1b,3a,12a-Trihydroxy-5b-cholanoic acid

Base Information

• Chemical Name: 1b,3a,12a-Trihydroxy-5b-cholanoic acid
• CAS No.: 80434-32-8
• Molecular Formula: C₂₄H₄₀O₅
• Molecular Weight: 408.579
• Wikidata: Q27161404
• Mol file: 80434-32-8.mol

Synonyms:1b,3a,12a-Trihydroxy-5b-cholanoic acid;1b,3a,12a-trihydroxy-5b-cholan-24-oic acid;CHEBI:89219;1b,3a,12a-Trihydroxy-5b-cholanoate;1b,3a,12a-trihydroxy-5b-cholan-24-oate;1,3,12-trihydroxy-(5b)-Cholan-24-oate;1,3,12-trihydroxy-(5b)-Cholan-24-oic acid;Q27161404

Chemical Property of 1b,3a,12a-Trihydroxy-5b-cholanoic acid

Chemical Property:

• PSA: 97.99000
• LogP: 3.44870
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 408.28757437
• Heavy Atom Count: 29
• Complexity: 637

Purity/Quality:

99%min ^*data from raw suppliers

1β-HydroxydeoxycholicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(C(CC(C4)O)O)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)C1CCC2[C@@]1([C@H](CC3C2CCC4[C@@]3([C@@H](C[C@H](C4)O)O)C)O)C
• Uses: 1β-Hydroxydeoxycholic Acid is an metabolite of Taurodeoxychloic Acid (T009000), a steroidal amphipathic hepatic bile salt formed in the liver through the conjugation of deoxycholate (S624090) with taurine (T007850).

Technology Process of 1b,3a,12a-Trihydroxy-5b-cholanoic acid

There total 16 articles about 1b,3a,12a-Trihydroxy-5b-cholanoic 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: 27.0%

Deoxycholic acid (83-44-3) → 1β,3α,12α-trihydroxy-5β-cholan-24-oic acid (80434-32-8,63266-91-1,70050-65-6)

Guidance literature:

With MicroCYP₀₀₂₉; Enzymatic reaction;

DOI:10.1002/jlcr.3495

Reference yield:

(R)-methyl 4-((1R,3S,5R,8S,9S,10S,12S,13R,14S,17R)-12-acetoxy-1,3-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate (104839-75-0) → 1β,3α,12α-trihydroxy-5β-cholan-24-oic acid (80434-32-8,63266-91-1,70050-65-6)

Guidance literature:

With lithium hydroxide; In methanol; for 1h; Heating;

DOI:10.1248/cpb.34.2890

Reference yield:

methyl deoxycholate (3245-38-3) → 1β,3α,12α-trihydroxy-5β-cholan-24-oic acid (80434-32-8,63266-91-1,70050-65-6)

Guidance literature:

Multi-step reaction with 10 steps

1: AgCO₃-Celite / toluene

2: 9 g / N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h

3: 138 mg / Br₂ / acetic acid / 1 h / Ambient temperature

4: 62 mg / Cr(OAc)2 / CHCl₃; acetic acid / 1 h / Ambient temperature

5: 26 mg / Li₂CO₃, LiBr / dimethylformamide / 4 h / 80 °C

6: 30 percent H₂O₂, 2 N NaOH / dioxane / 24 h / Ambient temperature

7: diethyl ether

8: 58 mg / Cr(OAc)2 / ethanol / 1 h / Ambient temperature

9: 15 mg / NaBH₄ / propan-2-ol / 0.5 h

10: 178 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; AgCO₃-Celite; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1248/cpb.34.2890

upstream raw materials:

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

(R)-methyl 4-((1R,3S,5R,8S,9S,10S,12S,13R,14S,17R)-12-acetoxy-1,3-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

(R)-methyl 4-((5R,8R,9S,10R,12S,13R,14S,17R)-12-acetoxy-10,13-dimethyl-3-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-17-yl)pentanoate

methyl deoxycholate

Refernces

• 1、 Hayes, Martin A.,Li, Xue-Qing,Gr?nberg, Gunnar,Diczfalusy, Ulf,Andersson, Tommy B.. "CYP3A specifically catalyzes 1β-hydroxylation of deoxycholic acid: Characterization and enzymatic synthesis of a potential novel urinary biomarker for CYP3A activity". . p. 1480 - 1489. Retrieved 2016/08/24.
• 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.