LBF20503HP01

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Upper classes: LB LBF



5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid
LBF20503HP01.png
Structural Information
5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid
  • 5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid
Formula C20H30O4
Exact Mass 334.21440944799997
Average Mass 334.4498
SMILES C(CC=CCC=CCC=CC=CC(OO)CCCC(O)=O)=CCC
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 mioglobin. It is produced from icosapentaenoate by 5-lipoxygenate of arachidonic acid Lee_TH et al..
5-Hydroperoxide derivative of icosapentaenoic acid, which is produced concomitantly with action of 15-lipoxygenase against arachidonate, is further metabolized to hydroxylate and leukotrienes, but their physiological activities remain to be clarified Lee_TH et al..
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(Me-ester; after reduction and TMS-derivatization) YamauchiRet al. OchiKet al. FurukawaMet al. HammarstromS: m/e=404[M]; 389[M-CH3]; 314[M-HOTMS]; 303[M-(CH2)3COOCH3]; 255[M-CH2CH=CH(CH2)3CH3]; 213[303-HOTMS]; 203[SMTO=CH(CH2)3COOCH3]
UV Spectra UV(Me-ester) YamauchiRet al.: conjugated diene: λ max=235.5nm; UV(after reduction) HammarstromS: conjugated diene: λ =max=235nm
IR Spectra IR(Me-ester) YamauchiRet al.: OOH group: 3400cm-1
NMR Spectra 1H-NMR YamauchiRet al.: OOH proton: 8.5ppm
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20503HP01 See above. Furukawa_M et al. 1984
n.a. LBF20503HP01 See above. Hammarstrom_S 1983
n.a. LBF20503HP01 See above. Lee_TH et al. 1985
n.a. LBF20503HP01 See above. Ochi_K et al. 1983
n.a. LBF20503HP01 See above. Yamauchi_R et al. 1983
n.a. LBF20503HP01 See above. Yamauchi_R et al. 1985