10-oxo-12(Z)-Octadecenoic Acid-d5

10-oxo-12(Z)-Octadecenoic acid-d5 is intended for use as an internal standard for the quantification of 10-oxo-12(Z)-octadecenoic acid (Cay-36977) by GC- or LC-MS. 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.Formal Name: (Z)-10-oxooctadec-12-enoic-17,17,18,18,18-d5 acid. Synonyms: 10-keto-12Z-Octadecenoic Acid-d5, 10-oxo-12-cis-Octadecenoic Acid-d5. Molecular Formula: C18H27D5O3. Formula Weight: 301.5. Purity: >99% deuterated forms (d1-d5). Formulation: (Request formulation change), A solution in ethanol. Solubility: Ethanol: 1 mg/ml. SMILES: O=C(C/C=C\CCCC([2H])([2H])C([2H])([2H])[2H])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-/i1D3,2D2. InChi Key: IEQLMTRAAYQDSD-PJKSMEJXSA-N.