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10-oxo-12(Z)-Octadecenoic Acid (Synonyms: 10-keto-12Z-Octadecenoic Acid, 10-oxo-12-cis-Octadecenoic Acid)

Katalog-Nr.GC52071

A metabolite of linoleic acid and an activator of TRPV1

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10-oxo-12(Z)-Octadecenoic Acid Chemische Struktur

Cas No.: 103521-29-5

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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

10-oxo-12(Z)-Octadecenoic acid is a metabolite of linoleic acid 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 . 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.

1.Kishino, S., Takeuchi, M., Park, S.-B., et al.Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid compositionProc. Natl. Acad. Sci. USA110(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 TRPV1FASEB J.3(11)5036-5048(2017)

Chemical Properties

Cas No. 103521-29-5 SDF Download SDF
Überlieferungen 10-keto-12Z-Octadecenoic Acid, 10-oxo-12-cis-Octadecenoic Acid
Canonical SMILES O=C(C/C=C\CCCCC)CCCCCCCCC(O)=O
Formula C18H32O3 M.Wt 296.5
Löslichkeit DMF: 10 mg/ml,DMSO: 5 mg/ml,Ethanol: 5 mg/ml,PBS (pH 7.2): insol Storage -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 3.3727 mL 16.8634 mL 33.7268 mL
5 mM 0.6745 mL 3.3727 mL 6.7454 mL
10 mM 0.3373 mL 1.6863 mL 3.3727 mL
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