Chenodeoxycholic acid diacetate methyl ester

Base Information

• Chemical Name: Chenodeoxycholic acid diacetate methyl ester
• CAS No.: 2616-71-9
• Molecular Formula: C29H46 O6
• Molecular Weight: 490.681
• European Community (EC) Number: 636-755-3
• UNII: X4FU9EI1O4
• DSSTox Substance ID: DTXSID30466756
• Nikkaji Number: J65.412D
• Wikidata: Q76421554
• Mol file: 2616-71-9.mol

Synonyms:Chenodeoxycholic acid diacetate methyl ester;2616-71-9;X4FU9EI1O4;Methyl chenodeoxycholate diacetate;UNII-X4FU9EI1O4;3alpha,7alpha-Diacetoxy-5beta-cholan-24-oic acid methyl ester;methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-diacetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate;Methyl 3alpha,7alpha-diacetoxy-5beta-cholan-24-oate;Cholan-24-oic acid, 3,7-bis(acetyloxy)-, methyl ester, (3alpha,5beta,7alpha)-;Cholan-24-oic acid, 3,7-bis(acetyloxy)-, methyl ester, (3.alpha.,5.beta.,7.alpha.)-;Cholane-24-oic acid, 3,7-bis-acetoxy-;Chenodeoxycholic acid, acetate-methyl ester;12-Desoxycholic acid diacetate methyl ester;Chenodesoxycholic acid diacetate methyl ester;Methyl 3,7-bis(acetyloxy)cholan-24-oate #;SCHEMBL3044260;DTXSID30466756;methyl (4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11aR)-4,7-bis(acetyloxy)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoate;3ALPHA,7ALPHA-DIACETOXY-5BETA-CHOLAN-24-OICACIDMETHYLESTER;MFCD00021165;AKOS024386251;chenodeoxycholic acid diac-etate methyl ester;J-016292;methyl 3alpha,7alpha-diacetyloxy-5beta-cholan-24-oate;METHYL 3.ALPHA.,7.ALPHA.-DIACETOXY-5.BETA.-CHOLAN-24-OATE;methyl (4R)-4-[(3R, 5S, 7R, 8R, 9S, 10S, 13R, 14S, 17R)-3, 7-diacetyloxy-10, 13-dimethyl-2, 3, 4, 5, 6, 7, 8, 9, 11, 12, 14, 15, 16, 17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate

Chemical Property of Chenodeoxycholic acid diacetate methyl ester

Chemical Property:

• Melting Point: 96-98 °C
• Boiling Point: 531.0±25.0 °C(Predicted)
• PSA: 78.90000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 5.70790
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 490.32943918
• Heavy Atom Count: 35
• Complexity: 824

Purity/Quality:

98%,99%, ^*data from raw suppliers

Chenodeoxycholic acid diacetate methyl ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)OC(=O)C)C)OC(=O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)OC(=O)C)C)OC(=O)C)C
• Uses: Chenodeoxycholic Acid Diacetate Methyl Ester can be used to treat disorders associated with defects of the cystic fibrosis transmembrane conductance regulator gene or protein.

Technology Process of Chenodeoxycholic acid diacetate methyl ester

There total 33 articles about Chenodeoxycholic acid diacetate methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

C29H45BrO6 → methyl 3α,7α-diacetoxy-5β-cholan-24-oate (2616-71-9)

Guidance literature:

With sodium tetrahydroborate; In dimethyl sulfoxide; at 15 - 25 ℃; for 0.5h;

Reference yield: 90.0%

chenodeoxycholic acid methyl ester (3057-04-3) + acetic anhydride (108-24-7) → methyl 3α,7α-diacetoxy-5β-cholan-24-oate (2616-71-9) + (4R)-methyl 4-((3R,5R,7R,10S,13R,17R)-3-acetoxy-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate (19684-68-5)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 16h;

Reference yield: 72.0%

methyl (3α,5β,7α)-3,7-diacetoxychol-16-en-24-oate (85198-69-2) → methyl 3α,7α-diacetoxy-5β-cholan-24-oate (2616-71-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In isopropyl alcohol;

DOI:10.1002/hlca.19840670229

upstream raw materials:

diazomethane

3α,7α-diacetoxy-24-phenyl-5β-cholan-24-oic acid

chenodeoxycholic acid methyl ester

acetic anhydride

Downstream raw materials:

chenodeoxycholic acid

methyl (3α,5β,7α)-3,7-diacetoxychol-16-en-24-oate

Chenodeoxycholic Acid

Refernces

• 1、 Iida, Takashi,Chang, Frederic C.. "Potential Bile Acid Metabolites. 3. A New Route to Chenodeoxycholic Acid". . p. 2786 - 2788. Retrieved 1981.
• 2、 WOOTTON,WIGGINS. "Studies in the bile acids. 2. The non-ketonic acids of human bile.". . p. 292 - 294. Retrieved 1953.
• 3、 -. "COMPOUNDS FOR USE IN THE TREATMENT OF LIVER DISEASE". . . Retrieved 2021/02/26.
• 4、 Májer, Ferenc,Sharma, Ruchika,Mullins, Claire,Keogh, Luke,Phipps, Sinead,Duggan, Shane,Kelleher, Dermot,Keely, Stephen,Long, Aideen,Radics, Gábor,Wang, Jun,Gilmer, John F.. "New highly toxic bile acids derived from deoxycholic acid, chenodeoxycholic acid and lithocholic acid". . p. 256 - 268. Retrieved 2014/01/17.