516-35-8

Usage

Uses

Used in Pharmaceutical Industry:
Taurochenodeoxycholic acid is used as an anti-inflammatory agent for its ability to inhibit hepatocyte apoptosis through the suppression of Bid translocation to mitochondria. This makes it a valuable compound in the development of treatments for various inflammatory conditions and liver-related diseases.
Used in Research Applications:
As a labelled analogue, Taurochenodeoxycholic acid is utilized in research to study its anti-inflammatory activity and its effects on hepatocyte apoptosis. This helps in understanding the underlying mechanisms of action and potential therapeutic applications in the field of medicine.

InChI:InChI=1/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16?,17-,18+,19+,20-,21-,22+,24-,25-,26+/m0/s1

Upstream product

• 107-35-7 Tau 
• 128-13-2 ursodeoxycholic acid 
• 51036-13-6 N-chlorotaurine 
• 196505-69-8 C₂₇H₄₄O₆ 
• 1260543-03-0 C₃₀H₄₄O₄ 
• 91613-11-5 4-nitrophenyl ursodeoxycholate 
• 35807-85-3 tauroursodeoxycholic acid sodium salt 
• 474-25-9 chenodeoxycholic acid 

Downstream Products

• 72732-24-2 trisodium taurochenodeoxycholate 3,7-disulfate 
• 75808-01-4 3α-hydroxy-7-carbonylcholanoyl-N-taurine 
• 1110779-44-6 C₄₈H₈₀O₄₀*C₂₆H₄₅NO₆S 
• 72732-24-2 trisodium tauroursodeoxycholate 3,7-disulfate 

Relevant academic research and scientific papers

Method for synthesizing tauroursodeoxycholic acid under promotion of trichloroisocyanuric acid

The invention relates to the technical field of medicine synthesis, in particular to a method for synthesizing tauroursodeoxycholic acid under the promotion of trichloroisocyanuric acid. The method sequentially comprises the following steps: an intermediate product synthesis step: reacting taurine under the action of trichloroisocyanuric acid to obtain a system I; synthesizing tauroursodeoxycholicacid, namely adding tauroursodeoxycholic acid and alkali into the system I, and reacting to obtain a system II; the synthetic method has the advantages of economy and environmental protection, is simple in operation process, is suitable for industrial expansion, and can be applied to production practice of tauroursodeoxycholic acid.

Synthetic method of tauroursodeoxycholic acid

The invention discloses a synthetic method of tauroursodeoxycholic acid. The synthetic method comprises the following steps: taking extracted or synthetic taurochenodeoxycholic acid as a raw material,obtaining a target product tauroursodeoxycholic acid crude product through 7 alpha-hydroxyl selective oxidation, 3 alpha-hydroxyl protection, 7-carbonyl selective oxidation, 7 alpha-hydroxyl sulfonylation, detosylation and alkaline hydrolysis reactions of the taurochenodeoxycholic acid, and finally obtaining the high-purity tauroursodeoxycholic acid through recrystallization purification. The tauroursodeoxycholic acid is obtained by using low-cost poultry bile as the raw material, the traditional steps of hydrolyzing and then condensing combined chenodeoxycholic acid are omitted, and a taurylamine structure is obtained directly; the target configuration product is obtained through selective oxidation, selective reduction and stereoselectivity elimination; in the whole technology, using high alkali, metallic sodium or valuable catalysts is avoided, and the whole technology presents a relatively efficient and safe chemical synthetic route. The technological process has the advantages ofbeing simple and controllable, high in purity, efficient, safe, environmentally-friendly and easy for industrialization, and has good application prospects in the field of pharmacy.

niu Huangxiong method for the preparation of sodium deoxycholate

The invention provides a method for preparing sodium tauroursodeoxycholate. The method comprises (1) using ursodesoxycholic acid as raw materials and getting a mixed anhydride solution through acetylation and chloride reactions; (2) dissolving taurine into a sodium carbonate solution to get a taurine sodium carbonate solution which is then added in drops into the mixed anhydride solution of step (1) with stirring, and then filtering precipitate to get a filtrate; (3) adjusting pH of the filtrate of step (2) to 6 to 7, concentrating and drying to get crude dried products of tauro-ursodesoxycholic acid; and (4) desalting purifying and re-crystallizing the concentrated dried products of step (3) to get the sodium tauroursodeoxycholate. The method is low in cost and short in technology route, with a yield up to 78%, and is suitable for industrial scale production.

Preparing method for tauro ursodesoxy cholic acid

The invention discloses a preparing method for tauro ursodesoxy cholic acid. The method comprises the following steps that firstly, ursodesoxycholic acid and a phenolic compound are added into a chloralkane organic solvent at the room temperature, the temperature is lowered to 10-20 DEG C, a condensing agent is added, thorough reaction is carried out under the temperature of 5-45 DEG C in a heat preservation mode after dripping is completed, filter liquor is concentrated after filtering to obtain a crude product, and the crude product is recrystallized to obtain a ursodesoxycholic acid phenolic ester refined product; secondly, taurine salt and a crown ether complexing agent are added into water to be dissolved, a taurine salt crown ether complex is obtained after concentration, the ursodesoxycholic acid phenolic ester refined product and the taurine salt crown ether complex are added into an organic solvent to be reacted, acid is added after thorough reaction and stirred, solids are separated out and filtered, a filter cake is dissolved in water, stirred and subjected to crystallization, and tauro ursodesoxy cholic acid is obtained. The synthetic method is low in cost, operation is simple and controllable, the product is high in yield and purity, meanwhile, the isomer impurity taurochenodeoxycholic acid of tauro ursodesoxy cholic acid can be well controlled, and the preparing method is suitable for industrial production.

Process for the preparation of tauroursodesoxycholic acid

The present invention relates to a novel method for preparing tauroursodeoxycholic acid which comprises a step of selective precipitation of the impurities present in the suspension obtained from the reaction of an aqueous solution of sodium taurinate with an acetonic solution of a mixed anhydride of ursodeoxycholic acid with an alkyl chloroformate.

Chemical synthesis, structural analysis, and decomposition of N-nitroso bile acid conjugates

N-nitrosoamides of 7β-hydroxylated bile acid conjugates, particularly of the ursodeoxycholic acid family have been synthesized. The products and synthetic intermediates were fully characterized by the results of high- resolution 1H NMR, FT-1R, FABMS and ESI-MS studies. The compounds, N- nitrosoglycoursodeoxycholic acid (NOGUDCA), N-nitrosoglycoursocholic acid (NOGUCA) and N-nitrosoglycodeoxycholic acid (NOGDCA) decomposed between pH 6 and 9 in aqueous bullet solutions, indicating a t( 1/2 ) of 5-7 h while N- nitrosotauroursodeoxycholic acid (NOTUDCA) indicated a much longer t( 1/2 ) of 15-17 h. These results suggest that the compounds are relatively stable and may enter the enterohepatic circulation. Their decomposition is similar to that of other N-nitrosamides, which generate alkylating agents and thereby act as DNA mutagens.

An improved procedure for the synthesis of glycine and taurine conjugates of bile acids

Glycine and taurine conjugates of 5β cholanic acids have been synthesized using improved procedures based on the peptide coupling reagent, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. The conjugates are obtained in chromatographically pure form in yields higher than 90%. The use of this procedure in the large scale preparation of choly[1,2 13C2]glycine is described.