2616-71-9

Basic information

• Product Name: 3ALPHA,7ALPHA-DIACETOXY-5BETA-CHOLAN-24-OIC ACID METHYL ESTER
• Synonyms: METHYLCHENODEOXYCHOLIC DIACETATE;3ALPHA,7ALPHA-DIACETOXY-5BETA-CHOLAN-24-OIC ACID METHYL ESTER;3ALPHA,7ALPHA-DIHYDROXY-5BETA-CHOLAN-24-OIC ACID METHYL ESTER 3,7-DIACETATE;5BETA-CHOLAN-24-OIC ACID-3ALPHA,7ALPHA-DIOL METHYL ESTER 3,7-DIACETATE;5BETA-CHOLANIC ACID-3ALPHA,7ALPHA-DIOL 3,7-DIACETATE METHYL ESTER;5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA-DIOL DIACETATE METHYL ESTER;3α,7α-diacetoxy-5β-cholan-24-oic acid methyl ester;CHENODEOXYCHOLIC ACID DIACETATE METH
• CAS NO: 2616-71-9
• Molecular Formula: C₂₉H₄₆O₆
• Molecular Weight: 490.67
• Mol File: 2616-71-9.mol

Chemical Properties

• Melting Point: 96-98 °C
• Boiling Point: 531.0±25.0 °C(Predicted)
• Appearance: /
• Density: 1.10±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3ALPHA,7ALPHA-DIACETOXY-5BETA-CHOLAN-24-OIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3ALPHA,7ALPHA-DIACETOXY-5BETA-CHOLAN-24-OIC ACID METHYL ESTER(2616-71-9)
• EPA Substance Registry System: 3ALPHA,7ALPHA-DIACETOXY-5BETA-CHOLAN-24-OIC ACID METHYL ESTER(2616-71-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36
• WGK Germany: 3
• Hazardous Substances Data: 2616-71-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3ALPHA,7ALPHA-DIACETOXY-5BETA-CHOLAN-24-OIC ACID METHYL ESTER is used as a therapeutic agent for treating disorders associated with defects of the cystic fibrosis transmembrane conductance regulator (CFTR) gene or protein. Its application is based on its ability to modulate the function of the CFTR protein, which is responsible for the transport of chloride ions across cell membranes. By improving the function of this protein, it can help alleviate the symptoms of cystic fibrosis and other related conditions.

Upstream product

• 3057-04-3 chenodeoxycholic acid methyl ester 
• 108-24-7 acetic anhydride 
• 82267-82-1 3α,7α-diacetoxy-12,12-ethanediyldimercapto-5β-cholan-24-oic acid methyl ester 
• 75-36-5 acetyl chloride 
• 85198-69-2 methyl (3α,5β,7α)-3,7-diacetoxychol-16-en-24-oate 
• 64144-66-7 (3α,5β,7α)-3,7-dihydroxyandrostan-17-one 
• 91378-51-7 7α-hydroxy-5β-androstane-3,17-dione 
• 85198-67-0 (Z)-(3α,5β,7α)-pregn-17(20)-ene-3,7-diol 
• 474-25-9 chenodeoxycholic acid 
• 2868-48-6 methyl hyodeoxycholate 
• 10190-22-4 3α,6α,7α-triol-5β-24-cholanoic acid methyl ester 
• 2862-62-6 3α-ol-6-oxo-5β-24-cholanoic acid methyl ester 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 

Downstream Products

• 474-25-9 chenodeoxycholic acid 
• 474-25-9 Chenodeoxycholic Acid 
• 85198-69-2 methyl (3α,5β,7α)-3,7-diacetoxychol-16-en-24-oate 

Relevant articles and documents

Preparation method of chenodeoxycholic acid

The invention belongs to the field of organic synthesis, and provides a preparation method of chenodeoxycholic acid, which comprises the following steps of: extracting chenodeoxycholic acid serving as one of main components in waste after chenodeoxycholic acid is extracted from duck gall paste, namely seal cholic acid, serving as a raw material; and the chenodeoxycholic acid is obtained by a propylidene protection method, acetylation, propylidene removal, methyl esterification, reaction with p-toluenesulfonyl chloride, bromine substitution, debromination, deprotection and the like. The method for preparing chenodeoxycholic acid is simple, the raw material source is rich, the product yield is high, and industrialization is easy to realize.

COMPOUNDS FOR USE IN THE TREATMENT OF LIVER DISEASE

Bile acid derivatives, methods of manufacture thereof, and uses thereof are disclosed herein. The bile acid derivatives have demonstrated potential as therapeutics for treating liver disease.

Method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid

The invention belongs to the field of organic synthesis of carbocyclic compounds, and particularly relates to a method for synthesizing 3alpha, 7alpha-dihydroxy-5-beta-cholanic acid from duck cholic acid. According to the method, chenodeoxycholic acid with purity of 97.6% is synthesized by using duck cholic acid as a raw material. The comprehensive yield is 87.8%, the purity of the product is highwhile a high-temperature reaction is avoided, and later impurity removal is simple and convenient.

New highly toxic bile acids derived from deoxycholic acid, chenodeoxycholic acid and lithocholic acid

We have prepared a new panel of 23 BA derivatives of DCA, chenodeoxycholic acid (CDCA) and lithocholic acid (LCA) in order to study the effect of dual substitution with 3-azido and 24-amidation, features individually associated with cytotoxicity in our previous work. The effect of the compounds on cell viability of HT-1080 and Caco-2 was studied using the 3-[4,5-dimethylthizol-2- yl]-2,5-diphenyltetrazolium bromide (MTT) assay. Compounds with high potency towards reduction of cell viability were further studied using flow cytometry in order to understand the mechanism of cell death. Several compounds were identified with low micromolar IC50 values for reducing cell viability in the Caco-2 and HT1080 cell lines, making them among the most potent BA apoptotic agents reported to date. There was no evidence of relationship between overall hydrophobicity and cytotoxicity supporting the idea that cell death induction by BAs may be structure-specific. Compounds derived from DCA caused cell death through apoptosis. There was some evidence of selectivity between the two cell lines studied which may be due to differing expression of CD95/FAS. The more toxic compounds increased ROS production in Caco-2 cells, and co-incubation with the antioxidant N-acetyl cysteine blunted pro-apoptotic effects. The properties these compounds suggest that there may be specific mechanism(s) mediating BA induced cell death. Compound 8 could be useful for investigating this phenomenon.

PURIFICATION PROCESS FOR CHENODEOXYCHOLIC ACID

The present invention relates to a process for purifying chenodeoxycholic acid (3α,7α-dihydroxy-5β-cholic acid). In particular, the present invention relates to a process for purifying chenodeoxycholic acid from low grade of chenodeoxycholic acid mixture in swine bile solid, with high yield and purity.

Stereoselective Introduction of Steroid Side Chains. Synthesis of Chenodeoxycholic Acid

A new short route to chenodeoxycholic acid has been developed.The synthesis is based on the stereoselective introduction of the steroidal side chain via an ene reaction of methyl acrylate and a (17Z)-ethylidene steroid prepared from androstenedione.

Potential Bile Acid Metabolites. 6. Stereoisomeric 3,7-Dihydroxy-5β-cholanic Acids

New synthetic routes to the four possible 3,7-dihydroxy acids are described.The principal reactions involved were inversions with DMF and Me2SO-crown ether and reduction of 12-oxo tosylhydrazones.Inversion of 3α-tosylates by the Me2SO-crown ether method succeeded but that of the corresponding mesylates did not.A table of 1H NMR chemical shift reference data of monosubstituted methyl cholanates pertinent to bile acid characterization has been expanded.

Process and intermediates for the synthesis of Vitamin D3 metabolites and chenodeoxycholic acid

The present disclosure is directed to a process for the synthesis of chenodeoxychloic acid, 25-hydroxycholesterol and 1α,25-dihydroxycholesterol from 17-keto steroids. A cholic acid side chain is stereospecifically introduced by reaction of the appropriate 17-keto steroid with ethyltriphenylphosphonium halides to produce the 17-ethylidene derivative which is allowed to react with acrylic acid esters or propiolic acid esters followed by hydrogenation.