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Basic Information
CAS No.: 571-20-0
Name: 5alpha-Androstane-3b,17b-diol
Article Data: 120
Molecular Structure:
Molecular Structure of 571-20-0 (5alpha-Androstane-3b,17b-diol)
Formula: C19H32 O2
Molecular Weight: 292.462
Synonyms: 5a-Androstane-3b,17b-diol (7CI,8CI); 3b,17b-Androstanediol; 3b,17b-Dihydroxy-5a-androstane; 3b-Adiol; Maxterone; NSC 50891
EINECS: 209-334-3
Density: 1.09g/cm3
Melting Point: 161 °C
Boiling Point: 415°Cat760mmHg
Flash Point: 186°C
Hazard Symbols: Xi
Risk Codes: 36/38
Safety: Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating vapors.
PSA: 40.46000
LogP: 3.75090
Synthetic route
1239-31-2

3β-acetoxy-5α-androstan-17-one

571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
With diisobutylaluminium hydride; nickel dichloride In dichloromethane; toluene at -78℃; for 0.25h; Inert atmosphere;99%
Multi-step reaction with 2 steps
1: 97 percent / NaBH4 / methanol / 1 h / 0 - 20 °C
2: 95 percent / NaOH / methanol / 0.17 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / 0.42 h / 20 °C / Inert atmosphere
2: potassium carbonate / methanol / 24 h / 20 °C / Inert atmosphere
View Scheme
481-29-8

Epiandrosterone

571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 20℃;95%
With ethanol; nickel Hydrogenation;
With hydrogenchloride; acetic acid; platinum Hydrogenation.;
3090-70-8

(3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
With sodium hydroxide In methanol for 0.166667h; Heating;95%
With potassium carbonate In methanol at 20℃; for 24h; Inert atmosphere;89%
With sodium hydroxide In methanol Yield given;
1239-31-2

3β-acetoxy-5α-androstan-17-one

A

3090-70-8

(3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

B

571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,4-dioxane; methanol for 6h; Ambient temperature; Yields of byproduct given;A 86%
B n/a
With sodium tetrahydroborate In 1,4-dioxane; methanol for 6h; Ambient temperature; Yields of byproduct given;A n/a
B 760 mg
16992-89-5

3α-hydroxyandrost-4-en-17β-yl acetate

A

571-20-0

5-androgen-3,17-diol

B

1852-53-5

androstanediol

C

17β-ethoxy-5β-androstane-3α,4β-diol

D

5β-androstane-3α,4β,17β-triol

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide; diborane Product distribution; multistep reaction: 1.) THF, 0 deg C, 4 h, 2.) overnight; hydroboration of androst-4-enes; stereochemical aspects;A n/a
B n/a
C 21%
D 63%
With sodium hydroxide; dihydrogen peroxide; diborane 1.) THF, 0 deg C, 4 h, 2.) overnight; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With sodium hydroxide; dihydrogen peroxide; diborane 1.) THF, 0 deg C, 4 h, 2.) overnight; Yield given. Multistep reaction. Yields of byproduct given;
846-46-8

androstanedione

A

481-29-8

Epiandrosterone

B

53-41-8

cis-androsterone

C

571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
for 504h; Rhodotorula mucilaginosa;A 18%
B 35%
C 30%
521-18-6

Stanolone

A

481-29-8

Epiandrosterone

B

53-41-8

cis-androsterone

C

846-46-8

androstanedione

D

571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
for 504h; Rhodotorula mucilaginosa;A 21%
B 33%
C 5%
D 33%
521-18-6

Stanolone

A

571-20-0

5-androgen-3,17-diol

B

27261-27-4

5α-androstane-3β,17β,16β-triol

C

121209-70-9

5α-androstane-2β,3α,16α,17β-tetrol

Conditions
ConditionsYield
With fungus Gnomonia fructicola In ethanol at 24 - 26℃; for 120h;A 3%
B 20%
C 3%
With fungus Gnomonia fructicola In ethanol at 24 - 26℃; for 120h;A 3%
B 20%
C 3%
846-46-8

androstanedione

A

481-29-8

Epiandrosterone

B

29907-31-1

11α-hydroxy-5α-androstane-3,17-dione

C

17752-36-2

3β,5α-dihydroxy-5α-androstan-17-one

D

571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
With Cephalosporium aphidicola In ethanol; dimethyl sulfoxide for 168h;A 9%
B 3.5%
C 1%
D 5.5%
71-23-8

propan-1-ol

481-29-8

Epiandrosterone

571-20-0

5-androgen-3,17-diol

Conditions
ConditionsYield
With sodium
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Chemistry

IUPAC Name:   (3S,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
Synonyms:  10,13-Dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3,17-diol ; 10,13-Dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol ; 10,13-Diméthylhexadécahydro-1H-cyclopenta[a]phénanthrène-3,17-diol ; androstane-3,17-diol ; 3.alpha-17.beta.-Dihydroxy-5.alpha.-androstane ; 3alpha,17alpha-Dihydroxy-5beta-androstane ; 3alpha,17-Dihydroxy-5beta-androstane ; 3beta,17alpha-Dihydroxy-5alpha-androstane ; 3-beta,17-beta-Androstanediol ; 3beta,17beta-Dihydroxy-5alpha-androstane ; 3-beta,17-beta-Dihydroxy-5-alpha-androstane
The Molecular Formula of   5-alpha-Androstane-3-beta-17-beta-diol (571-20-0):C19H32O2
The Molecular Weight of   5-alpha-Androstane-3-beta-17-beta-diol (571-20-0):292.456180 g/mol
The Molecular Structure of   5-alpha-Androstane-3-beta-17-beta-diol (571-20-0):
Index of Refraction: 1.546
Molar Refractivity: 84.95 cm3
Molar Volume: 268.1 cm3
Polarizability: 33.67x 10-24cm3
Surface Tension: 42.6 dyne/cm
Density: 1.09 g/cm
Flash Point: 186 °C
Enthalpy of Vaporization: 77.17 kJ/mol
Boiling Point: 415 °C at 760 mmHg
Vapour Pressure: 1.27E-08 mmHg at 25°C 

Uses

5-alpha-Androstane-3-beta-17-beta-diol (571- 20-0) can be used as anabolic agent.

Safety Profile

Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating vapors.