5alpha-Androstane-3beta,17beta-diol

Base Information

• Chemical Name: 5alpha-Androstane-3beta,17beta-diol
• CAS No.: 571-20-0
• Molecular Formula: C19H32 O2
• Molecular Weight: 292.462
• Hs Code.: 29144000
• European Community (EC) Number: 209-334-3
• NSC Number: 50891
• UNII: 6J0K4253QD
• DSSTox Substance ID: DTXSID8022379
• Nikkaji Number: J58.219K
• Wikipedia: 3%CE%B2-Androstanediol
• Wikidata: Q4641516
• Metabolomics Workbench ID: 35336
• ChEMBL ID: CHEMBL316048
• Mol file: 571-20-0.mol

Synonyms:571-20-0;3beta-androstanediol;5alpha-Androstane-3beta,17beta-diol;5alpha-Androstan-3beta,17beta-diol;3beta androstanediol;3beta,17beta-Dihydroxy-5alpha-androstane;CHEBI:18329;3.beta.,17.beta.-Androstanediol;(3beta,5alpha,17beta)-androstane-3,17-diol;5-ALPHA-ANDROSTANE-3-BETA,17BETA-DIOL;Androstanediol;UNII-6J0K4253QD;3-beta,17-beta-Androstanediol;5.alpha.-Androstane-3.beta.,17.beta.-diol;3.beta.,17.beta.-Dihydroxy-5.alpha.-androstane;6J0K4253QD;3beta,17beta-Androstanediol (VAN);EINECS 209-334-3;NSC 50891;NSC-50891;BRN 2559488;5-alpha-ANDROSTANE-3-beta,17-beta-DIOL;3-beta,17-beta-Dihydroxy-5-alpha-androstane;4-06-00-06096 (Beilstein Handbook Reference);(3S,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol;Androstane-3,17-diol #;Androstane-3,17-diol, (3.beta.,5.alpha.,17.beta.)-;MAXTERONE;3b,17b-Androstanediol;Androstane-3,17-diol, (3beta,5alpha,17beta)-;(3.beta.,5.alpha.,17.beta.)-Androstane-3,17-diol;3.BETA.-ADIOL;Androstane-3,17-diol, (3-beta,5-alpha,17-beta)-;3beta,17beta-Androstanediol;Androstan-3beta,17beta-diol;BIDD:ER0165;SCHEMBL867704;5a-an-drostane-3b,17b-diol;3.BETA.-ANDROSTANEDIOL;CHEMBL316048;DTXSID8022379;3b,17b-Dihydroxy-5a-androstane;TQP0570;(3S,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol;NSC50891;BDBM50474606;LMST02020053;5-alpha-androstan-3beta,17beta-diol;AKOS015964921;DB03882;Androstane-3, (3.beta.,5.alpha.,17.beta.)-;Q4641516;W-105485;Androstane-3,17-diol, (3-beta,5-alpha,17-beta)- (9CI);(3S,5S,8R,10S,13S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol

Chemical Property of 5alpha-Androstane-3beta,17beta-diol

Chemical Property:

• Vapor Pressure: 1.27E-08mmHg at 25°C
• Melting Point: 161 °C
• Refractive Index: 1.4709 (estimate)
• Boiling Point: 415°Cat760mmHg
• PKA: 15.07±0.70(Predicted)
• Flash Point: 186°C
• PSA: 40.46000
• Density: 1.09g/cm³
• LogP: 3.75090
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 292.240230259
• Heavy Atom Count: 21
• Complexity: 422

Purity/Quality:

99%, ^*data from raw suppliers

5α-Androstane-3β,17β-diol(Dihydroepiandrosterone) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 24-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4O)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)O
• Uses: 5α-Androstane-3β,17β-diol is a metabolite of Testosterone (T155000).

Technology Process of 5alpha-Androstane-3beta,17beta-diol

There total 134 articles about 5alpha-Androstane-3beta,17beta-diol 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: 99.0%

3β-acetoxy-5α-androstan-17-one (1239-31-2) → 5-androgen-3,17-diol (571-20-0)

Guidance literature:

With diisobutylaluminium hydride; nickel dichloride; In dichloromethane; toluene; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.3184/174751911X13050949941793

Reference yield: 95.0%

(3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (3090-70-8) → 5-androgen-3,17-diol (571-20-0)

Guidance literature:

With sodium hydroxide; In methanol; for 0.166667h; Heating;

DOI:10.1007/s10600-007-0041-1

Reference yield: 95.0%

Epiandrosterone (481-29-8) → 5-androgen-3,17-diol (571-20-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃;

DOI:10.1021/jacs.8b12552

upstream raw materials:

propan-1-ol

Epiandrosterone

Perbenzoic acid

pregnenolone acetate

Downstream raw materials:

androstane-3,17-dione

androstanedione

(5α)-androstane-3,17-dione

(S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one

Refernces

• 1、 Llabrés i Xamena, F. X.,Mautschke, H.-H.. "One-Step Chemo-, Regio- and Stereoselective Reduction of Ketosteroids to Hydroxysteroids over Zr-Containing MOF-808 Metal-Organic Frameworks". . p. 10766 - 10775. Retrieved 2021/06/15.
• 2、 Wan, Runlan,Kong, Xi,Yang, Youzhe,Tao, Siwen,Chen, Youyou,Teichmann, Alexander Tobias,Wieland, Frank Heinrich. "Role of human 3α-hydroxysteroid dehydrogenase isoforms (AKR1C1-AKR1C3) in the extrahepatic metabolism of the steroidal aromatase inactivator Formestane". . . Retrieved 2019/12/23.