10448-96-1

Basic information

• Product Name: Almestrone
• Synonyms: Almestrone;3-Hydroxy-7a-methylestra-1,3,5(10)-trien-17-one;3-Hydroxy-7α-methylestra-1,3,5(10)-trien-17-one;NSC 134712;SR 16279;U 24704;Estra-1,3,5(10)-trien-17-one,3-hydroxy-7-Methyl-, (7a)-;(7R,8R,9S,13S,14S)-3-hydroxy-7,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS NO: 10448-96-1
• Molecular Formula: C₁₉H₂₄O₂
• Molecular Weight: 284.39
• Mol File: 10448-96-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 231-233 °C
• Boiling Point: 448.7 °C at 760 mmHg
• Flash Point: 191.2 °C
• Appearance: /
• Density: 1.127g/cm³
• Vapor Pressure: 1.14E-08mmHg at 25°C
• Refractive Index: 1.57
• PKA: 10.25±0.60(Predicted)
• CAS DataBase Reference: Almestrone(CAS DataBase Reference)
• NIST Chemistry Reference: Almestrone(10448-96-1)
• EPA Substance Registry System: Almestrone(10448-96-1)

Safety Data

• Hazardous Substances Data: 10448-96-1(Hazardous Substances Data)

Usage

General Description

Almestrone is a synthetic androgenic steroid with anabolic properties. It is used for treating conditions such as muscle wasting, osteoporosis, and hormonal imbalances. Almestrone works by promoting the growth and development of muscle tissue, increasing bone density, and stimulating secondary sexual characteristics in men. It is considered a controlled substance and is not approved for use in most countries, as it can cause serious side effects such as liver toxicity, cardiovascular issues, and hormonal imbalances. Almestrone should only be used under the supervision of a qualified healthcare provider and with careful monitoring due to its potential for abuse and misuse.

InChI:InChI=1/C19H24O2/c1-11-9-12-10-13(20)3-4-14(12)15-7-8-19(2)16(18(11)15)5-6-17(19)21/h3-4,10-11,15-16,18,20H,5-9H2,1-2H3

Synthetic route

4-estrene-7α-methyl-3,17-dione → 7α-Methylestrone (10448-96-1)

Conditions	Yield
With oxygen; copper(ll) bromide In acetonitrile at 40℃; for 1.5 - 26h; Quantum yield;	73%
With oxygen; copper dichloride In acetonitrile at 40℃; for 5h;	52%
With copper(ll) bromide In acetinitrile at 40℃; for 18h;

7α-Methylestrone (10448-96-1) + methyl iodide (74-88-4) → 4-methoxy 7α-methylestrone

Conditions	Yield
With potassium carbonate In dichloromethane; water; acetone	100%

trifluoromethylsulfonic anhydride (358-23-6) + 7α-Methylestrone (10448-96-1) → 7α-methyl-3-trifluoromethanesylfonyloxyestra-1,3,5(10)-trien-17-one (156078-51-2)

Conditions	Yield
With 2,6-dimethylpyridine In diethyl ether; dichloromethane at 0℃; for 0.666667h;	96%

Isopropenyl acetate (108-22-5) + 7α-Methylestrone (10448-96-1) → 7α-methylestrone acetate (36014-09-2) + 7α-methylestra-1,3,5(10),16-tetraene-3,17-diol diacetate (28838-19-9)

Conditions	Yield
With sulfuric acid for 2h; Heating;	A 23% B 54%

7α-Methylestrone (10448-96-1) → 16α-bromo-3-hydroxy-7α-methylestra-1,3,5(10)-trien-17-one (146016-30-0)

Conditions	Yield
With copper(ll) bromide In chloroform; ethyl acetate for 3h; Heating;
Multi-step reaction with 3 steps 1: 54 percent / H2SO4 / 2 h / Heating 2: 65 percent / acetate buffer, Br2 / acetic acid; diethyl ether / 0.25 h / 0 °C 3: 74.5 percent / conc. H2SO4 / ethanol / Ambient temperature View Scheme

7α-Methylestrone (10448-96-1) → 4-fluoro-7α-methylestrone (151160-22-4) + 2-fluoro-7α-methylestrone (151160-20-2)

Conditions	Yield
With N-fluoropyridinium triflate In 1,1,2-trichloroethane Heating; Title compound not separated from byproducts;

7α-Methylestrone (10448-96-1) → 16α-bromo-7α-methyl-3-trifluoromethanesulfonylestra-1,3,5(10)-trien-17-one (156078-53-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature View Scheme

7α-Methylestrone (10448-96-1) → 7α-methyl-3-trifluoromethanesylfonyloxy-17-acetoxyestra-1,3,5(10),16-tetraene (156078-52-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating View Scheme

7α-Methylestrone (10448-96-1) → (7R,8R,9S,13S,14S,16R,17S)-16-Fluoro-7,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

Conditions

Yield

Multi-step reaction with 8 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 29 percent / KOH / methanol / 5 h / Ambient temperature 8: 27 percent / LiAlH4 / diethyl ether / 0.25 h / -78 °C View Scheme

7α-Methylestrone (10448-96-1) → (7R,8R,9S,13S,14S,16R,17R)-16-Fluoro-7,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

Conditions

Yield

Multi-step reaction with 8 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 29 percent / KOH / methanol / 5 h / Ambient temperature 8: 66 percent / LiAlH4 / diethyl ether / 0.25 h / -78 °C View Scheme

7α-Methylestrone (10448-96-1) → [18F]-16beta-Fluoro-7alpha-methylestradiol

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 95 percent / LiAlH4 / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) from 0 deg C to RT, 25 min View Scheme

7α-Methylestrone (10448-96-1) → (7R,8R,9S,13S,14S,16R)-16-Fluoro-3-hydroxy-7,13-dimethyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one (156078-59-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 29 percent / KOH / methanol / 5 h / Ambient temperature View Scheme

7α-Methylestrone (10448-96-1) → (7R,8R,9S,13S,14S,16S)-16-Fluoro-3-hydroxy-7,13-dimethyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

Conditions

Yield

Multi-step reaction with 7 steps 1: 96 percent / 2,6-lutidine / CH2Cl2; diethyl ether / 0.67 h / 0 °C 2: 85 percent / conc. H2SO4 / 3.5 h / Heating 3: 77 percent / N-bromosuccinimide (NBS) / CCl4 / 21 h / Ambient temperature 4: 58 percent / 1 N aq. NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 95 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C 6: 81 percent / (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 30 percent / KOH / methanol / 5 h / Ambient temperature View Scheme

Relevant articles and documents

Synthesis of 7-alpha-methylestrone

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PROCESS FOR PRODUCTION OF STEROID COMPOUND

The present invention relates to a process for production of a steroid compound having a partial structure represented by Formula (2) by oxidizing a steroid compound having a partial structure represented by Formula (1), without the need of any special apparatus, in a safe and economical manner, with less adverse affect on environment, in a simple and high efficient manner. Specifically, the invention relates to a process for producing a steroid compound having a partial structure of ring A and ring B of the steroid skeleton represented by Formula (2): wherein R represents a hydrogen atom or C1-6 alkyl group, comprising the step of reacting a steroid compound having a partial structure of ring A and ring B of the steroid skeleton represented by Formula (1): wherein R is the same as above; with a catalytic amount of copper halide in the presence of oxygen.