4993-32-2

Usage

Uses

A metabolite of Androstenedione.

InChI:InChI=1/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h12,14-17,19-20H,2-10H2,1H3/t12?,14?,15?,16?,17-,18?/m0/s1

Upstream product

• 3962-66-1 estra-5⁽¹⁰⁾-en-3,17-dione 
• 14646-92-5 3β-Hydroxy-oestr-5(10)-en-17-on-3-acetat 
• 3461-67-4 3β-Acetoxy-Δ⁵-androsten-17-on-19-saeure 
• 2857-42-3 3β-acetoxy-19-hydroxyandrost-5-en-17-one 
• 3494-09-5 3-ethoxy-17β-hydroxy-1,3,5(10)-estratriene 
• 1091-93-6 3-methoxy-17-hydroxyestra-2,5⁽¹⁰⁾-diene 
• 3461-60-7 3β-Hydroxyestr-5(10)-en-17-one 
• 1089-78-7 17β-hydroxy-estr-5(10)-en-3-one 

Relevant academic research and scientific papers

An easy stereoselective synthesis of 5(10)-estrene-3β,17α-diol, a biological marker of pregnancy in the mare

5(10)-Estrene-3β,17α-diol is an essential reference material for doping analysis in horse-racing laboratories. It is used to detect misuse, for doping purpose, of the pregnancy status in the mare. Its stereoselective synthesis from 17β-estradiol-3-methyl ether (prepared from estrone or 17β-estradiol) was performed in four steps: (1) Mitsunobu inversion of the 17β-alcohol; (2) Birch reduction of the aromatic ring; (3) stereoselective reduction of the 3-ketone via Noyori asymmetric transfer hydrogenation; (4) chemoenzymatic purification.

Reduction of steroidal ketones with amine - Boranes

Complexes of secondary amines with borane, R2NH·BH 3, surpass sodium borohydride as reducing agents for saturated and unsaturated steroidal 3-, 12-, 17-, and 20-ketones as regards chemo- and regioselectivity and mildness of the reaction conditions. In the case of 12-ketones, stereoselectivity is also improved.

Formation of 5α steroids by biotranformation involving the 5 α-reductase activity of Penicillium decumbens

The biotransformation of a series of Δ4-3-ketosteroids by the Penicillium decumbens ATCC 10436 has been investigated. Conversion to the 5α-dihydrosteroid was observed substrates of the androsterone and pregne series: the reaction is tolerant of non-polar substituents (Cl and CH3) at C-4 of the substrate, but does not occur in the presence of a 4-hydroxyl group, or with additional unsaturation at the Δ1 or Δ6 positions. A-nor, B-nor, 3-deoxy-, and 3,5-cycloandrostanes are not reduced, but 6-methylenestestosterone is converted to a 6-methylene-5α-dihydro derivative. Several biotransformations are reported which involve oxidoreductase activity at C-3 and/or C-17, either concomitant or independent of Δ4 reduction: the substrate specificity of the oxidoreductase processes has been examined and defined by the use of 3α-hydroxy, 3β-hydroxy, 3-keto, 17β-keto substituted steroids. In this way, the existence in P. decumbens of 3β-hydroxy-3-keto and 17β-hydroxy-17-keto oxidoreductases has been demonstrated.