Product Name

  • Name

    5-androstene-3,17-dione

  • EINECS
  • CAS No. 571-36-8
  • Article Data37
  • CAS DataBase
  • Density 1.11 g/cm3
  • Solubility
  • Melting Point 158 °C
  • Formula C19H26O2
  • Boiling Point 423.7 °C at 760 mmHg
  • Molecular Weight 286.414
  • Flash Point 158.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 571-36-8 (5-androstene-3,17-dione)
  • Hazard Symbols
  • Synonyms 5-Androsten-3,17-dione;NSC 12873;D5-Androstene-3,17-dione;
  • PSA 34.14000
  • LogP 4.08740

Synthetic route

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
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

Androstenedione

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
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

dehydroepiandrosterone

A

Androstenedione
63-05-8

Androstenedione

B

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
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

(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

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
With zinc In ethanol; water at 20℃; for 72h; Inert atmosphere;52%
dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

A

androst-4,6-diene-3,17-dione
633-34-1

androst-4,6-diene-3,17-dione

B

5-androstenedione
571-36-8

5-androstenedione

C

Androsta-1,4-diene-3,17-dione
897-06-3

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

Conditions
ConditionsYield
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%
...Expand
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-androstenediol

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
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

3-hydroxy-3,5-androstadien-17-one

A

Androstenedione
63-05-8

Androstenedione

B

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
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

3-hydroxy-3,5-androstadien-17-one

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
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

dehydroepiandrosterone

bromine
7726-95-6

bromine

acetic acid
64-19-7

acetic acid

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
nachfolgendes Behandeln mit CrO3 und Erwaermen des Reaktionsprodukts mit Zink-Pulver und Methanol;
...Expand
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-androstenediol

water
7732-18-5

water

bromine
7726-95-6

bromine

acetic acid
64-19-7

acetic acid

CrO3

CrO3

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
weitere Verbindung: Essigsaeure; Kochen des Reaktionsprodukts in Methanol mit Zink-Pulver;
...Expand
Androstenedione
63-05-8

Androstenedione

A

6α-hydroxy-androst-4-ene-3,17-dione
24704-84-5

6α-hydroxy-androst-4-ene-3,17-dione

B

5-androstenedione
571-36-8

5-androstenedione

C

6β-perhydroxyandrost-4-ene-3,17-dione

6β-perhydroxyandrost-4-ene-3,17-dione

D

6α-perhydroxyandrost-4-ene-3,17-dione

6α-perhydroxyandrost-4-ene-3,17-dione

E

androst-4-ene-3,6,17-trione
2243-06-3

androst-4-ene-3,6,17-trione

F

6β-hydroxy-4-androstene-3,17-dione
63-00-3

6β-hydroxy-4-androstene-3,17-dione

Conditions
ConditionsYield
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
...Expand
prasterone acetate
853-23-6

prasterone acetate

5-androstenedione
571-36-8

5-androstenedione

Conditions
ConditionsYield
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

5-androstenedione

ethylene glycol
107-21-1

ethylene glycol

3,3,17,17-diethylenedioxyandrost-5-ene
4966-70-5

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

Conditions
ConditionsYield
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

5-androstenedione

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;
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

5-androstenedione
571-36-8

5-androstenedione

androsten-3,5-dienyl-17-one 3-triflate
95667-41-7

androsten-3,5-dienyl-17-one 3-triflate

Conditions
ConditionsYield
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 dichloromethane81%
5-androstenedione
571-36-8

5-androstenedione

(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

(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

Conditions
ConditionsYield
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-androstenedione

5-hydro-3-oxaoctafluoropentanesulfonyl fluoride
104729-49-9

5-hydro-3-oxaoctafluoropentanesulfonyl fluoride

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

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
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene50%
lead(IV) acetate

lead(IV) acetate

5-androstenedione
571-36-8

5-androstenedione

4α-acetoxyandrost-5-ene-3,17-dione
1140823-19-3

4α-acetoxyandrost-5-ene-3,17-dione

Conditions
ConditionsYield
With acetic acid In toluene at 15 - 20℃; for 26h;25%
5-androstenedione
571-36-8

5-androstenedione

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

3α-hydroxy-androst-5-en-17-one
2283-82-1

3α-hydroxy-androst-5-en-17-one

Conditions
ConditionsYield
With ethanol; nickel Hydrogenation;
5-androstenedione
571-36-8

5-androstenedione

5-androgen-3,17-diol
571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
With fermenting yeast
5-androstenedione
571-36-8

5-androstenedione

androstene-(5)-dione-(3.17)-dioxime

androstene-(5)-dione-(3.17)-dioxime

5-androstenedione
571-36-8

5-androstenedione

androst-4-ene-3,6,17-trione
2243-06-3

androst-4-ene-3,6,17-trione

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane at 25℃; ultrasonic irradiation; Yield given;
5-androstenedione
571-36-8

5-androstenedione

3-hydroxy-3,5-androstadien-17-one
1229-13-6

3-hydroxy-3,5-androstadien-17-one

Conditions
ConditionsYield
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

5-androstenedione

(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

(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

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 25℃; Rate constant; Equilibrium constant; Mechanism; μ=1.0 with KCl;
5-androstenedione
571-36-8

5-androstenedione

6α-Chlor-androst-4-en-3,17-dion
50433-82-4

6α-Chlor-androst-4-en-3,17-dion

Conditions
ConditionsYield
With pyridine; sulfuryl dichloride
5-androstenedione
571-36-8

5-androstenedione

ethylene glycol
107-21-1

ethylene glycol

A

3,3,17,17-diethylenedioxyandrost-5-ene
4966-70-5

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

B

3,17-bis-cycloethylenedioxy-androst-5-ene
981-08-8

3,17-bis-cycloethylenedioxy-androst-5-ene

C

3,3-ethylenedioxy-5-androsten-17-one
3754-63-0

3,3-ethylenedioxy-5-androsten-17-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;
...Expand
5-androstenedione
571-36-8

5-androstenedione

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

acetic acid
64-19-7

acetic acid

Androstenedione
63-05-8

Androstenedione

...Expand
ethanol
64-17-5

ethanol

5-androstenedione
571-36-8

5-androstenedione

diluted aqueous sulfuric acid

diluted aqueous sulfuric acid

Androstenedione
63-05-8

Androstenedione

...Expand
ethanol
64-17-5

ethanol

5-androstenedione
571-36-8

5-androstenedione

fermenting upper yeast

fermenting upper yeast

A

testosterone
58-22-0

testosterone

B

5-androgen-3,17-diol
571-20-0

5-androgen-3,17-diol

...Expand
ethanol
64-17-5

ethanol

5-androstenedione
571-36-8

5-androstenedione

Raney nickel

Raney nickel

A

dehydroepiandrosterone
53-43-0

dehydroepiandrosterone

B

3α-hydroxy-androsten-(5)-one-(17)

3α-hydroxy-androsten-(5)-one-(17)

Conditions
ConditionsYield
Hydrogenation;
...Expand

Androst-5-ene-3,17-dione Specification

The CAS register number of Androst-5-ene-3,17-dione is 571-36-8. It also can be called as 5-Androsten-3,17-dione and the systematic name about this chemical is androst-5-ene-3,17-dione. The molecular formula about this chemical is C19H26O2 and the molecular weight is 286.4085. This chemical can be used in biochemistry.

Physical properties about Androst-5-ene-3,17-dione are: (1)ACD/LogP: 3.01; (2)ACD/LogD (pH 5.5): 3.01; (3)ACD/LogD (pH 7.4): 3.01; (4)ACD/BCF (pH 5.5): 113.59; (5)ACD/BCF (pH 7.4): 113.59; (6)ACD/KOC (pH 5.5): 1029.98; (7)ACD/KOC (pH 7.4): 1029.98; (8)#H bond acceptors: 2; (9)Polar Surface Area: 34.14Å2; (10)Index of Refraction: 1.551; (11)Molar Refractivity: 81.71 cm3; (12)Molar Volume: 255.8 cm3; (13)Polarizability: 32.39x10-24cm3; (14)Surface Tension: 42.6 dyne/cm; (15)Enthalpy of Vaporization: 67.81 kJ/mol; (16)Boiling Point: 423.7 °C at 760 mmHg; (17)Vapour Pressure: 2.19E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C4C/C3=C/C[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/h3,14-16H,4-11H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
(3)InChIKey: SQGZFRITSMYKRH-QAGGRKNEBS
(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/h3,14-16H,4-11H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
(5)Std. InChIKey: SQGZFRITSMYKRH-QAGGRKNESA-N

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