Androst-5-en-3beta-ol

Base Information

• Chemical Name: Androst-5-en-3beta-ol
• CAS No.: 1476-64-8
• Molecular Formula: C19H30 O
• Molecular Weight: 274.447
• UNII: 498C13Y7JP
• Nikkaji Number: J683.146J
• Wikidata: Q27259258
• Mol file: 1476-64-8.mol

Synonyms:5-androsten-3-ol;androst-5-en-3 beta-ol;androst-5-en-3-ol

Chemical Property of Androst-5-en-3beta-ol

Chemical Property:

• Vapor Pressure: 1.37E-07mmHg at 25°C
• Refractive Index: 1.551
• Boiling Point: 387.1°Cat760mmHg
• Flash Point: 160.2°C
• PSA: 20.23000
• Density: 1.05g/cm³
• LogP: 4.70020
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 274.229665576
• Heavy Atom Count: 20
• Complexity: 439

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC1C3CC=C4CC(CCC4(C3CC2)C)O
• Isomeric SMILES: C[C@@]12CCC[C@H]1[C@@H]3CC=C4C[C@H](CC[C@@]4([C@H]3CC2)C)O

Technology Process of Androst-5-en-3beta-ol

There total 23 articles about Androst-5-en-3beta-ol 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: 98.0%

dehydroepiandrosterone (53-43-0) → androst-5-en-3β-ol (1476-64-8,25706-90-5)

Guidance literature:

With potassium hydroxide; hydrazine hydrate; In diethylene glycol; a) 120 deg C, 1 h, b) 230 deg C, 3.5 h;

DOI:10.1016/0968-0896(96)00018-1

Reference yield: 98.0%

prasterone acetate (853-23-6) → androst-5-en-3β-ol (1476-64-8,25706-90-5)

Guidance literature:

prasterone acetate; With hydrazine hydrate; In 2-ethoxy-ethanol; Inert atmosphere; Heating;

With potassium hydroxide; In 2-ethoxy-ethanol; at 136 ℃; for 3h;

DOI:10.1016/j.bmcl.2010.10.044

Reference yield: 72.0%

(3S,8S,9S,10R,13S,14S,17S)-17-(1-hydroxy-1-(4-methoxyphenyl)ethyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol → androst-5-en-3β-ol (1476-64-8,25706-90-5)

Guidance literature:

With 2,3,5-trimethyl-pyridine; [Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)₂(5,5'-bis(trifluoromethyl)-2,2'-bipyridyl)](PF₆); thiophenol; In dichloromethane; at 20 ℃; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1021/jacs.6b06517

upstream raw materials:

dehydroepiandrosterone

17-semicarbazone of 3β-hydroxyandrost-5-en-17-one

sodium ethanolate

3β-acetoxy-17-(2-carbamoylhydrazono)-5-androstene

Downstream raw materials:

(5R,6R,8S,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one

3β-hydroxy-Δ⁵-androsten-7-one acetate

androsta-3,5-dien-7-one

5α-hydroxy-6-oxoandrostane-3β-yl acetate

Refernces

• 1、 Huang-Minlon. "-". . p. 3301. Retrieved 1949.
• 2、 Yao, Juan,Ye, Weijian,Liu, Jinliang,Liu, Juanjuan,Wang, Cunde. "Synthesis and cytotoxicity of (3β)-3-acetyloxy-5(6)-androsten-7-one oxime and 3,5(6)-androstadien-7-one oxime". . p. 1839 - 1843. Retrieved 2014.
• 3、 Chang, Kai-Hsuan,Jenkins, Malikah N.,Wu, Hsin-Ru,Li, Wen-Shan. "A selective Cu(II)/Fe(III)-mediated hydrogenation of steroidal haloalkenes in the presence of hydrazine". . p. 1351 - 1354. Retrieved 2003.
• 4、 Chupina, L. N.,Rulin, V. A.,Shner, V. F.,Suvorov, N. N.,Kotelevtseva, N. V.,et al.. "SYNTHESIS AND EXAMINATION OF THE ANTICHOLESTEREMIC AND ANTIMICROBIAL ACTIVITY OF HYDROGENATED A AND B INDOLE ANALOGS OF STEROIDS". . p. 368 - 372. Retrieved 1982.
• 5、 Yayla, Hatice G.,Wang, Huaiju,Tarantino, Kyle T.,Orbe, Hudson S.,Knowles, Robert R.. "Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O-H Bonds". supporting information. p. 10794 - 10797. Retrieved 2016/09/09.