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pseudodiosgenin
diosgenin
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 20℃; for 12h; Cycloaddition; | 100% |
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
diosgenin
Conditions | Yield |
---|---|
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 2.3h; Catalytic behavior; Temperature; Time; Solvent; Reagent/catalyst; | 99% |
Conditions | Yield |
---|---|
With potassium hydrogensulfate; silica gel In methanol at 65℃; for 5h; | 90% |
Aspergillus niger; |
3-O-(tert-butyldiphenylsilyl)diosgenin
diosgenin
Conditions | Yield |
---|---|
With perchloric acid on silica gel In acetonitrile at 50℃; for 0.5h; chemoselective reaction; | 84% |
pseudodiosgenin
A
(3β,20R,22R,25R)-spirosol-5-en-3-ol
B
diosgenin
Conditions | Yield |
---|---|
With acetic acid at 20℃; Cycloaddition; | A 68.3% B 12.6% |
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In tetrahydrofuran Electrochemical reaction; | A 53% B 47% |
methanol
A
methyl D-glucopyranoside
B
methyl xyloside
C
methyl L-rhamnopyranoside
D
diosgenin
Conditions | Yield |
---|---|
With hydrogenchloride for 2.5h; Product distribution; Heating; | A n/a B n/a C n/a D 50.8% |
methanol
A
methyl D-glucopyranoside
B
methyl xyloside
C
methyl L-rhamnopyranoside
D
diosgenin
Conditions | Yield |
---|---|
With hydrogenchloride for 2.5h; Product distribution; Heating; | A n/a B n/a C n/a D 50.6% |
diosgenin
Conditions | Yield |
---|---|
With silica gel | 50% |
25R-spirost-5-en-3β-yl diphenyl phosphate
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
A
3β-O-(1',2':3',4'-di-O-isopropylidene-α-D-galactopyranos-6'-yl)-(25R)-spirost-5-ene
B
diosgenin
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In dichloromethane at 25℃; Molecular sieve; Inert atmosphere; Electrochemical reaction; | A 37% B 7% |
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. |