3alpha,17beta-Dihydroxy-5alpha-androstane

Base Information

• Chemical Name: 3alpha,17beta-Dihydroxy-5alpha-androstane
• CAS No.: 1852-53-5
• Molecular Formula: C19H32O2
• Molecular Weight: 292.462
• Hs Code.: 29144000
• NSC Number: 9899
• Mol file: 1852-53-5.mol

Synonyms: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;Androstanediol;Androstane-3.alpha.,17.beta.-diol;Etiocholane-3.alpha.,17.beta.-diol;Androstane-3,17-diol #;5.alpha.-Androstane-3.alpha.,17.beta.-androstanediol;NSC-9899;5.alpha.-Androstane-3.alpha.,17.beta.-diol;3.alpha.,17.beta.-Dihydroxy-5.alpha.-androstane;Androstane-3,17-diol, (3beta,5alpha,17beta)-;Androstane-3,17-diol, (3-beta,5-alpha,17-beta)-;Oprea1_827742;SCHEMBL12657941;NSC9899;CBMYJHIOYJEBSB-UHFFFAOYSA-N;(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;AKOS004903575;LS-19355;PD015599;FT-0602847;FT-0602849;FT-0662153;FT-0662158;Androstane-3, (3.alpha.,5.alpha.,17.beta.)-;(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

Chemical Property of 3alpha,17beta-Dihydroxy-5alpha-androstane

Chemical Property:

• Vapor Pressure: 1.27E-08mmHg at 25°C
• Melting Point: 236-236.5 °C
• Refractive Index: 1.546
• Boiling Point: 415 °C at 760 mmHg
• 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-3α,17β-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4O)C)O

Technology Process of 3alpha,17beta-Dihydroxy-5alpha-androstane

There total 114 articles about 3alpha,17beta-Dihydroxy-5alpha-androstane 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: 96.0%

cis-androsterone (53-41-8) → androstanediol (1852-53-5)

Guidance literature:

With iron(II) chloride tetrahydrate; lithium; In tetrahydrofuran; mineral oil; at 20 ℃; for 4h; Reagent/catalyst; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.5b01232

Reference yield: 90.0%

4-Androstene-3alpha,17beta-diol (1852-61-5) → androstanediol (1852-53-5)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 35 - 40 ℃; for 3h; Solvent; Temperature;

Reference yield: 21.0%

3α-hydroxyandrost-4-en-17β-yl acetate (16992-89-5) → 5-androgen-3,17-diol (571-20-0) + androstanediol (1852-53-5) + 17β-ethoxy-5β-androstane-3α,4β-diol + 5β-androstane-3α,4β,17β-triol

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; diborane; Product distribution; multistep reaction: 1.) THF, 0 deg C, 4 h, 2.) overnight; hydroboration of androst-4-enes; stereochemical aspects;

upstream raw materials:

cis-androsterone

3α-hydroxy-5α-androstan-16-one

Stanolone

4-Androstene-3alpha,17beta-diol

Downstream raw materials:

androstane-3,17-dione

androstanedione

α-androstan-3,17-dion

β-androstan-3,17-dion

Refernces

• 1、 Tindall,French,Nayfeh. "Estradiol-17β inhibition of androgen uptake, metabolism and binding in epididymis of adult male rats in vivo: A comparison with cyproterone acetate". . p. 257 - 268. Retrieved 1981.
• 2、 Raju, Uma,Blaustein, Ancel,Levitz, Mortimer. "CONJUGATION OF ANDROGENS AND ESTROGENS BY HUMAN BREAST TUMORS IN VITRO". . p. 685 - 696. Retrieved 1980.
• 3、 Ruzicka,Goldberg,Meyer. "-". . p. 210,215. Retrieved 1935.
• 4、 Boutin, Sophie,Roy, Jenny,Maltais, René,Poirier, Donald. "Formation of 5α-dihydrotestosterone from 5α-androstane-3α,17β-diol in prostate cancer LAPC-4 cells – Identifying inhibitors of non-classical pathways producing the most potent androgen". . . Retrieved 2020.
• 5、 Carmichael, Rejean,Belanger, Alain. "STUDY OF THE DIRECT EFFECT OF LHRH AGONIST ON TESTICULAR 17-HYDROXYLASE AND 5α-REDUCTASE ACTIVITIES IN NON-HYPOPHYSECTOMIZED ADULT RATS TREATED WITH AN ANTI-LUTEINIZING HORMONE SERUM". . p. 1 - 12. Retrieved 1984.
• 6、 -. "A 5 α- androstanedione method for the preparation of". Paragraph 0038; 0039. . Retrieved 2017/01/12.