Home>>Lipids>> Cyclooxygenase>>(±)5(6)-DiHET

(±)5(6)-DiHET

(Synonyms: (±)5,6-DiHETrE) 目录号 : GC40270

A racemic version of a CYP450 pathway metabolite of arachidonic acid

(±)5(6)-DiHET Chemical Structure

Cas No.:213382-49-1

规格 价格 库存 购买数量
25μg
¥1,268.00
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50μg
¥2,415.00
现货
100μg
¥4,557.00
现货
250μg
¥10,141.00
现货

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Sample solution is provided at 25 µL, 10mM.

Description

5(6)-DiHET is a fully racemic version of the enantiomeric forms biosynthesized from 5(6)-EET by epoxide hydrolases. [1] 5(6)-DiHET can be used to quantify 5(6)-EET due to the conversion of 5(6)-EET to 5(6)-δ-lactone in solution. [2]  5(6)-DiHET activates large conductance calcium-activated potassium (BK) channels in smooth muscle cells from rat small coronary arteries. [3 It is a substrate for sheep seminal vesicle COX, producing 5,6-dihydroxy prostaglandin E1 and F1α metabolites in vitro. [4] 5(6)-DiHET levels decrease in plasma in a high-fat diet-induced rat model of hyperlipidemia.[5]

Reference:
[1]. 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).
[2]. Rashid, M., Manivet, P., Nishio, H., et al. Identification of the binding sites and selectivity of sarpogrelate, a novel 5-HT2 antagonist, to human 5-HT2A, 5-HT2B and 5-HT2C receptor subtypes by molecular modeling. Life Sci. 73(2), 193-207 (2003).
[3]. Lu, T., Katakam, P.V.G., VanRollins, M., et al. Dihydroxyeicosatrienoic acids are potent activators of Ca2+-activated K+ channels in isolated rat coronary arterial myocytes. J. Physiol. 534(Pt 3), 651-667 (2001).
[4]. Oliw, E.H. Biosynthesis of 5,6-dihydroxyprostaglandin E1 and F1α from 5,6-dihydroxyeicosatrienoic acid by ram seminal vesicles. Biochim. Biophys. Acta. 795(2), 384-391 (1984).
[5]. Miao, H., Zhao, Y.-H., Vaziri, N.D., et al. Lipidomics biomarkers of diet-induced hyperlipidemia and its treatment with Poria cocos. J. Agric. Food Chem. 64(4), 969-979 (2016).

化学性质

Cas No. 213382-49-1 SDF
别名 (±)5,6-DiHETrE
化学名 (±)5,6-dihydroxy-8Z,11Z,14Z-eicosatrienoic acid
Canonical SMILES CCCCC/C=C\C/C=C\C/C=C\C[C@@H](O)[C@@H](O)CCCC(O)=O
分子式 C20H34O4 分子量 338.5
溶解度 50mg/mL in DMSO, 50mg/mL in DMF 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 2.9542 mL 14.771 mL 29.5421 mL
5 mM 0.5908 mL 2.9542 mL 5.9084 mL
10 mM 0.2954 mL 1.4771 mL 2.9542 mL
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