39663-17-7

Upstream product

• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 564-33-0 11α-hydroxyandrost-4-ene-3,17-dione 
• 142886-25-7 11α-acetoxy-3β-(tert-butyldimethylsiloxy)-25-hydroxy-4'-phenyl-5,8-<1,2>epi<1,2,4>triazolo-5α,8α-cholest-6-ene-3',5'-dione 
• 147832-99-3 3β-(tert-butyldimethylsiloxy)-11α,25-dihydroxy-4'-phenyl-5,8-<1,2>epi<1,2,4>triazolo-5α,8α-cholest-6-ene-3',5'-dione 
• 132787-58-7 (5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-11α-yl 4-carboxybutyrate 
• 147833-00-9 (5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-25-hydroxy-9,10-secocholesta-5,7,10(19)-trien-11α-yl 3-carboxypropionate 
• 147832-98-2 (5Z,7E)-(3S)-3,25-dihydroxy-9,10-secocholesta-5,7,10(19)-trien-11α-yl 3-carboxypropionate 
• 132787-59-8 (5Z,7E)-(3S)-3,25-dihydroxy-9,10-secocholesta-5,7,10(19)-trien-11α-yl 4-carboxybutyrate 
• 132787-57-6 (5Z,7E)-(3S)-3-(tert-butyldimethylsiloxy)-9,10-secocholesta-5,7,10(19)-triene-11α,25-diol 
• 2140-46-7 25-hydroxychlolesterol 

Relevant academic research and scientific papers

Potential of Azadirachta indica cell suspension culture to produce biologically active metabolites of dehydroepiandrosterone

Dehydroepiandrosterone (1) was investigated for biotransformation studies using the plant cell suspension culture of Azadirachta indica A. Juss. for the first time, yielding metabolites 2-6: 5α,3,17-androstanedione (2), 5-androstene-3β,17β-diol (3), 3β-hydroxyandrostan-17-one (4), 3β,11α-dihydroxy-5-androsten-17-one (5), and 3β,7α- dihydroxy-5-androsten-17-one (6), whose structures were solved through modern spectroscopic methods. All five compounds 2-6 have not been reported obtained by this way before. This is a new method to biosynthesize compounds 2-6 employing cultured cells of A. indica. Metabolites 2, 3, and 6 are important biologically active compounds, whereas 4 is a precursor for the production of the 7-hydroxylated compound having antiglucocorticoid and neuroprotective effects.

Microbial Baeyer-Villiger oxidation of steroidal ketones using Beauveria bassiana: Presence of an 11α-hydroxyl group essential to generation of D-homo lactones

This paper demonstrates for the first time transformation of a series of 17-oxo steroidal substrates (epiandrosterone, dehydroepiandrosterone, androstenedione) by the most frequently used whole cell biocatalyst, Beauveria bassiana, to 11α-hydroxy-17a-oxa-d-homo-androst-17-one products, in the following sequence of reactions: 11α-hydroxylation and subsequent Baeyer-Villiger oxidation to a ring-D lactone. 11α-Hydroxyprogesterone, the product of the first stage of the progesterone metabolism, was further converted along two routes: hydroxylation to 6β,11α- dihydroxyprogesterone or 17β-acetyl chain degradation leading to 11α-hydroxytestosterone, the main metabolite of the substrate. Part of 11α-hydroxytestosterone underwent a rare reduction to 11α-hydroxy- 5β-dihydrotestosterone. The experiments have demonstrated that the Baeyer-Villiger monooxygenase produced by the strain catalyzes solely oxidation of C-20 or C-17 ketones with 11α-hydroxyl group. 17-Oxo steroids, beside the 11α-hydroxylation and Baeyer-Villiger oxidation, also underwent reduction to 17β-alcohols; activity of 17β-hydroxysteroid dehydrogenase (17β-HSD) has significant impact on the amount of the formed ring-D δ-lactone.

The hydroxylation of Δ5-androstenes by Cephalosporium aphidicola

Whereas the major hydroxylation product of 3β-hydroxy-5α-androstan- 17-one by Cephalosporium aphidicola is the 11α-alcohol, the presence of a Δ5-double bond in the substrate leads to non-stereospecific allylic hydroxylation at C-7. Hydroxylation at C-11 became a minor transformation and there was no detectable hydroxylation at C-14.