Taurochenodeoxycholic acid

Taurochenodeoxycholic acid is one of the main bioactive substances of animals' bile acid.

Solid

Taurochenodeoxycholic acid is a bile acid taurine conjugate of chenodeoxycholic acid. It has a role as a mouse metabolite and a human metabolite. It derives from a chenodeoxycholic acid. It is a conjugate acid of a taurochenodeoxycholate.|Taurochenodeoxycholic acid is an experimental drug that is normally produced in the liver. Its physiologic function is to emulsify lipids such as cholesterol in the bile. As a medication, taurochenodeoxycholic acid reduces cholesterol formation in the liver, and is likely used as a choleretic to increase the volume of bile secretion from the liver and as a cholagogue to increase bile discharge into the duodenum. It is also being investigated for its role in inflammation and cancer therapy.|A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.

Under room temperature, will be of ursodesoxycholic acid 10.0g (25.4mmol) and P-nitro phenol 3.54g (25.4mmol) by adding 100 ml methylene chloride, stirring cooling to 10-20°C. Dropwise N, N '-dicyclohexyl carbodiimide 5.25g (25.4mmol) dichloromethane solution, completion of the dropping, 20-45 °C reaction 2 hours, filtering, for removing insoluble matter, the filtrate concentrated to obtain yellowish oily 12.59g, yield 96.3percent.The above-mentioned oil to b the nitrile is heavy crystallization, to obtain white adhesive material, directly used for the next step reaction.Under room temperature, the taurine potassium 18-crown -6 complexes 15.73g (36.8mmol) and such oils by adding dichloromethane in sheet, stirring. Reaction at room temperature 5 hours later, TLC (ethyl acetate: petroleum ether = 1:1) monitoring, the reaction is complete. Adding 0.21g glacial acetic acid, stirring a large amount of solid precipitated, filtering to obtain the white solid, the above-mentioned white solid by adding 20 ml in water, stirring crystallization. Filtering and drying to obtain solid 11.56g, total yield 84.7percent (purity 99.8percent, HPLC), deoxycholic acid niu Huange not be detected, the largest unknown shan Za 0.04percent.Under room temperature, will be of ursodesoxycholic acid 10.0g (25.4mmol) and phenol 2.39g (25.4mmol) by adding 100 ml methylene chloride, stirring cooling to 10-20°C. Dropwise N, N '-dicyclohexyl carbodiimide 5.25g (25.4mmol) dichloromethane solution, completion of the dropping, 5-20 °C reaction 2 hours, filtering, for removing insoluble matter, the filtrate concentrated to obtain yellowish oily 11.45g, yield 96.0percent.The above-mentioned oil to b the nitrile is heavy crystallization, to obtain white adhesive material, directly used for the next step reaction.Under room temperature, the taurine potassium 18-crown -6 complexes 15.68g (36.7mmol) and such oils by adding dichloromethane in sheet, stirring. Reaction at room temperature 5 hours later, TLC (ethyl acetate: petroleum ether = 1:1) monitoring, the reaction is complete. Adding 0.19g glacial acetic acid, stirring a large amount of solid precipitated, filtering to obtain the white solid, the above-mentioned white solid by adding 20 ml in water, stirring crystallization. Filtering and drying to obtain solid 11.63g, the overall yield is 85.2percent (purity 99.7percent, HPLC), deoxycholic acid niu Huange not be detected, the largest unknown shan Za 0.04percent.

Taurochenodeoxycholic Acid is a bile acid conjugate and metabolite Taurolithocholic Acid (T009100) with antiinflammatory activity. Taurochenodeoxycholic Acid has been shown to inhibit hepatocyte apoptosis through suppression of Bid translocation to mitochondria.

Molecular Weight:499.7
XLogP3:3.6
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:499.29675933
Monoisotopic Mass:499.29675933
Topological Polar Surface Area:132
Heavy Atom Count:34
Complexity:858
Defined Atom Stereocenter Count:10
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes