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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

16(17)-EpDPE

Cayman Chemical Item Number 10174

16,17-epoxy Docosapentaenoic Acid; 16,17 EDP

16(17)-EpDPE

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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. 16(17)-EpETE is the DHA homolog of 14(15)-EpETrE, derived via epoxidation of the 16,17-double bond of docosahexaenoic acid (DHA). The EDHF activity of 16(17)-EpDPE has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a murine inflammation model.4

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 123 574-580 (1998).

2 Fisslthaler, B., Popp, R., Kiss, L., et al. Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature 401 493-497 (1999).

3 Baron, A., Frieden, M., and Bény, J. Epoxyeicosatrienoic acids activate a high-conductance, Ca2+-dependent K+ channel on pig coronary artery endothelial cells. J Physiol 504 537-543 (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).

Synonyms
  • 16,17-epoxy Docosapentaenoic Acid
  • 16,17 EDP
Formal Name (±)16(17)-​epoxy-​4Z,​7Z,​10Z,​13Z,​19Z-​docosapentaenoic acid
Molecular Formula C22H32O3
Formula Weight 344.5
Formulation A solution in ethanol
Purity ≥90%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CC/C=C\C[C@H]​1O[C@H]​1C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)​O

Background Reading

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 123 574-580 (1998).

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).

Fisslthaler, B., Popp, R., Kiss, L., et al. Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature 401 493-497 (1999).

Baron, A., Frieden, M., and Bény, J. Epoxyeicosatrienoic acids activate a high-conductance, Ca2+-dependent K+ channel on pig coronary artery endothelial cells. J Physiol 504 537-543 (1997).

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16(17)-EpDPE is available in the following screening library:

Size Price Quantity Subtotal
25 µg $33.00 $0.00
50 µg $63.00 $0.00
100 µg $119.00 $0.00
500 µg $528.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

(±)14(15)-EET
14(15)-EpETE
19(20)-EpDPE
(±)5(6)-EET
(±)8(9)-EET
Docosahexaenoic Acid
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