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Usage

Uses

Used in Pharmaceutical Industry:
Glycochenodeoxycholic Acid is used as a therapeutic agent for treating various liver and gallbladder disorders. Its application reason is due to its ability to dissolve cholesterol gallstones and improve bile flow, which aids in the treatment of these conditions.
Used in Diagnostic Industry:
Glycochenodeoxycholic Acid is used as a diagnostic agent for bile duct imaging and evaluation of the biliary system. Its application reason is its ability to enhance the visualization of the bile ducts and provide a clearer understanding of any abnormalities or blockages.
Used in Nutritional Industry:
Glycochenodeoxycholic Acid is used as a supplement to aid in the digestion and absorption of dietary fats and fat-soluble vitamins. Its application reason is its role in emulsifying fats, which facilitates their breakdown and absorption in the body.
Used in Cosmetic Industry:
Glycochenodeoxycholic Acid is used as an ingredient in certain cosmetic products, particularly those targeting skin health and appearance. Its application reason is its potential to improve skin hydration and reduce the appearance of blemishes and acne.

InChI:InChI=1/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19?,20?,21-,24?,25+,26-/m1/s1

Upstream product

• 474-25-9 chenodeoxycholic acid 
• 174069-12-6 3α,7α-dihydroxy-5β-cholan-24-oic acid 2,5-dioxopyrrolidin-1-yl ester 
• 115488-03-4 glycine ursodeoxycholic acid ethyl ester 
• 56-40-6 glycine 
• 128-13-2 ursodeoxycholic acid 
• 178437-09-7 3α,7β-dihydroxy-5β-cholan-24-oic acid 2,5-dioxo-pyrrolidin-1-yl ester 

Relevant academic research and scientific papers

Glycocholic acid ester, preparation method thereof and preparation method of glycocholic acid

The invention provides a preparation method of glycocholic acid ester, glycocholic acid ester and a preparation method of glycocholic acid, according to the preparation method of glycocholic acid ester, an aza-carbene derivative is used as a condensation reagent, and synthesis of glycocholic acid ester can be efficiently completed through a one-pot method in a wide solvent range. The yield can reach 90% or above, the reaction conditions are mild, and the method can be suitable for preparation of most glycocholic acid esters and can be better suitable for amplification and industrial production.

Synthesis, anticancer activities, antimicrobial activities and bioavailability of berberine-bile acid analogues

Fifteen berberine-bile acid analogues were synthesized. Anticancer activities of these analogues compared with berberine (BBR) were evaluated in vitro; among the analogues, A4, B4, and B5 had higher cytotoxicity than that of BBR. Most of the analogues showed higher antimicrobial activity against Staphylococcus aureus ATCC 25923 and Staphylococcus albus ATCC 8799 than that of BBR, but Bacillus subtilis AS 1.398 and Escherichia coli ATCC 31343 were not sensitive to all of the analogues. A4 and B4 were stable in the serum stability assay. B4 showed promising oral bioavailability in mice.

Continuous flow synthesis and scale-up of glycine- and taurine-conjugated bile salts

A multi-gram scale protocol for the N-acyl amidation of bile acids with glycine and taurine has been successfully developed under continuous flow processing conditions. Selecting ursodeoxycholic acid (UDCA) as the model compound and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) as the condensing agent, a modular mesoreactor assisted flow set-up was employed to significantly speed up the optimization of the reaction conditions and the flow scale-up synthesis. The results in terms of yield, in line purification, analysis, and implemented flow set-up for the reaction optimization and large scale production are reported and discussed.

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.