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103521-29-5

103521-29-5 Structure

103521-29-5 Structure
IdentificationBack Directory
[Name]

12-Octadecenoic acid, 10-oxo-, (12Z)-
[CAS]

103521-29-5
[Synonyms]

12-Octadecenoic acid, 10-oxo-, (12Z)-
[Molecular Formula]

C18H32O3
[MOL File]

103521-29-5.mol
[Molecular Weight]

296.44
Chemical PropertiesBack Directory
[Boiling point ]

447.4±28.0 °C(Predicted)
[density ]

0.953±0.06 g/cm3(Predicted)
[storage temp. ]

-20°C
[solubility ]

DMF: 10 mg/ml,DMSO: 5 mg/ml,Ethanol: 5 mg/ml,PBS (pH 7.2): insol
[form ]

Solid
[pka]

4.78±0.10(Predicted)
[color ]

White to off-white
Safety DataBack Directory
[Symbol(GHS) ]


GHS02,GHS07
[Signal word ]

Danger
[Hazard statements ]

H225-H319
[Precautionary statements ]

P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
Hazard InformationBack Directory
[Uses]

10-Oxo-12(Z)-octadecenoic acid is an ester product.
[Biological Activity]

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.
[storage]

-20°C
[References]

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)
103521-29-5 suppliers list
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