Identification | Back Directory | [Name]
(+/-)14(15)-EPOXY-5Z,8Z,11Z,17Z-EICOSATETRAENOIC ACID | [CAS]
131339-24-7 | [Synonyms]
14(15)-EPETE RGZIXZYRGZWDMI-IXQKDQKQSA-N 14,15-EPOXY EICOSATETRAENOIC ACID (+/-)14(15)-EPOXY-5Z,8Z,11Z,17Z-EICOSATETRAENOIC ACID (+/-)14(15)-EPOXY-5Z,8Z,11Z,17Z-EICOSATETRAENOIC ACID 5,8,11-Tridecatrienoic acid, 13-[(2R,3S)-3-(2Z)-2-penten-1-yl-2-oxiranyl]-, (5Z,8Z,11Z)-rel- | [Molecular Formula]
C20H30O3 | [MDL Number]
MFCD08056091 | [MOL File]
131339-24-7.mol | [Molecular Weight]
318.45 |
Hazard Information | Back Directory | [Description]
EDHF (endothelium-derived hyperpolarizing factor) is an unidentified mediator released from vascular endothelial cells in response to acetylcholine and bradykinin which is distinct from the NOS- (nitric oxide) and COX-derived (prostacyclin) vasodilators.1,2 Cytochrome P450 (CYP450) metabolism of polyunsaturated fatty acids, produces epoxides such as (±)14(15)-EpETrE which are prime candidates for the actual active mediator.3 However, the CYP450 metabolites of eicosapentaenoic acid (EPA; ) and docosahexaenoic acid (DHA; ) have been little studied relative to arachidonate epoxygenase metabolites. (±)14(15)-EpETE is the ω-3 homolog of 14(15)-EpETrE, derived via epoxidation of the 14,15-double bond of EPA. The EDHF activity of (±)14(15)-EpETE has not yet been determined. | [References]
1. Chataigneau, T., Félétou, M., Duhault, J., et al. Epoxyeicosatrienoic acids, potassium channel blockers, and endothelium-dependent hyperpolarization in the guinea-pig carotid artery Br. J. Pharmacol. 123(3),574-580(1998). 2. Fisslthaler, B., Popp, R., Kiss, L., et al. Cytochrome P450 2C is an EDHF synthase in coronary arteries Nature 401(6752),493-497(1999). 3. Baron, A., Frieden, M., and Bény, J.L. Epoxyeicosatrienoic acids activate a high-conductance, Ca2+-dependent K+ channel on pig coronary artery endothelial cells J. Physiol. 504(Pt 3),537-543(1997). |
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