(±)19(20)-EpDPA


CAS No. :

(±)19(20)-EpDPA,
Product Details
Cat No:R043730
Synonyms:​(±)19,20 EDP;​(±)19,20-epoxy Docosapentaenoic Acid;​(±)19,20-epoxy DPA;​(±)19,20-EpDPE
Molecular Formula:C22H32O3
Molecular Weight:344.5
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Cat No:R043730
Product-Name:(±)19(20)-EpDPA
InChI:InChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,15-13-,16-14-/t20-,21+/m1/s1
InChIKey:OSXOPUBJJDUAOJ-MWEXLPNRSA-N
SMILES:CC[C@@H]1[C@@H](O1)C/C=CC/C=CC/C=CC/C=CC/C=CCCC(O)=O
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. Cytochrome P450 (CYP450) metabolism of polyunsaturated fatty acids produces epoxides such as (±)14(15)-EpETrE (Item No. 50651) which are prime candidates for the actual active mediator. However, the CYP450 metabolites of eicosapentaenoic acid (EPA; Item No. 90110) and docosahexaenoic acid (DHA; Item No. 90310) have been little studied relative to arachidonate epoxygenase metabolites. ​(±)19(20)-EpDPA is a DHA epoxygenase metabolite, derived via epoxidation of the ω-3 double bond of DHA. The EDHF activity of (±)19(20)-EpDPA has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a mouse inflammation model.
1.Chataigneau, T.,Félétou, M.,Duhault, J., et al. Epoxyeicosatrienoic acids, potassium channel blockers, and endothelium-dependent hyperpolarization in the guinea-pig carotid artery. British Journal of Pharmacology 123, 574-580 (1998).
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