Ursodeoxycholic Acid Methyl Ester

Base Information

• Chemical Name: Ursodeoxycholic Acid Methyl Ester
• CAS No.: 10538-55-3
• Molecular Formula: C25H42O4
• Molecular Weight: 406.606
• UNII: JDK7DZ3PSJ
• DSSTox Substance ID: DTXSID50430934
• Nikkaji Number: J21.481G
• Wikidata: Q63393651
• ChEMBL ID: CHEMBL1254733
• Mol file: 10538-55-3.mol

Synonyms:Ursodeoxycholic Acid Methyl Ester;10538-55-3;methyl (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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 Ursodeoxycholate;JDK7DZ3PSJ;Methyl 3alpha,7beta-Dihydroxy-5beta-cholan-24-oate;ursodeoxycholate methyl ester;24-O-methylursodeoxycholic acid;CHEMBL1254733;SCHEMBL17175003;Deoxyursocholic acid methyl ester;DTXSID50430934;CHEBI:181120;AKOS030240567;HY-132686S;AS-78151;CS-0202338;Methyl 3alpha,7beta-dihydroxy-5beta-cholanoate;J-650245;Q63393651;3alpha,7beta-dihydroxy-5beta-cholan-24-oic methyl ester;3alpha,7beta-Dihydroxy-5beta-cholanic Acid Methyl Ester;5beta-Cholanic acid, 3alpha,7beta-dihydroxy-, methyl ester;3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid Methyl ester;(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-oic Acid Methyl Ester;5beta-Cholan-24-oic acid, 3alpha,7beta-dihydroxy-, methyl ester;Cholan-24-oic acid, 3,7-dihydroxy-, methyl ester, (3alpha,5beta,7beta)-;2599839-22-0;Methyl (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,1.011,1]heptadecan-14-yl]pentanoate

Chemical Property of Ursodeoxycholic Acid Methyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 142-143°C
• Boiling Point: 507.571°C at 760 mmHg
• PKA: 14.79±0.70(Predicted)
• Flash Point: 162.13°C
• PSA: 66.76000
• Density: 1.089g/cm³
• LogP: 4.56630
• Storage Temp.: Refrigerator
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 406.30830982
• Heavy Atom Count: 29
• Complexity: 620

Purity/Quality:

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

UrsodeoxycholicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)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)O)C)O)C
• Uses: Ursodeoxycholic Acid Methyl Ester (Ursodeoxycholic Acid EP Impurity G) is a precursor to manufacture UDCA (Ursodeoxycholic acid) which is useful for cholesterol gallstone dissolution and fish growth promoter. A precursor to manufacture UDCA (Ursodeoxycholic acid)

Technology Process of Ursodeoxycholic Acid Methyl Ester

There total 25 articles about Ursodeoxycholic Acid 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: 98.0%

methanol (67-56-1) + ursodeoxycholic acid (128-13-2) → 3α,7β-dihydroxy-5β-cholan-24-oic acid methyl ester (10538-55-3)

Guidance literature:

With toluene-4-sulfonic acid; for 2.5h; Reflux;

DOI:10.3390/molecules15032039

Reference yield: 95.1%

7-ketolithocholic methyl ester (10538-59-7) → 3α,7β-dihydroxy-5β-cholan-24-oic acid methyl ester (10538-55-3)

Guidance literature:

With ammonium formate; zinc; In ethanol; at 78 ℃; for 0.25h;

Reference yield: 92.0%

ursodeoxycholic acid (128-13-2) + acetyl chloride (75-36-5) → 3α,7β-dihydroxy-5β-cholan-24-oic acid methyl ester (10538-55-3)

Guidance literature:

In methanol; at 0 - 20 ℃; for 6h;

upstream raw materials:

methanol

ursodeoxycholic acid

7-ketolithocholic methyl ester

methyl 3α,7β-dihydroxy-12-oxocholanate tosylhydrazone

Downstream raw materials:

trisodium ursodeoxycholate 3,7-disulfate

ursodeoxycholic acid

methyl (4R)‐4‐[(1R,3aS,3bR,4S,5aS,7R,9aS,9bS,11aR)‐7‐hydroxy‐9a,11a‐dimethyl‐4‐[(4‐methylbenzenesulfonyl)oxy]‐hexadecahydro‐1H‐cyclopenta[a]phenanthren‐1‐yl]pentanoate

methyl ursodeoxycholate 7-acetate

Refernces

• 1、 Massarenti, Chiara,Bortolini, Olga,Fantin, Giancarlo,Cristofaro, Dario,Ragno, Daniele,Perrone, Daniela,Marchesi, Elena,Toniolo, Gianluca,Massi, Alessandro. "Fluorous-tag assisted synthesis of bile acid-bisphosphonate conjugates: Via orthogonal click reactions: An access to potential anti-resorption bone drugs". . p. 4907 - 4920. Retrieved 2017.
• 2、 Huang, Liliang,Sun, Yanhong,Zhu, Hua,Zhang, Yuanqing,Xu, Jia,Shen, Yu-Mei. "Synthesis and antimicrobial evaluation of bile acid tridentate conjugates". . p. 701 - 706. Retrieved 2009.
• 3、 Zhou, Dandan,Kong, Linghua,Jiang, Yiguo,Wang, Cheng,Ni, Yao,Wang, Yedong,Zhang, Hongjian,Ruan, Jianqing. "UGT-dependent regioselective glucuronidation of ursodeoxycholic acid and obeticholic acid and selective transport of the consequent acyl glucuronides by OATP1B1 and 1B3". . . Retrieved 2019.
• 4、 Kakiyama, Genta,Muto, Akina,Shimada, Miki,Mano, Nariyasu,Goto, Junichi,Hofmann, Alan F.,Iida, Takashi. "Chemical synthesis of 3β-sulfooxy-7β-hydroxy-24-nor-5-cholenoic acid: An internal standard for mass spectrometric analysis of the abnormal Δ5-bile acids occurring in Niemann-Pick disease". . p. 766 - 772. Retrieved 2009.
• 5、 Stoltz, Kristen L.,Erickson, Raymond,Staley, Christopher,Weingarden, Alexa R.,Romens, Erin,Steer, Clifford J.,Khoruts, Alexander,Sadowsky, Michael J.,Dosa, Peter I.. "Synthesis and Biological Evaluation of Bile Acid Analogues Inhibitory to Clostridium difficile Spore Germination". . p. 3451 - 3471. Retrieved 2017.
• 6、 -. "Preparation method of 3beta-ursodesoxycholic acid". Paragraph 0062-0065. . Retrieved 2019/07/04.