33526-41-9

Usage

Uses

1. Used in Pharmaceutical Industry:
(6S,17S)-10,13,17-trimethyl-6,17-bis(trimethylsilyloxy)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one is used as a pharmaceutical candidate for [application reason]. Its unique molecular structure and chemical properties make it a potential candidate for the development of new drugs or drug delivery systems.
2. Used in Chemical Research:
(6S,17S)-10,13,17-trimethyl-6,17-bis(trimethylsilyloxy)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one is used as a research compound for [application reason]. Its complex structure and properties can be valuable for studying various chemical reactions and mechanisms, contributing to the advancement of chemical science.
3. Used in Material Science:
(6S,17S)-10,13,17-trimethyl-6,17-bis(trimethylsilyloxy)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one is used as a material component for [application reason]. Its specific properties may be harnessed to develop new materials with unique characteristics, such as improved stability, reactivity, or selectivity.
4. Used in Analytical Chemistry:
(6S,17S)-10,13,17-trimethyl-6,17-bis(trimethylsilyloxy)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one is used as an analytical reference standard for [application reason]. Its distinct chemical features can be utilized for the identification and quantification of similar compounds in various analytical techniques.

Upstream product

• 72-63-9 metandienone 
• 58-18-4 17-methyltestosterone 
• 136693-32-8 (8R,9S,10R,13S,14S,17S)-10,13,17-Trimethyl-3,17-bis-trimethylsilanyloxy-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclopenta[a]phenanthrene 

Relevant academic research and scientific papers

Steroids' transformations in Penicillium notatum culture

The application of Penicillium notatum genus for biotransformations of steroids has been investigated. The reactions observed include insertion of an oxygen atom into D-ring of steroids, 15α-hydroxylation of 17α-methyl testosterone derivatives, ester bond hydrolysis, and degradation of a testosterone derivatives side chain. Microbial production of testolactones, the biologically active compounds, was also achieved using this strain in up to 98% yield.

Natural Product Diversification by One-Step Biocatalysis using Human P450 3A4

Efficient synthetic techniques for the diversification of natural products are incremental for drug discovery processes of the pharmaceutical industry because these complex bioactive compounds often require an adjustment of properties. Human liver P450 3A4, key player of the body's detoxification system and decisive factor of a drug's metabolic fate, is renowned for its broad substrate scope including many natural products. In this study, we investigated the synthetic potential of human P450 3A4 for the diversification of natural product classes and isolated the produced metabolites of six selected natural products at a preparative 100-mg scale. Aided by efficient expression levels in P. pastoris, this whole-cell biocatalyst was found to be highly effective at the intended job allowing the identification of a total of 31 authentic human metabolites, many of them for the first time. By revealing an unprecedented degree of diversification, this study extends the synthetic repertoire for efficient enzymatic natural product modification in a one-step fashion and adds a completely new view to an old enzyme traditionally used for inhibition and toxicology studies.

Biotransformation of dianabol with the filamentous fungi and β-glucuronidase inhibitory activity of resulting metabolites

Biotransformation of the anabolic steroid dianabol (1) by suspended-cell cultures of the filamentous fungi Cunninghamella elegans and Macrophomina phaseolina was studied. Incubation of 1 with C. elegans yielded five hydroxylated metabolites 2-6, while M. phaseolina transformed compound 1 into polar metabolites 7-11. These metabolites were identified as 6β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (2), 15α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (3), 11α,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (4), 6β,12β,17β-trihydroxy-17α-methylandrost-1,4-dien-3-one (5), 6β,15α,17β-trihydroxy-17α-methylandrost-1,4-dien-3-one (6), 17β-hydroxy-17α-methylandrost-1,4-dien-3,6-dione (7), 7β,17β,-dihydroxy-17α-methylandrost-1,4-dien-3-one (8), 15β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (9), 17β-hydroxy-17α-methylandrost-1,4-dien-3,11-dione (10), and 11β,17β-dihydroxy-17α-methylandrost-1,4-dien-3-one (11). Metabolite 3 was also transformed chemically into diketone 12 and oximes 13, and 14. Compounds 6 and 12-14 were identified as new derivatives of dianabol (1). The structures of all transformed products were deduced on the basis of spectral analyses. Compounds 1-14 were evaluated for β-glucuronidase enzyme inhibitory activity. Compounds 7, 13, and 14 showed a strong inhibition of β-glucuronidase enzyme, with IC50 values between 49.0 and 84.9 μM.

Fungal transformation of methyltestosterone by the soil ascomycete Acremonium strictum to some hydroxy derivatives of 17-methylsteroid

The ascomycete Acremonium strictum was used for the biotransformation of methyltestosterone (1), a pharmaceutical steroid substance, into some steroid derivatives (6β-hydroxy-17α-methyltestosterone (2), 6β,12β-dihydroxy-17α-methyltestosterone (3), 7β-hydroxy-17α-methyltestosterone (4), 6β,17β-dihydroxy- 17α-methylandrosta-1,4-dien-3-one (5), and 3,17β-dihydroxy-17α- methylestra-1,3,5(10)-triene (6). The fermentation was carried out in Sabouraud-dextrose broth (SDB) supplemented with 1 mM of the substrate, and the temperature and aeration rate were adjusted to 30 C and 150 rpm, respectively. The biotransformation characteristics observed were hydoxylations at C-6β, C-7β, and C-12β, 1,2-dehydrogenation, and ring A aromatization. The best fermentation conditions, such as temperature, substrate concentration, pH, incubation period, and aeration, were found to be 25 C, 1 mM, pH 6.5, 6 days, and 150 rpm, respectively, for maximum biotransformation of 1.

Metabolism of anabolic steroids in humans: Synthesis of 6β-hydroxy metabolites of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and metandienone

Hydroxylation at position 6β of testosterone I (17β-hydroxyandrost-4- en-3-one) and the anabolic steroids 17α-methyltestosterone II (17β-hydroxy- 17α-methylandrost-4-en-3-one), metandienone III (17β-hydroxy-17α- methylandrosta-1,4-dien-3-one), 4-chloro-1,2-dehydro-17α-methyltestosterone IV (4-chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one), and fluoxymesterone V (9-fluoro-11β, 17β-dihydroxy-17a-methylandrost-4-en-3- one) was achieved via light-induced autooxidation of the corresponding trimethylsilyl 3,5-dienol ethers dissolved in isopropanol or ethanol. The reaction further yielded the 6α-hydroxy isomer in low amounts. The 6β- hydroxy isomers of I-V and the 6α-hydroxy isomers of I, III, and IV were isolated and characterized by 1H and 13C NMR, high-performance liquid chromatography, gas chromatography, and mass spectrometry. Human excretion studies with single administered doses of boldenone (17β-hydroxyandrosta- 1,4-dien-3-one), 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, metandienone, 17α-methyltestosterone, and [16,16,17- 2H3]testosterone showed that 6β-hydroxylation is the major metabolic pathway in the metabolism of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and metandienone, whereas for boldenone, 17α- methyltestosterone, and testosterone, 6β hydroxylation is negligable.