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 (Item No. 36977) by GC- or LC-MS. 10-oxo-12(Z)-Octadecenoic acid is a metabolite of linoleic acid (Item Nos. 90150 | 90150.1 | 21909) and an activator of transient receptor potential vanilloid 1 (TRPV1).1,2 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.1 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).2 It also induces inward currents in HEK293 cells expressing TRPV1, an effect that can be blocked by the TRPV1 antagonist capsazepine (Item No. 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.WARNING This product is not for human or veterinary use.

[1] SHIGENOBU KISHINO. Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2013, 110 44: 17808-17813. DOI: 10.1073/pnas.1312937110
[2] MINJI KIM. 10-oxo-12(Z)-octadecenoic acid, a linoleic acid metabolite produced by gut lactic acid bacteria, enhances energy metabolism by activation of TRPV1[J]. FASEB Journal, 2017, 31 11: 5036-5048. DOI: 10.1096/fj.201700151r