3alpha,6alpha,12alpha-Trihydroxy-5beta-cholan-24-oic Acid

Base Information

• Chemical Name: 3alpha,6alpha,12alpha-Trihydroxy-5beta-cholan-24-oic Acid
• CAS No.: 21066-18-2
• Molecular Formula: C₂₄H₄₀O₅
• Molecular Weight: 408.579
• DSSTox Substance ID: DTXSID90864976
• Nikkaji Number: J906.647K
• Wikidata: Q63393132
• Metabolomics Workbench ID: 36322
• Mol file: 21066-18-2.mol

Synonyms:3 alpha,6 alpha,12 alpha-trihydroxy-5 beta-cholanoic acid;3,6,12-TCNA;3,6,12-trihydroxycholanoic acid;3,6,12-trihydroxycholanoic acid, (3alpha,5beta,6beta,12alpha)-isomer

Chemical Property of 3alpha,6alpha,12alpha-Trihydroxy-5beta-cholan-24-oic Acid

Chemical Property:

• Vapor Pressure: 4.59E-16mmHg at 25°C
• Boiling Point: 583.9°C at 760 mmHg
• Flash Point: 321°C
• PSA: 97.99000
• Density: 1.184g/cm³
• LogP: 3.44870
• XLogP3: 3.6
• 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% ^*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(CC3C2CC(C4C3(CCC(C4)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]2C[C@@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C

Technology Process of 3alpha,6alpha,12alpha-Trihydroxy-5beta-cholan-24-oic Acid

There total 14 articles about 3alpha,6alpha,12alpha-Trihydroxy-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: 70.0%

methyl 3α,6α,12α-trihydroxy-5β-cholanoate (134526-11-7) → 3α,6α,12α-trihydroxy-5β-cholan-24-oic acid (21066-18-2)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 20 ℃;

Reference yield:

cholic acid (81-25-4) → 3α,6α,12α-trihydroxy-5β-cholan-24-oic acid (21066-18-2)

Guidance literature:

Multi-step reaction with 11 steps

1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

2: N-Bromosuccinimide / acetone; water / 20 °C

3: 2,6-dimethylpyridine / dichloromethane / 20 °C

4: boron trifluoride diethyl etherate / dichloromethane / -80 °C

5: sodium tetrahydroborate; methanol / tetrahydrofuran / 0 °C

6: pyridine; dmap / 80 °C

7: ozone / dichloromethane / -78 °C

8: samarium diiodide / tetrahydrofuran; methanol / 20 °C / Inert atmosphere

9: borane tert-butylamine / dichloromethane / 0 - 20 °C

10: hydrogenchloride / methanol / 0 - 20 °C

11: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; N-Bromosuccinimide; samarium diiodide; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; water; borane tert-butylamine; potassium carbonate; ozone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 4: |Mukaiyama Aldol Addition;

Reference yield:

methyl cholate (1448-36-8) → 3α,6α,12α-trihydroxy-5β-cholan-24-oic acid (21066-18-2)

Guidance literature:

Multi-step reaction with 10 steps

1: N-Bromosuccinimide / acetone; water / 20 °C

2: 2,6-dimethylpyridine / dichloromethane / 20 °C

3: boron trifluoride diethyl etherate / dichloromethane / -80 °C

4: sodium tetrahydroborate; methanol / tetrahydrofuran / 0 °C

5: pyridine; dmap / 80 °C

6: ozone / dichloromethane / -78 °C

7: samarium diiodide / tetrahydrofuran; methanol / 20 °C / Inert atmosphere

8: borane tert-butylamine / dichloromethane / 0 - 20 °C

9: hydrogenchloride / methanol / 0 - 20 °C

10: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; N-Bromosuccinimide; samarium diiodide; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; water; borane tert-butylamine; ozone; In tetrahydrofuran; methanol; dichloromethane; water; acetone; 3: |Mukaiyama Aldol Addition;

upstream raw materials:

3α,6α,12α-triacetoxy-5β-cholan-24-oic acid methyl ester

3α,6α,12α-triacetoxy-7,7-ethanediyldimercapto-5β-cholan-24-oic acid methyl ester

methyl 3α,6α,12α-triacetoxy-7-oxo-5β-cholan-24-oate

methyl 3α,6α,12α-trihydroxy-5β-cholanoate