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Cas Database

Name	5-alpha-Dihydroprogesterone	EINECS	209-297-3
CAS No.	566-65-4	Density	1.048 g/cm³
PSA	34.14000	LogP	4.80340
Solubility	N/A	Melting Point	200 °C
Formula	C₂₁H₃₂O₂	Boiling Point	429.2 °C at 760 mmHg
Molecular Weight	316.484	Flash Point	160.3 °C
Transport Information	N/A	Appearance	White solid
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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;	Article Data	62

5-alpha-Dihydroprogesterone Synthetic route

: 516-53-0
(20R)-5α-Pregnandiol-(3β.20)

: 566-65-4
dihydroprogesterone

Conditions

Conditions	Yield
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

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

: 6170-12-3
5α-pregnanedione-(3,20)-dioxime

: 566-65-4
dihydroprogesterone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With 3,3-dimethyldioxirane In acetone for 18h; Ambient temperature;	82%

: 516-55-2
isopregnanolone

: 566-65-4
dihydroprogesterone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

5-alpha-Dihydroprogesterone 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.

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