Dehydroandrosterone

Base Information

• Chemical Name: Dehydroandrosterone
• CAS No.: 2283-82-1
• Molecular Formula: C19H28O2
• Molecular Weight: 288.43
• DSSTox Substance ID: DTXSID20177384
• Nikkaji Number: J156.541I
• Wikipedia: Dehydroandrosterone
• Wikidata: Q28130029
• Metabolomics Workbench ID: 35381
• Mol file: 2283-82-1.mol

Synonyms:Dehydroandrosterone;2283-82-1;Isoandrostenolone;5-Androsten-3alpha-ol-17-one;(3R,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one;Prasterone, 3alpha-Isomer;Androst-5-en-17-one, 3-hydroxy-, (3alpha)-;5-Androsten-3.beta.-ol-17-one;5-Androstene-3.beta.-ol-17-one;5-Androsten-3-.beta.-ol-17-one;3-.beta.-Hydroxy-5-androsten-17-one;3.beta.-Hydroxyandrost-5-en-17-one #;Dehydro Androsterone;Androst-5-en-3a-ol-17-one;D5-Androstene-3a-ol-17-one;SCHEMBL1251757;3a-Hydroxy-5-androsten-17-one;3a-hydroxyandrost-5-en-17-one;DTXSID20177384;3a-hydroxy-Androst-5-en-17-one;LMST02020103;3alpha-Hydroxy-androst-5-ene-17-one;BCP9000597;Androst-5-en-17-one, 3.alpha.-hydroxy-;CS-0450124;Androst-5-en-17-one, 3-hydroxy-, (3.alpha.)-;(3aS,3bR,7R,9aR,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one;(3R,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one

Chemical Property of Dehydroandrosterone

Chemical Property:

• Vapor Pressure: 4.54E-09mmHg at 25°C
• Melting Point: 148 °C
• Refractive Index: 1.56
• Boiling Point: 426.7 °C at 760 mmHg
• PKA: 15.02±0.60(Predicted)
• Flash Point: 182.1 °C
• PSA: 37.30000
• Density: 1.12 g/cm³
• LogP: 3.87920
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 288.208930132
• Heavy Atom Count: 21
• Complexity: 508

Purity/Quality:

99%, ^*data from raw suppliers

DehydroAndrosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(C4)O)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@H](C4)O)C
• Uses: Dehydro Androsterone is an Androsterone (A637535) analogue.

Technology Process of Dehydroandrosterone

There total 30 articles about Dehydroandrosterone 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-5-androsten-17-one (853-23-6,5223-99-4,18462-31-2,33203-18-8,33855-01-5,104597-49-1) → dehydroepiandrosterone (53-43-0,571-35-7,2283-82-1,24357-33-3,25375-38-6,102340-20-5)

Guidance literature:

With Aliquat 336; potassium hydroxide; In water; at 60 ℃; for 1.5h;

DOI:10.1039/c2gc16328d

Reference yield: 95.8%

(3R,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (5223-99-4) → 3α-hydroxy-androst-5-en-17-one (2283-82-1)

Guidance literature:

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

Reference yield: 80.0%

17,17-ethylenedioxy-androst-5-ene-3α-ol (14456-21-4) → 3α-hydroxy-androst-5-en-17-one (2283-82-1)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/j.steroids.2010.10.005

upstream raw materials:

3β-acetoxy-5-androsten-17-one

cis-androsterone

6β-methoxy-3α,5α-cyclo-14β-androstan-17-one

(3S,8R,9S,10R,13S,16R)-16-Bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one

Downstream raw materials:

5-androstene-3α,16α-diol-17-one

dehydroepiandrosterone

prasterone acetate

Androstenedione

Refernces

• 1、 Parasram, Marvin,Chuentragool, Padon,Wang, Yang,Shi, Yi,Gevorgyan, Vladimir. "General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols". supporting information. p. 14857 - 14860. Retrieved 2017/10/31.
• 2、 Cui, Xiaoxue,Li, Bo,Liu, Tianzhen,Li, Chunbao. "A practical solution for aqueous reactions of water-insoluble high-melting-point organic substrates". supporting information; experimental part. p. 668 - 672. Retrieved 2012/06/01.