17?-HYDROXY-5 -ANDROSTAN-3-ONE

Base Information

• Chemical Name: 17?-HYDROXY-5 -ANDROSTAN-3-ONE
• CAS No.: 571-24-4
• Molecular Formula: C₁₉H₃₀O₂
• Molecular Weight: 290.446
• Mol file: 571-24-4.mol

Synonyms:

Chemical Property of 17?-HYDROXY-5 -ANDROSTAN-3-ONE

Chemical Property:

• Melting Point: 171 - 174°C
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)

Purity/Quality:

99% ^*data from raw suppliers

17α-Hydroxy-5α-androstan-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 17α-Hydroxy-5α-androstan-3-one is a metabolite of epi-testosterone (T155005). It functions similar to other testosterone analogs, maintaining cell conformation in epithelial cells.

Technology Process of 17?-HYDROXY-5 -ANDROSTAN-3-ONE

There total 25 articles about 17?-HYDROXY-5 -ANDROSTAN-3-ONE 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: 76.0%

C22H36OS2 → stanolone (521-18-6,571-22-2,571-24-4,2150-84-7,5692-03-5,29873-50-5,35456-91-8,35457-09-1,36027-76-6,64282-57-1,124377-49-7)

Guidance literature:

C₂₂H₃₆OS₂; With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 20 ℃; for 24h;

With water; In acetonitrile; for 0.0833333h;

DOI:10.1002/ejoc.202000979

Reference yield: 70.0%

C26H33NO5 → 5alpha-Androstane-17alpha-ol-3-one (571-24-4)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 6h;

DOI:10.1016/j.bmcl.2018.09.031

Reference yield: 67.0%

epitestosterone (481-30-1) → 5alpha-Androstane-17alpha-ol-3-one (571-24-4) + 5beta-Androstane-17alpha-ol-3-one (5692-03-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1002/oms.1210200808

upstream raw materials:

3-oxo-5α-androstan-17α-yl cyclohexanecarboxylate

epitestosterone

5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate

3-oxoandrost-4-en-17α-yl benzoate

Downstream raw materials:

dihydrotestosterone p-chlorophenoxyisobutyrate

2-(4-Chloro-phenoxy)-2-methyl-propionic acid (5S,10R,13S,17S)-3-[2-(4-chloro-phenoxy)-2-methyl-propionyloxy]-10,13-dimethyl-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

dihydrotestosterone propionate

Propionic acid (5S,10R,13S,17S)-10,13-dimethyl-17-propionyloxy-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Refernces

• 1、 Boutin, Sophie,Maltais, René,Roy, Jenny,Poirier, Donald. "Synthesis of 17β-hydroxysteroid dehydrogenase type 10 steroidal inhibitors: Selectivity, metabolic stability and enhanced potency". . . Retrieved 2020/10/22.
• 2、 Parr, Maria K.,Zapp, Josef,Becker, Michael,Opfermann, Georg,Bartz, Ulrike,Schaenzer, Wilhelm. "Steroidal isomers with uniform mass spectra of their per-TMS derivatives: Synthesis of 17-hydroxyandrostan-3-ones, androst-1-, and -4-ene-3,17-diols". . p. 545 - 551. Retrieved 2008/02/02.