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566-65-4

Basic Information
CAS No.: 566-65-4
Name: 5-alpha-Dihydroprogesterone
Article Data: 62
Molecular Structure:
Molecular Structure of 566-65-4 (5-alpha-Dihydroprogesterone)
Formula: C21H32O2
Molecular Weight: 316.484
Synonyms: 5a-Pregnane-3,20-dione (8CI);5a-Pregnanedione (7CI);(+)-(5a)-Pregnane-3,20-dione;3,20-Allopregnanedione;3,20-Dioxo-5a-pregnane;5a-Dihydroprogesterone;NSC 18319;
EINECS: 209-297-3
Density: 1.048 g/cm3
Melting Point: 200 °C
Boiling Point: 429.2 °C at 760 mmHg
Flash Point: 160.3 °C
Appearance: White solid
PSA: 34.14000
LogP: 4.80340
Synthetic route
516-53-0

(20R)-5α-Pregnandiol-(3β.20)

566-65-4

dihydroprogesterone

Conditions
ConditionsYield
With Jones reagent In acetone at 10℃;96%
With chromium(VI) oxide; acetic acid
7680-01-5

3β-methoxy-5α-pregnane-20-one

566-65-4

dihydroprogesterone

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone for 18h; Ambient temperature;95%
6170-12-3

5α-pregnanedione-(3,20)-dioxime

566-65-4

dihydroprogesterone

Conditions
ConditionsYield
With acetyl chloride; sodium nitrite In dichloromethane at 20℃;90%
57-83-0

Progesterone

A

566-65-4

dihydroprogesterone

B

15114-79-1

20-hydroxy-Δ4-progest-3-one

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; methylcopper; diisobutylaluminium hydride In tetrahydrofuran; diethyl ether; hexane at -50℃; for 2h;A 84%
B 5.9%

1-((3S,5S,8R,9S,10S,13S,14S,17S)-3-Benzyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone

566-65-4

dihydroprogesterone

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone for 18h; Ambient temperature;82%
516-55-2

isopregnanolone

566-65-4

dihydroprogesterone

Conditions
ConditionsYield
With sodium hypochlorite; acetic acid; sodium bromide In tetrahydrofuran at 20 - 40℃; for 2h;81%
With sodium hypochlorite; sodium bromide In water; acetic acid at 20℃; for 2h;79%
With chromium(VI) oxide; acetic acid
57-83-0

Progesterone

A

566-65-4

dihydroprogesterone

B

128-23-4

pregnanedione

C

40135-22-6

allopregnanolone

D

4320-08-5

3-hydroxy-5β-pregnan-20-one

Conditions
ConditionsYield
With hydrogen; Cu/Al2O3 In toluene at 60℃; under 760 Torr;A 14%
B 49%
C 2%
D 8%
57-83-0

Progesterone

566-65-4

dihydroprogesterone

Conditions
ConditionsYield
In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;45%
With Chlorella vulgaris C211/8k; 4,4'-butylidenebis(6-tert-butyl-m-cresol) at 20℃; for 360h; Reduction; illumination;17.3%
With Penicillium digitatum MRC 500787; MYB medium (malt extract 2percent, glucose 1percent, bacteriological peptone 1percent, yeast extract 0.3percent) In N,N-dimethyl-formamide at 24℃; for 120h;12.3%
566-88-1

dihydrocholesterone

A

566-65-4

dihydroprogesterone

B

69483-56-3

5α-cholestane-3,11-dione

C

2243-09-6

5α-cholestane-3,6-dione

D

13400-67-4

3,7-dioxo-5α-cholestane

Conditions
ConditionsYield
With pyridine; oxygen; acetic acid; zinc; iron In water for 5h; Ambient temperature; Gif system; Further byproducts given;A 4.6%
B 1.1%
C 4.1%
D 3.8%
566-88-1

dihydrocholesterone

A

566-65-4

dihydroprogesterone

B

2243-09-6

5α-cholestane-3,6-dione

C

13400-67-4

3,7-dioxo-5α-cholestane

D

108393-74-4

(5S,8R,9S,10S,13S,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,16-dione

Conditions
ConditionsYield
With pyridine; oxygen; acetic acid; zinc; iron In water for 5h; Ambient temperature; Gif system; Further byproducts given;A 4.6%
B 4.1%
C 3.8%
D 2.1%
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Specification

The 5-alpha-Dihydroprogesterone, with the CAS registry number 566-65-4, is also known as Pregnane-3,20-dione, (5-alpha)- (9CI). It belongs to the product category of Steroids. Its EINECS registry number is 209-297-3. This chemical's molecular formula is C21H32O2 and molecular weight is 316.48. Its IUPAC name is called (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one. This chemical's classification codes are Drug / Therapeutic Agent; Hormone.

Physical properties of 5-alpha-Dihydroprogesterone: (1)ACD/LogP: 4.31; (2)ACD/LogD (pH 5.5): 4.31; (3)ACD/LogD (pH 7.4): 4.31; (4)ACD/BCF (pH 5.5): 1115.92; (5)ACD/BCF (pH 7.4): 1115.92; (6)ACD/KOC (pH 5.5): 5285.61; (7)ACD/KOC (pH 7.4): 5285.61; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.515; (11)Molar Refractivity: 91.11 cm3; (12)Molar Volume: 301.8 cm3; (13)Surface Tension: 37.2 dyne/cm; (14)Density: 1.048 g/cm3; (15)Flash Point: 160.3 °C; (16)Enthalpy of Vaporization: 68.44 kJ/mol; (17)Boiling Point: 429.2 °C at 760 mmHg; (18)Vapour Pressure: 1.43E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
(2)Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCC(=O)C4)C)C
(3)InChI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
(4)InChIKey: XMRPGKVKISIQBV-BJMCWZGWSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 80mg/kg (80mg/kg)   Journal of Medicinal Chemistry. Vol. 11, Pg. 117, 1968.
mouse LDLo intravenous 10mg/kg (10mg/kg)   Journal of Medicinal Chemistry. Vol. 11, Pg. 117, 1968.