21080-62-6

Basic information

• Product Name: 3,7-dihydroxyandrostan-17-one
• Synonyms: 3,7-dihydroxyandrostan-17-one
• CAS NO: 21080-62-6
• Molecular Formula: C19H30O3
• Molecular Weight: 306.4397
• Mol File: 21080-62-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 454.7°Cat760mmHg
• Flash Point: 242.9°C
• Appearance: /
• Density: 1.158g/cm³
• Vapor Pressure: 3.51E-10mmHg at 25°C
• Refractive Index: 1.556
• PKA: 14.75±0.70(Predicted)
• CAS DataBase Reference: 3,7-dihydroxyandrostan-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-dihydroxyandrostan-17-one(21080-62-6)
• EPA Substance Registry System: 3,7-dihydroxyandrostan-17-one(21080-62-6)

Safety Data

• Hazardous Substances Data: 21080-62-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H30O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h11-15,17,20-21H,3-10H2,1-2H3/t11?,12?,13-,14-,15?,17-,18-,19-/m0/s1

Upstream product

• 1852-53-5 androstanediol 
• 53-41-8 cis-androsterone 

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.

Microbiological hydroxylation. Part XX. Hydroxylation of dioxygenated 5alpha-androstanes with the fungi Absidia regnieri and Syncephelastrum racemosum.

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