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131339-24-7

131339-24-7 Structure

131339-24-7 Structure
IdentificationBack 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
Chemical PropertiesBack Directory
[solubility ]

DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS (pH 7.2): 1 mg/ml
Safety DataBack Directory
[Symbol(GHS) ]


GHS02,GHS07
[Signal word ]

Danger
[Hazard statements ]

H225-H319
[Precautionary statements ]

P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
Hazard InformationBack 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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