2243-05-2

Usage

Uses

Used in Pharmaceutical Industry:
5α-Androstane-3,6,17-trione is used as an active pharmaceutical ingredient for the development of drugs that target hormonal imbalances. Its role as an aromatase inhibitor makes it a potential candidate for treating conditions related to androgen deficiency or for applications in hormone therapy.
Used in Research Applications:
In the field of research, 5α-Androstane-3,6,17-trione serves as a valuable compound for studying the effects of aromatase inhibition on various biological processes. It can be used to investigate the role of androgens in different physiological and pathological conditions, contributing to a better understanding of hormonal regulation and its impact on health.
Used in Forensic Applications:
5α-Androstane-3,6,17-trione is employed as a reference material in forensic science, particularly in the analysis and identification of designer drugs and their metabolites. Its regulated status in the United States makes it a relevant compound for forensic laboratories to detect and analyze in cases involving the use or distribution of controlled substances.
Used in Sports Anti-Doping:
As an analog of an aromatase inhibitor, 5α-Androstane-3,6,17-trione may be used in the development of tests and methods for detecting the use of performance-enhancing drugs in sports. Its presence in an athlete's system could indicate the use of banned substances, aiding anti-doping agencies in their efforts to maintain fair competition and ensure the integrity of sports.

Upstream product

• 39933-10-3 3β,5-dihydroxy-5α-androstane-6,17-dione 3-acetate 
• 63-05-8 Androstenedione 
• 846-46-8 androstanedione 
• 481-29-8 Epiandrosterone 
• 53-43-0 dehydroepiandrosterone 
• 58-22-0 testosterone 

Downstream Products

• 203737-93-3 istaroxime 
• 1046809-08-8 3-[O-(2-aminoethyl)oxime]-(5α)-androstene-3,6,17-trione 
• 18529-66-3 6β,17β-dihydroxy-5α-androstan-3-one 
• 4601-47-2 (3R,5S,8R,9S,10R,13S,14R)-3-Hydroxy-10,13-dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-6,17-dione 
• 22630-54-2 3α,6α-Dihydroxy-5α-androstan-17-on 
• 4601-47-2 3β-hydroxy-5α-androstane-6,17-dione 
• 53512-53-1 3α-hydroxy-5α-androstane-6,17-dione 

Relevant academic research and scientific papers

Biotransformation of testosterone by Ulocladium chartarum MRC 72584

The incubation of testosterone 1 with Ulocladium chartarum MRC 72584 has been reported. U. chartarum MRC 72584 hydroxylated testosterone 1 at C-7β, C-6β, C-14α and C-12β, accompanied by a 5α-reduction and oxidations at C-6 and at C-17.

Studies on Bacillus stearothermophilus: Part IV. Influence of enhancers on biotransformation of testosterone

The impact of chemical enhancers on the biotransformation of testosterone has been exploited. Application of crude cell concentrates to produce Bacillus stearothermophilus-mediated bioconversion of testosterone at 65°C for 72 h has been examined. After incubation, the xenobiotic substrate was added to the concentrated whole cell suspensions. The enhancer molecules were included in the whole cell suspension. The resultant products, after extraction into an organic solvent, were purified by thin layer chromatography and identification was carried out through spectroscopic data. Five steroid metabolites 9,10-seco-4-androstene-3,9,17-trione, 5α-androstan-3,6,17-trione, 17β-hydroxy-5α-androstan-3,6-dione, 3β,17β- dihydroxyandrost-4-ene-6-one and 17β-hydroxyandrost-4,6-diene-3-one were identified as biotransformation products of testosterone. A possible biosynthetic route for these bioconversion products is postulated.

Microbial transformation of dehydroepiandrosterone (DHEA) by some fungi

In this work, biotransformations of dehydroepiandrosterone (DHEA) 1 by Ulocladium chartarum MRC 72584, Cladosporium sphaerospermum MRC 70266 and Cladosporium cladosporioides MRC 70282 have been reported. U. chartarum MRC 72584 mainly hydroxylated 1 at C-7α and C-7β, accompanied by a minor hydroxylation at C-4β, a minor epoxidation from the β-face and a minor oxidation at C-7 subsequent to its hydroxylations. 3β,7β-Dihydroxy-5β,6β-epoxyandrostan-17-one 6, 3β,4β,7α-trihydroxyandrost-5-en-17-one 7 and 3β,4β,7β-trihydroxyandrost-5-en-17-one 8 from this incubation were identified as new metabolites. C. sphaerospermum MRC 70266 converted some of 1 into a 3-keto-4-ene steroid and then hydroxylated at C-6α, C-6β and C-7α, accompanied a minor 5α-reduction and a minor oxidation at C-6 following its hydroxylations. C. sphaerospermum MRC 70266 also hydroxylated some of 1 at C-7α and C-7β. C. cladosporioides MRC 70282 converted almost half of 1 into a 3-keto-4-ene steroid and then hydroxylated at C-6α and C-6β. C. cladosporioides MRC 70282 also reduced some of 1 at C-17.

Microbial transformation of androstenedione by Cladosporium sphaerospermum and Ulocladium chartarum

In this work, incubations of androstenedione 1 with Cladosporium sphaerospermum MRC 70266 and Ulocladium chartarum MRC 72584 have been reported. C. sphaerospermum MRC 70266 mainly hydroxylated 1 at C-6β, accompanied by a hydroxylation at C-15α, a reduction at C-17, a 5α-reduction and oxidations at C-6 and C-16 following hydroxylations. U. chartarum MRC 72584 hydroxylated 1 at C-6β, C-7α, C-7β and C-14α, accompanied by an oxidation at C-6 following its hydroxylation, a reduction at C-17 and a 5α-reduction. 6β,17β-Dihydroxyandrost-4-en-3,16-dione 8, one of the metabolites from the incubation of 1 with C. sphaerospermum MRC 70266, was determined as a new compound.

The iron(II) complex [Fe(CF3SO3)2(mcp)] as a convenient, readily available catalyst for the selective oxidation of methylenic sites in alkanes

The efficient and selective oxidation of secondary C-H sites of alkanes is achieved by using low catalyst loadings of a non-expensive, readily available iron catalyst [Fe(II)(CF3SO3)2(mcp)], {Fe-mcp, [mcp=N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)cyclohexane-trans-1,2-diamine]}, and hydrogen peroxide (H2O2) as oxidant, via a simple reaction protocol. Natural products are selectively oxidized and isolated in synthetically amenable yields. The easy access to large quantities of the catalyst and the simplicity of the C-H oxidation procedure make this system a particularly convenient tool to carry out alkane C-H oxidation reactions on the preparative scale, and in short reaction times.

Reactions of 5-Hydroxy-6-oxo Steroids. II. New Aromatization Reactions of Steroids

Reactions of 3β-acetoxy-5α-hydroxy-6-oxo steroids with hydrobromic, trichloroacetic, and perchloric acids are described.It has been established that in reactions with HBraq 1-methyl-A-aromatic compounds 2 are formed, whereas with CCl3COOH formation of 2 and A-aromatic derivatives 7 take place.Dienones 3, the tentative intermediates of aromatization process, arise in all the experiments.It has been noticed that CCl3COOH catalyze tha introduction of acetoxyl group at C-7 position with simultaneous lack of 5α-hydroxyl substituent (compounds 8a, 8c and 9c).