>>Analytical Standards>>(±)16(17)-EpDPA

(±)16(17)-EpDPA (Synonyms: (±)16,17 EDP, (±)16,17-epoxy Docosapentaenoic Acid, (±)16,17-epoxy DPA, (±)16,17-EpDPE)

Catalog No.GC41194

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.

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(±)16(17)-EpDPA Chemical Structure

Cas No.: 155073-46-4

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25μg
US$57.00
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50μg
US$108.00
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100μg
US$204.00
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500μg
US$904.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

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 and docosahexaenoic acid 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]

Reference:
[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).

Chemical Properties

Cas No. 155073-46-4 SDF
Synonyms (±)16,17 EDP, (±)16,17-epoxy Docosapentaenoic Acid, (±)16,17-epoxy DPA, (±)16,17-EpDPE
Chemical Name (±)16,17-epoxy-4Z,7Z,10Z,13Z,19Z-docosapentaenoic acid
Canonical SMILES CC/C=C\C[C@@H]1[C@@H](O1)C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O
Formula C22H32O3 M.Wt 344.5
Solubility DMF: 50 mg/ml,DMSO: 50 mg/ml,Ethanol: 50 mg/ml,PBS (pH 7.2): 1 mg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 2.9028 mL 14.5138 mL 29.0276 mL
5 mM 0.5806 mL 2.9028 mL 5.8055 mL
10 mM 0.2903 mL 1.4514 mL 2.9028 mL
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Review for (±)16(17)-EpDPA

Average Rating: 5 ★★★★★ (Based on Reviews and 40 reference(s) in Google Scholar.)

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