| Identification | Back Directory | [Name]
(±)16(17)-EpDPA | [CAS]
155073-46-4 | [Synonyms]
(±)16(17)-EpDPA
BCTXZWCPBLWCRV-QCAYAECISA-N
(±)16(17)-EpDPA MaxSpec Standard | [Molecular Formula]
C22H32O3 | [MOL File]
155073-46-4.mol | [Molecular Weight]
344.49 |
| Chemical Properties | Back Directory | [Boiling point ]
462.5±33.0 °C(Predicted) | [density ]
0.994±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS (pH 7.2): 1 mg/ml | [pka]
4.58±0.10(Predicted) |
| 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)-EET 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. (±)16(17)-EpDPA is the DHA homolog of (±)14(15)-EpETrE, derived via epoxidation of the 16,17-double bond of DHA. The EDHF activity of (±)16(17)-EpDPA has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a mouse inflammation model.4 | [Uses]
(±)16(17)-EpDPA is the DHA homolog of (±)14(15)-EpETrE, derived via epoxidation of the 16,17-double bond of DHA. | [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).
4. Serhan, C.N., Hong, S., Gronert, K., et al. Resolvins: A family of bioactive products of ω-3 fatty acid transformation circuits by aspirin treatment that counter proinflammation signals J. Exp. Med. 196(8),1025-1037(2002). |
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