571-40-4

Basic information

• Product Name: 5-Androstenedione
• Synonyms: 1,(a)-Androstene-3,17-Dione;5α-Androst-1-ene-3,17-dione;WJIQCDPCDVWDDE-WZNAKSSCSA-N
• CAS NO: 571-40-4
• Molecular Formula: C₁₉H₂₆O₂
• Molecular Weight: 286.412
• EINECS: 571-400-4
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 571-40-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 140-142 °C
• Boiling Point: 418.8 °C at 760 mmHg
• Flash Point: 156.6 °C
• Appearance: /
• Density: 1.099 g/cm³
• CAS DataBase Reference: 5-Androstenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Androstenedione(571-40-4)
• EPA Substance Registry System: 5-Androstenedione(571-40-4)

Safety Data

• Hazardous Substances Data: 571-40-4(Hazardous Substances Data)

Usage

Uses

Δ1-Androstenedione as a prodrug of Δ1-Testosterone (T155010).

Synthetic route

androstanedione (846-46-8) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With palladium(II) trifluoroacetate; oxygen; acetic acid; dimethyl sulfoxide at 80℃; under 760.051 Torr; for 12h;	93%
With trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 60℃; for 40h; Temperature; regioselective reaction;	63%
With periodic acid; tert-butyl alcohol
With 3-ketosteroid Δ1-dehydrogenase Enzymatic reaction;

1-testosterone (65-06-5) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With chromium(VI) oxide In water; acetic acid at 25 - 30℃; for 1h;	88.9%

androstanedione (846-46-8) → Androsta-1,4-diene-3,17-dione (897-06-3) + 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 70℃; for 24h;	A 4% B 84%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 70℃; for 24h; Dehydrogenation;	A 4% B 84%

Stanolone (521-18-6) → androstanedione (846-46-8) + 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With 1-tosyloxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one In dichloromethane at 20℃; for 10h;	A 45% B 17%

Epiandrosterone (481-29-8) → testosterone (58-22-0) + 3β,11α-dihydroxy-5α-androstan-17-one (25848-75-3) + 3beta-7alpha-Dihydroxy-5alpha-androstane-17-one (25848-68-4) + 3beta-7beta-Dihydroxy-5alpha-androstane-17-one (25848-69-5) + 1α,3β-dihydroxy-5α-androstan-17-one (2260-01-7) + Androsta-1,4-diene-3,17-dione (897-06-3) + 1-dehydrotestosterone (846-48-0) + 6β-hydroxytestosterone (62-99-7, 2944-87-8, 34096-63-4, 34442-08-5, 145772-79-8) + 5α-androst-1-ene-3,17-dione (571-40-4) + 6β-hydroxy-4-androstene-3,17-dione (63-00-3)

Conditions	Yield
With malt extract; disodium hydrogenphosphate; calcium(II) chloride dihydrate; magnesium(II) chloride hexahydrate; strontium (III) chloride hexahydrate; potassium chloride; boric acid; sodium hydrogencarbonate; sodium sulfate; sodium chloride; potassium bromide; potassium hydroxide In water; N,N-dimethyl-formamide at 32℃; for 168h; pH=8; Enzymatic reaction;	A 2% B 2% C 2% D 3% E 5% F 5% G 3% H 2% I 2% J 32%

...Expand

2,4,6-trimethyl-pyridine (108-75-8) + 2α-bromo-3,17-dioxo-5α-androstane (28507-01-9) → Androstenedione (63-05-8) + 5α-androst-1-ene-3,17-dione (571-40-4)

5α-cholest-1-en-3-one (601-55-8) → 5α-androst-1-ene-3,17-dione (571-40-4)

(5S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (65556-93-6) → 5α-androst-1-ene-3,17-dione (571-40-4)

androstanedione (846-46-8) → Androstenedione (63-05-8) + Androsta-1,4-diene-3,17-dione (897-06-3) + 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With Phenylselenyl chloride; dihydrogen peroxide Yield given. Multistep reaction. Yields of byproduct given;

2α-bromo-3,17-dioxo-5α-androstane (28507-01-9) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With lithium carbonate; lithium bromide

17β-hydroxy-5α-androsten-(1)-one-(3) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid

2α-bromo-4α-androstanedione-(3.17) → Androstenedione (63-05-8) + 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With 2,3,5-trimethyl-pyridine

Androsta-1,4-diene-3,17-dione (897-06-3) → Androstenedione (63-05-8) + androstane-3,17-dione (1229-12-5) + 5α-androst-1-ene-3,17-dione (571-40-4) + 5β-Androst-1-ene-3,17-dione (571-39-1)

Conditions	Yield
With sodium hydroxide; hydrogen; palladium on activated charcoal In methanol Further byproducts.;	A 29 % Chromat. B 16 % Chromat. C 2 % Chromat. D 23 % Chromat.

(5S,8R,9S,10S,13S,14S,17S)-2-bromo-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate (952222-37-6) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99.6 percent / lithium bromide; lithium carbonate / dimethylformamide / 0.5 h / Heating 2: 99.8 percent / sodium hydroxide / methanol / 2 h / 20 °C 3: 88.9 percent / chromium trioxide / acetic acid; H2O / 1 h / 25 - 30 °C View Scheme

stanolone acetate (1164-91-6) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / hydrogen chloride; bromine / acetic acid / 1 h / 20 - 25 °C 2: 99.6 percent / lithium bromide; lithium carbonate / dimethylformamide / 0.5 h / Heating 3: 99.8 percent / sodium hydroxide / methanol / 2 h / 20 °C 4: 88.9 percent / chromium trioxide / acetic acid; H2O / 1 h / 25 - 30 °C View Scheme

(5α,17β)-3-oxoandrost-1-en-17-yl acetate (64-82-4, 6656-41-3, 21507-42-6, 25615-33-2, 54631-35-5, 79732-37-9, 97413-69-9) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99.8 percent / sodium hydroxide / methanol / 2 h / 20 °C 2: 88.9 percent / chromium trioxide / acetic acid; H2O / 1 h / 25 - 30 °C View Scheme

Stanolone (521-18-6) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridinium chlorochromate 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; trifluoroacetic acid / dimethyl sulfoxide; fluorobenzene / 40 h / 60 °C View Scheme

5α-androst-1-ene-3,17-dione (571-40-4) + thiourea (17356-08-0) → C20H30N2O2S

Conditions	Yield
With sodium ethanolate In ethanol for 1h; Heating;	90%

thioacetic acid (507-09-5) + 5α-androst-1-ene-3,17-dione (571-40-4) → 1α-acetylsulfanyl-5α-androstane-3,17-dione (102443-87-8)

Conditions	Yield
UV-Licht.Irradiation;
im UV-Licht;

5α-androst-1-ene-3,17-dione (571-40-4) → androstanedione (846-46-8)

Conditions	Yield
With methanol; palladium on activated charcoal; Lindlar's catalyst Hydrogenation;

5α-androst-1-ene-3,17-dione (571-40-4) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
With fermenting yeast

5α-androst-1-ene-3,17-dione (571-40-4) → 5α-androstene-(1)-dione-(3.17)-dioxime

5α-androst-1-ene-3,17-dione (571-40-4) → 1α,2α-epoxy-5α-androstane-3,17-dione (3308-50-7)

Conditions	Yield
With methanol; sodium hydroxide; dihydrogen peroxide

5α-androst-1-ene-3,17-dione (571-40-4) + isopropyl alcohol (67-63-0) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
With sodium

5α-androst-1-ene-3,17-dione (571-40-4) + methylmagnesium bromide (75-16-1) → 1α-methyl-5α-androstane-3,17-dione (1423-99-0)

Conditions	Yield
With copper(l) chloride

5α-androst-1-ene-3,17-dione (571-40-4) + methylmagnesium bromide (75-16-1) → dimethylandrostanolone (2881-21-2)

Conditions	Yield
With copper(l) chloride

5α-androst-1-ene-3,17-dione (571-40-4) + methylmagnesium bromide (75-16-1) → 3ξ,17β-Dihydroxy-3ξ,17α-dimethyl-androsten-(1)

Conditions	Yield
With copper(l) chloride

5α-androst-1-ene-3,17-dione (571-40-4) + methylmagnesium bromide (75-16-1) → 3ξ-Hydroxy-3ξ-methyl-5α-androsten-(1)-on-(17)

Conditions	Yield
With copper(l) chloride

methanol (67-56-1) + 5α-androst-1-ene-3,17-dione (571-40-4) + palladium/calcium carbonate → androstanedione (846-46-8)

Conditions	Yield
Hydrogenation;

5α-androst-1-ene-3,17-dione (571-40-4) + aq.-ethanolic solution + fermenting yeast → 5α-androstanediol-(3β.17ξ)

5α-androst-1-ene-3,17-dione (571-40-4) + isopropyl alcohol (67-63-0) + sodium → 5α-androstanediol-(3β.17ξ)

5α-androst-1-ene-3,17-dione (571-40-4) → 5α-androst-1-ene-3α,17α-diol + 5α-androst-1-ene-3β,17α-diol + 5α-androst-1-ene-3α,17β-diol (38859-38-0) + 5α-androst-1-ene-3β,17β-diol

Conditions	Yield
With potassium tri-sec-butyl-borohydride In various solvent(s) at 20℃; for 1h;	A 1 % Chromat. B 9 % Chromat. C 8 % Chromat. D 51 % Chromat.

Upstream product

• 846-46-8 (5ξ)-androstane-3,17-dione 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 28507-01-9 2α-bromo-5α-androstane-3,17-dione 
• 521-18-6 Stanolone 
• 481-29-8 Epiandrosterone 
• 64-82-4 (5α,17β)-3-oxoandrost-1-en-17-yl acetate 
• 1164-91-6 stanolone acetate 
• 952222-37-6 (5S,8R,9S,10S,13S,14S,17S)-2-bromo-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate 
• 897-06-3 Androsta-1,4-diene-3,17-dione 
• 65-06-5 1-testosterone 
• 846-46-8 androstanedione 
• 65556-93-6 (5S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one 
• 601-55-8 5α-cholest-1-en-3-one 
• 846-46-8 (5ξ)-androstane-3,17-dione 

Downstream Products

• 571-20-0 5-androgen-3,17-diol 
• 897-06-3 Androsta-1,4-diene-3,17-dione 
• 23633-63-8 5α-androst-1-en-3β-ol-17-one 
• 5424-40-8 3β,17β-diacetoxy-5α-androstane 
• 846-46-8 androstanedione 
• 2881-21-2 1α,17α-Dimethyl-17β-hydroxy-5α-androstan-3-on 

Relevant articles and documents

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2-Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents

Two powerful hypervalent iodine(V) oxidants, DMP-OTs (1-tosyloxy-1,1-diacetoxy-1H-1λ5-benzo[d][1,2]iodoxol-3-one) and IBX-OTs (1-tosyloxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one) show high reactivity in the oxidation of structurally complex primary and secondary alcohols, which are highly functionalized polyketide or terpene fragments or steroids. The yields of the corresponding carbonyl compounds are even higher for the protocol that uses pyridine as additive. The oxidations proceed very rapidly at room temperature leaving the protective groups and π-systems intact and affording the corresponding carbonyl compounds in good to excellent yields. Moreover, IBX-OTs is an efficient reagent for the oxidative dehydrogenation of steroidal alcohols to the corresponding enones. (Figure presented.).

Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis

Mild and regioselective conversion of 3-keto-5α- and 3-keto-5β-steroids (trans A/B- and cis A/B-ring juncture, respectively) to the corresponding enones (Δ1- and Δ4-3- ketones) by treatment with o-iodoxybenzoic acid (IBX) catalyzed by trifluoroacetic acid (TFA) in DMSO, is described. The IBX-mediated reaction involved dehydrogenation of the α- and β-hydrogen atoms of the 3-ketones to give the enones regioselectively in good isolated yields without concomitant formation of related dienones and trienones.