Eicosanoid

DATA No : XPR6302 INFORMANT : Shouzo Yamamoto

NAME : (Z,Z,Z)-11,12-Epoxy-5,8,14-eicosatrienoic acid

COMMON NAME	:	11(12)OXIDO-5,8,14-EICOSATRIENOIC ACID
SYMBOL	:	11,12-EET
FORMULA	:	C₂₀H₃₂O₃ MOL.WT (average) : 318.450

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BIOLOGICAL ACTIVITY

The compound relaxes intestinal artery, inhibits vasopressin-dependent water flow in urinary bladder, and regulates intracellular calcium level (Ref. 0078).

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	11(R),12(S)-EET METHYL ESTER ; [a]=+4.94(C=1.64 ,ACETONE) (Ref. 1098) 11(S),12(R)-EET METHYL ESTER ; [a]=-2.34(C=0.66, CHLOROFORM) (Ref. 1099)

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	¹H-NMR(CDCl₃) : d 5.54-5.20(m, 6H), 3.61(s, 3H), 3.00-2.68(m, 4H), 2.37-2.00(m, 10H), 1.81-1.54(m, 2H), 1.46-1.13(m, 6H), 0.88(t, J=7Hz, 3H) (Ref. 1098)

MASS SPECTRA	:	METHYL ESTER ; m/e 340(M⁺), 322, 309, 227, 155 (Ref. 1096)

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat (Ref. 0076) or rabbit (Ref. 0077).

CHEMICAL SYNTHESIS

(Ref. 1098)
[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)

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[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)

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[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)

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[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)

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[1098]

AUTHOR	:	Mosset,P., Yadagiri,P., Lumin,S., Capdevila,J. and Falck,J.R.
TITLE	:	Arachidonic Epoxygenase: Total Synthesis of Both Enantiomers of 8,9- and 11,12-epoxyeicosatrienoic Acid.
JOURNAL	:	Tetrah. Lett.
VOL	:	27 PAGE : 6035 -6038 (1986)

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[1099]

AUTHOR	:	Falck,J.R., Manna,S. and Capdevila,J.
TITLE	:	Enantiospecific Synthesis of Methyl 11,12- and 14,15-Epoxyeicosatrienoate.
JOURNAL	:	Tetrah. Lett.
VOL	:	25 PAGE : 2443 -2446 (1984)

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