4-Androsten-3beta-ol-17-one

Base Information

• Chemical Name: 4-Androsten-3beta-ol-17-one
• CAS No.: 571-44-8
• Molecular Formula: C₁₉H₂₈O₂
• Molecular Weight: 288.43
• UNII: 8U3PGO66GQ
• DSSTox Substance ID: DTXSID50433223
• Nikkaji Number: J1.767.620B
• Wikipedia: 4-Dehydroepiandrosterone
• Wikidata: Q4637119
• Pharos Ligand ID: FS11BS7A2NRP
• ChEMBL ID: CHEMBL1077603
• Mol file: 571-44-8.mol

Synonyms:571-44-8;4-Androsten-3beta-ol-17-one;3beta-Hydroxy-4-androstenone;3Beta-hydroxyandrost-4-en-17-one;8U3PGO66GQ;UNII-8U3PGO66GQ;4-Androstene-3beta-ol,17-one;CHEMBL1077603;Androst-4-en-17-one, 3-hydroxy-, (3beta)-;(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one;3-Hydroxy-4-androstenone;3|A-Hydroxy-4-androstenone;SCHEMBL2507308;3b-hydroxyandrost-4-ene-17-one;DTXSID50433223;VMYTXBKVYDESSJ-USOAJAOKSA-N;3beta-Hydroxyandrosta-4-ene-17-one;BDBM50388396;3.BETA.-HYDROXY-4-ANDROSTENONE;4-androstene-3,17-dione-delta-4-dione;4-ANDROSTEN-3.BETA.-OL-17-ONE;4-ANDROSTENE-3.BETA.-OL,17-ONE;3.BETA.-HYDROXYANDROST-4-EN-17-ONE;Q4637119;ANDROST-4-EN-17-ONE, 3-HYDROXY-, (3.BETA.)-

Chemical Property of 4-Androsten-3beta-ol-17-one

Chemical Property:

• Melting Point: 135-137 °C
• Boiling Point: 428.5±45.0 °C(Predicted)
• PKA: 14.39±0.60(Predicted)
• Density: 1.12±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 288.208930132
• Heavy Atom Count: 21
• Complexity: 508

Purity/Quality:

99% ^*data from raw suppliers

3β-Hydroxy-4-androstenone 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(C=C1CCC3C2CCC4(C3CCC4=O)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
• Uses: Testosterone (T155000) derivative. It is a potent androgen with anabolic properties.

Technology Process of 4-Androsten-3beta-ol-17-one

There total 2 articles about 4-Androsten-3beta-ol-17-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: 40.0%

androsterone → 3-alpha-hydroxy-androst-4-en-17-one (571-44-8,2791-99-3,86420-28-2) + 3α-hydroxy-androst-5-en-17-one (53-43-0,571-35-7,2283-82-1,24357-33-3,25375-38-6,102340-20-5)

Guidance literature:

androsterone; With 1-(diphenylphosphino)ferrocene-1-(di-tert-butylphosphino)ferrocene; palladium diacetate; caesium carbonate; In benzene; at 20 ℃; Inert atmosphere; Glovebox; Irradiation;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; benzene; at 20 ℃; Overall yield = 43 %; regioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/jacs.7b08459

Reference yield:

cis-androsterone (53-41-8) → 3-alpha-hydroxy-androst-4-en-17-one (571-44-8,2791-99-3,86420-28-2) + 3α-hydroxy-androst-5-en-17-one (53-43-0,571-35-7,2283-82-1,24357-33-3,25375-38-6,102340-20-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: palladium diacetate; caesium carbonate; 1-(diphenylphosphino)ferrocene-1-(di-tert-butylphosphino)ferrocene / benzene / 20 °C / Inert atmosphere; Glovebox; Irradiation

2.2: 20 °C / Inert atmosphere; Glovebox

With 1H-imidazole; 1-(diphenylphosphino)ferrocene-1-(di-tert-butylphosphino)ferrocene; palladium diacetate; caesium carbonate; In tetrahydrofuran; benzene;

DOI:10.1021/jacs.7b08459

Reference yield: 80.0%

3β-hydroxyandrost-4-en-17-one (571-44-8) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Guidance literature:

DOI:10.1021/ja00310a046

upstream raw materials:

cis-androsterone

Downstream raw materials:

Androstenedione

16α-Fluor-3β-acetoxy-androsten-(5)-on-(17)

Refernces