Glycoursodeoxycholic acid

Base Information

• Chemical Name: Glycoursodeoxycholic acid
• CAS No.: 64480-66-6
• Deprecated CAS: 474-26-0,2273-95-2
• Molecular Formula: C₂₆H₄₃NO₅
• Molecular Weight: 449.631
• UNII: PF1G5J2X2A
• ChEMBL ID: CHEMBL409348
• DSSTox Substance ID: DTXSID20862344
• Metabolomics Workbench ID: 36676
• Nikkaji Number: J398.522I
• Wikidata: Q27077819
• Mol file: 64480-66-6.mol

Synonyms:glycine ursodeoxycholic acid;glycoursodeoxycholic acid

Chemical Property of Glycoursodeoxycholic acid

Chemical Property:

• Melting Point: 232-235°C
• PSA: 106.86000
• LogP: 3.98500
• Storage Temp.: -20°C Freezer
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 449.31412347
• Heavy Atom Count: 32
• Complexity: 727

Purity/Quality:

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

Glycoursodeoxycholic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCC(=O)NCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)NCC(=O)O)[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: As a metabolite of Ursodeoxycholic Acid, Glycoursodeoxycholic Acid is used as an anticholelithogenic A metabolite of Ursodeoxycholic Acid, which is used as an anticholelithogenic.

Technology Process of Glycoursodeoxycholic acid

There total 10 articles about Glycoursodeoxycholic acid 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%

glycine ursodeoxycholic acid ethyl ester (115488-03-4) → glycoursodeoxycholic acid (640-79-9,13164-20-0,64480-66-6,66255-07-0,93861-57-5,93861-58-6,130008-98-9,132437-62-8,139894-85-2,2273-95-2)

Guidance literature:

With methanol; potassium carbonate; for 1h; Reagent/catalyst; Reflux;

Reference yield: 91.0%

ursodeoxycholic acid (128-13-2) + glycine (56-40-6,18875-39-3,25718-94-9) → glycoursodeoxycholic acid (640-79-9,13164-20-0,64480-66-6,66255-07-0,93861-57-5,93861-58-6,130008-98-9,132437-62-8,139894-85-2,2273-95-2)

Guidance literature:

ursodeoxycholic acid; glycine; With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide; In water; acetonitrile; tert-butyl alcohol; at 20 - 80 ℃;

With hydrogenchloride; In water; pH=2;

DOI:10.1039/c2ob25528f

Reference yield:

3α,7β-dihydroxy-5β-cholan-24-oic acid 2,5-dioxo-pyrrolidin-1-yl ester (178437-09-7) → glycoursodeoxycholic acid (640-79-9,13164-20-0,64480-66-6,66255-07-0,93861-57-5,93861-58-6,130008-98-9,132437-62-8,139894-85-2,2273-95-2)

Guidance literature:

With triethylamine; glycine; In dimethyl sulfoxide; at 20 ℃; for 4h;

DOI:10.2174/157018012800673010

upstream raw materials:

chenodeoxycholic acid

3α,7α-dihydroxy-5β-cholan-24-oic acid 2,5-dioxopyrrolidin-1-yl ester

glycine ursodeoxycholic acid ethyl ester

glycine

Refernces

• 1、 Li, Qingyong,He, Wuna,Zhang, Li,Zu, Yuangang,Zhu, Qiaochu,Deng, Xiaoqiu,Zhao, Tengfei,Gao, Wenqing,Zhang, Baoyou. "Synthesis, anticancer activities, antimicrobial activities and bioavailability of berberine-bile acid analogues". scheme or table. p. 573 - 580. Retrieved 2012/08/08.
• 2、 Dayal, Bishambar,Bhojawala, Jalpa,Rapole, Keshava R.,Pramanik, Birendra N.,Ertel, Norman H.,Shefer, Sarah,Salen, Gerald. "Chemical synthesis, structural analysis, and decomposition of N-nitroso bile acid conjugates". . p. 885 - 890. Retrieved 2007/10/03.