(±)5(6)-EET

5(6)-EET is a fully racemic version of the enantiomeric forms biosynthesized from arachidonic acid (Cay-90010) by cytochrome P450 enzymes. In solution, 5(6)-EET degrades into 5,6-DiHET and 5(6)-delta-lactone, which can be converted to 5(6)-DiHET and quantified by GC-MS. In neuroendocrine cells, such as the anterior pituitary and pancreatic islets, 5(6)-EET has been implicated in the mobilization of calcium and hormone secretion. 5(6)-EET is an inhibitor of T-type voltage-gated calcium channels (Cav3) that inhibits isoforms Cav3.1, Cav3.2 (IC50 = 0.54 µM), and Cav3.3 and decreases nifedipine-resistant phenylephrine-induced vasoconstriction in isolated mouse mesenteric arteries via Cav3.2 blockade when used at a concentration of 3 µM. In addition, it is a substrate of COX-1 and COX-2, as measured by oxygen consumption and product formation assays when used at a concentration of 50 µM. (±)5(6)-EET is provided as a mixture of the free acid and lactone. Formal Name: (±)5,6-epoxy-8Z,11Z,14Z-eicosatrienoic acid. CAS Number: 87173-80-6. Synonyms: (±)5,6-EpETrE. Molecular Formula: C20H32O3. Formula Weight: 320.5. Purity: >95% (mixture of free acid and lactone). Formulation: A solution in methyl acetate. Solubility: DMF: >50 mg/ml (per Rao Maddipati), DMSO: >50 mg/ml (per Rao Maddipati), Ethanol: >50 mg/ml (per Rao Maddipati), PBS pH 7.2: >1 mg/ml (from 13(S)-HODE). SMILES: CCCCC/C=C\C/C=C\C/C=C\C[C@@H](O1)[C@@H]1CCCC(O)=O. InChi Code: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-/t18-,19+/m1/s1. InChi Key: VBQNSZQZRAGRIX-GSKBNKFLSA-N.