LBF21503HO04: Difference between revisions

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|LipidBank=DFA8100
|LipidBank=DFA8100
|LipidMaps=LMFA03070017
|LipidMaps=LMFA03070017
|SysName=Methyl 11-Hydroperoxy-5,8,12,14,17-Icosapentaenoate
|SysName=Methyl-11-hydroperoxy-5,8,12,14,17-eicosapentaenoic acid
|Common Name=&&Methyl 11-Hydroperoxy-5,8,12,14,17-Icosapentaenoate&&
|Common Name=&&Methyl-11-hydroperoxy-5,8,12,14,17-eicosapentaenoic acid&&
|Mass Spectra=GC-EI-MS(after reduction and TMS-derivatization)[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(Me-ester: after reduction, hydrogenation and TMS-derivatization) [[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]
|Mass Spectra=GC-EI-MS(after reduction and TMS-derivatization)[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(Me-ester: after reduction, hydrogenation and TMS-derivatization) [[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]
|UV Spectra=conjugated diene: <FONT FACE="Symbol">l</FONT>max=235.5nm [[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]
|UV Spectra=conjugated diene: lambda max=235.5nm [[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]
|IR Spectra=OOH group: 3400cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]
|IR Spectra=OOH group: 3400cm^{-1} [[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: OOH proton: 8.5ppm
|NMR Spectra=^1 H-NMR[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]: OOH proton: 8.5ppm
|Source=Autooxidation of icosapentaenoate[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]. Oxidation of icosapentaenoate by singlet-oxygen[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]. Oxidation of icosapentaenoate in the presence of myoglobin.
|Source=Autooxidation of icosapentaenoate[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]. Oxidation of icosapentaenoate by singlet-oxygen[[Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897|{{RelationTable/GetFirstAuthor|Reference:Yamauchi_R:Yamada_T:Kato_K:Ueno_Y:,Agric. Biol. Chem.,1983,47,2897}}]]. Oxidation of icosapentaenoate in the presence of myoglobin<!--8110-->.
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=
|Metabolism=
|Note=Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides])<!--8110-->.
}}
}}


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{{Lipid/Footer}}

Latest revision as of 08:59, 2 June 2010

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Upper classes: LB LBF



Methyl-11-hydroperoxy-5,8,12,14,17-eicosapentaenoic acid
LBF21503HO04.png
Structural Information
Methyl-11-hydroperoxy-5,8,12,14,17-eicosapentaenoic acid
  • Methyl-11-hydroperoxy-5,8,12,14,17-eicosapentaenoic acid
Formula
Exact Mass
Average Mass
SMILES
Physicochemical Information
Autooxidation of icosapentaenoate Yamauchi_R et al.. Oxidation of icosapentaenoate by singlet-oxygen Yamauchi_R et al.. Oxidation of icosapentaenoate in the presence of myoglobin.
Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides]).
Spectral Information
Mass Spectra GC-EI-MS(after reduction and TMS-derivatization) YamauchiRet al.: m/e=404[M]; 389[M-CH3] 314[M-HOTMS], GC-EI-MS(Me-ester: after reduction, hydrogenation and TMS-derivatization) YamauchiRet al.: m/e=399[M-CH3]; 383[M-OCH3]; 367[399-CH3OH]
UV Spectra conjugated diene: λ max=235.5nm YamauchiRet al.
IR Spectra OOH group: 3400cm-1 YamauchiRet al.
NMR Spectra 1H-NMR YamauchiRet al.: OOH proton: 8.5ppm
Other Spectra
Chromatograms