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7-Keto-dehydroepiandrosterone
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Name

7-Keto-dehydroepiandrosterone

 EINECS 1592732-453-0
CAS No. 566-19-8 Density 1.19 g/cm3
PSA 54.37000 LogP 3.05820
Solubility N/A 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 N/A Appearance White powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 566-19-8 (7-Keto-dehydroepiandrosterone) Hazard Symbols N/A
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)-;

Article Data 30

7-Keto-dehydroepiandrosterone Synthetic route

53-43-0

dehydroepiandrosterone

566-19-8

5-androstene-3β-ol-7,17-dione

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
7745-40-6, 14456-21-4

3β-hydroxy-17,17-ethylenedioxo-5-androstene

566-19-8

5-androstene-3β-ol-7,17-dione

Conditions
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
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
ConditionsYield
With Cunninghamella elegans In ethanol for 72h; Further byproducts given;A 5.4%
B 9%
C 4.1%
D 1.1%
853-23-6

prasterone acetate

1189-85-1

di-tert-butyl chromate

566-19-8

5-androstene-3β-ol-7,17-dione

Conditions
ConditionsYield
und anschliessend Hydrolysieren;
853-23-6

prasterone acetate

566-19-8

5-androstene-3β-ol-7,17-dione

Conditions
ConditionsYield
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
ConditionsYield
With sodium carbonate In methanol
With sodium hydrogencarbonate In methanol307 mg

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;

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