24-norursodeoxycholic acid

Base Information

• Chemical Name: 24-norursodeoxycholic acid
• CAS No.: 99697-24-2
• Molecular Formula: C₂₃H₃₈O₄
• Molecular Weight: 378.552
• Mol file: 99697-24-2.mol

Synonyms:24-Norursodeoxycholicacid; 3a,7b-Dihydroxy-24-nor-5b-cholan-23-oic acid; Norursodeoxycholic acid

Chemical Property of 24-norursodeoxycholic acid

Chemical Property:

• Vapor Pressure: 9.33E-14mmHg at 25°C
• Boiling Point: 536.7°Cat760mmHg
• PKA: 4.71±0.10(Predicted)
• Flash Point: 292.4°C
• PSA: 77.76000
• Density: 1.142g/cm³
• LogP: 4.08780
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

24-NorUrsodeoxycholicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ursodeoxycholic Acid (U850000) derivative. 24-norUrsodeoxycholic acid is superior to Ursodeoxycholic acid in the treatment of sclerosing cholangitis in Mdr2 (Abcb4) knockout mice.

Technology Process of 24-norursodeoxycholic acid

There total 5 articles about 24-norursodeoxycholic 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: 98.0%

3α,7β-dihydroxy-24-nor-5β-cholan-23-oic acid potassium salt (1380159-64-7) → Norursodeoxycholic acid (99697-24-2)

Guidance literature:

With perlite; In water; isopropyl alcohol; at 0 - 80 ℃; for 4h; Product distribution / selectivity;

Reference yield: 97.0%

3α,7β-diformyloxy-24-nor-5β-cholan-23-nitrile (118316-07-7) → Norursodeoxycholic acid (99697-24-2)

Guidance literature:

With potassium hydroxide; In methanol; water; for 48h; Reflux; Inert atmosphere;

DOI:10.1021/jm500889f

Reference yield:

3α,7β-dihydroxy-24-nor-5β-cholan-23-nitrile (118316-12-4) → Norursodeoxycholic acid (99697-24-2)

Guidance literature:

3α,7β-dihydroxy-24-nor-5β-cholan-23-nitrile; With sodium hydroxide; In propan-1-ol; for 20h; Autoclave; Reflux;

With hydrogenchloride; at 55 - 65 ℃; pH=1 - 2;

upstream raw materials:

3α,7β-dihydroxy-24-nor-5β-cholan-23-oic acid potassium salt

3α,7β-dihydroxy-24-nor-5β-cholan-23-nitrile

ursodeoxycholic acid

(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-bis(formyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

Downstream raw materials:

23-p-toluenesulfoxy-24-nor-5β-cholane-3α,7β-diol

sodium 3α,7β-dihydroxy-24-nor-5β-cholane-23-sulfonate

Refernces

• 1、 Sepe, Valentina,Renga, Barbara,Festa, Carmen,Damore, Claudio,Masullo, Dario,Cipriani, Sabrina,Di Leva, Francesco Saverio,Monti, Maria Chiara,Novellino, Ettore,Limongelli, Vittorio,Zampella, Angela,Fiorucci, Stefano. "Modification on ursodeoxycholic acid (UDCA) scaffold. Discovery of bile acid derivatives as selective agonists of cell-surface G-protein coupled bile acid receptor 1 (GP-BAR1)". . p. 7687 - 7701. Retrieved 2014/12/12.
• 2、 -. "Optimized synthesis of pure, non-polymorphic, crystalline bile acids with defined particle size". Page/Page column 8-9. . Retrieved 2012/07/03.