571-36-8

Basic information

• Product Name: 5-androstene-3,17-dione
• Synonyms: 5-ANDROSTENE-3,17-DIONE PRODUCEDASREQUESTOCKTED,TRADING;5-ANDOSTERONE-3,17-DIONE;Androst-5-ene-3,17-dione;(8R,9S,10R,13S,14S)-10,13-dimethyl-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione;(8R,9S,10R,13S,14S)-10,13-dimethyl-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-quinone
• CAS NO: 571-36-8
• Molecular Formula: C₁₉H₂₆O₂
• Molecular Weight: 286.4085
• Mol File: 571-36-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 423.7 °C at 760 mmHg
• Flash Point: 158.4 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 2.19E-07mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: 5-androstene-3,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-androstene-3,17-dione(571-36-8)
• EPA Substance Registry System: 5-androstene-3,17-dione(571-36-8)

Safety Data

• Hazardous Substances Data: 571-36-8(Hazardous Substances Data)

Usage

Definition

ChEBI: An androstanoid that is androst-5-ene bearing two oxo substituents at positions 3 and 17.

InChI:InChI=1/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,14-16H,4-11H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

Synthetic route

dehydroepiandrosterone (53-43-0) → 5-androstenedione (571-36-8)

Conditions	Yield
Oppenauer oxidation;	85%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 1h; Ambient temperature;	78%
With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane; water at 25℃; for 2h;	78%

Androstenedione (63-05-8) → 5-androstenedione (571-36-8)

Conditions	Yield
Stage #1: Androstenedione With potassium tert-butylate In tert-butyl alcohol at 35 - 40℃; for 1.5h; Inert atmosphere; Stage #2: With acetic acid In water; tert-butyl alcohol at 20 - 25℃; Temperature; Reagent/catalyst;	83%
With potassium hydroxide; sodium hydrogencarbonate; acetic acid In 1,2-dimethoxyethane for 15h; Ambient temperature;	75%
With potassium tert-butylate; tert-butyl alcohol

dehydroepiandrosterone (53-43-0) → Androstenedione (63-05-8) + 5-androstenedione (571-36-8)

Conditions	Yield
With Celite; pyridinium chlorochromate In dichloromethane for 3.5h; Ambient temperature; Yields of byproduct given;	A n/a B 53%
With chromic acid In acetone at 0℃; for 0.0666667h; Title compound not separated from byproducts;

(8R,9S,10R,13S,14S)-6-bromo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthrene-3,17(2H,6H)-dione (38632-00-7, 61145-67-3, 64395-40-0) → 5-androstenedione (571-36-8)

Conditions	Yield
With zinc In ethanol; water at 20℃; for 72h; Inert atmosphere;	52%

dehydroepiandrosterone (53-43-0) → androst-4,6-diene-3,17-dione (633-34-1) + 5-androstenedione (571-36-8) + Androsta-1,4-diene-3,17-dione (897-06-3)

Conditions	Yield
With 2,2'-bipyridylchromium peroxide In benzene for 3h; Product distribution; Heating; effect of various chromium(VI) based oxidants;	A 40% B 10% C 8%
With 2,2'-bipyridylchromium peroxide In benzene for 3h; Heating;	A 40% B 10% C 8%

5-androstenediol (521-17-5, 1963-03-7, 4593-57-1, 4593-58-2, 14504-94-0, 16895-59-3, 47122-33-8, 64162-67-0, 75767-22-5, 139973-51-6, 151284-19-4) → 5-androstenedione (571-36-8)

Conditions	Yield
With bromine; acetic acid anschliessendes Behandeln mit CrO3 und Erwaermen des Reaktionsprodukts mit Zink-Pulver und Methanol;

3-hydroxy-3,5-androstadien-17-one (1229-13-6) → Androstenedione (63-05-8) + 5-androstenedione (571-36-8)

Conditions	Yield
With sodium acetate; acetic acid In methanol; water at 25℃; Rate constant; Mechanism; μ = 0.09;

3-hydroxy-3,5-androstadien-17-one (1229-13-6) → 5-androstenedione (571-36-8)

Conditions	Yield
With sodium hydroxide; 3-oxo-Δ5-steroid isomerase In methanol; water Rate constant; pH 5.0 to 5.1;
With acetic acid; sodium chloride In methanol at 6.5℃; pH=3.9 - 5.1; Kinetics; Further Variations:; Temperatures;
With phosphate buffer; D38E mutant of 3-oxo-Δ5 steroid isomerase In methanol at 15.3℃; pH=7.0; Kinetics; Further Variations:; Temperatures;

dehydroepiandrosterone (53-43-0) + bromine (7726-95-6) + acetic acid (64-19-7) → 5-androstenedione (571-36-8)

Conditions	Yield
nachfolgendes Behandeln mit CrO3 und Erwaermen des Reaktionsprodukts mit Zink-Pulver und Methanol;

5-androstenediol (521-17-5, 1963-03-7, 4593-57-1, 4593-58-2, 14504-94-0, 16895-59-3, 47122-33-8, 64162-67-0, 75767-22-5, 139973-51-6, 151284-19-4) + water (7732-18-5) + bromine (7726-95-6) + acetic acid (64-19-7) + CrO3 → 5-androstenedione (571-36-8)

Conditions	Yield
weitere Verbindung: Essigsaeure; Kochen des Reaktionsprodukts in Methanol mit Zink-Pulver;

Androstenedione (63-05-8) → 6α-hydroxy-androst-4-ene-3,17-dione (24704-84-5) + 5-androstenedione (571-36-8) + 6β-perhydroxyandrost-4-ene-3,17-dione + 6α-perhydroxyandrost-4-ene-3,17-dione + androst-4-ene-3,6,17-trione (2243-06-3) + 6β-hydroxy-4-androstene-3,17-dione (63-00-3)

Conditions	Yield
Stage #1: Androstenedione With potassium tert-butylate In tert-butyl alcohol at 30 - 35℃; for 1h; Inert atmosphere; Stage #2: With acetic acid In water Stage #3: With D-glucose; glucose dehydrogenase (CDX-901)_; ketoreductase from Sphingomonas wittichii; NAD; NADP In aq. phosphate buffer; tert-butyl methyl ether at 45℃; for 65h; pH=6.5; Enzymatic reaction;	A 4 mg B n/a C n/a D n/a E 9 mg F 8 mg

prasterone acetate (853-23-6) → 5-androstenedione (571-36-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium methylate; potassium carbonate / ethanol / 1 h / 80 °C 2: aluminum isopropoxide / toluene; cyclohexanone / 3 h / 100 °C 3: potassium tert-butylate / tert-butyl alcohol / 6 h View Scheme

5-androstenedione (571-36-8) + ethylene glycol (107-21-1) → 3,3,17,17-diethylenedioxyandrost-5-ene (4966-70-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Heating / reflux;	99%
With toluene-4-sulfonic acid In toluene for 5h;	92%
toluene-4-sulfonic acid In toluene for 12h; Reflux;

5-androstenedione (571-36-8) → Androstenedione (63-05-8)

Conditions	Yield
With potassium hydroxide In methanol; water Ambient temperature;	97%
With sodium hydroxide In methanol; water at 25℃;
With sodium hydroxide; 3-oxo-Δ5-steroid isomerase In methanol; water Rate constant; pH 5.0 to 5.1;

trifluoromethylsulfonic anhydride (358-23-6) + 5-androstenedione (571-36-8) → androsten-3,5-dienyl-17-one 3-triflate (95667-41-7)

Conditions	Yield
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane for 2.5h; Ambient temperature;	83%
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane	81%

5-androstenedione (571-36-8) → (8R,9S,10R,13S,14S)-4-diazo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthrene-3,17(2H,4H)-dione (1150096-91-5)

Conditions	Yield
Stage #1: 5-androstenedione With 3-carbonxybenzenesulfonyl azide In acetonitrile at 20℃; for 0.333333h; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 2h; Inert atmosphere;	63%
With 3-carbonxybenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃; Inert atmosphere;	62%

5-androstenedione (571-36-8) + 5-hydro-3-oxaoctafluoropentanesulfonyl fluoride (104729-49-9) → 1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-ethoxy)-ethanesulfonic acid (8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene	50%

lead(IV) acetate + 5-androstenedione (571-36-8) → 4α-acetoxyandrost-5-ene-3,17-dione (1140823-19-3)

Conditions	Yield
With acetic acid In toluene at 15 - 20℃; for 26h;	25%

5-androstenedione (571-36-8) → dehydroepiandrosterone (53-43-0) + 3α-hydroxy-androst-5-en-17-one (2283-82-1)

Conditions	Yield
With ethanol; nickel Hydrogenation;

5-androstenedione (571-36-8) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
With fermenting yeast

5-androstenedione (571-36-8) → androstene-(5)-dione-(3.17)-dioxime

5-androstenedione (571-36-8) → androst-4-ene-3,6,17-trione (2243-06-3)

Conditions	Yield
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane at 25℃; ultrasonic irradiation; Yield given;

5-androstenedione (571-36-8) → 3-hydroxy-3,5-androstadien-17-one (1229-13-6)

Conditions	Yield
With sodium hydroxide; acetic acetate In methanol; water at 25℃; Rate constant; Equilibrium constant;
With deuteriated sodium hydroxide; deuteroacetic acid In deuteromethanol; water-d2 at 12.8℃; pH=4.5 - 5.5; Kinetics; Further Variations:; Temperatures;

5-androstenedione (571-36-8) → (8R,9S,10R,13S,14S)-10,13-Dimethyl-17-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol anion (121375-08-4)

Conditions	Yield
With sodium hydroxide In methanol; water at 25℃; Rate constant; Equilibrium constant; Mechanism; μ=1.0 with KCl;

5-androstenedione (571-36-8) → 6α-Chlor-androst-4-en-3,17-dion (50433-82-4)

Conditions	Yield
With pyridine; sulfuryl dichloride

5-androstenedione (571-36-8) + ethylene glycol (107-21-1) → 3,3,17,17-diethylenedioxyandrost-5-ene (4966-70-5) + 3,17-bis-cycloethylenedioxy-androst-5-ene (981-08-8) + 3,3-ethylenedioxy-5-androsten-17-one (3754-63-0)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;

5-androstenedione (571-36-8) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) → Androstenedione (63-05-8)

ethanol (64-17-5) + 5-androstenedione (571-36-8) + diluted aqueous sulfuric acid → Androstenedione (63-05-8)

ethanol (64-17-5) + 5-androstenedione (571-36-8) + fermenting upper yeast → testosterone (58-22-0) + 5-androgen-3,17-diol (571-20-0)

ethanol (64-17-5) + 5-androstenedione (571-36-8) + Raney nickel → dehydroepiandrosterone (53-43-0) + 3α-hydroxy-androsten-(5)-one-(17)

Conditions	Yield
Hydrogenation;

Upstream product

• 53-43-0 3ξ-hydroxy-androst-5-en-17-one 
• 521-17-5 androst-5-ene-3β,17β-diol 
• 521-17-5 androst-5-ene-3β,17β-diol 
• 53-43-0 dehydroepiandrosterone 
• 521-17-5 5-androstenediol 
• 63-05-8 Androstenedione 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 7732-18-5 water 
• 853-23-6 prasterone acetate 
• 38632-00-7 (8R,9S,10R,13S,14S)-6-bromo-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthrene-3,17(2H,6H)-dione 
• 1229-13-6 3-hydroxy-3,5-androstadien-17-one 

Downstream Products

• 63-05-8 Androstenedione 
• 2243-06-3 androst-4-ene-3,6,17-trione 
• 58-22-0 testosterone 
• 571-20-0 5-androgen-3,17-diol 
• 53-43-0 dehydroepiandrosterone 
• 853-23-6 prasterone acetate 
• 1383292-25-8 dehydroepiandrosterone p-nitrobenzoate 
• 2283-82-1 3α-hydroxy-androst-5-en-17-one 
• 1912-63-6 10,13-Dimethyl-1,2,7,8,9,10,11,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthren-17-one 
• 105079-63-8 17-Oxo-3-(phenylethynyl)-androsta-3,5-diene 
• 181770-80-9 3,3-(ethylenedioxy)-6β-(dimethylphenylsiloxy)-5β-androstane-7-one 
• 181770-78-5 (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-10,13-dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,17-dione 
• 181770-90-1 (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-3-eth-(E)-ylidene-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one 
• 181770-92-3 (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-3-eth-(Z)-ylidene-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one 

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The invention provides a method for preparing 4-androstenedione from dehydroepiandrosterone acetate. The method comprises the following steps: carrying out a hydrolysis reaction on dehydroepiandrosterone acetate to obtain dehydroepiandrosterone, carrying out an oxidation reaction on the dehydroepiandrosterone to obtain crude 4-androstenedione, adding methanol and dichloroethane to the crude 4-androstenedione, and performing purification to obtain refined 4-androstenedione, wherein the obtained refined 4-androstenedione can be further reacted with potassium tert-butoxide to obtain 5-androstenedione. The method for preparing 4-androstenedione from dehydroepiandrosterone acetate has the following advantages: the preparation process is simple and feasible, and the production rate is improved,so the production values of enterprises are improved; and the cheap dehydroepiandrosterone acetate is used as the raw material to prepare the 4-androstenedione greatly demanded on the market, and the4-androstenedione is reacted to further prepare the 5-androstenedione, so the production cost of the enterprise is saved.

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