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512-04-9

Basic Information
CAS No.: 512-04-9
Name: Spirost-5-en-3-ol,(3b,25R)-
Article Data: 52
Cas Database
Molecular Structure:
Molecular Structure of 512-04-9 (Spirost-5-en-3-ol,(3b,25R)-)
Formula: C27H42O3
Molecular Weight: 414.629
Synonyms: 25D-Spirost-5-en-3b-ol (6CI,7CI);Spirost-5-en-3b-ol, (25R)- (8CI);(25R)-Spirost-5-en-3b-ol;25a-Spirost-5-en-3b-ol;NSC 33396;Nitogenin;
EINECS: 208-134-3
Density: 1.13 g/cm3
Melting Point: 205-208 °C
Boiling Point: 527.1 °C at 760 mmHg
Flash Point: 272.6 °C
Solubility: chloroform: 20 mg/mL, clear, slightly yellow
Appearance: Flaky or needle crystal
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37
Transport Information: N/A
PSA: 38.69000
LogP: 5.71390
Synthetic route
6808-14-6, 7662-13-7

pseudodiosgenin

512-04-9

diosgenin

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; for 12h; Cycloaddition;100%
86533-55-3

tert-butyldimethyl(((2’R,4S,5’R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5’,6a,8a,9-tetramethyl-1,3,3’,4,4’,5,5’,6,6a,6b,6’,7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2’,1’:4,5]indeno[2,1-b]furan-10,2’-pyran]-4-yl)oxy)silane

512-04-9

diosgenin

Conditions
ConditionsYield
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 2.3h; Catalytic behavior; Temperature; Time; Solvent; Reagent/catalyst;99%
1061-54-7

diosgenin acetate

512-04-9

diosgenin

Conditions
ConditionsYield
With potassium hydrogensulfate; silica gel In methanol at 65℃; for 5h;90%
Aspergillus niger;
324740-29-6

3-O-(tert-butyldiphenylsilyl)diosgenin

512-04-9

diosgenin

Conditions
ConditionsYield
With perchloric acid on silica gel In acetonitrile at 50℃; for 0.5h; chemoselective reaction;84%
Conditions
ConditionsYield
With acetic acid at 20℃; Cycloaddition;A 68.3%
B 12.6%
1061-54-7

diosgenin acetate

A

16863-51-7

(25R)-5-spirostene

B

512-04-9

diosgenin

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In tetrahydrofuran Electrochemical reaction;A 53%
B 47%
Conditions
ConditionsYield
With hydrogenchloride for 2.5h; Product distribution; Heating;A n/a
B n/a
C n/a
D 50.8%
Conditions
ConditionsYield
With hydrogenchloride for 2.5h; Product distribution; Heating;A n/a
B n/a
C n/a
D 50.6%

C27H44O4

512-04-9

diosgenin

Conditions
ConditionsYield
With silica gel50%
1414891-45-4

25R-spirost-5-en-3β-yl diphenyl phosphate

4064-06-6

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

A

1456599-14-6

3β-O-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)-(25R)-spirost-5-ene

B

512-04-9

diosgenin

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In dichloromethane at 25℃; Molecular sieve; Inert atmosphere; Electrochemical reaction;A 37%
B 7%
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Specification

The systematic name of Diosgenin is (3beta,25R)-spirost-5-en-3-ol . With the CAS registry number 512-04-9, it is also named as 22alpha-Spirost-5-en-3beta-ol ; 5-19-03-00030 (Beilstein Handbook Reference) ; Nitogenin ; SP 37 ; (20R,25R)-Spirost-5-en-3beta-ol ; Spirost-5-en-3-beta-ol, (25R)- ; (2S,4aR,4bS,5'R,6aS,6bR,7S,8R,9aS,10aS,10bS)-4a,5',6a,7-Tetramethyl-1,2,3,3',4,4',4a,4b,5,5',6,6',6a,6b,7,9a,10,10a,10b,11-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-8,2'-pyran]-2-ol .

The Diosgenin is flaky or needle crystal which is soluble in gasoline, ethanol, chloroform and other organic solvents, insoluble in water. The product's categories are pharmaceutical intermediates, fine chemical & intermediates, APIs, biochemistry, steroids and the group of Dioscin.

The sugar-free (aglycone), Diosgenin is used for the commercial synthesis of cortisone, pregnenolone and other steroid products. It is also the precursor for the semisynthesis of progesterone which in turn was used in early combined oral contraceptive pills.

The Diosgenin is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If swallowed, wash out mouth with water provided person is conscious. If inhaled, remove to fresh air. If breathing becomes difficult, call a physician. In case of skin contact, flush with copious amounts of water for at least 15 minutes. Remove contaminated clothing and shoes. If you want to contact this product, you must wear suitable protective clothing and gloves.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.84 ; (2)# of Rule of 5 Violations: 1 ; (3)ACD/LogD (pH 5.5): 5.84 ; (4)ACD/LogD (pH 7.4): 5.84 ; (5)ACD/BCF (pH 5.5): 16089.87 ; (6)ACD/BCF (pH 7.4): 16089.87 ; (7)ACD/KOC (pH 5.5): 35697.48 ; (8)ACD/KOC (pH 7.4): 35697.48 ; (9)#H bond acceptors: 3 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 1 ; (12)Index of Refraction: 1.564 ; (13)Molar Refractivity: 119.36 cm3 ; (14)Molar Volume: 366.8 cm3 ; (15)Polarizability: 47.31×10-24 cm3 ; (16)Surface Tension: 44.7 dyne/cm ; (17)Enthalpy of Vaporization: 92.22 kJ/mol ; (18)Vapour Pressure: 2.59E-13 mmHg at 25°C ; (19)Exact Mass: 414.313395 ; (20)MonoIsotopic Mass: 414.313395 ; (21)Topological Polar Surface Area: 38.7 ; (22)Heavy Atom Count: 30.

People can use the following data to convert to the molecule structure. SMILES: O1[C@@H]4[C@H]([C@@H]([C@]12OC[C@@H](CC2)C)C)[C@@]5(C)CC[C@@H]3[C@@]6(C(=C/C[C@H]3[C@@H]5C4)\C[C@@H](O)CC6)C; InChI: InChI=1/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1.

The following is the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3564mg/kg (3564mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Pharmaceutical Chemistry Journal Vol. 11, Pg. 1095, 1977.
mouse LD50 oral > 8gm/kg (8000mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Pharmaceutical Chemistry Journal Vol. 11, Pg. 1095, 1977.
rat LD50 intraperitoneal 4872mg/kg (4872mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Pharmaceutical Chemistry Journal Vol. 11, Pg. 1095, 1977.
rat LD50 oral > 8gm/kg (8000mg/kg)   Pharmaceutical Chemistry Journal Vol. 11, Pg. 1095, 1977.