2089-06-7

Usage

Uses

5α-Pregnane-3,11,20-trione is a Progesterone metabolite.

InChI:InChI=1/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h13,15-17,19H,4-11H2,1-3H3/t13-,15-,16+,17-,19+,20-,21+/m0/s1

Upstream product

• 565-97-9 3β,20β_F-dihydroxy-5α-pregnan-11-one 
• 96005-68-4 12α-bromo-5α-pregnane-3,11,20-trione 
• 565-96-8 11α-hydroxy-5β-pregnane-3,20-dione 
• 80-75-1 11-alpha-hydroxyprogesterone 
• 3676-17-3 5α-pregnane-3β,11β,20-triol 
• 64-19-7 acetic acid 
• 115485-77-3 3β,20β_F-diacetoxy-9,11α-epoxy-5α-pregnan-7-one 
• 102291-06-5 3,3,20,20-Bis--5α-pregn-9(11)-en 
• 516-15-4 11-Ketoprogesterone 
• 28445-05-8 5α-pregn-16-ene-3,11,20-trione 
• 55647-25-1 5α-pregnane-3β,11α,20β_F-triol 
• 565-99-1 UC₁₀₁₇ 

Downstream Products

• 565-99-1 UC₁₀₁₇ 
• 26039-99-6 5α-Pregnan-11-on 
• 7339-06-2 1-Androsten-(5α)-3,11,17-trion 
• 3676-17-3 5α-pregnane-3β,11β,20β_F-triol 
• 641-85-0 5α-pregnane 
• 23930-19-0 Alphaxalone 

Relevant academic research and scientific papers

First synthesis of a C-homosteroid from pregn-4-ene-3,11,20-trione

(3α,5α)-3-Hydroxy-C-homopregnane-11,20-dione (3) was prepared in eleven steps from the commercially available pregn-4-ene-3,11,20-trione (4) via the 11-oxo-13-formyl-12,13-secopregnane intermediate 11 (Scheme 2). Subjection of this secopregnane to an intramolecular aldol condensation afforded the α,β-unsaturated key intermediate C-homopregn-12-en-11-one 12. Copyright

NEUROACTIVE STEROIDS AND METHODS OF PREPARATION

Disclosed are neuroactive steroid anaesthetic agents, methods for their preparation and compositions comprising the same. The invention provides scaled up and/or GMP methods for preparing neuroactive steroids, such as alfaxalone, alfadolone and alfadolone acetate.

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.