LBF20406HP09

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Upper classes: LB LBF



8,15-Dihydroperoxy-5,9,11,13-eicosatetraenoic acid
LBF20406HP09.png
Structural Information
8,15-Dihydroperoxy-5,9,11,13-eicosatetraenoic acid
  • 8,15-Dihydroperoxy-5,9,11,13-eicosatetraenoic acid
Formula C20H32O6
Exact Mass 368.219888756
Average Mass 368.46448
SMILES C(CCC(OO)C=CC=CC=CC(OO)CC=CCCCC(O)=O)CC
Physicochemical Information
Autooxidation of arachidonic acid Yamagata_S et al.. In degradation products of 15-hydroperoxides of arachidonic acid in the presence of Fe(III)-ascorbic acid. Oxidation of arachidonic acid by singlet-oxygen Terao_J et al.. It is produced enzymatically from 15-HPETE in vivo(8,15-DHPETE). It is produced from 15-HPETE by soy bean lipoxygenase Bild_GS et al..
Spectral Information
Mass Spectra EI-MS(Me-ester; after reduction) Bild_GS et al.: m/e=350[M]; 332[M-H2O]; 301[332-OCH3]; 261[332-(CH2)4CH3]; 209[M-CH=CH(CH2)4COOCH3]; 191[209-H2O]; GC-EI-MS(Me-ester; after reduction, hydrogenation and TMS) YamagataSet al. TeraoJet al.: m/e=487[M-CH3]; 431[M-(CH2)4CH3]; 359[M-(CH2)6COOCH3]
UV Spectra UV(Me-ester) TeraoJet al. conjugated triene: 270nm and 281nm
IR Spectra IR(Me-estre) TeraoJet al.OOH group: 3400cm-1, IR(after reduction) Bild_GS et al. trans unsaturation: 968cm-1, OH group: 1040, 3540cm-1
NMR Spectra 1H-NMR(Me-ester) TeraoJet al. OOH: 8.3ppm, 1H-NMR(after reduction) Bild_GS et al. C8, C15: 4.2ppm; OH: 6.3ppm
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406HP09 See above. Bild_GS et al. 1977
n.a. LBF20406HP09 See above. Terao_J et al. 1981
n.a. LBF20406HP09 See above. Yamagata_S et al. 1983