Back to HOME

Eicosanoid


DATA No : XPR6300 INFORMANT : Shouzo Yamamoto

NAME : (Z,Z,Z)-5,6-Epoxy-8,11,14-eicosatrienoic acid

COMMON NAME: 5(6)OXIDO-8,11,14-EICOSATRIENOIC ACID
SYMBOL: 5,6-EET
FORMULA: C20H32O3 MOL.WT (average) : 318.450


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
The compound is active in stimulated secretion of somatostatin, insulin and glucagon, vasodilataion and regulation of intracellular calcium (Ref. 0078).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:METHYL ESTER ; m/e 334(M+), 316, 303, 283, 267, 233, 190, 176, 163,143(base peak) (Ref. 1095). METHYL ESTER ; m/e 334(M+), 316, 303, 285, 245 (Ref. 1096)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsomes of rat (Ref. 0076) or rabbit (Ref. 0077).
CHEMICAL SYNTHESIS
(Ref. 1097)
[Table 0001]
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0076]
AUTHOR:Chacos,N., Falck,J.R., Wixtrom,C., and Capdevilla,J.
TITLE:Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. PubMed ID:6803794
JOURNAL:Biochem. Biophpys. Res. Commun.
VOL:104 PAGE : 916 -922 (1982)
[TOP]

[0077]
AUTHOR:Oliw,E.H., Guengerich,F.P., and Oates,J.A.
TITLE:Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. PubMed ID:6803794
JOURNAL:J. Biol. Chem.
VOL:257 PAGE : 3771 -3779 (1982)
[TOP]

[0078]
AUTHOR:Fitzpatrick, F. A., and Murphy, R. C.
TITLE:Cytochrome P-450 metabolism of arachidonic acid: formation and biological actions of "epoxygenase"-derived eicosanoids PubMed ID:3072574
JOURNAL:Pharmacol Rev.
VOL:40 PAGE : 229-241 (1988)
[TOP]

[1095]
AUTHOR:Chacos,N., Falck,J.R., Wixtrom,C. and Capdevila,J.
TITLE:Novel Epoxides Formed during the Liver Cytochrome P-450 Oxidation of Arachidonic Acid. PubMed ID:6803794
JOURNAL:Biochem. Biophys. Res. Commun.
VOL:104 PAGE : 916 -822 (1982)
[TOP]

[1096]
AUTHOR:Oliw,E.H., Guengerich,F.P. and Oates,J.A.
TITLE:Oxygenation of Arachidonic Acid by Hepatic Monooxygenases. Isolation and Metabolism of Four Epoxide Intermediates. PubMed ID:6801052
JOURNAL:J. Biol. Chem.
VOL:257 PAGE : 3771 -3781 (1982)
[TOP]

[1097]
AUTHOR:Moustakis,C.A., Viala,J., Capdevila,J. and Falck,J.R.
TITLE:Total Synthesis of the Cytochrome p-450 Epoxygenase Metabolites 5(R),6(S)-, 5(S),6(R)-, and 14(R),15(S)-Epoxyeicosatrienoic Acid (EET) and Hydration Products 5(R),6(R)- and 14(R),15(R)-Dihydroxyeicosatrienoic Acid (DHET).
JOURNAL:J. Am. Chem. Soc.
VOL:107 PAGE : 5283 -5285 (1985)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.