1057-07-4

Basic information

• Product Name: Androstanolone 17-benzoate
• Synonyms: 5-ALPHA-ANDROSTAN-17-BETA-OL-3-ONE HEXAHYDROBENZOATE;5ALPHA-ANDROSTAN-17BETA-OL-3-ONE BENZOATE;5ALPHA-ANDROSTAN-17BETA-OL-3-ONE 17-BENZOATE;5ALPHA-DIHYDROTESTOSTERONE BENZOATE;3-OXO-5A-ANDROSTAN-17B-YL BENZOATE;ANDROSTANOLONE 17-BENZOATE;17BETA-HYDROXY-5ALPHA-ANDROSTAN-3-ONE 17-BENZOATE;DIHYDROTESTOSTERONE HEXAHYDROBENZOATE
• CAS NO: 1057-07-4
• Molecular Formula: C₂₆H₃₄O₃
• Molecular Weight: 394.55
• EINECS: 213-891-8
• Product Categories: Steroids
• Mol File: 1057-07-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 155 °C
• Boiling Point: 505.6 °C at 760 mmHg
• Flash Point: 216.7 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 2.4E-10mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: Androstanolone 17-benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Androstanolone 17-benzoate(1057-07-4)
• EPA Substance Registry System: Androstanolone 17-benzoate(1057-07-4)

Safety Data

• Hazard Codes: Xn
• Statements: 63
• Safety Statements: 36/37
• RTECS: BV8058500
• Hazardous Substances Data: 1057-07-4(Hazardous Substances Data)

Usage

General Description

Androstanolone 17-benzoate, also known as stanolone benzoate, is a synthetic androgen and anabolic steroid with a chemical structure similar to the male hormone testosterone. It is a derivative of dihydrotestosterone and is commonly used in the treatment of hypogonadism and androgen deficiency in men. Androstanolone 17-benzoate is also used in combination with other hormones for hormone replacement therapy, and as a performance-enhancing drug in sports and bodybuilding due to its ability to increase muscle mass and strength. However, it is important to note that the use of Androstanolone 17-benzoate for non-medical purposes is illegal and poses serious health risks.

InChI:InChI=1/C26H34O3/c1-25-14-12-19(27)16-18(25)8-9-20-21-10-11-23(26(21,2)15-13-22(20)25)29-24(28)17-6-4-3-5-7-17/h3-7,18,20-23H,8-16H2,1-2H3/t18-,20-,21-,22-,23-,25-,26-/m0/s1

Synthetic route

Stanolone (521-18-6) + benzoyl chloride (98-88-4) → stanolone benzoate (1057-07-4)

Conditions	Yield
In pyridine at 60℃; for 2h;	96%

3β-Hydroxy-17β-benzoyloxy-5α-androstan (6242-26-8) → stanolone benzoate (1057-07-4)

Conditions	Yield
With 4-Benzoylpyridine In acetone at 20℃; for 46h; UV-irradiation; Inert atmosphere;	76%

17β-benzoyloxy-5α-androstanol-(3α) → stanolone benzoate (1057-07-4)

Conditions	Yield
With chromic acid; acetic acid

C10H9FeCONHNH3(1+)*Cl(1-)={C10H9FeCONHNH3}Cl + stanolone benzoate (1057-07-4) → C10H9FeC27H35N2O3

Conditions	Yield
In ethanol; acetic acid boiling;	84%
In ethanol; acetic acid

ferrocenylcarbonylhydrazine + stanolone benzoate (1057-07-4) → C10H9FeC27H35N2O3

Conditions	Yield
In ethanol; acetic acid boiling;	84%
In ethanol; acetic acid

indole (120-72-9) + stanolone benzoate (1057-07-4) → 2-(indol-3-yl)dihydrotestosterone benzoate (74252-30-5)

Conditions	Yield
With perchloric acid In N,N-dimethyl-formamide for 3h; Heating;	72%

stanolone benzoate (1057-07-4) → 5α-hydroxy-3-oxo-5α-androstan-17β-yl benzoate (26128-31-4) + 6α-hydroxy-3-oxo-5α-androstan-17β-yl benzoate

Conditions	Yield
With iodosylbenzene; 5,10,15,20-tetrakis-5-(2,2'-bi-Py)porphyrin Mn(III) chloride; copper(II) bis(trifluoromethanesulfonate) In water; acetonitrile at 20℃; for 16h;	A 36% B 45%

stanolone benzoate (1057-07-4) + indole-2,3-dione (91-56-5) → Benzoic acid (5S,8R,9S,10S,13S,14S,17S)-2-(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
With diethylamine In ethanol Heating;	30%

benzilic hydrazide (13050-38-9) + stanolone benzoate (1057-07-4) → benzilic acid-(17β-benzoyloxy-5α-androstan-3-ylidenehydrazide)

Conditions	Yield
With methanol; acetic acid

stanolone benzoate (1057-07-4) + methylmagnesium bromide (75-16-1) → 3β-methyl-5α-androstane-3α,17β-diol (2233-69-4) + 3α-methyl-5α-androstane-3β,17β-diol (2066-31-1)

Conditions	Yield
With diethyl ether

stanolone benzoate (1057-07-4) → 2.2-dibromo-17β-benzoyloxy-5α-androstanone-(3)

Conditions	Yield
With hydrogen bromide; bromine; acetic acid

Diethyl-2-(dimethylamino)-ethoxycarbonylmethylphosponat (26559-63-7) + stanolone benzoate (1057-07-4) → Benzoic acid (5S,8R,9S,10S,13S,14S,17S)-3-[1-(2-dimethylamino-ethoxycarbonyl)-meth-(E)-ylidene]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

Conditions	Yield
(i) NaH, 1,2-dimethoxy-ethane, (ii) /BRN= 3122672/; Multistep reaction;

diethyl 2-(cyclohexylimino)ethylphosphonate (20061-84-1) + stanolone benzoate (1057-07-4) → seq.trans-3-Formylmethylen-17β-benzoyloxy-5α-androstan (19897-11-1)

Conditions	Yield
(i) NaH, (ii) aq. oxalic acid; Multistep reaction;

stanolone benzoate (1057-07-4) → 3β-Hydroxy-17β-benzoyloxy-5α-androstan (6242-26-8)

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate

stanolone benzoate (1057-07-4) + thiourea (17356-08-0) → 17β-benzoyloxy-(2ξ,3ξ,5α)-2,3-dihydro-androstano[2,3-d]isoxazol-3'-ylamine (68432-14-4)

Conditions	Yield
With 2-Methylnaphthalene

stanolone benzoate (1057-07-4) + urea (57-13-6) → 17β-benzoyloxy-(2ξ,3ξ,5α)-2,3-dihydro-androstano[2,3-d]isoxazol-3'-ylamine (68432-14-4)

Conditions	Yield
With 2-Methylnaphthalene

stanolone benzoate (1057-07-4) → Benzoic acid (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-hexadecahydro-spiro[cyclopenta[a]phenanthrene-3,3'-diaziridin]-17-yl ester

Conditions	Yield
With tert-butylhypochlorite; ammonia In dichloromethane at 20℃; for 48h;

stanolone benzoate (1057-07-4) → 2α-Brom-17β-benzoyloxy-5α-androstanon-(3) (96192-10-8)

Conditions	Yield
With pyridinium hydrobromide perbromide In tetrahydrofuran
With bromine In acetic acid for 3h; Ambient temperature;	5.1 g

stanolone benzoate (1057-07-4) → 17β-Benzoyloxy-3-chlor-Δ2-α-androsten (17444-85-8)

Conditions	Yield
With phosphorus pentachloride In tetrachloromethane

stanolone benzoate (1057-07-4) + methylmagnesium bromide (75-16-1) + acetic anhydride (108-24-7) → 17β-acetoxy-3-methyl-5α-androstan-3α-ol (2611-37-2) + 17β-acetoxy-3-methyl-5α-androstan-3β-ol (2066-32-2)

Conditions	Yield
(i) Et2O, (ii) /BRN= 385737/, Py; Multistep reaction;

methanol (67-56-1) + stanolone benzoate (1057-07-4) → 17β-Benzoyloxy-3,3-dimethoxy-5α-androstan

stanolone benzoate (1057-07-4) → 5α-androst-1-en-3-one-17β-yl benzoate (1971-67-1)

Conditions	Yield
(i) Br2, aq. HBr, AcOH, (ii) LiBr, Li2CO3; Multistep reaction;
Multi-step reaction with 2 steps 1: 5.1 g / Br2 / acetic acid / 3 h / Ambient temperature 2: CaCO3 / N,N-dimethyl-acetamide / 0.33 h / Heating View Scheme

stanolone benzoate (1057-07-4) + hydrogen bromide (10035-10-6, 12258-64-9) + bromine (7726-95-6) + acetic acid (64-19-7) → 17β-benzoyloxy-2α,4α-dibromo-5α-androstan-3-one (115385-19-8)

Conditions	Yield
20-std. Aufbewahren des Reaktionsgemisches;

stanolone benzoate (1057-07-4) + hydrogen bromide (10035-10-6, 12258-64-9) + bromine (7726-95-6) + acetic acid (64-19-7) → 2.2-dibromo-17β-benzoyloxy-5α-androstanone-(3)

stanolone benzoate (1057-07-4) → 1-testosterone (65-06-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 5.1 g / Br2 / acetic acid / 3 h / Ambient temperature 2: CaCO3 / N,N-dimethyl-acetamide / 0.33 h / Heating 3: 82.6 percent / 5percent methanolic NaOH / 2 h / Heating View Scheme

stanolone benzoate (1057-07-4) → 1β,17β-dihydroxyandrost-4-en-3-one (19418-63-4)

Conditions

Yield

Multi-step reaction with 9 steps 1: 5.1 g / Br2 / acetic acid / 3 h / Ambient temperature 2: CaCO3 / N,N-dimethyl-acetamide / 0.33 h / Heating 3: 82.6 percent / 5percent methanolic NaOH / 2 h / Heating 4: 69.9 percent / Mo(CO)6, t-butylhydroperoxide / CH2Cl2 / Heating 5: 69.9 percent / SeO2, CH3COOH / 2-methyl-propan-2-ol / 24 h / Heating 6: 67.5 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 7: 76 percent / LiAlH4 / tetrahydrofuran / 3.5 h / Ambient temperature 8: 97 percent / MnO2 / CHCl3 / 21 h 9: 56 percent / 30percent aq. HF / acetonitrile / 1.5 h View Scheme

stanolone benzoate (1057-07-4) → 5α-androst-1β,2β-epoxude-3-on-17β-ol (135415-79-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 5.1 g / Br2 / acetic acid / 3 h / Ambient temperature 2: CaCO3 / N,N-dimethyl-acetamide / 0.33 h / Heating 3: 82.6 percent / 5percent methanolic NaOH / 2 h / Heating 4: 69.9 percent / Mo(CO)6, t-butylhydroperoxide / CH2Cl2 / Heating View Scheme

stanolone benzoate (1057-07-4) → androst-4-en-1β,2β-epoxide-3-on-17β-ol (112192-79-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 5.1 g / Br2 / acetic acid / 3 h / Ambient temperature 2: CaCO3 / N,N-dimethyl-acetamide / 0.33 h / Heating 3: 82.6 percent / 5percent methanolic NaOH / 2 h / Heating 4: 69.9 percent / Mo(CO)6, t-butylhydroperoxide / CH2Cl2 / Heating 5: 69.9 percent / SeO2, CH3COOH / 2-methyl-propan-2-ol / 24 h / Heating View Scheme

stanolone benzoate (1057-07-4) → androst-4-en-1β,3-diol-17β-silyl ether (135359-58-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: 5.1 g / Br2 / acetic acid / 3 h / Ambient temperature 2: CaCO3 / N,N-dimethyl-acetamide / 0.33 h / Heating 3: 82.6 percent / 5percent methanolic NaOH / 2 h / Heating 4: 69.9 percent / Mo(CO)6, t-butylhydroperoxide / CH2Cl2 / Heating 5: 69.9 percent / SeO2, CH3COOH / 2-methyl-propan-2-ol / 24 h / Heating 6: 67.5 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 7: 76 percent / LiAlH4 / tetrahydrofuran / 3.5 h / Ambient temperature View Scheme

Upstream product

• 6242-26-8 3β-Hydroxy-17β-benzoyloxy-5α-androstan 
• 42723-50-2 dl-O-(Δ¹-20-oxo-5β-pregnen-17-yl)acetone oxime 
• 42723-64-8 dl-Δ¹-5β-androsten-17β-ol benzoate 
• 98-88-4 benzoyl chloride 
• 1971-67-1 dl-Δ¹-5β-androsten-3-oxo-17β-ol benzoate 
• 521-18-6 Stanolone 
• 42722-79-2 dl-17-hydroxy-Δ¹-5β-pregnen-20-ol 
• 42723-62-6 dl-Δ¹-5β-androsten-17-one 
• 894-65-5 dl-Δ¹-5β-androsten-17β-ol 

Downstream Products

• 42723-68-2 Benzoic acid (5R,8S,9R,10S,13R,14R,17R)-4-bromo-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester 
• 17444-85-8 17β-Benzoyloxy-3-chlor-Δ²-α-androsten 
• 2088-71-3 testosterone benzoate 
• 903-27-5 17β-Acetoxy-3-methyl-5α-androst-2-en 
• 1424-00-6 mesterolone 
• 2639-53-4 (5α,17β)-androst-2-en-17-ol 
• 115385-19-8 17β-benzoyloxy-2α,4α-dibromo-5α-androstan-3-one 
• 126541-29-5 3-azi-5α-androstan-17β-yl benzoate 
• 65-06-5 1-testosterone 
• 26128-31-4 5α-hydroxy-3-oxo-5α-androstan-17β-yl benzoate 
• 1971-67-1 5α-androst-1-en-3-one-17β-yl benzoate 
• 96192-10-8 2α-Brom-17β-benzoyloxy-5α-androstanon-(3) 
• 74252-30-5 2-(indol-3-yl)dihydrotestosterone benzoate 
• 68432-14-4 17β-benzoyloxy-(2ξ,3ξ,5α)-2,3-dihydro-androstano[2,3-d]isoxazol-3'-ylamine 

Relevant articles and documents

Regioselective oxidation of steroids by a manganese porphyrin carrying metal coordinating groups

A manganese porphyrin having tour 2,2′-bipyridyl groups on its meso positions was synthesized. In the presence of Cu2+ ions it catalyzes the regioselective oxidation of steroid substrates carrying auxiliary metal coordinating groups.