LBF20406HP02

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Upper classes: LB LBF



8-Hydroperoxy- 5,9,11,14 -eicosatetraenoic acid
LBF20406HP02.png
Structural Information
8-Hydroperoxy- 5,9,11,14 -eicosatetraenoic acid
  • 8-Hydroperoxy- 5,9,11,14 -eicosatetraenoic acid
Formula C20H32O4
Exact Mass 336.23005951199997
Average Mass 336.46567999999996
SMILES C(CC=CCC=CC=CC(OO)CC=CCCCC(O)=O)CCC
Physicochemical Information
Autooxidation of arachidonic acid Terao_J et al. Yamagata_S et al. Porter_NA et al.. Oxidation of arachidonic acid by singlet-oxygen Terao_J et al. Porter_NA et al.. Reaction products between arachidonic acid and lipoxygenase from living cells(8-HPETE) Spector_AA et al..
8-HPETE generated by 8-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE.

Terao_J et al.

Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation Terao_J et al. Yamagata_S et al. Peers_KE et al.. However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol Porter_NA et al. Terao_J et al. Peers_KE et al..
Spectral Information
Mass Spectra GC-EI-MS(Me-ester; after reduction and TMS) TeraoJet al.[[Reference:Terao_J:Matsushita_S:,Agric. Biol. Chem.,1981,45,587

TeraoJet al.]] RabinovitchHet al.: m/e=406[M]; 316[M-HOTMS]; 65[SMTO=CHCH=CHCH=CHCH2CH=CH(CH2)4CH3]; GC-EI-MS(Me-ester; after reduction and TBDMS)(114): m/e=448[M], 391[M-(CH3)3C]; GC-EI-MS(Me-ester;after reduction, hydrogenation and TMS)

UV Spectra UV[[Reference:Porter_NA:Logan_J:Kontoyiannidou_V:,J. Org. Chem.,1979,44,3177

Porter_NA et al.]] conjugated diene: λ max=235nm, UV(Me-ester) TeraoJet al. conjugated diene: λ max=232.5nm, UV(Me-ester; after reduction) Porter_NA et al. conjugated trans, cis diene: λ max=236nm, conjugated trans, trans diene: λ max=232.5nm

IR Spectra IR(me-ester; after reduction)[[Reference:Porter_NA:Wolf_RA:Yarbro_EM:Weenen_H:,Biochem. Biophys. Res. Commun.,1979,89,1058

Porter_NA et al.]] conjugated trans, cis diene: 985, 950cm-1, conjugated trans, trans diene: 989cm-1; IR(Me-ester) TeraoJet al.: OOH group: 3400cm-1

NMR Spectra 1H-NMR(Me-ester) TeraoJet al.: OOH: 8.3ppm
Other Spectra Hydrogenation and TBDMS TeraoJet al.
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406HP02 See above. Pace-Asciak_CR et al. 1983
n.a. LBF20406HP02 See above. Peers_KE et al. 1983
n.a. LBF20406HP02 See above. Porter_NA et al. 1981
n.a. LBF20406HP02 See above. Porter_NA et al. 1979
n.a. LBF20406HP02 See above. Porter_NA et al. 1979
n.a. LBF20406HP02 See above. Rabinovitch_H et al. 1981
n.a. LBF20406HP02 See above. Spector_AA et al. 1988
n.a. LBF20406HP02 See above. Terao_J et al. 1981
n.a. LBF20406HP02 See above. Terao_J et al. 1981
n.a. LBF20406HP02 See above. Yamagata_S et al. 1983