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| CAS No.: | 566-65-4 |
|---|---|
| Name: | 5-alpha-Dihydroprogesterone |
| Molecular Structure: | |
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|
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| 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 |
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- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
| Conditions | Yield |
|---|---|
| With Jones reagent In acetone at 10℃; | 96% |
| With chromium(VI) oxide; acetic acid |
| Conditions | Yield |
|---|---|
| With 3,3-dimethyldioxirane In acetone for 18h; Ambient temperature; | 95% |
| Conditions | Yield |
|---|---|
| With acetyl chloride; sodium nitrite In dichloromethane at 20℃; | 90% |
| 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% |
- 566-65-4
dihydroprogesterone
| Conditions | Yield |
|---|---|
| With 3,3-dimethyldioxirane In acetone for 18h; Ambient temperature; | 82% |
| 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 | Yield |
|---|---|
| With hydrogen; Cu/Al2O3 In toluene at 60℃; under 760 Torr; | A 14% B 49% C 2% D 8% |
| 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 | 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 | 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% |
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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. |