5alpha-Androstane-3b,17b-diol supplier

Name
5alpha-Androstane-3b,17b-diol
EINECS 209-334-3
CAS No. 571-20-0
Article Data120
CAS DataBase
Density 1.09g/cm³
Solubility
Melting Point 161 °C
Formula C19H32 O2
Boiling Point 415°Cat760mmHg
Molecular Weight 292.462
Flash Point 186°C
Transport Information
Appearance
Safety Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating vapors.
Risk Codes 36/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5a-Androstane-3b,17b-diol (7CI,8CI); 3b,17b-Androstanediol; 3b,17b-Dihydroxy-5a-androstane; 3b-Adiol; Maxterone; NSC 50891
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
for 504h; Rhodotorula mucilaginosa;	A 18% B 35% C 30%

...Expand

: 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

Conditions	Yield
for 504h; Rhodotorula mucilaginosa;	A 21% B 33% C 5% D 33%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
With Cephalosporium aphidicola In ethanol; dimethyl sulfoxide for 168h;	A 9% B 3.5% C 1% D 5.5%

...Expand

: 71-23-8
propan-1-ol

: 481-29-8
Epiandrosterone

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

Conditions

Conditions	Yield
With sodium

: 93-59-4
Perbenzoic acid

: 906-83-2
pregnenolone acetate

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

Conditions

Conditions	Yield
With chloroform Kochen des Reaktionsprodukts mit wss.-methanol. KOH;

: 60-29-7
diethyl ether

: 481-29-8
Epiandrosterone

: 10557-57-0
propylmagnesium iodide

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

...Expand

: 60-29-7
diethyl ether

: 1239-31-2
3β-acetoxy-5α-androstan-17-one

: 1068-56-0
isopropylmagnesium iodide

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

Conditions

Conditions	Yield
Versetzen mit wss.HCl und Erwaermen des Reaktionsprodukts mit methanol.KOH;

...Expand

: 64-17-5
ethanol

: 65-06-5
1-testosterone

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

Conditions

Conditions	Yield
Behandeln mit gaerender Hefe;

: 58-22-0
testosterone

A: 521-18-6
Stanolone

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

Conditions

Conditions	Yield
With diethyl ether; palladium Hydrogenation;

: 58-22-0
testosterone

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

Conditions

Conditions	Yield
With rot causing bacteria

: 53-43-0
dehydroepiandrosterone

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

Conditions

Conditions	Yield
With acetic acid; platinum Hydrogenation;
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol Luche Cerium Reduction;

: 846-46-8
androstanedione

A: 481-29-8
Epiandrosterone

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

Conditions

Conditions	Yield
bei der Einwirkung von Faeulnisbakterien;

: 846-46-8
androstanedione

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

Conditions

Conditions	Yield
With rot causing bacteria in a(n) aqueous yeast-suspension at 36 - 37℃;
With ethanol; sodium
With fermenting yeast
With ethanol; sodium

: 571-36-8
5-androstenedione

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

Conditions

Conditions	Yield
With fermenting yeast

: 906-83-2
pregnenolone acetate

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

Conditions

Conditions	Yield
With potassium sulfate; dipotassium peroxodisulfate; sulfuric acid; acetic acid at 25℃; Kochen des Reaktionsprodukts mit aethanol. KOH;

: 1239-31-2
3β-acetoxy-5α-androstan-17-one

: 1068-56-0
isopropylmagnesium iodide

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

Conditions

Conditions	Yield
With diethyl ether Versetzen mit wss. HCl und Erhitzen des Reaktionsprodukts mit methanol. KOH;

: 571-40-4
5α-androst-1-ene-3,17-dione

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

Conditions

Conditions	Yield
With fermenting yeast

: 122747-40-4
3β-acetoxy-17β-cyclohexanecarbonyloxy-5α-androstane

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

Conditions

Conditions	Yield
With potassium hydroxide

: 571-40-4
5α-androst-1-ene-3,17-dione

: 67-63-0
isopropyl alcohol

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

Conditions

Conditions	Yield
With sodium

: 481-29-8
Epiandrosterone

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

B: 6247-88-7
(3β,5α,13α)-3-hydroxyandrostane-17-one

C: 138313-21-0
3β-hydroxy-13,17-seco-5α-androst-13-en-17-aldehyde

Conditions

Conditions	Yield
With triethylamine In acetonitrile for 0.916667h; Product distribution; Mechanism; Ambient temperature; Irradiation; other steroides; var. solvents; var. time;

...Expand

: 58-22-0
testosterone

A: 481-29-8
Epiandrosterone

B: 521-18-6
Stanolone

C: 53-41-8
cis-androsterone

D: 846-46-8
androstanedione

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

F: 1852-53-5
androstanediol

Conditions

Conditions	Yield
With total testicular homogenate of adult Sprague-Dawley rats treated with 6, des-Gly-NH210>LHRH ethylamide Product distribution; metabolism, <3H>labelled study, further: equine antibovine LH serum (JOAN-5-31-67);

...Expand

: 58-22-0
testosterone

A: 521-18-6
Stanolone

B: 53-41-8
cis-androsterone

C: 846-46-8
androstanedione

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

E: 1852-53-5
androstanediol

Conditions

Conditions	Yield
With carbon dioxide; 5α-reductase in testicular cells of adult male Sprague-Dawley rats; oxygen; NADP at 37℃; for 1.5h; Product distribution; Kinetics; <3H>labelled, metabolism with or without 7α-hydroxytestosterone;

...Expand

: 58-22-0
testosterone

A: 521-18-6
Stanolone

B: 571-22-2
5β-androstan-17β-ol-3-one

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

D: 1156-92-9
4-androstenediol

E: 1852-61-5
4-Androstene-3alpha,17beta-diol

Conditions

Conditions	Yield
With H2SiEt2; Rh-(R,R)-(+)-DIOP for 24h; Product distribution; other reducing agents;

...Expand

: 521-18-6
Stanolone

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

Conditions

Conditions	Yield
With potassium phosphate buffer; 3β,20β-hydroxysteroid oxidoreductase from sheep fetal blood; NADPH at 37℃; for 0.5h; Product distribution; Kinetics; Km = 74 μM, Vmax = 1.3 nmol min-1 (nmol of enzyme)-1;
Multi-step reaction with 2 steps 1: 5 percent / 504 h / Rhodotorula mucilaginosa 2: 30 percent / 504 h / Rhodotorula mucilaginosa View Scheme
With potassium phosphate; recombinant human aldo-keto reductase 1C1; NADPH In methanol at 37℃; pH=7; Kinetics; Reagent/catalyst; Concentration; aq. phosphate buffer; Enzymatic reaction; stereoselective reaction;
With aldo-keto reductase 1D1 E120H mutant; NADPH In acetonitrile at 37℃; pH=6; Kinetics; aq. phosphate buffer; Enzymatic reaction;
With potassium phosphate; rabbit aldose reductase-like protein AKR1B19; NADP In methanol at 37℃; pH=7.4; Kinetics; Enzymatic reaction;

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

: 108-24-7
acetic anhydride

: 5424-40-8
3β,17β-diacetoxy-5α-androstane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 0.0111667h; microwave irradiation;	100%

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

: 846-46-8
androstanedione

Conditions

Conditions	Yield
With sodium hypochlorite In acetic acid at 15 - 25℃;	96%
at 25℃; for 25h; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.01M KOH/t-butanol - water (1:1);	80%
In acetone at 20℃; for 48h; UV-irradiation; Inert atmosphere;	44%
With tert-butyl alcohol; N-bromoacetamide
With chromium(VI) oxide; acetic acid

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

: 98-59-9
p-toluenesulfonyl chloride

: 5α-androstane-3β,17β-diol di-p-toluenesulfonate

Conditions

Conditions	Yield
With pyridine at 28℃; for 48h;	87%

: 112-77-6
(Z)-9-octadecenoyl chloride

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

: 1239669-31-8
5α-androstane-3β,17β-diol dioleate

Conditions

Conditions	Yield
With dmap; 1-butyl-3-methylimidazolium chloride In pyridine at 40℃; for 0.0166667h; Microwave irradiation; Ionic liquid;	85%

: 371-27-7
2,2,2-trifluoroethylbutyrate

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

: 113999-46-5
Butyric acid (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Conditions

Conditions	Yield
In acetone at 45℃; for 23h; with Chromobacterium viscosum lipase;	83%

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

: 162465-84-1
1-(p-dimethylaminobenzoyl)-1,2,4-triazole

: 5α-androstane-3β,17β-diol bis(p-dimethylaminobenzoate)

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 24h; Ambient temperature;	77%

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

: 36239-09-5
ethyl chlorocarbonylacetate

: 3β,17β-diethylmalonate-5α-androstane

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	75%

: 7459-33-8
linoleyl chloride

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

: 1239669-32-9
5α-androstane-3β,17β-diol dilinoleate

Conditions

Conditions	Yield
With dmap; 1-butyl-3-methylimidazolium chloride In pyridine at 40℃; for 0.0166667h; Microwave irradiation; Ionic liquid;	74%

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

: trifluoroethyl levulinate

: 5α-androstane-3β,17β-diol-3-levulinate

Conditions

Conditions	Yield
With Candida antarctica lipase B In tetrahydrofuran at 45℃; for 60h;	71%

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

: 3-((1R,4aS,4bS,7S,8aS,10aS)-7-hydroxy-2,4b-dimethyltetradecahydrophenanthren-1-yl)propanal

Conditions

Conditions	Yield
With tetrabutylphosphonium dimethyl phosphate; 2,4,6-Triisopropylthiophenol; [Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF6 In toluene at 20℃; for 24h; Glovebox; Sealed tube; Irradiation;	69%

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

: 185049-55-2
3-(4-tert-butylphenyl)glutaric anhydride

: 3-(4-tert-Butyl-phenyl)-pentanedioic acid mono-{(3S,5S,8R,9S,10S,13S,14S,17S)-3-[3-(4-tert-butyl-phenyl)-4-carboxy-butyryloxy]-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl} ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	67%

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

: 5,10,15-triphenyl-20-p-benzoic acid porphyrin

: 5α-androstane-3β,17β-diol bis(p-(10',15',20'-triphenyl-5'-porphyrinyl)benzoate)

Conditions

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 12h; Ambient temperature;	64%

: 371-27-7
2,2,2-trifluoroethylbutyrate

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

: 113999-47-6
butyric acid-(3β-hydroxy-5α-androstanyl-(17β)-ester)

Conditions

Conditions	Yield
In acetone at 45℃; for 168h; with Bacillus subtilis protease;	60%

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

A: 481-29-8
Epiandrosterone

B: 846-46-8
androstanedione

Conditions

Conditions	Yield
With potato dextrose broth medium In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436;	A 60% B 10%

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

: 149707-76-6
O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) trichloroacetimidate

: C87H84O20

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 3h;	36%

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

A: 481-29-8
Epiandrosterone

B: 521-18-6
Stanolone

C: 846-46-8
androstanedione

Conditions

Conditions	Yield
at 25℃; for 12h; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.01M KOH/t-butanol - water (1:1);	A 3% B 28% C 30%

...Expand

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

: 183901-63-5
2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

: C87H84O20

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 3h;	15%

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

: 32212-65-0
5alpha-Androstane-3beta,11beta,17beta-triol

Conditions

Conditions	Yield
With Aspergillus tamarii KITA (QM 1223) In N,N-dimethyl-formamide at 30℃; for 120h; Microbiological reaction;	1%

: 110-86-1
pyridine

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

: 75-36-5
acetyl chloride

: 10437-36-2
5α-androstane-3-β,17β-diol 17-acetate

...Expand

5alpha-Androstane-3b,17b-diol Chemical Properties

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/cm³
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

5alpha-Androstane-3b,17b-diol Uses

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

5alpha-Androstane-3b,17b-diol Safety Profile

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

Product Name

5alpha-Androstane-3b,17b-diol

Synthetic route

5alpha-Androstane-3b,17b-diol Chemical Properties

5alpha-Androstane-3b,17b-diol Uses

5alpha-Androstane-3b,17b-diol Safety Profile

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