2607-14-9

Upstream product

• 3091-03-0 17α-hydroxy-17β-methylandrost-5-en-3β-ol 
• 108-94-1 cyclohexanone 
• 53-43-0 dehydroepiandrosterone 
• 145-13-1 Pregnenolone 
• 846-45-7 17-Methylene-4-androstene-3-one 
• 58-18-4 17-methyltestosterone 
• 143579-42-4 methyltestosterone 17β-sulfate pyridinium salt 
• 35900-10-8 17,20-epoxy-21-nor-pregn-4-en-3-one 
• 101123-01-7 Sulfuric acid mono-((8R,9S,10R,13S,14S,17S)-10,13,17-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl) ester 

Downstream Products

• 88495-36-7 17α-hydroxy-17β-methyl-5β-androstan-3-one 
• 846-45-7 17-Methylene-4-androstene-3-one 

Relevant academic research and scientific papers

Synthesis and X-ray crystallographic analysis of 17α-hydroxy-17- methylandrost-4-ene-17-one

17α-Hydroxy-17-methylandrost-4-ene-17-one is a complex of two steroid molecules with water and its crystal structure has been determined by X-ray crystallographic techniques. The transparent plate-like crystals of this compound crystallized in the orthorhombic space group P212 121, with unit cell parameters: a = 6.382(2), b = 12.841(5), c = 43.350(2) A, λ(Mo Kα) = 0.71073 A, Z = 8. The structure has been solved by direct methods and refined to R = 0.047, wR = 0.086. There are two crystallographically independent molecules, I and II, in the asymmetric unit. In both the molecules, rings A and D adopt a distorted half-chair conformation while rings B and C exist in chair conformation. The crystal structure is stabilized by intermolecular O-H...O and C-H...O hydrogen bonds.

17-Epimerization of 17α-methyl anabolic steroids in humans: metabolism and synthesis of 17α-hydroxy-17β-methyl steroids

The 17-epimers of the anabolic steroids bolasterone (I), 4-chlorodehydromethyltestosterone (II), fluoxymesterone (III), furazabol (IV), methanedienone (V), mestanolone (VI), methyltestosterone (VII), methandriol (VIII), oxandrolone (IX), oxymesterone (X), oxymetholone (XI), stanozolol (XII), and the human metabolites 7α,17α-dimethyl-5β-androstane-3α,17β-diol (XIII) (metabolite of I), 6β-hydroxymetandienone (XIV) (metabolite of V), 17α-methyl-5β-androst-1-ene-3α,17β-diol (XV) (metabolite of V), 3'-hydroxystanozolol (XVI) (metabolite of XII), as well as the reference substances 17β-hydroxy-17α-methyl-5β-androstan-3-one (XVII), 17β-hydroxy-17α-methyl-5β-androst-1-en-3-one (XVIII) (also a metabolite of V), the four isomers 17α-methyl-5α-androstane-3α,17β-diol (XIX) (also a metabolite of VI, VII, and XI), 17α-methyl-5α-androstane-3β,17β-diol (XX), 17α-methyl-5β-androstane-3α,17β-diol (XXI) (also a metabolite of V, VII, and VIII), 17α-methyl-5β-androstane-3β,17β-diol (XXII), and 17β-hydroxy-7α,17α-dimethyl-5β-androstan-3-one (XXIII) were synthesized via a 17β-sulfate that spontaneously hydrolyzed in water to several dehydration products, and to the 17α-hydroxy-17β-methyl epimer.The 17β-sulfate was prepared by reaction of the 17β-hydroxy-17α-methyl steroid with sulfur trioxide pyridine complex.The 17β-methyl epimers are eluted in gas chromatography as trimethylsilyl derivatives from a capillary SE-54 or OV-1 column 70-170 methylen units before the corresponding 17α-methyl epimer.The electron impact mass spectra of the underivatized and trimethylsilylated epimers are in most cases identical and only for I, II, and V was a differentiation between the 17-epimers possible. 1H nuclear magnetic resonance (NMR) spectra show for the 17β-methyl epimer a chemical shift for the C-18 protons (singlet) of about 0.175 ppm (in deuterochloroform) to a lower field. 13C NMR spectra display differences for the 17-epimeric steroids in shielding effects for carbons 12-18 and 20.Excretion studies with I-XII with identification and quantification of 17-epimeric metabolites indicate that the extent of 17-epimerization depends on the A-ring structure and shows a great variation for the different 17α-methyl anabolic steroids.Keywords: anabolic steroids; 17-epimerization; nuclear magnetic resonance; Kovats indices; mass spectrometry; metabolism; gas chromatography

Studies on anabolic steroids. 9. Tertiary sulfates of anabolic 17α-methyl steroids: synthesis and rearrangement

A simple and convenient method has been developed to prepare sulfates of anabolic 17β-hydroxy-17α-methyl steroids.The sulfates of methandienone, 17α-methyltestosterone, mestanolone, oxandrolone, and stanozolol were prepared.Different A-ring functions were not affected under the sulfation condition.The buffered hydrolyses of these sulfates provided the 17-epimers of the original steroids and 17,17-dimethyl-18-nor-13(14)-ene steroids, presumably via the 17-carbocations. Keywords: steroids, tertiary sulfates; 17α-methyl steroids; 17β-methyl steroids; 17,17-dimethyl-18-norandrost-13(14)-enes; NMR