7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one

Base Information

• Chemical Name: 7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one
• CAS No.: 547-97-7
• Molecular Formula: C₂₇H₄₆O₃
• Molecular Weight: 418.66
• UNII: JXG7DN7KC6
• DSSTox Substance ID: DTXSID00415291
• Nikkaji Number: J2.755.946H
• Wikidata: Q27105610
• Metabolomics Workbench ID: 36785
• Mol file: 547-97-7.mol

Synonyms:7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one;547-97-7;JXG7DN7KC6;5beta-Cholesten-7alpha,12alpha-diol-3-one;(5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one;7alpha,12alpha-Dihydroxy-5beta-cholestane-3-one;(5beta,7alpha,12alpha)-7,12-Dihydroxycholestan-3-one;Cholestan-3-one, 7,12-dihydroxy-, (5beta,7alpha,12alpha)-;(5S,7S,8R,9R,10R,12R,13S,14S,17R)-10,13-Dimethyl-17-((2R)-6-methylheptan-2-yl)-7,12-bis(oxidanyl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta(a)phenanthren-3-one;7|A,12|A-Dihydroxy-5|A-cholestan-3-one;(1R,3aS,3bR,4R,5aR,9aS,9bS,11S,11aR)-4,11-Dihydroxy-9a,11a-dimethyl-1-((2R)-6-methylheptan-2-yl)-hexadecahydro-1H-cyclopenta(a)phenanthren-7-one;(1R,3aS,3bR,4R,5aR,9aS,9bS,11S,11aR)-4,11-dihydroxy-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-hexadecahydro-1H-cyclopenta[a]phenanthren-7-one;5beta-cholestane-7alpha,12alpha-diol-3-one;5beta-cholestan-7alpha,12alpha-diol-3-one;UNII-JXG7DN7KC6;C05453;CHEBI:2288;SCHEMBL2508888;DTXSID00415291;LMST04030113;7a,12a-Dihydroxy-5ss-cholestan-3-on;7?,12?-Dihydroxy-5?-cholestan-3-one;Q27105610;(5beta,7alpha,12alpha)-7,12-Dihydroxy-cholestan-3-one;7 alpha ,12 alpha -Dihydroxy-5 beta -cholestan-3-one

Chemical Property of 7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one

Chemical Property:

• Melting Point: 202-205°C
• PSA: 57.53000
• LogP: 5.61840
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 418.34469533
• Heavy Atom Count: 30
• Complexity: 644

Purity/Quality:

99% ^*data from raw suppliers

7α,12α-Dihydroxy-5β-cholestan-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(C(CC3C2C(CC4C3(CCC(=O)C4)C)O)O)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[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(CCC(=O)C4)C)O)O)C
• Uses: Substrate for 3α-Hydroxysteroid Dehydrogenase in primary bile acid biosynthesis.

Technology Process of 7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one

There total 12 articles about 7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one 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%

7α,12α-diacetoxy-5β-cholestan-3-one (120174-41-6) → 7α,12α-dihydroxy-5β-cholestan-3-one (547-97-7)

Guidance literature:

With water; potassium hydroxide; In methanol; at 30 ℃; for 16h;

DOI:10.1016/j.steroids.2013.05.011

Reference yield:

cholic acid (81-25-4) → 7α,12α-dihydroxy-5β-cholestan-3-one (547-97-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dmap / pyridine / 1 h / 40 °C

2.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 2 h / 20 °C

2.2: 2 h / 0 °C

3.1: potassium bromide; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0 °C

4.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C

4.2: 0.25 h / 0 °C

5.1: hydrogen; palladium 10% on activated carbon / methanol; ethyl acetate; acetic acid / 3 h / 20 °C

6.1: hydrogenchloride / methanol; water / 6 h / 30 °C

7.1: Jones reagent / acetone; dichloromethane / 0.5 h / 0 °C

8.1: potassium hydroxide; water / methanol / 16 h / 30 °C

With hydrogenchloride; dmap; sodium hypochlorite; Jones reagent; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; water; hydrogen; chloroformic acid ethyl ester; triethylamine; potassium bromide; potassium hydroxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; acetic acid; ethyl acetate; acetone; 4.2: |Wittig Olefination;

DOI:10.1016/j.steroids.2013.05.011

Reference yield:

cholic acid 3,7,12-triacetate (52840-09-2) → 7α,12α-dihydroxy-5β-cholestan-3-one (547-97-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 2 h / 20 °C

1.2: 2 h / 0 °C

2.1: potassium bromide; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C

3.2: 0.25 h / 0 °C

4.1: hydrogen; palladium 10% on activated carbon / methanol; ethyl acetate; acetic acid / 3 h / 20 °C

5.1: hydrogenchloride / methanol; water / 6 h / 30 °C

6.1: Jones reagent / acetone; dichloromethane / 0.5 h / 0 °C

7.1: potassium hydroxide; water / methanol / 16 h / 30 °C

With hydrogenchloride; sodium hypochlorite; Jones reagent; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; water; hydrogen; chloroformic acid ethyl ester; triethylamine; potassium bromide; potassium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetic acid; ethyl acetate; acetone; 3.2: |Wittig Olefination;

DOI:10.1016/j.steroids.2013.05.011

upstream raw materials:

5β-Cholestane-3α,7α,12α-triol

cholic acid

cholic acid 3,7,12-triacetate

3α,7α,12α-triacetoxy-5β-cholane-24-ol

Downstream raw materials:

7α,12α-dihydroxy-4-cholesten-3-one