7-Keto-dehydroepiandrosterone supplier

Name
7-Keto-dehydroepiandrosterone
EINECS 1592732-453-0
CAS No. 566-19-8
Article Data30
CAS DataBase
Density 1.19 g/cm³
Solubility
Melting Point 240.0-244.0oC
Formula C₁₉H₂₆O₃
Boiling Point 477.1 °C at 760 mmHg
Molecular Weight 302.414
Flash Point 256.5 °C
Transport Information
Appearance White powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Androst-5-ene-7,17-dione,3b-hydroxy- (8CI);3b-Hydroxy-5-androstene-7,17-dione;5-Androsten-3b-ol-7,17-dione;7-Keto-DHEA;7-Oxo-DHEA;Androst-5-ene-7,17-dione,3-hydroxy-, (3b)-;
PSA 54.37000
LogP 3.05820

Synthetic route

: 53-43-0
dehydroepiandrosterone

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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%

: 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

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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

: 53-43-0
dehydroepiandrosterone

A: 566-19-8
5-androstene-3β-ol-7,17-dione

B: 2487-48-1, 7522-54-5, 62357-03-3, 53-00-9
3β,7α-dihydroxyandrost-5-ene-17-one

C: 2487-48-1
5-androsten-3β,7β-diol-17-one

Conditions

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%

...Expand

: 7745-40-6, 14456-21-4
3β-hydroxy-17,17-ethylenedioxo-5-androstene

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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

: 853-23-6
prasterone acetate

A: 566-19-8
5-androstene-3β-ol-7,17-dione

B: 2487-48-1, 7522-54-5, 62357-03-3, 53-00-9
3β,7α-dihydroxyandrost-5-ene-17-one

C: 2487-48-1
5-androsten-3β,7β-diol-17-one

D: 58211-52-2
3β,14α-dihydroxyandrost-5-en-7,17-dione

Conditions

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%

...Expand

: 53-43-0
dehydroepiandrosterone

A: 566-19-8
5-androstene-3β-ol-7,17-dione

B: 2487-48-1, 7522-54-5, 62357-03-3, 53-00-9
3β,7α-dihydroxyandrost-5-ene-17-one

C: 2487-48-1
5-androsten-3β,7β-diol-17-one

D: 3β,7β-dihydroxy-5β,6β-epoxyandrostan-17-one

E: 3β,4β,7β-trihydroxyandrost-5-en-17-one

F: 3β,7α-dihydroxy-5β,6β-epoxyandrostan-17-one

G: 3β,4β,7α-trihydroxyandrost-5-en-17-one

Conditions

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%

...Expand

: 853-23-6
prasterone acetate

A: 566-19-8
5-androstene-3β-ol-7,17-dione

B: 2487-48-1
5-androsten-3β,7β-diol-17-one

C: 58324-06-4
5,6β-epoxy-3β,12α-dihydroxy-5β-androstan-17-one

D: 58211-52-2
3β,14α-dihydroxyandrost-5-en-7,17-dione

Conditions

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

...Expand

: 853-23-6
prasterone acetate

: 1189-85-1
di-tert-butyl chromate

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

Conditions	Yield
und anschliessend Hydrolysieren;

: 853-23-6
prasterone acetate

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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

: 53-43-0
dehydroepiandrosterone

A: 566-19-8
5-androstene-3β-ol-7,17-dione

B: 2487-48-1, 7522-54-5, 62357-03-3, 53-00-9
3β,7α-dihydroxyandrost-5-ene-17-one

C: 2697-85-0, 62357-04-4, 2226-66-6
Androst-5-ene-3beta,7alpha,17beta-triol

Conditions

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;

...Expand

: 7-oxo-dehydroepiandrosterone-3β-sulfate

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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

: 202415-77-8
5-androsten-7,17-dione-3β-ol ethylene ketal tert-butyldimethylsilyl ether

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; methanol

: 853-23-6
prasterone acetate

KMnO4: KMnO4

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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

: 2487-48-1, 7522-54-5, 62357-03-3, 53-00-9
3β,7α-dihydroxyandrost-5-ene-17-one

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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.

: 2487-48-1
5-androsten-3β,7β-diol-17-one

: 566-19-8
5-androstene-3β-ol-7,17-dione

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 108-24-7
acetic anhydride

: 1449-61-2
3-O-acetyl-7-oxo-dehydroepiandrosterone

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 18162-48-6
tert-butyldimethylsilyl chloride

: 157302-54-0
(3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5-ene-7,17-dione

Conditions

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

: 288-32-4
1H-imidazole

to-butyldimethysilyl chloride: to-butyldimethysilyl chloride

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 3β-t-butyldimethylsilyloxyandrost-5-ene-7,17-dione

Conditions

Conditions	Yield
In N-methyl-acetamide	92.6%

...Expand

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 541-41-3
chloroformic acid ethyl ester

: 3β-carboethoxyandrost-5-ene-7,17-dione

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 541-41-3
chloroformic acid ethyl ester

: 3β-carboethoxyandrost-5-ene-7,17-dione

Conditions

Conditions	Yield
In pyridine	90%

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 2697-85-0
5-androstene-3β,7β,17β-triol

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 1420-49-1
androsta-3,5-diene-7,17-dione

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: C21H20Cl5NO3

: 1454311-30-8
androst-5-en-7,17-dione-3β-yl 2-[4-N,N-bis(2-chloroethyl)amino-phenyl]butanoate

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 543-27-1
isobutyl chloroformate

: 3β-carboiso-butoxyandrost-5-ene-7,17-dione

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 3β-hydroxy-5,17-dioxo-5,7-seco-B-norandrost-7-oic acid

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 2937-50-0
Allyl chloroformate

: 3β-carboallyloxyandrost-5-ene-7,17-dione

Conditions

Conditions	Yield
In tetrahydrofuran-pyridine	78%

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 543-27-1
isobutyl chloroformate

: 3β-carboisobutoxyandrost-5-ene-7,17-dione

Conditions

Conditions	Yield
In pyridine	78%

: 110-87-2
3,4-dihydro-2H-pyran

: 566-19-8
5-androstene-3β-ol-7,17-dione

A: 102890-86-8
3β-(2-tetrahydropyranyloxy)-androst-5-ene-7,17-dione

B: 1420-49-1
androsta-3,5-diene-7,17-dione

Conditions

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

...Expand

: 7452-59-7
octyl chloroformate

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 3β-carbooctyloxyandrost-5-ene-7,17-dione

Conditions

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

: 7452-59-7
octyl chloroformate

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 1056899-12-7
3β-carbooctyloxyandrost-5-ene-7,17-dione

Conditions

Conditions	Yield
In pyridine	65%

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 3β-carbo(9-fluorenyl)methoxyandrost-5-ene-7,17-dione

Conditions

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

: 566-19-8
5-androstene-3β-ol-7,17-dione

: androst-5-ene-3,7,17-trione

Conditions

Conditions	Yield
With cyclohexanone; aluminum isopropoxide; toluene

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 98-59-9
p-toluenesulfonyl chloride

: 897039-72-4
3β-Tosyloxy-androsten-(5)-dion-(7,17)

Conditions

Conditions	Yield
With pyridine

: 186581-53-3, 908094-01-9
diazomethane

: 566-19-8
5-androstene-3β-ol-7,17-dione

: (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

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

: 106-31-0
butanoic acid anhydride

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 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

Conditions	Yield
With pyridine

: 112-16-3
n-dodecanoyl chloride

: 566-19-8
5-androstene-3β-ol-7,17-dione

: 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

Conditions	Yield
With pyridine

7-Keto-dehydroepiandrosterone Specification

7-Keto-dehydroepiandrosterone has the IUPAC Name of (3S,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17-dione. With the CAS NO.566-19-8, it is also called 7-Keto DHEA; 7-Oxo-DHEA; DHEA, 7-keto-; UNII-2334LJD2E9; 3beta-Hydroxyandrost-5-ene-7,17-dione. 7-Oxodehydroepiandrosterone (CAS NO.566-19-8) is used as a pharmaceutical intermediates.

Physical properties about 7-Keto-dehydroepiandrosterone are: (1)ACD/LogP: 1.669; (2)ACD/LogD (pH 5.5): 1.67; (3)ACD/LogD (pH 7.4): 1.67; (4)ACD/BCF (pH 5.5): 10.93 ; (5)ACD/BCF (pH 7.4): 10.93; (6)ACD/KOC (pH 5.5): 192.76; (7)ACD/KOC (pH 7.4): 192.76; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.569; (12)Molar Refractivity: 83.229 cm³; (13)Molar Volume: 253.886 cm³; (14)Polarizability: 32.995 10-24cm³; (15)Surface Tension: 48.1559982299805 dyne/cm; (16)Density: 1.191 g/cm³; (17)Flash Point: 256.478 °C; (18)Enthalpy of Vaporization: 85.408 kJ/mol; (19)Boiling Point: 477.144 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/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;
(2)InChIKey=KPRGOTLNGIBVFL-GINZOMEDSA-N;
(3)SmilesC1[C@@H](CC2=CC([C@H]3[C@@H]4CCC([C@@]4(C)CC[C@H]3[C@@]2(C1)C)=O)=O)O;

Product Name

7-Keto-dehydroepiandrosterone

Synthetic route

7-Keto-dehydroepiandrosterone Specification

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