Androsterone

Base Information

• Chemical Name: Androsterone
• CAS No.: 53-41-8
• Molecular Formula: C19H30O2
• Molecular Weight: 290.446
• Hs Code.: 29379000
• European Community (EC) Number: 200-173-4
• NSC Number: 9898
• UNII: C24W7J5D5R
• DSSTox Substance ID: DTXSID3036525
• Nikkaji Number: J4.145I
• Wikipedia: Androsterone
• Wikidata: Q422469
• NCI Thesaurus Code: C29783
• Pharos Ligand ID: FSK6GW2AG8W8
• Metabolomics Workbench ID: 35312
• ChEMBL ID: CHEMBL87285
• Mol file: 53-41-8.mol

Synonyms:3 alpha Hydroxy 5 alpha Androstan 17 One;3-alpha-Hydroxy-5-alpha-Androstan-17-One;5 alpha Androstan 3 alpha ol 17 one;5 alpha-Androstan-3 alpha-ol-17-one;Androsterone;Epiandrosterone

Chemical Property of Androsterone

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Vapor Pressure: 1.5E-08mmHg at 25°C
• Melting Point: 181-184 °C(lit.)
• Refractive Index: 1.536
• Boiling Point: 413.139 °C at 760 mmHg
• PKA: 15.14±0.60(Predicted)
• Flash Point: 176.377 °C
• PSA: 37.30000
• Density: 1.085 g/cm³
• LogP: 3.95910
• Storage Temp.: −20°C
• Water Solubility.: 11.5mg/L(23.5 oC)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 290.224580195
• Heavy Atom Count: 21
• Complexity: 459

Purity/Quality:

99% ^*data from raw suppliers

Androsterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 22-24/25-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
• Uses: It was isolated from male urine after removed of the phenolic estrogen fraction. Typical urinary 17-oxosteroid, formed by the metabolic reduction of testosterone. Less potent than testosterone.

Technology Process of Androsterone

There total 84 articles about Androsterone 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: 100.0%

(3R,5S,8R,9S,10S,13S,14S)-10,13-Dimethyl-3-(tetrahydro-furan-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-one (111222-34-5) → cis-androsterone (53-41-8)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; for 1h; Ambient temperature;

DOI:10.1055/s-1987-27903

Reference yield: 94.6%

androsterone acetate (1164-95-0) → cis-androsterone (53-41-8)

Guidance literature:

With methanol; sodium hydroxide; at 40 ℃; for 4h; Inert atmosphere;

Reference yield: 78.0%

2-Oxo-propionic acid (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester → cis-androsterone (53-41-8) + androstanedione (846-46-8)

Guidance literature:

With Oxone; edetate disodium; sodium hydrogencarbonate; In water; acetonitrile; at 20 ℃; for 120h;

DOI:10.1021/jo0347011

upstream raw materials:

dehydroepiandrosterone

Androstenedione

3β-chloro-5α-androstan-17-one

androstanedione

Downstream raw materials:

Epiandrosterone

androstanedione

androstanediol

5α-androst-2-en-17-one

Refernces

• 1、 Solum, Eirik Johansson,Mohamed, Yasser Mahmoud A.. "Convenient stereoselective synthesis of some 3-aminosteroid scaffolds". . p. 1159 - 1164. Retrieved 2019.
• 2、 Ke, Yanxiong,Lu, Guangying,Ren, Jiangmeng,Wang, Di,Zeng, Bu-Bing. "Catalytic removal of tert-butyldimethylsilyl (TBS) ether by PVP-I". . . Retrieved 2019/09/06.