Homoursodeoxycholic acid

Base Information

• Chemical Name: Homoursodeoxycholic acid
• CAS No.: 102044-28-0
• Molecular Formula: C₂₅H₄₂O₄
• Molecular Weight: 406.606
• Nikkaji Number: J1.518.590B
• Metabolomics Workbench ID: 72036
• Mol file: 102044-28-0.mol

Synonyms:homoursodeoxycholic acid;HUDCA

Chemical Property of Homoursodeoxycholic acid

Chemical Property:

• Vapor Pressure: 9.33E-15mmHg at 25°C
• Boiling Point: 557.6°Cat760mmHg
• Flash Point: 305.1°C
• PSA: 77.76000
• Density: 1.115g/cm³
• LogP: 4.86800
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 406.30830982
• Heavy Atom Count: 29
• Complexity: 620

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CCCC(=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

Technology Process of Homoursodeoxycholic acid

There total 6 articles about Homoursodeoxycholic 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-diformyloxy-5β-cholan-26-oic acid (116989-42-5) → homo-ursodeoxycholic acid (102044-28-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 60 ℃; for 2h;

DOI:10.1002/jps.2600770710

Reference yield:

(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 (6058-15-7,6159-50-8) → homo-ursodeoxycholic acid (102044-28-0)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl chloride / 3 h

2: 4.2 g / triethylamine / diethyl ether / 0.5 h / 0 °C

3: 71 percent / dioxane; H₂O / Ambient temperature; Irradiation

4: 98 percent / 3 M NaOH / ethanol / 2 h / 60 °C

With sodium hydroxide; oxalyl dichloride; triethylamine; In 1,4-dioxane; diethyl ether; ethanol; water;

DOI:10.1002/jps.2600770710

Reference yield:

Formic acid (3R,5S,7S,8R,9S,10S,13R,14S,17R)-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-7-formyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester (80724-83-0,79066-13-0) → homo-ursodeoxycholic acid (102044-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 4.2 g / triethylamine / diethyl ether / 0.5 h / 0 °C

2: 71 percent / dioxane; H₂O / Ambient temperature; Irradiation

3: 98 percent / 3 M NaOH / ethanol / 2 h / 60 °C

With sodium hydroxide; triethylamine; In 1,4-dioxane; diethyl ether; ethanol; water;

DOI:10.1002/jps.2600770710

upstream raw materials:

3α,7β-diformyloxy-5β-cholan-26-oic 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

Formic acid (3R,5S,7S,8R,9S,10S,13R,14S,17R)-17-((R)-3-chlorocarbonyl-1-methyl-propyl)-7-formyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

3α,7β-diformyloxy-25-diazo-5β-cholan-24-one

Refernces

• 1、 Roda,Grigolo,Roda,Simoni,Pellicciari,Natalini,Fini,Labate. "Quantitative relationship between bile acid structure and biliary lipid secretion in rats". . p. 596 - 605. Retrieved 1988.