5alpha-Androst-16-en-3beta-ol

Base Information

• Chemical Name: 5alpha-Androst-16-en-3beta-ol
• CAS No.: 7148-51-8
• Molecular Formula: C19H30O
• Molecular Weight: 274.447
• NSC Number: 65888
• UNII: EPQ9QH9KXZ
• DSSTox Substance ID: DTXSID90905050
• Nikkaji Number: J104.458C
• Wikipedia: 3%CE%B2-Androstenol
• Wikidata: Q39088119
• Mol file: 7148-51-8.mol

Synonyms:5 alpha-androst-16-en-3 beta-ol;5 alpha-androst-16-en-3 beta-ol, (3alpha,5beta)-isomer;5 alpha-androst-16-en-3 beta-ol, (3beta)-isomer

Chemical Property of 5alpha-Androst-16-en-3beta-ol

Chemical Property:

• Vapor Pressure: 4E-07mmHg at 25°C
• Melting Point: 123-124 °C
• Refractive Index: 1.54
• Boiling Point: 374.1 °C at 760 mmHg
• PKA: 14.84±0.60(Predicted)
• Flash Point: 156.5 °C
• PSA: 20.23000
• Density: 1.037 g/cm³
• LogP: 4.55610
• 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: 428

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Androst-16-en-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CC=C2)CCC4C3(CCC(C4)O)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CC[C@@H]4[C@@]3(CC[C@@H](C4)O)C
• Uses: A metabolite of 16-Androstene.

Technology Process of 5alpha-Androst-16-en-3beta-ol

There total 49 articles about 5alpha-Androst-16-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: 75.4%

17-iodo-3β-hydroxy-5α-androstan-16-ene (95043-81-5) → 5α-androst-16-en-3β-ol (7148-51-8)

Guidance literature:

With diethylene glycol monoethyl ether sodium salt; In 1,4-dioxane; at 100 ℃; for 92h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

Reference yield: 65.0%

16R-bromopregnane-3S,20S-diol (939496-37-4) → 16S,20S-epoxypregnane-3S-ol + 5α-androst-16-en-3β-ol (7148-51-8)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 60 ℃; for 18h;

DOI:10.1016/j.tetlet.2007.05.126

Reference yield: 58.0%

cis-androsterone (53-41-8) → androstenol (3597-54-4,4572-71-8,7148-51-8,14152-27-3,18485-74-0,19321-55-2,64681-01-2,86335-09-3,86335-14-0,86335-15-1,103615-88-9,103615-90-3,1153-51-1)

Guidance literature:

cis-androsterone; With toluene-4-sulfonic acid hydrazide; In ethanol; for 2h; Reflux;

With methyllithium; In diethyl ether; at 22 ℃; for 16.5h;

DOI:10.1002/cbdv.201300286

upstream raw materials:

17-Iodandrost-16-en-3β-ol

17-Brom-androst-16-en-3β-ol

5α-androst-16-en-3-one

aluminum isopropoxide

Downstream raw materials:

5α-androstan-3β-ol

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

3β,16α-dihydroxy-5α-androstane

5α-androst-16-en-3-one

Refernces

• 1、 -. "Synthetic method of androst-16-en-3beta-ol". Paragraph 0036-0065. . Retrieved 2020/08/07.
• 2、 Koch, Vanessa,Nieger, Martin,Br?se, Stefan. "Stille and Suzuki Cross-Coupling Reactions as Versatile Tools for Modifications at C-17 of Steroidal Skeletons – A Comprehensive Study". . p. 832 - 840. Retrieved 2017/03/11.