571-20-0

Basic information

• Product Name: 5alpha-Androstane-3b,17b-diol
• Synonyms: 3b,17b-dihydroxy-5a-androstane;3BETA,17BETA-DIHYDROXY-5ALPHA-ANDROSTANE;5ALPHA-ANDROSTAN-3BETA,17BETA-DIOL;5 ALFA-ANDROSTANE-3BETA, 17BETA-DIOL;5ALPHA-ANDROSTANE-3BETA,17BETA-DIOL;5A-ANDROSTEN-3B,17B-DIOL;5A-ANDROSTEN-3BETA,17BETA-DIOL;5A-ANDROSTAN-3B,17B-DIOL
• CAS NO: 571-20-0
• Molecular Formula: C19H32O2
• Molecular Weight: 292.46
• EINECS: 209-334-3
• Product Categories: Steroids;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals
• Mol File: 571-20-0.mol
• Article Data: 45

Chemical Properties

• Melting Point: 161 °C
• Boiling Point: 374.38°C (rough estimate)
• Flash Point: 186°C
• Appearance: /
• Density: 1.0164 (rough estimate)
• Vapor Pressure: 1.27E-08mmHg at 25°C
• Refractive Index: 1.4709 (estimate)
• PKA: 15.07±0.70(Predicted)
• CAS DataBase Reference: 5alpha-Androstane-3b,17b-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 5alpha-Androstane-3b,17b-diol(571-20-0)
• EPA Substance Registry System: 5alpha-Androstane-3b,17b-diol(571-20-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 24-45
• RTECS: BV8044320
• Hazardous Substances Data: 571-20-0(Hazardous Substances Data)

Usage

Uses

5α-Androstane-3β,17β-diol is a metabolite of Testosterone (T155000).

Definition

ChEBI: An androstane-3,17-diol that is 5alpha-androstane substituted by beta-hydroxy groups at positions 3 and 17. It is a metabolite of dihydrotestosterone.

InChI:InChI=1/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1

Synthetic route

3β-acetoxy-5α-androstan-17-one (1239-31-2) → 5-androgen-3,17-diol (571-20-0)

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

Epiandrosterone (481-29-8) → 5-androgen-3,17-diol (571-20-0)

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

(3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (3090-70-8) → 5-androgen-3,17-diol (571-20-0)

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;

3β-acetoxy-5α-androstan-17-one (1239-31-2) → (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (3090-70-8) + 5-androgen-3,17-diol (571-20-0)

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

3α-hydroxyandrost-4-en-17β-yl acetate (16992-89-5) → 5-androgen-3,17-diol (571-20-0) + androstanediol (1852-53-5) + 17β-ethoxy-5β-androstane-3α,4β-diol + 5β-androstane-3α,4β,17β-triol

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;

androstanedione (846-46-8) → Epiandrosterone (481-29-8) + cis-androsterone (53-41-8) + 5-androgen-3,17-diol (571-20-0)

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

Stanolone (521-18-6) → Epiandrosterone (481-29-8) + cis-androsterone (53-41-8) + androstanedione (846-46-8) + 5-androgen-3,17-diol (571-20-0)

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

Stanolone (521-18-6) → 5-androgen-3,17-diol (571-20-0) + 5α-androstane-3β,17β,16β-triol (27261-27-4) + 5α-androstane-2β,3α,16α,17β-tetrol (121209-70-9)

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%

androstanedione (846-46-8) → Epiandrosterone (481-29-8) + 11α-hydroxy-5α-androstane-3,17-dione (29907-31-1) + 3β,5α-dihydroxy-5α-androstan-17-one (17752-36-2) + 5-androgen-3,17-diol (571-20-0)

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

propan-1-ol (71-23-8) + Epiandrosterone (481-29-8) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
With sodium

Perbenzoic acid (93-59-4) + pregnenolone acetate (906-83-2) → 5-androgen-3,17-diol (571-20-0)

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

diethyl ether (60-29-7) + Epiandrosterone (481-29-8) + propylmagnesium iodide (10557-57-0) → 5-androgen-3,17-diol (571-20-0)

diethyl ether (60-29-7) + 3β-acetoxy-5α-androstan-17-one (1239-31-2) + isopropylmagnesium iodide (1068-56-0) → 5-androgen-3,17-diol (571-20-0)

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

ethanol (64-17-5) + 1-testosterone (65-06-5) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
Behandeln mit gaerender Hefe;

testosterone (58-22-0) → Stanolone (521-18-6) + 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
With diethyl ether; palladium Hydrogenation;

testosterone (58-22-0) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
With rot causing bacteria

dehydroepiandrosterone (53-43-0) → 5-androgen-3,17-diol (571-20-0)

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

androstanedione (846-46-8) → Epiandrosterone (481-29-8) + 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
bei der Einwirkung von Faeulnisbakterien;

androstanedione (846-46-8) → 5-androgen-3,17-diol (571-20-0)

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

5-androstenedione (571-36-8) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
With fermenting yeast

pregnenolone acetate (906-83-2) → 5-androgen-3,17-diol (571-20-0)

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

3β-acetoxy-5α-androstan-17-one (1239-31-2) + isopropylmagnesium iodide (1068-56-0) → 5-androgen-3,17-diol (571-20-0)

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

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

Conditions	Yield
With fermenting yeast

3β-acetoxy-17β-cyclohexanecarbonyloxy-5α-androstane (122747-40-4) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
With potassium hydroxide

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

Epiandrosterone (481-29-8) → 5-androgen-3,17-diol (571-20-0) + (3β,5α,13α)-3-hydroxyandrostane-17-one (6247-88-7) + 3β-hydroxy-13,17-seco-5α-androst-13-en-17-aldehyde (138313-21-0)

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

testosterone (58-22-0) → Epiandrosterone (481-29-8) + Stanolone (521-18-6) + cis-androsterone (53-41-8) + androstanedione (846-46-8) + 5-androgen-3,17-diol (571-20-0) + androstanediol (1852-53-5)

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);

testosterone (58-22-0) → Stanolone (521-18-6) + cis-androsterone (53-41-8) + androstanedione (846-46-8) + 5-androgen-3,17-diol (571-20-0) + androstanediol (1852-53-5)

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;

testosterone (58-22-0) → Stanolone (521-18-6) + 5β-androstan-17β-ol-3-one (571-22-2) + 5-androgen-3,17-diol (571-20-0) + 4-androstenediol (1156-92-9) + 4-Androstene-3alpha,17beta-diol (1852-61-5)

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

Stanolone (521-18-6) → 5-androgen-3,17-diol (571-20-0)

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;

5-androgen-3,17-diol (571-20-0) + acetic anhydride (108-24-7) → 3β,17β-diacetoxy-5α-androstane (5424-40-8)

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

5-androgen-3,17-diol (571-20-0) → androstanedione (846-46-8)

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

5-androgen-3,17-diol (571-20-0) + p-toluenesulfonyl chloride (98-59-9) → 5α-androstane-3β,17β-diol di-p-toluenesulfonate

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

(Z)-9-octadecenoyl chloride (112-77-6) + 5-androgen-3,17-diol (571-20-0) → 5α-androstane-3β,17β-diol dioleate (1239669-31-8)

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

2,2,2-trifluoroethylbutyrate (371-27-7) + 5-androgen-3,17-diol (571-20-0) → Butyric acid (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester (113999-46-5)

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

5-androgen-3,17-diol (571-20-0) + 1-(p-dimethylaminobenzoyl)-1,2,4-triazole (162465-84-1) → 5α-androstane-3β,17β-diol bis(p-dimethylaminobenzoate)

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

5-androgen-3,17-diol (571-20-0) + ethyl chlorocarbonylacetate (36239-09-5) → 3β,17β-diethylmalonate-5α-androstane

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

linoleyl chloride (7459-33-8) + 5-androgen-3,17-diol (571-20-0) → 5α-androstane-3β,17β-diol dilinoleate (1239669-32-9)

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

5-androgen-3,17-diol (571-20-0) + trifluoroethyl levulinate → 5α-androstane-3β,17β-diol-3-levulinate

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

5-androgen-3,17-diol (571-20-0) → 3-((1R,4aS,4bS,7S,8aS,10aS)-7-hydroxy-2,4b-dimethyltetradecahydrophenanthren-1-yl)propanal

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%

5-androgen-3,17-diol (571-20-0) + 3-(4-tert-butylphenyl)glutaric anhydride (185049-55-2) → 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	Yield
With toluene-4-sulfonic acid In toluene Heating;	67%

5-androgen-3,17-diol (571-20-0) + 5,10,15-triphenyl-20-p-benzoic acid porphyrin → 5α-androstane-3β,17β-diol bis(p-(10',15',20'-triphenyl-5'-porphyrinyl)benzoate)

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

2,2,2-trifluoroethylbutyrate (371-27-7) + 5-androgen-3,17-diol (571-20-0) → butyric acid-(3β-hydroxy-5α-androstanyl-(17β)-ester) (113999-47-6)

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

5-androgen-3,17-diol (571-20-0) → Epiandrosterone (481-29-8) + androstanedione (846-46-8)

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

5-androgen-3,17-diol (571-20-0) + O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) trichloroacetimidate (149707-76-6) → C87H84O20

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

5-androgen-3,17-diol (571-20-0) → Epiandrosterone (481-29-8) + Stanolone (521-18-6) + androstanedione (846-46-8)

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%

5-androgen-3,17-diol (571-20-0) + 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (183901-63-5) → C87H84O20

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

5-androgen-3,17-diol (571-20-0) → 5alpha-Androstane-3beta,11beta,17beta-triol (32212-65-0)

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

pyridine (110-86-1) + 5-androgen-3,17-diol (571-20-0) + acetyl chloride (75-36-5) → 5α-androstane-3-β,17β-diol 17-acetate (10437-36-2)

Upstream product

• 71-23-8 propan-1-ol 
• 481-29-8 Epiandrosterone 
• 60-29-7 diethyl ether 
• 1239-31-2 3β-acetoxy-5α-androstan-17-one 
• 1068-56-0 isopropylmagnesium iodide 
• 64-17-5 ethanol 
• 65-06-5 1-testosterone 
• 846-46-8 androstanedione 
• 571-40-4 5α-androst-1-ene-3,17-dione 
• 67-63-0 isopropyl alcohol 
• 10467-10-4 ethylmagnesium iodide 
• 71-43-2 benzene 
• 53-43-0 dehydroepiandrosterone 
• 64-19-7 acetic acid 

Downstream Products

• 53-41-8 epiandrosterone 
• 846-46-8 androstanedione 
• 3090-70-8 (3S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 1229-12-5 androstane-3,17-dione 
• 846-46-8 androstanedione 
• 481-29-8 Epiandrosterone 
• 19316-62-2 5-alpha-Androstane-3-beta,7-alpha,17-beta-triol 
• 521-18-6 Stanolone 
• 63-05-8 Androstenedione 
• 49644-04-4 5α-androstane-3β,6α,17β-triol 
• 32212-65-0 5α-androstan-3β,11β,17β-triol 
• 3597-54-4 androstenol 
• 53-41-8 cis-androsterone 
• 198560-58-6 3-(4-tert-Butyl-phenyl)-4-(2-sulfo-ethylcarbamoyl)-butyric acid (3S,5S,6S,8R,9S,10R,13S,14S,17S)-17-[3-(4-tert-butyl-phenyl)-4-(2-sulfo-ethylcarbamoyl)-butyryloxy]-6-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 

Relevant articles and documents

Formation of 5α-dihydrotestosterone from 5α-androstane-3α,17β-diol in prostate cancer LAPC-4 cells – Identifying inhibitors of non-classical pathways producing the most potent androgen

5α-Dihydrotestosterone (5α-DHT) possesses a great affinity for the androgen receptor (AR), and its binding to AR promotes the proliferation of prostate cancer (PC) cells in androgen-dependent PC. Primarily synthesized from testosterone (T) in testis, 5α-DHT could also be produced from 5α-androstane-3α,17β-diol (3α-diol), an almost inactive androgen, following non-classical pathways. We reported the chemical synthesis of non-commercially available [4-14C]-3α-diol from [4-14C]-T, and the development of a biological assay to identify inhibitors of the 5α-DHT formation from radiolabeled 3α-diol in LAPC-4 cell PC model. We measured the inhibitory potency of 5α-androstane derivatives against the formation of 5α-DHT, and inhibition curves were obtained for the most potent compounds (IC50 = 1.2–14.1 μM). The most potent inhibitor 25 (IC50 = 1.2 μM) possesses a 4-(4-CF3-3-CH3O-benzyl)piperazinyl methyl side chain at C3β and 17β-OH/17α-C[tbnd]CH functionalities at C17 of a 5α-androstane core.

A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions

We report a general protocol for the light-driven isomerization of cyclic aliphatic alcohols to linear carbonyl compounds. These reactions proceed via proton-coupled electron-transfer activation of alcohol O-H bonds followed by subsequent C-C β-scission of the resulting alkoxy radical intermediates. In many cases, these redox-neutral isomerizations proceed in opposition to a significant energetic gradient, yielding products that are less thermodynamically stable than the starting materials. A mechanism is presented to rationalize this out-of-equilibrium behavior that may serve as a model for the design of other contrathermodynamic transformations driven by excited-state redox events.