7801-12-9

Basic information

• Product Name: 3α,11α-Dihydroxy-5α-androstan-17-one
• CAS NO: 7801-12-9
• Molecular Formula: C19H30O3
• Molecular Weight: 306.4397
• Mol File: 7801-12-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3α,11α-Dihydroxy-5α-androstan-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3α,11α-Dihydroxy-5α-androstan-17-one(7801-12-9)
• EPA Substance Registry System: 3α,11α-Dihydroxy-5α-androstan-17-one(7801-12-9)

Safety Data

• Hazardous Substances Data: 7801-12-9(Hazardous Substances Data)

Upstream product

• 963-74-6 5alpha-androstan-17-one 
• 53-41-8 cis-androsterone 
• 1852-53-5 androstanediol 

Relevant articles and documents

Microbial Baeyer-Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway

Beauveria bassiana KCH 1065, as was recently demonstrated, is unusual amongst fungal biocatalysts in that it converts C19 3-oxo-4-ene and 3β-hydroxy-5-ene as well as 3β-hydroxy-5α-saturated steroids to 11α-hydroxy ring-D lactones. The Baeyer-Villiger monooxygenase (BVMO) of this strain is distinguished from other enzymes catalyzing BVO of steroidal ketones by the fact that it oxidizes solely substrates with 11α-hydroxyl group. The current study using a series of 5α-saturated steroids (androsterone, 3α-androstanediol and androstanedione) has highlighted that a small change of the steroid structure can result in significant differences of the metabolic fate. It was found that the 3α-stereochemistry of hydroxyl group restricted "normal" binding orientation of the substrate within 11α-hydroxylase and, as a result, androsterone and 3α-androstanediol were converted into a mixture of 7β-, 11α- and 7α-hydroxy derivatives. Hydroxylation of androstanedione occurred only at the 11α-position, indicating that the 3-oxo group limits the alternative binding orientation of the substrate within the hydroxylase. Only androstanedione and 3α-androstanediol were metabolized to hydroxylactones. The study uniquely demonstrated preference for oxidation of equatorial (11α-, 7β-) hydroxyketones by BVMO from B. bassiana. The time course experiments suggested that the activity of 17β-HSD is a factor determining the amount of produced ring-D lactones. The obtained 11α-hydroxylactones underwent further transformations (oxy-red reactions) at C-3. During conversion of androstanedione, a minor dehydrogenation pathway was observed with generation of 11α,17β-dihydroxy-5α-androst-1-en-3-one. The introduction of C1C2 double bond has been recorded in B. bassiana for the first time.