29873-50-5

Upstream product

• 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 
• 57-83-0 Progesterone 
• 63-05-8 Androstenedione 
• 58-22-0 testosterone 
• 68-96-2 17-hydroxyprogesterone 
• 481-30-1 epitestosterone 

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 
• 17006-60-9 3α-ethynyl-3β-hydroxyandrostan-17-one 
• 65-06-5 17-Hydroxy-androst-1-en-3-on 

Relevant academic research and scientific papers

The source of follicular androgens in the hamster follicle

The comparative ability of granulosa cells and theca of the hamster preovulatory follicle to produce androgens in vitro from endogenous and exogenous substrates was assessed. The results indicate that theca are the major source of follicular androstenedione, but that the granulosa cells may be the major source of follicular testosterone. Theca and granulosa cells accumulate comparable amounts of dihydrotestosterone from exogenous androstenedione and testosterone and both may be a significant source of follicular DHT. LH stimulates the conversion of progesterone and 17α-OH progesterone to androstenedione, testosterone and DHT in theca. LH does not stimulate the conversion of androstenedione to testosterone or DHT, and that of testosterone to DHT in either granulosa cells or theca. FSH, in granulosa cells but not in theca, stimulates the conversion of androstenedione to testosterone but it has no effect in DHT accumulation from exogenous testosterone.

Microbial transformations of testosterone to 5α-dihydrotestosterone by two species of Penicillium: P. chrysogenum and P. crustosum

Two species of Penicillium - P. chrysogenum and P. crustosum - were cultured in presence of [3H]testosterone as a substrate. Both species were shown to reduce the 4,5-double bond in testosterone to give dihydrotestosterone (DHT). The steroids produced were 5α- dihydrotestosterone, DHT, 3α-hydroxy-5β-androstan-17-one, 3α-hydroxy-5α- androstan-17-one, 4-androstene-3,17-dione, and 5α-androstane-3,17-dione. These products implicate the presence of the 5α-reductase, with maximal activity at pH 6 and 8, in both species of Penicillium. The presence of DHT in the growth medium and not in the mycelium suggests that DHT is excreted into the medium.

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.