571-24-4

Basic information

• Product Name: 17?-HYDROXY-5 -ANDROSTAN-3-ONE
• Synonyms: 17?-HYDROXY-5 -ANDROSTAN-3-ONE;(5S,8R,9S,10S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS NO: 571-24-4
• Molecular Formula: C₁₉H₃₀O₂
• Molecular Weight: 290.4403
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 571-24-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: 17?-HYDROXY-5 -ANDROSTAN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 17?-HYDROXY-5 -ANDROSTAN-3-ONE(571-24-4)
• EPA Substance Registry System: 17?-HYDROXY-5 -ANDROSTAN-3-ONE(571-24-4)

Safety Data

• Hazardous Substances Data: 571-24-4(Hazardous Substances Data)

Usage

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.

Upstream product

• 103133-50-2 3-oxo-5α-androstan-17α-yl cyclohexanecarboxylate 
• 481-30-1 epitestosterone 
• 1259-22-9 5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate 
• 36025-82-8 3-oxoandrost-4-en-17α-yl benzoate 
• 853-23-6 prasterone acetate 
• 1639-43-6 androstenediol-3-acetate 
• 40768-03-4 androst-5-ene-3β,17α-diyl 3-acetate 17-benzoate 
• 150054-83-4 3β-hydroxy-5α-androstan-17α-yl cyclohexanecarboxylate 
• 40768-04-5 3β-hydroxyandrost-5-en-17α-yl benzoate 
• 100428-85-1 17α-hydroxyandrost-5-en-3β-yl 3-acetate 
• 481-30-1 epitestosterone 
• 17291-35-9 3-Oxo-5α-androstan-17β-ol-toluol-p-sulfonat 
• 71120-50-8 Pyridine-3-sulfonic acid (5S,10S,13S,17S)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester 

Downstream Products

• 64919-12-6 dihydrotestosterone p-chlorophenoxyisobutyrate 
• 88674-60-6 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 
• 855-22-1 dihydrotestosterone propionate 
• 88674-61-7 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 
• 10148-98-8 (3S,5S,8R,9S,10S,13S,14S,17S)-3-ethynyl-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol 
• 65-06-5 17-Hydroxy-androst-1-en-3-on 
• 17006-60-9 3α-ethynyl-3β-hydroxyandrostan-17-one 

Relevant articles and documents

Identification of steroidal derivatives inhibiting the transformations of allopregnanolone and estradiol by 17β-hydroxysteroid dehydrogenase type 10

17β-Hydroxysteroid dehydrogenase type 10 (17β-HSD10) is a mitochondrial enzyme known for its potential role in Alzheimer's Disease (AD). 17β-HSD10, by its oxidative activity, could decrease the concentration of two important neurosteroids, allopregnanolone (ALLOP) and 17β-estradiol (E2), respectively preventing their neurogenesis and neuroprotective effects. Since the inhibition of 17β-HSD10 could lead to a new treatment for AD, we developed two biological assays using labeled ALLOP or E2 as substrates to measure the inhibitory activity of compounds against pure 17β-HSD10 protein. After the optimization of different parameters (time, concentration of enzyme, substrate and cofactor), analogs of the first reported steroidal inhibitor of 17β-HSD10 in intact cells were screened to determine their inhibitory potency for the ALLOP or the E2 oxidation. One compound, androstane derivative 5, possesses the best dual inhibition against both transformations (ALLOP, IC50 = 235 μM and E2, IC50 = 610 μM). Some compounds are dual inhibitors to a lesser extent, and others seem selective for one of the transformations in particular. By developing two reliable assays and by identifying a first generation of steroidal inhibitors of pure 17β-HSD10, this preliminary study opens the door to new and more potent inhibitors.

Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN

A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also shown that nitrogenated substrates such as hydrazones, N-tosylhydrazones, and ketimines reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.

PREPARATION OF UNLABELLED AND 3H>-LABELLED EPITESTOSTERONE AND ITS METABOLITES

Cold as well as 3H>-labelled substrates and metabolites IX-XI, XV, XVI, XX-XXII, XXIV, XXV and XXVIII were prepared by catalytic hydrogenation of epitestosterone (VIII) and Λ1-dehydroepitestosterone (XIII).The key step in the preparation of compound XXVIII was reaction of 3β-tosylates XXVI and XXX with potassium nitrite in dimethyl sulfoxide.