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.

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1. Kishino, S., Takeuchi, M., Park, S.-B., et al. Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition. Proc. Natl. Acad. Sci. USA 110(44), 17808-17813 (2013).

2. Kim, M., Furuzono, T., Yamakuni, K., et al. 10-oxo-12(Z)-octadecenoic acid, a linoleic acid metabolite produced by gut lactic acid bacteria, enhances energy metabolism by activation of TRPV1. The FASEB Journal 3(11), 5036-5048 (2017).