10-oxo-12(Z)-Octadecenoic Acid

10-oxo-12(Z)-Octadecenoic acid is a metabolite of linoleic acid (Cay-90150, Cay-90150.1, Cay-21909) and an activator of transient receptor potential vanilloid 1 (TRPV1). It is formed from linoleic acid by conjugated linoleic acid dehydrogenase (CLA-DH) via a 10-hydroxy-12(Z)-octadecenoic acid intermediate and can also be produced from linoleic acid by gut microbiota. 10-oxo-12(Z)-Octadecenoic acid (100 µM) selectively increases calcium levels in HEK293 cells expressing TRPV1 over those expressing TRPV2, TRPV3, TRPV4, and TRP melastatin 8 (TRPM8). It also induces inward currents in HEK293 cells expressing TRPV1, an effect that can be blocked by the TRPV1 antagonist capsazepine (Cay-10007518). Dietary administration of 10-oxo-12(Z)-octadecenoic acid (0.1% w/w) reduces weight gain and adipose tissue weight and increases the expression of the gene encoding mitochondrial uncoupling protein 1 (Ucp1) in wild-type, but not Trpv1 knockout, mice fed a high-fat diet. It also decreases plasma glucose and triglyceride levels in diabetic KKAy mice fed a high-fat diet.CAS Number: 103521-29-5. Synonyms: 10-keto-12Z-Octadecenoic Acid, 10-oxo-12-cis-Octadecenoic Acid. Molecular Formula: C18H32O3. Formula Weight: 296.5. Purity: >95%. Formulation: (Request formulation change), A solution in ethanol. Solubility: DMF: 10 mg/ml, DMSO: 5 mg/ml, Ethanol: 5 mg/ml, PBS (pH 7.2): insol. SMILES: O=C(C/C=C\CCCCC)CCCCCCCCC(O)=O. InChi Code: InChI=1S/C18H32O3/c1-2-3-4-5-8-11-14-17(19)15-12-9-6-7-10-13-16-18(20)21/h8,11H,2-7,9-10,12-16H2,1H3,(H,20,21)/b11-8-. InChi Key: IEQLMTRAAYQDSD-FLIBITNWSA-N.