(±)2-(14,15-Epoxyeicosatrienoyl) Glycerol

2-Arachidonoyl glycerol (2-AG) is an endogenous central cannabinoid (CB1) receptor agonist that is present at relatively high levels in the central nervous system. 2-AG is hydrolyzed by the enzyme monoacylglycerol lipase, terminating its biological activity, and metabolism by cyclooxygenase-2 and lipoxygenases has been documented. The related endocannabinoid, 2-arachidonoyl ethanolamide (AEA), can be metabolized by cytochrome P450 (CYP450) enzymes in human liver and kidney to a number of epoxy-ethanolamide derivatives. (±)2-(14,15-Epoxyeicosatrienoyl) Glycerol ((±)2-14,15-EG) is a novel CYP450 metabolite of 2-AG in the kidney. (±)2-14,15-EG is a potent mitogen for renal epithelial cells, increasing DNA synthesis in LLCPKcl4 cells at concentrations as low as 100 nM and doubling cell proliferation rates at 1 µM. In these cells, (±)2-14,15-EG activates the metalloprotease ADAM17, which cleaves proTGF-alpha and releases TGF-alpha as a ligand that initiates the EGFR-ERK signalling pathway.Formal Name: (5Z,8Z,11Z)-13-(3-pentyl-2-oxiranyl)-5,8,11-tridecatrienoic acid, (±)2-hydroxy-1-(hydroxymethyl)ethyl ester. CAS Number: 848667-56-1. Synonyms: (±)2-14,15-EG. Molecular Formula: C23H38O5. Formula Weight: 394.5. Purity: >95%. Formulation: (Request formulation change), A solution in acetonitrile. Solubility: DMF: 10 mg/ml, DMSO: 10 mg/ml, Ethanol: 50 mg/ml, PBS (pH 7.2): 0.15 mg/ml. SMILES: O=C(OC(CO)CO)CCC/C=C\C/C=C\C/C=C\C[C@H](O1)[C@H]1CCCCC. InChi Code: InChI=1S/C23H38O5/c1-2-3-12-15-21-22(28-21)16-13-10-8-6-4-5-7-9-11-14-17-23(26)27-20(18-24)19-25/h4,6-7,9-10,13,20-22,24-25H,2-3,5,8,11-12,14-19H2,1H3/b6-4-,9-7-,13-10-/t21-,22+/m1/s1. InChi Key: LPMVKZXODWQHGJ-LPGBQIIWSA-N. Side Chain Carbon Sum: 20:3.