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63-05-8

Basic Information
CAS No.: 63-05-8
Name: Androst-4-ene-3,17-dione
Molecular Structure:
Molecular Structure of 63-05-8 (Androst-4-ene-3,17-dione)
Formula: C19H26O2
Molecular Weight: 286.45
Synonyms: 17-Ketotestosterone;3,17-Dioxoandrost-4-ene;4-Androstene-3,17-dione;Androstenedione;Fecundin;NSC 9563;SKF 2170;D4-Androstene-3,17-dione;Androstenedione;4-Androstenedione;
EINECS: 200-554-5
Density: 1.11 g/cm3
Melting Point: 170-171 °C(lit.)
Boiling Point: 431.4 °C at 760 mmHg
Flash Point: 161.1 °C
Solubility: 57.28mg/L(25 oC)
Appearance: white to off-white solid
Hazard Symbols: HarmfulXn
Risk Codes: 40
Safety: 22-24/25-36
Transport Information:
PSA: 34.14000
LogP: 4.08740
Synthetic route
58-22-0

testosterone

63-05-8

Androstenedione

Conditions
ConditionsYield
With Jones reagent In acetone at 0℃; Jones Oxidation;100%
With oxygen; nitrosonium tetrafluoroborate In dichloromethane at 20℃; for 4h;99%
With N-chloro-succinimide; dodecyl methyl sulfide; triethylamine In toluene at -40℃; for 16h; Corey-Kim oxidation;97%
25375-38-6

3-hydroxy-5-androsten-17-one

63-05-8

Androstenedione

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ferric nitrate In ethyl acetate at 0℃; for 65h; Reagent/catalyst;100%
68-96-2

17-hydroxyprogesterone

63-05-8

Androstenedione

Conditions
ConditionsYield
In water; acetonitrile at 20℃; Electrochemical reaction;99%
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane; acetonitrile for 0.75h;95%
With chromium(VI) oxide; acetic acid
4966-70-5

3,3,17,17-diethylenedioxyandrost-5-ene

63-05-8

Androstenedione

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 40℃; for 2h; pH=3; Temperature; Green chemistry;98.6%
With sulfuric acid; water; silica gel In toluene for 2h;92%
Multi-step reaction with 4 steps
1: hydrogenchloride / water; acetone / pH 1-6
2: potassium tert-butylate / tetrahydrofuran / Inert atmosphere; Reflux
3: tetrahydrofuran / Acidic conditions
4: sodium hydrogencarbonate; ruthenium trichloride; Oxone / ethyl acetate; acetonitrile; water / -20 - 30 °C
View Scheme
2283-82-1

3α-hydroxy-androst-5-en-17-one

63-05-8

Androstenedione

Conditions
ConditionsYield
With calcium hypochlorite; acetic acid In ethyl acetate at 30℃; for 1h; Temperature; Green chemistry;98.5%
81176-75-2

(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[α]phenanthrene-3,17-diol

63-05-8

Androstenedione

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane for 0.5h;98%
With 9-fluorenone; oxygen In dimethyl sulfoxide at 20℃; Irradiation;72%
571-36-8

5-androstenedione

63-05-8

Androstenedione

Conditions
ConditionsYield
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;
162657-73-0

3-cycloethylenedithio-17-cycloethylenedioxy-androst-4-ene

63-05-8

Androstenedione

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In benzene at 80℃; for 5h;90%
53-43-0

dehydroepiandrosterone

A

63-05-8

Androstenedione

B

5982-99-0

androstane-3,17-dione

Conditions
ConditionsYield
aluminum oxide; copper In toluene at 60℃;A 12%
B 88%
152-58-9

Cortexolone

63-05-8

Androstenedione

Conditions
ConditionsYield
In water; acetonitrile at 20℃; Electrochemical reaction;86%
With ammonium hydroxide; iodine In water; acetonitrile at 50℃; for 24h;78%
With manganese(IV) oxide In chloroform for 4h; Heating;67.6%
152-58-9, 601-05-8, 3614-16-2, 122405-55-4

17,21-dihydroxy-pregn-3,20-dione

63-05-8

Androstenedione

Conditions
ConditionsYield
With sodium methylate In 1,4-dioxane for 3h; Heating;86%
897-06-3

Androsta-1,4-diene-3,17-dione

63-05-8

Androstenedione

Conditions
ConditionsYield
With sodium hydroxide; iron pentacarbonyl In methanol; water at 50 - 60℃; for 16h;85%
With thallium(III) nitrate trihydrate In diethylene glycol dimethyl ether for 24h; Ambient temperature;29%
With hydrogen; silica gel; copper In toluene at 60℃; under 760 Torr; for 5h;
/PBKTC004-1620/

/PBKTC004-1620/

63-05-8

Androstenedione

Conditions
ConditionsYield
IrH5(P-(i-Pr)3)2 In various solvent(s) at 100℃; for 28h;83%
53-43-0

dehydroepiandrosterone

63-05-8

Androstenedione

Conditions
ConditionsYield
With <(C4Ph4COHOCC4Ph4)(μ-H)><(CO)4Ru2>; acetone at 56℃; for 24h;81%
Behandeln mit verschiedenen Dehydrierungsmitteln;
Einwirkung von Flavobacterium-Arten;
1156-92-9

4-androstenediol

63-05-8

Androstenedione

Conditions
ConditionsYield
at 25℃; for 25h; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.01M KOH/t-butanol - water (1:1);80%
103708-01-6

3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>androsta-3,4-diene-17-one

63-05-8

Androstenedione

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 60℃; for 12h;80%
With sulfuric acid In tetrahydrofuran at 60℃; for 12h;80%
76183-49-8

3-(m-chlorobenzoyloxy)androsta-3,5-dien-17-one

63-05-8

Androstenedione

Conditions
ConditionsYield
With potassium hydroxide In methanol for 1h; Heating;74%
57-88-5

cholesterol

A

63-05-8

Androstenedione

B

897-06-3

Androsta-1,4-diene-3,17-dione

C

40736-33-2

(20S)-20-hydroxymethylpregn-4-en-3-one

D

80981-37-9

24-norchol-4-ene-3,22-dione

E

80981-38-0

24-norchola-1,4-diene-3,22-dione

F

35525-27-0

(20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one

Conditions
ConditionsYield
Product distribution; degradation by the Mycobacterium mutant CCM 3528;A n/a
B 0.20 g
C n/a
D 0.36 g
E 1.21 g
F 71%
51154-62-2

(8S,9S,10R,13S,14S,Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

A

63-05-8

Androstenedione

B

68-96-2

17-hydroxyprogesterone

C

1662-06-2

17alpha,20beta-Dihydroxypregn-4-en-3-one

Conditions
ConditionsYield
With ruthenium trichloride; Oxone; sodium hydrogencarbonate In water; ethyl acetate; acetonitrile at -20 - 30℃;A 10%
B 70%
C 20%

A

63-05-8

Androstenedione

B

68-96-2

17-hydroxyprogesterone

C

17ξ,20ξ-epoxy-pregna-Δ4-dien-3-one

Conditions
ConditionsYield
With ruthenium trichloride; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 20℃;A 10%
B 70%
C 20%
110801-53-1

(8R,9S,10R,13S,14S)-10,13-Dimethyl-17-[1-tripropylsilanyloxy-eth-(Z)-ylidene]-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

63-05-8

Androstenedione

Conditions
ConditionsYield
With potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid68%

C22H31NOS2

63-05-8

Androstenedione

Conditions
ConditionsYield
With silica gel; copper(II) sulfate In toluene for 30h; Heating;62%
57-83-0

Progesterone

A

63-05-8

Androstenedione

B

4416-57-3

testololactone

Conditions
ConditionsYield
With penicillium citreo-viride A.C.C.C. 0402 In acetone at 27.5℃; for 120h; Microbiological reaction;A 8.4%
B 60.9%

pregn-4-ene-3ξ,17α,20ξ-triol

A

63-05-8

Androstenedione

B

68-96-2

17-hydroxyprogesterone

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane; acetonitrile for 0.75h;A 60%
B 20%
315-37-7

testosterone heptanoate

A

58-22-0

testosterone

B

63-05-8

Androstenedione

Conditions
ConditionsYield
With Fusarium fujikuroi PTCC 5144 In ethanol; water at 26℃; for 312h; Reagent/catalyst; Microbiological reaction;A 20%
B 17%
C 59%
1229-12-5

androstane-3,17-dione

63-05-8

Androstenedione

Conditions
ConditionsYield
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;54%
With sodium In methanol at 20℃; for 1h;
Multi-step reaction with 2 steps
1: 72percent HClO4 / ethyl acetate / 0.5 h / Ambient temperature
2: CrO3*2Py (Collins oxidant) / CH2Cl2 / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: HBr; acetic acid; bromine
2: pyridine
View Scheme
501433-34-7

5α/β-androst-3-en-17-one

A

63-05-8

Androstenedione

B

1229-12-5

androstane-3,17-dione

C

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
Multistep reaction;A n/a
B n/a
C 54%
63-05-8

Androstenedione

122-51-0

orthoformic acid triethyl ester

972-46-3

3-ethoxyandrosta-3,5-dien-17-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran; ethanol at 45℃; for 2h; Inert atmosphere;100%
With toluene-4-sulfonic acid In ethanol at 20 - 25℃;99.2%
Stage #1: Androstenedione; orthoformic acid triethyl ester With toluene-4-sulfonic acid In ethanol at 40℃; for 6.5h;
Stage #2: With triethylamine In ethanol at 5℃; for 0.5h; Temperature;
97%
63-05-8

Androstenedione

1852-61-5

4-Androstene-3alpha,17beta-diol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; Temperature; Solvent; Reagent/catalyst;100%
With potassium borohydride In methanol
63-05-8

Androstenedione

81176-75-2

(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[α]phenanthrene-3,17-diol

Conditions
ConditionsYield
With lithium borohydride In diethyl ether for 2h; Product distribution; Heating; other solvents and reducing agents also investigated;100%
With lithium borohydride In diethyl ether for 2h; Heating;100%
63-05-8

Androstenedione

149-73-5

trimethyl orthoformate

57144-06-6

3-methoxyandrosta-3,5-dien-17-one

Conditions
ConditionsYield
With p-toluenesulfonic acid hydrochloride In methanol at 35 - 45℃; for 5.25h; Inert atmosphere;100%
With toluene-4-sulfonic acid In tetrahydrofuran at 30℃; for 4h; Temperature; Inert atmosphere;100%
With toluene-4-sulfonic acid In tetrahydrofuran at 5℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere;97.3%
63-05-8

Androstenedione

75-86-5

2-hydroxy-2-methylpropanenitrile

77881-13-1

17β-cyano-17α-hydroxy-4-androsten-3-one

Conditions
ConditionsYield
With sodium carbonate In methanol; water at 17 - 40℃; for 29h; pH=8 - 9;100%
With water; sodium carbonate In methanol at 38 - 42℃; for 4h; pH=8 - 9;100%
With methanol; potassium hydroxide at 50℃; for 6h; Autoclave; Large scale;95.9%

potassium cyanide

63-05-8

Androstenedione

77881-13-1

17β-cyano-17α-hydroxy-4-androsten-3-one

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 2h; Inert atmosphere; regioselective reaction;100%
63-05-8

Androstenedione

1229-12-5

androstane-3,17-dione

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; for 24h;99.26%
With palladium 10% on activated carbon; hydrogen at 20℃; under 760.051 Torr; for 23h;74%
With hydrogen; palladium on activated charcoal In ethyl acetate Ambient temperature;
Multi-step reaction with 2 steps
1: 467 mg / Zn; glacial acetic acid / 0.17 h
View Scheme
63-05-8

Androstenedione

108-24-7

acetic anhydride

4968-05-2

androstane-3,5-dien-17-one-3β-ol acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 35 - 45℃; for 12h;99%
With toluene-4-sulfonic acid for 0.05h; microwave irradiation;97%
With toluene-4-sulfonic acid at 65℃; for 1.5h;76%
63-05-8

Androstenedione

564-33-0

11α-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
With Gelasinospora retispora GRK002 In methanol; water at 34℃; for 144h; pH=5; Microbiological reaction;98%
With Beauveria bassiana CCTCC AF206001 In water for 24h; pH=6.0; Microbiological reaction;90.9%
mit Hilfe von Rhizopus arrhizus;
63-05-8

Androstenedione

A

53-42-9

Etiocholanolone

B

1229-12-5

androstane-3,17-dione

Conditions
ConditionsYield
With foie de boeuf; levure de boulanger; tampon phosphate In water at 37℃; for 144h; Clostridium paraputrificum ATCC No. 25780; Yields of byproduct given;A 98%
B n/a
With foie de boeuf; levure de boulanger; tampon phosphate In water at 37℃; for 144h; Clostridium paraputrificum ATCC No. 25780; Yields of byproduct given;A n/a
B 85%
With foie de boeuf; levure de boulanger; tampon phosphate In water at 37℃; for 144h; Product distribution; Clostridium paraputrificum ATCC No. 25780; composition of the culture medium, different species and influence of the steroid concentration examined;
63-05-8

Androstenedione

74-86-2

acetylene

434-03-7

levonorgestrel

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; ethanol95%
Stage #1: acetylene With potassium hydroxide In tetrahydrofuran; ethanol at 3℃; for 2h; Inert atmosphere;
Stage #2: Androstenedione In tetrahydrofuran; ethanol for 2h; Temperature; Solvent; Reagent/catalyst;
109.3 g
63-05-8

Androstenedione

122-51-0

orthoformic acid triethyl ester

57144-06-6

3-methoxyandrosta-3,5-dien-17-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran; chloroform at 38℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;94.27%
1445-45-0

Trimethyl orthoacetate

63-05-8

Androstenedione

57144-06-6

3-methoxyandrosta-3,5-dien-17-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran; methanol at 30℃; for 4h; Inert atmosphere; Industrial scale;94%
63-05-8

Androstenedione

58-22-0

testosterone

Conditions
ConditionsYield
With zygowilliopsis sp. WY7905 In aq. phosphate buffer at 30℃; for 24h; pH=8; Enzymatic reaction; stereoselective reaction;93%
With potassium borohydride In tetrahydrofuran; dichloromethane; water at -10 - -5℃; Temperature;93%
With Trichoderma virens In ethanol at 24℃; for 96h; Microbiological reaction;60%
63-05-8

Androstenedione

21749-63-3

2-(methylamino)benzenethiol

C26H33NOS

Conditions
ConditionsYield
In dichloromethane for 48h; Heating;93%
63-05-8

Androstenedione

260352-51-0

C19H25IO2

Conditions
ConditionsYield
Stage #1: Androstenedione With trimethylsilylazide In dichloromethane at 0℃; for 2h;
Stage #2: With pyridine; iodine In dichloromethane at 0 - 20℃;
93%
63-05-8

Androstenedione

3066-12-4

11α,17β-dihydroxyandrost-4-ene-3-one

Conditions
ConditionsYield
With Beauveria bassiana CCTCC AF206001 In water for 48h; pH=7.0; Microbiological reaction;91.3%
(microbiological transformation);
63-05-8

Androstenedione

4-androsten-3,17-dione-2,2,4,6,6,16,16-d7

Conditions
ConditionsYield
With hydrogenchloride; deuteromethanol In water at 56℃; Temperature; Inert atmosphere;91%
63-05-8

Androstenedione

86420-28-2

dehydroisoandrosterone

Conditions
ConditionsYield
With titanium(IV) isopropylate; 2,2'-azobis(isobutyronitrile); diphenylstibane In toluene at 90℃; for 16h;90%
63-05-8

Androstenedione

846-46-8

androstanedione

Conditions
ConditionsYield
With sodium dithionite; phase transfer catalyst; sodium hydrogencarbonate In toluene for 4h; Heating;88%
With hydrogen; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate In dichloromethane for 4h;70%
biochem. proc. with 5α-reductase of Penicillin decumbens;70%
63-05-8

Androstenedione

7191-30-2

2,2-dibutyl-1,3,2-dithiastannolane

A

63910-90-7

4-Androstene-3,17-dione 3-ethylene dithioacetal

B

10455-49-9

4-Androstene-3,17-dione 3,17-bis(ethylene dithioacetal)

Conditions
ConditionsYield
di-n-butylbis(trifluoromethanesulfonyloxy)stannane In 1,2-dichloro-ethane at 20℃; for 4h;A 87%
B 7%
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  • Androst-4-ene-3,17-dione CAS NO.63-05-8

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    Androst-4-ene-3,17-dione CAS NO.63-05-8

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    Details Product Name: Androstenedione Synonyms: 3,17-Dioxoandrost-4-Ene;delta-(sup4)-Androsten-3,17-dione;delta(Sup4)-Androstene-3,17-dione;delta4-androsten-3,17-dione;delta-4-

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    CAS:63-05-8 Androstenedione

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    Details Details 4-Androstenedione Formula: C19H26O2 CAS 63-05-8 Molecular Weight: 286.45 EINECS: 200-554-5 Assay: 99% Appearance: white crystalline odourless solid Package: 1kg/foil bag o

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    63-05-8 Androst-4-ene-3,17-dione

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    Androstenedione cas 63-05-8

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History

Androstenedione was manufactured as a dietary supplement, often called andro for short.
Andro was legal and able to be purchased over the counter and consequently it was common use in Major League Baseball throughout the 1990s by record-breaking sluggers like Mark McGwire. The supplement is banned by the World Anti-Doping Agency, and hence from the Olympic Games.
On March 12, 2004, the Anabolic Steroid Control Act of 2004 was introduced into the United States Senate. The law took effect on January 20, 2005. Surprisingly, andro was legally defined as an anabolic steroid, even though there is scant evidence that androstenedione itself is anabolic in nature.
On April 11, 2004, the United States Food and Drug Administration banned the sale of Andro.
Androstenedione is currently banned by the US military.

Specification

The Androstenedione is an organic compound with the formula C19H26O2. The IUPAC name of this chemical is (8R,9S,10R,13S,14S)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione. With the CAS registry number 63-05-8, it is also named as 4-Androsten-3,17-dione. The product's categories are Pharmaceutical Intermediates; Steroids; Metabolites & Impurities. Besides, it is a white to off-white solid, which should be stored in a closed place. It is used for biochemical studies.

Physical properties about Androstenedione are: (1)ACD/LogP: 2.90; (2)ACD/LogD (pH 5.5): 2.9; (3)ACD/LogD (pH 7.4): 2.9; (4)ACD/BCF (pH 5.5): 93.64; (5)ACD/BCF (pH 7.4): 93.64; (6)ACD/KOC (pH 5.5): 896.96; (7)ACD/KOC (pH 7.4): 896.96; (8)#H bond acceptors: 2; (9)Polar Surface Area: 34.14 Å2; (10)Index of Refraction: 1.551; (11)Molar Refractivity: 81.71 cm3; (12)Molar Volume: 255.8 cm3; (13)Polarizability: 32.39×10-24cm3; (14)Surface Tension: 42.6 dyne/cm; (15)Density: 1.11 g/cm3; (16)Flash Point: 161.1 °C; (17)Enthalpy of Vaporization: 68.71 kJ/mol; (18)Boiling Point: 431.4 °C at 760 mmHg; (19)Vapour Pressure: 1.2E-07 mmHg at 25°C.

Preparation: this chemical can be prepared by 17-hydroxy-androst-4-en-3-one. This reaction will need reagent CrO3 and acetic acid.



Uses of Androstenedione: it can be used to produce 5,17-dioxo-3,5-seco-A-nor-androstan-3-oic acid. It will need reagent KMnO4 and acetone.

When you are using this chemical, please be cautious about it as the following:
It has limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing, do not breathe dust and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C4/C=C3/CC[C@@H]2[C@H](CC[C@@]1(C(=O)CC[C@H]12)C)[C@@]3(C)CC4
(2)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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
(3)InChIKey: AEMFNILZOJDQLW-QAGGRKNEBJ
(4)Std. InChI: InChI=1S/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
(5)Std. InChIKey: AEMFNILZOJDQLW-QAGGRKNESA-N