&&Methyl-10,12-Epidioxy-9-Hydroperoxy-13,15-Octadecadienoate&&
|Common Name=&&Methyl-10,12-epidioxy-9-hydroperoxy-13,15-octadecadienoate&&
|Mass Spectra=GC-EI-MS(after reduction(PH3P) and TMS)[[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]]: m/e=397[M-CH3]; 259[SMTO=CH(CH2)7COOCH3]; GC-EI-MS(after reduction with NaBH4 or KI andTMS)[[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055}}]]: m/e=259[SMTO=CH(CH2)7COOCH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2CH3]
|Mass Spectra=GC-EI-MS(after reduction(PH3P) and TMS)[[Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:Weisleder_D:,Lipids,1981,16,439}}]]: m/e=397[M-CH3]; 259[SMTO=CH(CH2)7COOCH3]; GC-EI-MS(after reduction with NaBH4 or KI andTMS)[[Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:Neff_WE:Rohwedder_WK:Khambay_BPS:Garwood_RF:Weedon_BCL:,Lipids,1977,12,1055}}]]: m/e=259[SMTO=CH(CH2)7COOCH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2CH3]
|UV Spectra=Conjugated diene: <FONT FACE="Symbol">l</FONT>max=231-236nm [[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[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:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365|{{RelationTable/GetFirstAuthor|Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365}}]][[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=231-236nm [[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]][[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:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365|{{RelationTable/GetFirstAuthor|Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365}}]][[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: 3520 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[free], 3700-3100cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>[bonded]; olefinic protons: 3020-3000cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>; CONJUGATE TRANS, CIS DIENES: 990-980cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP>, 955-947cm<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:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365|{{RelationTable/GetFirstAuthor|Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365}}]][[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}}]]
|IR Spectra=OOH group: 3520 cm^{-1}[free], 3700-3100cm^{-1}[bonded]; olefinic protons: 3020-3000cm^{-1}; CONJUGATE TRANS, CIS DIENES: 990-980cm^{-1}, 955-947cm^{-1}<!--8079-->[[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:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365|{{RelationTable/GetFirstAuthor|Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365}}]][[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}}]]
|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}}]][[Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365|{{RelationTable/GetFirstAuthor|Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365}}]]: C9: 3.92-4.21; C10: 4.45-4.47; C11: 2.19-2.47, 2.81-2.87; C12: 4.77-4.80; C13: 5.57-5.62; C14: 6.65-6.68; C15: 5.96-6.65; C16: 5.50-5.55; OOH: 9.05-9.56ppm; J13-14=15Hz[C13-14 : trans]; J15-16=10Hz[C15-16: cis]13C-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}}]]: C9: 86.0; C10, 12: 83.8, 83.0
|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}}]][[Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365|{{RelationTable/GetFirstAuthor|Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365}}]]: C9: 3.92-4.21; C10: 4.45-4.47; C11: 2.19-2.47, 2.81-2.87; C12: 4.77-4.80; C13: 5.57-5.62; C14: 6.65-6.68; C15: 5.96-6.65; C16: 5.50-5.55; OOH: 9.05-9.56ppm; J13-14=15Hz[C13-14 : trans]; J15-16=10Hz[C15-16: cis]13C-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}}]]: C9: 86.0; C10, 12: 83.8, 83.0
|Source=Auto oxydation of linoleate[[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:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365|{{RelationTable/GetFirstAuthor|Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365}}]]. Oxydation of linoleate in the presence of Fe(III)-ascorbic acid[[Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84|{{RelationTable/GetFirstAuthor|Reference:Toyoda_I:Terao_J:Matsushita_S:,Lipids,1982,17,84}}]]. 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}}]][[Reference:Neff_WE:Frankel_EN:,Lipids,1984,19,952|{{RelationTable/GetFirstAuthor|Reference:Neff_WE:Frankel_EN:,Lipids,1984,19,952}}]]. Production mechanism[[Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Prog. Lipid Res.,1984,23,197}}]][[Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73}}]].
|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}}]].
|Note=Major secondary products of linolenate by autooxidation[[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 formed through 1, 3 cyclization of 12-peroxy radical of linolenate[[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}}]]<!--8027-->[[Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73|{{RelationTable/GetFirstAuthor|Reference:Frankel_EN:,Chem. Phys. Lipids,1987,44,73}}]][[Reference:Chan_HWS:Coxon_DT:Peers_KE:Price_KR:,Food Chemistry,1982,9,21|{{RelationTable/GetFirstAuthor|Reference:Chan_HWS:Coxon_DT:Peers_KE:Price_KR:,Food Chemistry,1982,9,21}}]][[Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365|{{RelationTable/GetFirstAuthor|Reference:Coxon_DT:Price_KR:Chan_HWS:,Chem. Phys. Lipids,1981,28,365}}]]. A level of epidioxy hydroperoxides produced by autooxidation of linolenate decreased by supplementation of antioxidants[[Reference:Peers_KE:Coxon_DT:Chan_HWS:,J. Sci. Food Agric.,1984,35,813|{{RelationTable/GetFirstAuthor|Reference:Peers_KE:Coxon_DT:Chan_HWS:,J. Sci. Food Agric.,1984,35,813}}]].
}}
}}


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Latest revision as of 21:00, 14 April 2010

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Upper classes: LB LBF



Methyl-10,12-epidioxy-9-hydroperoxy-13,15-octadecadienoate
LBF18203HP01.png
Structural Information
Methyl-10,12-epidioxy-9-hydroperoxy-13,15-octadecadienoic acid
  • Methyl-10,12-epidioxy-9-hydroperoxy-13,15-octadecadienoate
Formula C19H32O6
Exact Mass 356.219888756
Average Mass 356.45378
SMILES C(O1)(CC(C=CC=CCC)O1)C(OO)CCCCCCCC(=O)OC
Physicochemical Information
Auto oxydation of linoleate Neff_WE et al. Coxon_DT et al.. Oxydation of linoleate in the presence of Fe(III)-ascorbic acid Toyoda_I et al.. Photoenhancemant of linoleate peroxydation[Type II] Neff_WE et al. Neff_WE et al.. Production mechanism Frankel_EN Frankel_EN .
It reacts with DNA in the presence of Fe ions and ascorbic acid Fujimoto_K et al..
Major secondary products of linolenate by autooxidation Frankel_EN Neff_WE et al.. It is formed through 1, 3 cyclization of 12-peroxy radical of linolenate Frankel_EN Frankel_EN Frankel_EN Chan_HWS et al. Coxon_DT et al.. A level of epidioxy hydroperoxides produced by autooxidation of linolenate decreased by supplementation of antioxidants Peers_KE et al..
Spectral Information
Mass Spectra GC-EI-MS(after reduction(PH3P) and TMS) Neff_WE et al.: m/e=397[M-CH3]; 259[SMTO=CH(CH2)7COOCH3]; GC-EI-MS(after reduction with NaBH4 or KI andTMS) Frankel_EN et al.: m/e=259[SMTO=CH(CH2)7COOCH3]; 183[SMTO=CH-CH=CH-CH=CH-CH2CH3]
UV Spectra Conjugated diene: λ max=231-236nm ToyodaIet al. Neff_WE et al. Coxon_DT et al. Neff_WE et al.
IR Spectra OOH group: 3520 cm-1[free], 3700-3100cm-1[bonded]; olefinic protons: 3020-3000cm-1; CONJUGATE TRANS, CIS DIENES: 990-980cm-1, 955-947cm-1 Neff_WE et al. Coxon_DT et al. Neff_WE et al. Neff_WE et al.
NMR Spectra 1H-NMR Neff_WE et al. Neff_WE et al. Coxon_DT et al.: C9: 3.92-4.21; C10: 4.45-4.47; C11: 2.19-2.47, 2.81-2.87; C12: 4.77-4.80; C13: 5.57-5.62; C14: 6.65-6.68; C15: 5.96-6.65; C16: 5.50-5.55; OOH: 9.05-9.56ppm; J13-14=15Hz[C13-14 : trans]; J15-16=10Hz[C15-16: cis]13C-NMR Neff_WE et al. Neff_WE et al.: C9: 86.0; C10, 12: 83.8, 83.0
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF18203HP01 See above. Chan_HWS et al. 1982
n.a. LBF18203HP01 See above. Coxon_DT et al. 1981
n.a. LBF18203HP01 See above. Frankel_EN 1987
n.a. LBF18203HP01 See above. Frankel_EN 1983
n.a. LBF18203HP01 See above. Frankel_EN 1984
n.a. LBF18203HP01 See above. Frankel_EN et al. 1977
n.a. LBF18203HP01 See above. Fujimoto_K et al. 1984
n.a. LBF18203HP01 See above. Neff_WE et al. 1981
n.a. LBF18203HP01 See above. Neff_WE et al. 1982
n.a. LBF18203HP01 See above. Peers_KE et al. 1984
n.a. LBF18203HP01 See above. Toyoda_I et al. 1982