LBF20406HP02

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA8080
LipidMaps	-
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20406HP02

8-Hydroperoxy- 5,9,11,14 -eicosatetraenoic acid
Structural Information
Systematic Name	8-Hydroperoxy- 5,9,11,14 -eicosatetraenoic acid
Common Name	8-Hydroperoxy- 5,9,11,14 -eicosatetraenoic acid
Symbol
Formula	C20H32O4
Exact Mass	336.23005951199997
Average Mass	336.46567999999996
SMILES	C(CC=CCC=CC=CC(OO)CC=CCCCC(O)=O)CCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	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..
Chemical Synthesis
Metabolism
Biological Activity	8-HPETE generated by 8-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE. Terao_J et al.
Genetic Information
Note	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