Home>>Analytical Standards>>(±)14(15)-EET

(±)14(15)-EET (Synonyms: (±)14,15-EET, (±)14,15-EpETrE)

Catalog No.GC40430

(±)14(15)-EET is biosynthesized in rat and rabbit liver microsomes by CYP450.

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(±)14(15)-EET Chemical Structure

Cas No.: 197508-62-6

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25μg
$67.00
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50μg
$121.00
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100μg
$214.00
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500μg
$668.00
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Sample solution is provided at 25 µL, 10mM.

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Description of (±)14(15)-EET

(±)14(15)-EET is a metabolite of arachidonic acid that is formed via epoxidation of arachidonic acid by cytochrome P450.[1],[2] It prevents increases in leukotriene B4, ICAM-1, and chemokine (C-C motif) ligand 1 (CCL2) induced by oxidized LDL in primary rat pulmonary artery endothelial cells (RPAECs) when used at a concentration of 1 μM.[3] (±)14(15)-EET induces dilation of preconstricted isolated canine coronary arterioles (EC50 = 0.2 pM).[4] It reduces myocardial infarct size as a percentage of the area at risk in a canine model of ischemia-reperfusion injury induced by left anterior descending coronary artery (LAD) occlusion when administered at a dose of 0.128 mg/kg prior to occlusion or reperfusion.[5]

Reference:
[1]. Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104(3), 916-922 (1982).
[2]. Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. J. Biol. Chem. 257(7), 3771-3781 (1982).
[3]. Jiang, J.-X., Zhang, S.-J., Xiong, Y.-K., et al. EETs attenuate ox-LDL-induced LTB4 production and activity by inhibiting p38 MAPK phosphorylation and 5-LO/BLT1 receptor expression in rat pulmonary arterial endothelial cells. PLoS One 10(6), e0128278 (2015).
[4]. Oltman, C.L., Weintraub, N.L., VanRollins, M., et al. Epoxyeicosatrienoic acids and dihydroxyeicosatrienoic acids are potent vasodilators in the canine coronary microcirculation. Circ. Res. 83(9), 932-939 (1998).
[5]. Nithipatikom, K., Moore, J.M., Isbell, M.A., et al. Epoxyeicosatrienoic acids in cardioprotection: Ischemic versus reperfusion injury. Am. J. Physiol. Heart Circ. Physiol. 291(2), H537-H542 (2006).

Chemical Properties of (±)14(15)-EET

Cas No. 197508-62-6 SDF
Synonyms (±)14,15-EET, (±)14,15-EpETrE
Chemical Name (±)14(15)-epoxy-5Z,8Z,11Z-eicosatrienoic acid
Canonical SMILES CCCCC[C@@H]1[C@@H](O1)C/C=C\C/C=C\C/C=C\CCCC(O)=O
Formula C20H32O3 M.Wt 320.5
Solubility DMF: >50 mg/ml (per Rao Maddipati),DMSO: >50 mg/ml (per Rao Maddipati),Ethanol: >50 mg/ml (per Rao Maddipati), Storage Store at -20°C; protect from light
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 of (±)14(15)-EET

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1 mg 5 mg 10 mg
1 mM 3.1201 mL 15.6006 mL 31.2012 mL
5 mM 0.624 mL 3.1201 mL 6.2402 mL
10 mM 0.312 mL 1.5601 mL 3.1201 mL
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