100239-44-9

Basic information

• Product Name: 3A-HYDROXYTIBOLONE
• Synonyms: 3A-HYDROXYTIBOLONE;(3A,7A,17A)-3,17-DIHYDROXY-7-METHYL-19-NORPREGN-5(10)-EN-20-YL-3-ONE;3-alpha-Hydroxytibolone;7β-Tibolone;(3R,7R,8R,9S,13S,14S,17R)-17-ethynyl-7,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS NO: 100239-44-9
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.46
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Steroids;Metabolites & Impurities
• Mol File: 100239-44-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 72-74°C
• Appearance: /
• Refractive Index: 1.578
• Storage Temp.: Controlled Substance, -20?C Freezer
• CAS DataBase Reference: 3A-HYDROXYTIBOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3A-HYDROXYTIBOLONE(100239-44-9)
• EPA Substance Registry System: 3A-HYDROXYTIBOLONE(100239-44-9)

Safety Data

• Hazardous Substances Data: 100239-44-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Powder

Uses

As a metabolite of Tibolone, 3α-Hydroxy Tibolone can be used as a synthetic steroid with weak estrogenic, androgenic and progestogenic activity and a pharamceutical used in the treatment of menopausal syndrome.

InChI:InChI=1/C21H30O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,15,17-19,22-23H,5-12H2,2-3H3/t13?,15-,17?,18?,19-,20+,21?/m1/s1

Upstream product

• 5630-53-5 tibolone 
• 158932-37-7 17α-ethynyl-7α-methyl-5(10)-estren-3ξ,17β-diol 
• 500019-11-4 17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-ξ3-yl acetate 
• 500019-09-0 17α-ethynyl-17β-hydroxy-7α-methyl-5(10)-estren-α3-yl acetate 

Downstream Products

• 1357075-90-1 3α-tiboloyl (S)-2-methoxy-2-phenylpent-3-ynoate 
• 1357075-89-8 3α-tibolol-3-yl (R)-2-methoxy-2-phenylpent-3-ynoate 
• 100239-45-0 (3β,7α,17α)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3,17-diol 

Relevant articles and documents

Enantioselective production of 3-hydroxy metabolites of tibolone by yeast reduction

The enantioselective reduction of tibolone into the corresponding 3α-hydroxy or 3β-hydroxy metabolite can be controlled by choosing suited strains of yeasts and biotransformation conditions. A restricted screening performed among 52 yeasts showed that the 3α-epimer was preferentially obtained with high epimeric purity with various strains (i.e. with Kluyveromyces lactis CBS 2359), while only Saccharomyces cerevisiae CBS 3093 gave the 3β-epimer as major product. The reduction of tibolone with K. lactis CBS 2359 and S. cerevisiae CBS 3093 was optimised. S. cerevisiae CBS 3093 furnished a 96:4 ratio of 3β/3α with complete molar conversion within 72 h when the initial concentration of substrate was below 2.5 g/L. K. lactis CBS 2359 gave a 99:1 ratio of 3α/3β with complete conversion in 64 h.

Stereochemical analysis of the 3α- and 3β-hydroxy metabolites of tibolone through NMR and quantum-chemical investigations. An experimental test of GIAO calculations

The configuration at C-3 of the 3α- and 3β-hydroxy metabolites of tibolone was studied by extensive application of one- and two-dimensional 1H and 13C NMR spectroscopy combined with molecular modeling performed at the B3LYP/6-31G(d)

Alpha-glucosidase and tyrosinase inhibitors from fungal hydroxylation of tibolone and hydroxytibolones

Sixteen new and one known metabolites 4-20 were obtained by incubation of tibolone (1) and hydroxytibolones (2 and 3) with various fungi. Their structures were elucidated by means of a homo and heteronuclear 2D NMR and by HREI-MS techniques. The relative stereochemistry was deduced by 2D NOESY experiment. Metabolites of tibolone (1) exhibited significant inhibitory activities against α-glucosidase and tyrosinase enzymes. Hydroxylations at C-6, C-10, C-11, C-15 positions and α,β-unsaturation at C-1/C-2, C-4/C-5 showed potent inhibitory activities against these enzymes.