3764-87-2

Basic information

• Product Name: Trestolone
• Synonyms: 19-nor-7a-methyltestosterone;7-ALPHA-METHYL-19-NORTESTOSTERONE;(7r)-17-hydroxy-7,13-dimethyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one;4-ESTREN-7-ALPHA-METHYL-17-BETA-OL-3-ONE;TRESTOLONE;17β-Hydroxy-7α-methylestr-4-en-3-one;7α-Methyl-19-nortestosterone;7α-Methyl-19-NT
• CAS NO: 3764-87-2
• Molecular Formula: C₁₉H₂₈O₂
• Molecular Weight: 288.42
• Product Categories: Steroid and Hormone
• Mol File: 3764-87-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 145-146 °C
• Boiling Point: 375.48°C (rough estimate)
• Flash Point: 187.3°C
• Appearance: /
• Density: 0.9447 (rough estimate)
• Vapor Pressure: 1.44E-09mmHg at 25°C
• Refractive Index: 1.6220 (estimate)
• PKA: 15.06±0.60(Predicted)
• Water Solubility: 92mg/L(37 oC)
• CAS DataBase Reference: Trestolone(CAS DataBase Reference)
• NIST Chemistry Reference: Trestolone(3764-87-2)
• EPA Substance Registry System: Trestolone(3764-87-2)

Safety Data

• Hazardous Substances Data: 3764-87-2(Hazardous Substances Data)

Usage

Uses

Trestolone is a synthetic androgen used as a potential hormonal male contraceptive method that induces a state of termporary infertility.

InChI:InChI=1/C19H28O2/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/h10-11,14-18,21H,3-9H2,1-2H3

Synthetic route

17β-[(tert-butyldimethylsilyl)oxy]-7α-methylestr-4-en-3-one → 7α-methyl-19-nortestosterone (3764-87-2)

Conditions	Yield
With water; sulfuric acid In acetone at 20℃; for 48h;	85%

C21H30O3 → 7beta-Methyl-19-nortestosterone + 7α-methyl-19-nortestosterone (3764-87-2)

Conditions	Yield
With water; potassium hydroxide In methanol; toluene at 40℃; for 2h; Inert atmosphere;	A 3% B 60.5%

7alpha-Methyl-19-nortestosterone acetate (6157-87-5) → 7α-methyl-19-nortestosterone (3764-87-2)

Conditions	Yield
Stage #1: 7alpha-Methyl-19-nortestosterone acetate With methanol; potassium hydroxide for 3 - 4h; Stage #2: With citric acid pH=6;

19-nortestosterone (434-22-0) → 7beta-Methyl-19-nortestosterone + 7α-methyl-19-nortestosterone (3764-87-2)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: perchloric acid / ethyl acetate; water / 8 h / 18 °C / Inert atmosphere 2.1: N-Bromosuccinimide / water; N,N-dimethyl-formamide / 1.17 h / 0 - 7 °C / Inert atmosphere 2.2: 1.58 h / 110 °C / Inert atmosphere 3.1: copper(l) iodide / tetrahydrofuran; Dimethyl ether / 0.5 h / 0 - 10 °C / Inert atmosphere 4.1: potassium hydroxide; water / methanol; toluene / 2 h / 40 °C / Inert atmosphere View Scheme

3,17β-diacetoxy-estra-3,5-diene (4999-76-2) → 7beta-Methyl-19-nortestosterone + 7α-methyl-19-nortestosterone (3764-87-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / water; N,N-dimethyl-formamide / 1.17 h / 0 - 7 °C / Inert atmosphere 1.2: 1.58 h / 110 °C / Inert atmosphere 2.1: copper(l) iodide / tetrahydrofuran; Dimethyl ether / 0.5 h / 0 - 10 °C / Inert atmosphere 3.1: potassium hydroxide; water / methanol; toluene / 2 h / 40 °C / Inert atmosphere View Scheme

7α-methyl-19-nortestosterone (3764-87-2) + ethylene glycol (107-21-1) → 7α-methyl-3,3-(ethylenedioxy)-5(10)-estren-7-ol (141664-11-1)

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In benzene at 72℃; for 1.5h;

7α-methyl-19-nortestosterone (3764-87-2) + ethylene glycol (107-21-1) → 7α-methyl-3,3-(ethylenedioxy)-5(10)-estren-7-ol (141664-11-1) + C21H32O3

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 43h; Heating; Title compound not separated from byproducts;

7α-methyl-19-nortestosterone (3764-87-2) + ethylene glycol (107-21-1) → 7α-methyl-3,3-(ethylenedioxy)-5(10)-estren-17-one (141664-12-2) + 3,3-ethylenedioxy-7α-methyl-5-estren-17-one

Conditions	Yield
With sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate 1.) benzene, reflux, 43 h, 2.) CH2Cl2, RT, 5.5 h; Yield given. Multistep reaction;
With sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate 1.) benzene, reflux, 43 h, 2.) CH2Cl2, RT, 5.5 h; Yield given. Multistep reaction. Title compound not separated from byproducts;

7α-methyl-19-nortestosterone (3764-87-2) + ethylene glycol (107-21-1) + lithium acetylide (70277-75-7) → 7α-methyl-17α-ethinyl-17β-hydroxy-4-estren-3-one (1162-60-3)

Conditions	Yield
Multistep reaction;

7α-methyl-19-nortestosterone (3764-87-2) + ethylene glycol (107-21-1) + lithium acetylide (70277-75-7) → 7α-methylnorethynodrel ethylene ketal (677299-58-0) + C23H32O3

Conditions	Yield
With sodium acetate; toluene-4-sulfonic acid; ethylenediamine; pyridinium chlorochromate Multistep reaction. Title compound not separated from byproducts;

7α-methyl-19-nortestosterone (3764-87-2) + methyllithium (917-54-4) → (7S,8R,9S,10R,13S,14S,17S)-3,7,13-Trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

Conditions	Yield
(i) THF, Et2O, (ii) aq. HCl, acetone; Multistep reaction;

7α-methyl-19-nortestosterone (3764-87-2) → (7S,8R,9S,10R,13S,14S,17S)-7,13-Dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

Conditions	Yield
(i) LiAlH4, THF, (ii) aq. HCl, acetone; Multistep reaction;

7α-methyl-19-nortestosterone (3764-87-2) + phenyllithium (591-51-5) → (7S,8R,9S,10R,13S,14S,17S)-7,13-Dimethyl-3-phenyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

Conditions	Yield
(i) THF, Et2O, (ii) aq. HCl, acetone; Multistep reaction;

3,3-Dimethylacryloyl chloride (3350-78-5) + 7α-methyl-19-nortestosterone (3764-87-2) → 3-Methyl-but-2-enoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

(Z)-9-octadecenoyl chloride (112-77-6) + 7α-methyl-19-nortestosterone (3764-87-2) → (Z)-Octadec-9-enoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

Cyclopentanecarboxylic acid chloride (4524-93-0) + 7α-methyl-19-nortestosterone (3764-87-2) → Cyclopentanecarboxylic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

n-dodecanoyl chloride (112-16-3) + 7α-methyl-19-nortestosterone (3764-87-2) → Dodecanoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

Nonanoyl chloride (764-85-2) + 7α-methyl-19-nortestosterone (3764-87-2) → Nonanoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

undec-10-enoyl chloride (38460-95-6) + 7α-methyl-19-nortestosterone (3764-87-2) → Undec-10-enoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

(E)-dec-2-enoyl chloride (110232-46-7) + 7α-methyl-19-nortestosterone (3764-87-2) → (E)-Dec-2-enoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

trans-chrotonyl chloride (625-35-4, 3488-22-0, 10487-71-5) + 7α-methyl-19-nortestosterone (3764-87-2) → (E)-But-2-enoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

3,3-dimethylbutanoic acid chloride (7065-46-5) + 7α-methyl-19-nortestosterone (3764-87-2) → 3,3-Dimethyl-butyric acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

pent-4-enoyl chloride (39716-58-0) + 7α-methyl-19-nortestosterone (3764-87-2) → Pent-4-enoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

chlorure d'acide ethyl-2 butyrique (2736-40-5) + 7α-methyl-19-nortestosterone (3764-87-2) → 2-Ethyl-butyric acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

undecanoyl chloride (17746-05-3) + 7α-methyl-19-nortestosterone (3764-87-2) → (7α,17β)-7-methyl-17-[(1-oxoundecyl)oxy]estr-4-en-3-one

Conditions	Yield
With pyridine at 20℃;
With sulfuric acid In ethyl acetate

heptadecanoyl chloride (40480-10-2) + 7α-methyl-19-nortestosterone (3764-87-2) → Heptadecanoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

cyclopentanepropanoyl chloride (104-97-2) + 7α-methyl-19-nortestosterone (3764-87-2) → 3-Cyclopentyl-propionic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

Benzyloxyacetyl chloride (19810-31-2) + 7α-methyl-19-nortestosterone (3764-87-2) → Benzyloxy-acetic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

4-heptylbenzoyl chloride (50606-96-7) + 7α-methyl-19-nortestosterone (3764-87-2) → 4-Heptyl-benzoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

p-ethylbenzoyl chloride (16331-45-6) + 7α-methyl-19-nortestosterone (3764-87-2) → 4-Ethyl-benzoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

4-propylbenzoyl chloride (52710-27-7) + 7α-methyl-19-nortestosterone (3764-87-2) → 4-Propyl-benzoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

4-butylbenzoyl chloride (28788-62-7) + 7α-methyl-19-nortestosterone (3764-87-2) → 4-Butyl-benzoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

4-pentylbenzoyl chloride (49763-65-7) + 7α-methyl-19-nortestosterone (3764-87-2) → 4-Pentyl-benzoic acid (7R,8R,9S,10R,13S,14S,17S)-7,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With pyridine at 20℃;

Upstream product

• 37648-63-8 N-phenyl-2-quinoxalinecarboxamide 
• 37647-52-2 10-(3-chlorophenyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indol-10-ol hydrochloride 
• 37647-52-2 10-(3-chlorophenyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indol-10-ol hydrochloride 
• 37646-31-4 6-Methyl-5-(1-oxo-3-phenyl-2-propenyl)-5H-1,3-dioxolo[4,5-f]indole-7-acetic acid 
• 37645-86-6 7-Acetyl-2-(1-acetyl-2-oxopropyl)-3,5-dimethylbenzofuran-6-ol 
• 37645-62-8 2-pentyl-1,3-thiazole 
• 37645-61-7 2-butylthiazole 
• 37645-41-3 2,4-Pyrimidinedicarboxylic acid (9CI) 
• 37645-36-6 4-methylpyridine-2,6-dicarboxylic acid 
• 3764-36-1 1-Nitro-4-(2,2,2-trifluoroethyl)benzene 
• 37643-54-2 N-[PHENYL-(TOLUENE-4-SULFONYL)METHYL]FORMAMIDE 
• 37643-42-8 1-(phenylsulfanyl)-2-[(phenylsulfanyl)methyl]undecan-2-ol 
• 37643-31-5 1,6,8,8-Tetramethyl-5-oxospiro[3.5]nonane-1-yl=acetate 
• 37642-93-6 4-(1-NAPHTHYLAMINO)-4-OXOBUTANOIC ACID 

Downstream Products

• 3764-94-1 5-CHLOROTRYPTAMINE HYDROCHLORIDE 
• 37649-86-8 1-(3-FLUOROPHENYL)PYRAZOLE 
• 3764-99-6 6-(4-bromophenyl)-2,2-dimethylpiperidin-4-one 
• 376-50-1 DIETHYL PERFLUOROADIPATE 
• 37650-49-0 ethyl 2-[(6-oxo-1-phenyl-1,6-dihydro-3-pyridazinyl)oxy]propanoate 
• 3765-12-6 Tetraethylammonium bis[salicylato-(2-)]borate 
• 37651-68-6 4-ethoxy-N,N-diethyl-N-methyl-4-oxobutan-1-aminium iodide 
• 37652-48-5 1-methyl-4-[2-(phenylsulfanyl)benzyl]piperazine (2E)-but-2-enedioate 
• 37652-51-0 1-[2-(phenylsulfanyl)benzyl]piperazine methanesulfonate (1:1) 
• 37652-54-3 1-(2-benzylbenzyl)-4-methylpiperazine (2E)-but-2-enedioate 
• 37652-55-4 4-(2-benzylbenzyl)-1,1-dimethylpiperazin-1-ium iodide 
• 37652-56-5 ethyl 4-(2-benzylbenzyl)piperazine-1-carboxylate (2E)-but-2-enedioate 
• 37652-58-7 1-(2-benzylbenzyl)piperazine (2E)-but-2-enedioate 
• 37652-60-1 1-[(2-benzylphenyl)methyl]-4-propan-2-yl-piperazine, but-2-enedioic ac id 

Recommend Products

• 141664-12-2  3,3-ethylenedioxy-7α-methyl-5(10)-estren-17-one 
• 107-21-1  ethylene glycol 
• 1162-60-3  7α-methyl-17α-ethinyl-17β-hydroxy-4-estren-3-one 
• 70277-75-7  lithium acetylide 
• 677299-58-0  7α-methylnorethynodrel ethylene ketal 
• 591-51-5  phenyllithium 
• 50606-96-7  4-heptylbenzoyl chloride 
• 16331-45-6  p-ethylbenzoyl chloride 
• 52710-27-7  4-propylbenzoyl chloride 
• 28788-62-7  4-butylbenzoyl chloride 
• 49763-65-7  4-pentylbenzoyl chloride 
• 50606-95-6  4-hexylbenzoyl chloride 
• 39649-71-3  4-hexyloxybenzoyl chloride