1beta,3alpha-Dihydroxy-5beta-cholan-24-oic Acid

Base Information

• Chemical Name: 1beta,3alpha-Dihydroxy-5beta-cholan-24-oic Acid
• CAS No.: 89238-74-4
• Molecular Formula: C₂₄H₄₀O₄
• Molecular Weight: 392.579
• DSSTox Substance ID: DTXSID801345695
• Nikkaji Number: J457.327G
• Wikidata: Q63391983
• Metabolomics Workbench ID: 36262
• Mol file: 89238-74-4.mol

Synonyms:1beta,3alpha-Dihydroxy-5beta-cholan-24-oic Acid;89238-74-4;(1beta,3alpha,5beta)-1,3-Dihydroxy-cholan-24-oic Acid;(4R)-4-[(1R,3S,5R,8S,9S,10S,13R,14S,17R)-1,3-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid;1beta,3alpha-dihydroxy-5beta-cholanoic acid;LMST04010020;CHEBI:182575;DTXSID801345695;1b,3a-Dihydroxy-5b-cholan-24-oic acid;Q63391983

Chemical Property of 1beta,3alpha-Dihydroxy-5beta-cholan-24-oic Acid

Chemical Property:

• XLogP3: 5.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 392.29265975
• Heavy Atom Count: 28
• Complexity: 605

Purity/Quality:

99% ^*data from raw suppliers

(1β,3α,5β)-1,3-Dihydroxy-cholan-24-oicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(C(CC(C4)O)O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3([C@@H](C[C@H](C4)O)O)C)C
• Uses: (1β,3α,5β)-1,3-Dihydroxy-cholan-24-oic Acid is a bile acid metabolite. Steroid compound.

Technology Process of 1beta,3alpha-Dihydroxy-5beta-cholan-24-oic Acid

There total 15 articles about 1beta,3alpha-Dihydroxy-5beta-cholan-24-oic 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: 94.0%

1β,3α-dihydroxy-5β-cholan-24-oic acid methyl ester (104854-46-8) → 1β,3α-dihydroxy-5β-cholan-24-oic acid (89238-74-4)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1081/SCC-100104006

Reference yield:

Lithocholic acid (434-13-9) → Murocholic acid (668-49-5) + Hyodeoxycholic Acid (83-49-8) + dehydrolithocholic acid (1553-56-6,19038-19-8,98524-66-4) + 1β,3α-dihydroxy-5β-cholan-24-oic acid (89238-74-4)

Guidance literature:

With pyridine; phosphate buffer; iodosylbenzene; catalyst; In methanol; water; dimethyl sulfoxide; at 20 ℃; pH=10; Further byproducts.;

DOI:10.1021/jo020174u

Reference yield:

dehydrolithocholic acid (1553-56-6,19038-19-8,98524-66-4) → 1β,3α-dihydroxy-5β-cholan-24-oic acid (89238-74-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / sodium methoxide / pyridine / 8 h / 20 °C

2: 67 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / benzene / 0.08 h / 20 °C

3: chlorotris(triphenylphosphine)rhodium / benzene / 3 h / Heating

4: 365 mg / methanol

5: 82 percent / dimethyldioxirane / CH₂Cl₂; CHCl₃ / 1 h / 20 °C

6: 78 percent / diphenyl diselenide; NaBH₄; acetic acid / ethanol / 0.33 h / 0 - 5 °C

7: 75 percent / Zn(BH₄)2 / diethyl ether; benzene / 0.5 h / 20 °C

8: 94 percent / potassium hydroxide / methanol

With potassium hydroxide; sodium tetrahydroborate; zinc(II) tetrahydroborate; diphenyl diselenide; sodium methylate; 3,3-dimethyldioxirane; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Wilkinson's catalyst; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; benzene;

DOI:10.1081/SCC-100104006

upstream raw materials:

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

Lithocholic acid

dehydrolithocholic acid

5β cholene-1, one-3, oate-24 de methyle

Refernces

• 1、 Yang, Jerry,Gabriele, Bartolo,Belvedere, Sandro,Huang, Ying,Breslow, Ronald. "Catalytic oxidations of steroid substrates by artificial cytochrome p-450 enzymes.". . p. 5057 - 5067. Retrieved 2007/10/03.
• 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.