566-19-8

Basic information

• Product Name: 7-Keto-dehydroepiandrosterone
• Synonyms: DEHYDROEPIANDROSTERONE, 7-KETO;5-androstene-3b-ol-7,17-dione;5-ANDROSTEN-3-BETA-OL-7,17-DIONE;7-KETO-DEHYDROEPIANDROSTERONE;7-KETO DHEA;7-hydroxydehydroepiandrosterone;7-Oxo-dehydroepiandrosterone;androst-5-ene-7,17-dione,3beta-hydroxy
• CAS NO: 566-19-8
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.41
• EINECS: 1592732-453-0
• Product Categories: Steroids & Hormones - 13C & 2H;Cnbio;steroids;Steroid and Hormone
• Mol File: 566-19-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 245-248 °C
• Boiling Point: 477.1 °C at 760 mmHg
• Flash Point: 256.5 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 4.15E-11mmHg at 25°C
• Refractive Index: 1.569
• PKA: 14.67±0.60(Predicted)
• CAS DataBase Reference: 7-Keto-dehydroepiandrosterone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Keto-dehydroepiandrosterone(566-19-8)
• EPA Substance Registry System: 7-Keto-dehydroepiandrosterone(566-19-8)

Safety Data

• Hazardous Substances Data: 566-19-8(Hazardous Substances Data)

Usage

Physiological effects

In the past ten years, a large number of studies have shown that 7-keto dehydroepiandrosterone has stronger physiological activity than DHEA, especially in anti-aging, enhancing immunity, improving memory, enhancing brain function, preventing Alzheimer’s and diabetes , It has a strong effect on reducing the risk of heart disease, losing weight, increasing bone density and muscle vitality.

InChI:InChI=1/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/m0/s1

Synthetic route

dehydroepiandrosterone (53-43-0) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With tert.-butylhydroperoxide; N-hydroxyphthalimide; cobalt(II) acetate In acetone at 20℃; for 5h; regioselective reaction;	81.1%
With N-hydroxyphthalimide; sodium dichromate; chromium(III) perchlorate In acetone at 20℃; for 48h; Product distribution / selectivity;	74.25%
With tert.-butylhydroperoxide; dirhodium(II) tetrakis(caprolactam) In water; 1,2-dichloro-ethane at 40℃; for 20h;	74%

(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-7(2H)-one (166173-97-3) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With perchloric acid; water In acetone at 20℃; for 20h;	65%

dehydroepiandrosterone (53-43-0) → 5-androstene-3β-ol-7,17-dione (566-19-8) + 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1, 7522-54-5, 62357-03-3, 53-00-9) + 5-androsten-3β,7β-diol-17-one (2487-48-1)

Conditions	Yield
With Mortierella isabellina AM212 fungal strain for 12h; Enzymatic reaction;	A 6% B 53.5% C 24%
With Absidia coerulea AM93 In acetone at 20℃; for 8h; Time; Enzymatic reaction;	A 5.5% B 22% C 49%

3β-hydroxy-17,17-ethylenedioxo-5-androstene (7745-40-6, 14456-21-4) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With CrO3/NHPI on activated clay In dichloromethane at 20℃;	40%

prasterone acetate (853-23-6) → 5-androstene-3β-ol-7,17-dione (566-19-8) + 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1, 7522-54-5, 62357-03-3, 53-00-9) + 5-androsten-3β,7β-diol-17-one (2487-48-1) + 3β,14α-dihydroxyandrost-5-en-7,17-dione (58211-52-2)

Conditions	Yield
With Cunninghamella elegans In ethanol for 72h; Further byproducts given;	A 5.4% B 26.8% C 9% D 1.1%
With Cunninghamella elegans In ethanol for 72h; Further byproducts given;	A 5.4% B 26.8% C 9% D 1.1%

dehydroepiandrosterone (53-43-0) → 5-androstene-3β-ol-7,17-dione (566-19-8) + 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1, 7522-54-5, 62357-03-3, 53-00-9) + 5-androsten-3β,7β-diol-17-one (2487-48-1) + 3β,7β-dihydroxy-5β,6β-epoxyandrostan-17-one + 3β,4β,7β-trihydroxyandrost-5-en-17-one + 3β,7α-dihydroxy-5β,6β-epoxyandrostan-17-one + 3β,4β,7α-trihydroxyandrost-5-en-17-one

Conditions	Yield
With Ulocladium chartarum MRC 72584 In water; N,N-dimethyl-formamide at 28℃; for 120h; Enzymatic reaction;	A 6% B 12% C 16% D 3% E 4% F 2% G 3%

prasterone acetate (853-23-6) → 5-androstene-3β-ol-7,17-dione (566-19-8) + 5-androsten-3β,7β-diol-17-one (2487-48-1) + 5,6β-epoxy-3β,12α-dihydroxy-5β-androstan-17-one (58324-06-4) + 3β,14α-dihydroxyandrost-5-en-7,17-dione (58211-52-2)

Conditions	Yield
With Cunninghamella elegans In ethanol for 72h; Further byproducts given;	A 5.4% B 9% C 4.1% D 1.1%

prasterone acetate (853-23-6) + di-tert-butyl chromate (1189-85-1) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
und anschliessend Hydrolysieren;

prasterone acetate (853-23-6) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With chromium(VI) oxide und anschliessend Hydrolysieren;

3-O-acetyl-7-oxo-dehydroepiandrosterone (1449-61-2) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With sodium carbonate In methanol
With sodium hydrogencarbonate In methanol	307 mg

dehydroepiandrosterone (53-43-0) → 5-androstene-3β-ol-7,17-dione (566-19-8) + 3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1, 7522-54-5, 62357-03-3, 53-00-9) + Androst-5-ene-3beta,7alpha,17beta-triol (2697-85-0, 62357-04-4, 2226-66-6)

Conditions	Yield
With fungus Fusarium oxysporum var. cubense In ethanol at 27℃; Product distribution; biotransformation; Microbiological reaction; fungus Fusarium oxysporum var. cubense (from rhizome of banana plant showing symptoms of Panama disease);
With fungus Fusarium oxysporum In ethanol at 27℃; for 180h; biotransformation; Title compound not separated from byproducts;

7-oxo-dehydroepiandrosterone-3β-sulfate → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With perchloric acid In ethyl acetate at 25℃; for 0.25h;	99.5 % Chromat.

5-androsten-7,17-dione-3β-ol ethylene ketal tert-butyldimethylsilyl ether (202415-77-8) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; methanol

prasterone acetate (853-23-6) + KMnO4 → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / N-hydroxyphthalimide, azobis(cyclohexane-carbonitrile), air / acetone; ethyl acetate / 9 h / Heating 2: Na2CO3 / methanol View Scheme

3β,7α-dihydroxyandrost-5-ene-17-one (2487-48-1, 7522-54-5, 62357-03-3, 53-00-9) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With polyoxyethylenesorbitan monooleate; soy protein, hydrolyzed; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; yiest; autolysed extract of In water for 144h; Enzymatic reaction;
With Mortierella isabellina AM212 fungal strain for 12h; Enzymatic reaction;	9.7 %Chromat.

5-androsten-3β,7β-diol-17-one (2487-48-1) → 5-androstene-3β-ol-7,17-dione (566-19-8)

Conditions	Yield
With Mortierella isabellina AM212 fungal strain for 12h; Enzymatic reaction;	32 %Chromat.

5-androstene-3β-ol-7,17-dione (566-19-8) + acetic anhydride (108-24-7) → 3-O-acetyl-7-oxo-dehydroepiandrosterone (1449-61-2)

Conditions	Yield
With toluene-4-sulfonic acid for 0.0333333h; microwave irradiation;	96%
for 3h; Reflux;	85%

5-androstene-3β-ol-7,17-dione (566-19-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5-ene-7,17-dione (157302-54-0)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h;	92.6%
With 1H-imidazole

1H-imidazole (288-32-4) + to-butyldimethysilyl chloride + 5-androstene-3β-ol-7,17-dione (566-19-8) → 3β-t-butyldimethylsilyloxyandrost-5-ene-7,17-dione

Conditions	Yield
In N-methyl-acetamide	92.6%

5-androstene-3β-ol-7,17-dione (566-19-8) + chloroformic acid ethyl ester (541-41-3) → 3β-carboethoxyandrost-5-ene-7,17-dione

Conditions	Yield
In pyridine at 0 - 5℃;	90%

5-androstene-3β-ol-7,17-dione (566-19-8) + chloroformic acid ethyl ester (541-41-3) → 3β-carboethoxyandrost-5-ene-7,17-dione

Conditions	Yield
In pyridine	90%

5-androstene-3β-ol-7,17-dione (566-19-8) → 5-androstene-3β,7β,17β-triol (2697-85-0)

Conditions	Yield
With sodium tetrahydroborate; cerium(III) chloride In methanol; dichloromethane at 0 - 5℃; for 0.5h; pH=15;	88%

5-androstene-3β-ol-7,17-dione (566-19-8) → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With perchloric acid In methanol; water at 20℃; for 12h;	80%

5-androstene-3β-ol-7,17-dione (566-19-8) + C21H20Cl5NO3 → androst-5-en-7,17-dione-3β-yl 2-[4-N,N-bis(2-chloroethyl)amino-phenyl]butanoate (1454311-30-8)

Conditions	Yield
With dmap In toluene for 1.5h; Inert atmosphere; Reflux;	80%

5-androstene-3β-ol-7,17-dione (566-19-8) + isobutyl chloroformate (543-27-1) → 3β-carboiso-butoxyandrost-5-ene-7,17-dione

Conditions	Yield
In pyridine at 0 - 5℃;	78%

5-androstene-3β-ol-7,17-dione (566-19-8) → 3β-hydroxy-5,17-dioxo-5,7-seco-B-norandrost-7-oic acid

Conditions	Yield
With potassium permanganate; sodium periodate; potassium carbonate In water; tert-butyl alcohol at 60℃; for 2.33333h;	78%

5-androstene-3β-ol-7,17-dione (566-19-8) + Allyl chloroformate (2937-50-0) → 3β-carboallyloxyandrost-5-ene-7,17-dione

Conditions	Yield
In tetrahydrofuran-pyridine	78%

5-androstene-3β-ol-7,17-dione (566-19-8) + isobutyl chloroformate (543-27-1) → 3β-carboisobutoxyandrost-5-ene-7,17-dione

Conditions	Yield
In pyridine	78%

3,4-dihydro-2H-pyran (110-87-2) + 5-androstene-3β-ol-7,17-dione (566-19-8) → 3β-(2-tetrahydropyranyloxy)-androst-5-ene-7,17-dione (102890-86-8) + androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 3h;	A 68% B 0.150 g

octyl chloroformate (7452-59-7) + 5-androstene-3β-ol-7,17-dione (566-19-8) → 3β-carbooctyloxyandrost-5-ene-7,17-dione

Conditions	Yield
In pyridine at 0 - 5℃;	65%

octyl chloroformate (7452-59-7) + 5-androstene-3β-ol-7,17-dione (566-19-8) → 3β-carbooctyloxyandrost-5-ene-7,17-dione (1056899-12-7)

Conditions	Yield
In pyridine	65%

5-androstene-3β-ol-7,17-dione (566-19-8) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → 3β-carbo(9-fluorenyl)methoxyandrost-5-ene-7,17-dione

Conditions	Yield
In pyridine at 20℃; for 1h;	57%

5-androstene-3β-ol-7,17-dione (566-19-8) → androst-5-ene-3,7,17-trione

Conditions	Yield
With cyclohexanone; aluminum isopropoxide; toluene

5-androstene-3β-ol-7,17-dione (566-19-8) + p-toluenesulfonyl chloride (98-59-9) → 3β-Tosyloxy-androsten-(5)-dion-(7,17) (897039-72-4)

Conditions	Yield
With pyridine

diazomethane (186581-53-3, 908094-01-9) + 5-androstene-3β-ol-7,17-dione (566-19-8) → (3aS,4R,5S,7aS)-5-((1R,4S)-4-Hydroxy-1-methyl-2-oxo-cyclohexyl)-7a-methyl-1-oxo-octahydro-indene-4-carboxylic acid methyl ester

Conditions	Yield
(i) aq. H2O2, KOH, MeOH, (ii) /BRN= 102415/; Multistep reaction;

butanoic acid anhydride (106-31-0) + 5-androstene-3β-ol-7,17-dione (566-19-8) → Butyric acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-7,17-dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions	Yield
With pyridine

n-dodecanoyl chloride (112-16-3) + 5-androstene-3β-ol-7,17-dione (566-19-8) → Dodecanoic acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-7,17-dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions	Yield
With pyridine

Upstream product

• 53-43-0 dehydroepiandrosterone 
• 1449-61-2 3-O-acetyl-7-oxo-dehydroepiandrosterone 
• 2487-48-1 3β,7α-dihydroxyandrost-5-ene-17-one 
• 2487-48-1 5-androsten-3β,7β-diol-17-one 
• 7745-40-6 3β-hydroxy-17,17-ethylenedioxo-5-androstene 
• 166173-97-3 (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-7(2H)-one 
• 853-23-6 prasterone acetate 
• 202415-77-8 5-androsten-7,17-dione-3β-ol ethylene ketal tert-butyldimethylsilyl ether 
• 1189-85-1 di-tert-butyl chromate 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 2697-85-0 5-androstene-3β,7β,17β-triol 
• 2226-65-5 3beta,17beta-Dihydroxyandrost-5-en-7-one 
• 2697-85-0 Androst-5-ene-3beta,7alpha,17beta-triol 
• 1454311-30-8 androst-5-en-7,17-dione-3β-yl 2-[4-N,N-bis(2-chloroethyl)amino-phenyl]butanoate 
• 1420-49-1 androsta-3,5-diene-7,17-dione 
• 115758-65-1 17β-Acetoxy-3β-tosyloxy-androsten-(5)-on-(7) 
• 1449-61-2 3-O-acetyl-7-oxo-dehydroepiandrosterone 
• 102890-86-8 3β-(2-tetrahydropyranyloxy)-androst-5-ene-7,17-dione 
• 897039-72-4 3β-Tosyloxy-androsten-(5)-dion-(7,17) 

Relevant articles and documents

Metal-Free Allylic Oxidation of Steroids Using TBAI/TBHP Organocatalytic Protocol

A mild, efficient and organocatalytic allylic oxidation of steroids using a TBAI/TBHP protocol has been developed. A range of bioactive Δ5-en-7-ones can be easily prepared from the corresponding Δ5-steroids. The methodology features several advantages, including readily available starting materials, environmentally benign oxidant, high functional group compatibility, and metal-free catalysis.

Biohydroxylation of 7-oxo-DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

Metabolism of steroids in healthy and unhealthy human organs is the subject of extensive clinical and biomedical studies. For this kind of investigations, it is essential that the reference samples of new derivatives of natural, physiologically active steroids (especially those difficult to achieve in the chemical synthesis) become available. This study demonstrated for the first time transformation of 7-oxo-DHEA—a natural metabolite of DHEA, using Syncephalastrum racemosum cells. The single-pulse fermentation of substrate produced two new hydroxy metabolites: 1β,3β-dihydroxy-androst-5-en-7,17-dione and 3β,12β-dihydroxy-androst-5-en-7,17-dione, along with the earlier reported 3β,9α-dihydroxy-androst-5-en-7,17-dione and 3β,17β-dihydroxy-androst-5-en-7-one. Simultaneously, the same metabolites, together with small quantities of 7α- and 7β-hydroxy-DHEA, as well as the products of their reduction at the C-17 were obtained after transformation of DHEA under pulse-feeding of the substrate. The observed reactions suggested that this micro-organism contains enzymes exhibiting similar activity to those present in human cells. Thus, the resulting compounds can be considered as potential components of the eukaryotic, including human, metabolome.