1beta-Hydroxycholic acid

Base Information

• Chemical Name: 1beta-Hydroxycholic acid
• CAS No.: 80875-94-1
• Molecular Formula: C24H40 O6
• Molecular Weight: 424.578
• DSSTox Substance ID: DTXSID001314707
• Nikkaji Number: J420.790D
• Metabolomics Workbench ID: 36355
• Mol file: 80875-94-1.mol

Synonyms:1,3,7,12-tetrahydroxycholanoic acid;1,3,7,12-THCA;1beta-hydroxycholic acid;CA-1beta-ol

Chemical Property of 1beta-Hydroxycholic acid

Chemical Property:

• Vapor Pressure: 4.89E-18mmHg at 25°C
• Refractive Index: 1.574
• Boiling Point: 621.3°C at 760 mmHg
• Flash Point: 343.5°C
• PSA: 118.22000
• Density: 1.242g/cm³
• LogP: 2.41950
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 424.28248899
• Heavy Atom Count: 30
• Complexity: 668

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(C(CC(C4)O)O)C)O)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3([C@@H](C[C@H](C4)O)O)C)O)O)C

Technology Process of 1beta-Hydroxycholic acid

There total 22 articles about 1beta-Hydroxycholic 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: 90.0%

methyl 7α,12α-diacetoxy-1β,3α-dihydroxy-5β-cholan-24-oate (104854-47-9) → 1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oic acid (80875-94-1,63266-89-7)

Guidance literature:

With water; sodium hydroxide; In methanol; at 120 ℃; for 13h;

Reference yield: 84.0%

isopropyl 1β,3α-dihydroxy-7α,12α-diacetoxy-5β-cholan-24-oate (1428531-74-1) → 1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oic acid (80875-94-1,63266-89-7)

Guidance literature:

With water; sodium hydroxide; In methanol; at 120 ℃; for 13h;

Reference yield:

methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate (14773-00-3) → 1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oic acid (80875-94-1,63266-89-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.32 g / N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 1 h

2: 180 mg / Br₂ / acetic acid / 1 h / Ambient temperature

3: 98 mg / Li₂CO₃, LiBr / dimethylformamide / 4 h / 80 °C

4: 63 mg / Zn dust / acetone; acetic acid / 0.5 h / Ambient temperature

5: 30 percent H₂O₂, 2 N NaOH / ethanol / 4 h / Ambient temperature

6: diethyl ether

7: 43 mg / Cr(OAc)2 / tetrahydrofuran; ethanol / 2 h / Ambient temperature

8: 38 mg / NaBH₄ / propan-2-ol / 1 h

9: 112 mg / 2 N LiOH / methanol / 1 h / Heating

With dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; bromine; lithium carbonate; chromium(II) acetate; triethylamine; lithium bromide; zinc; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; acetone;

DOI:10.1248/cpb.34.2890

upstream raw materials:

1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oic acid methyl ester

methyl 7α,12α-diacetoxy-1β,3α-dihydroxy-5β-cholan-24-oate

methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate

methyl 3-keto-7,12-diacetylcholate

Downstream raw materials:

methyl 3,7,12-triacetoxycholan-24-oate

Refernces

• 1、 -. "ROR GAMMA MODULATORS". Page/Page column 57. . Retrieved 2013/04/10.
• 2、 Tohma,Mahara,Takeshita,Kurosawa,Ikegawa,Nittono. "Synthesis of the 1β-hydroxylated bile acids and identification of 1β,3α,7α-trihydroxy- and 1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oic acids in human meconium". . p. 3071 - 3073. Retrieved 2007/10/02.