3066-12-4

Basic information

• Product Name: 11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• Synonyms: 11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;(8S,9S,10R,11R,13S,14S,17S)-11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;11.alpha.-hydroxy Testosterone (DEA Schedule III)
• CAS NO: 3066-12-4
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.427
• Mol File: 3066-12-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 476.2°Cat760mmHg
• Flash Point: 255.9°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 4.56E-11mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(3066-12-4)
• EPA Substance Registry System: 11,17-dihydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(3066-12-4)

Safety Data

• Hazardous Substances Data: 3066-12-4(Hazardous Substances Data)

Usage

Description

11α-hydroxy Testosterone is a metabolite of testosterone, produced by the cytochrome P450 (CYP) isoform CYP3A. It can also be generated from testosterone by a mutant of CYP107A1 and from 11α-hydroxy progesterone by the fungus B. bassiana. The biological activity of this metabolite has not been elucidated.

InChI:InChI=1/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-17,21-22H,3-8,10H2,1-2H3

Upstream product

• 521-17-5 5-androstenediol 
• 58-22-0 testosterone 
• 53-43-0 dehydroepiandrosterone 
• 63-05-8 Androstenedione 
• 57-83-0 Progesterone 
• 80-75-1 11-alpha-hydroxyprogesterone 

Downstream Products

• 15375-19-6 (5α)-androst-9(11)-ene-3,17-dione 
• 1429-06-7 5α-androstane-3,11,17-trione 
• 25788-56-1 11α,17β-dihydroxy-5α-androstan-3-one 
• 32326-39-9 3β,11α,17β-trihydroxy-5α-androstane 

Relevant articles and documents

Transformation of androst-4-ene-3,17-dione and androsta-1,4-diene-3,17-dione by means of Beauveria sp. II

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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.