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Name Diosgenin
EINECS208-134-3
CAS No. 512-04-9
Density1.13 g/cm³
PSA38.69000
LogP5.71390
Solubilitychloroform: 20 mg/mL, clear, slightly yellow
Melting Point205-208 °C
FormulaC₂₇H₄₂O₃
Boiling Point527.1 °C at 760 mmHg
Molecular Weight414.629
Flash Point272.6 °C
Transport InformationN/A
AppearanceFlaky or needle crystal
Safety26-36/37
Risk Codes36/37/38
Molecular Structure
Hazard SymbolsXi
SynonymsXi
Article Data52

Diosgenin Synthetic route

: 6808-14-6, 7662-13-7
pseudodiosgenin

: 512-04-9
diosgenin

Conditions

Conditions	Yield
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

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%

: 1061-54-7
diosgenin acetate

: 512-04-9
diosgenin

Conditions

Conditions	Yield
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

Conditions	Yield
With perchloric acid on silica gel In acetonitrile at 50℃; for 0.5h; chemoselective reaction;	84%

: 6808-14-6, 7662-13-7
pseudodiosgenin

A: 470-05-3, 470-06-4, 512-04-9, 512-06-1, 31356-47-5, 51195-66-5, 66289-52-9, 89299-45-6, 125710-71-6
(3β,20R,22R,25R)-spirosol-5-en-3-ol

B: 512-04-9
diosgenin

Conditions

Conditions	Yield
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

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In tetrahydrofuran Electrochemical reaction;	A 53% B 47%

: 67-56-1
methanol

: trigoneoside Vb

A: 97-30-3, 617-04-9, 709-50-2, 1824-94-8, 2152-78-5, 3396-99-4, 6819-48-3, 18469-06-2, 20550-04-3, 22277-65-2, 29411-57-2, 35437-40-2, 35437-43-5, 36191-11-4, 36191-12-5, 39598-79-3, 39598-80-6, 39598-89-5, 51023-63-3, 51223-62-2, 51224-38-5, 51224-39-6, 51224-40-9, 51224-41-0, 51819-81-9, 51819-82-0, 51819-83-1, 56688-81-4, 62279-53-2, 64281-79-4, 64281-80-7, 64912-19-2, 66101-73-3, 78184-90-4, 84368-39-8, 84368-40-1, 84368-41-2, 92142-37-5, 93302-26-2, 103421-28-9, 115794-08-6, 3149-68-6
methyl D-glucopyranoside

B: 91-09-8, 612-05-5, 1825-00-9, 2500-78-9, 3867-83-2, 3945-28-6, 5328-63-2, 6206-67-3, 6207-01-8, 6207-03-0, 7404-24-2, 17289-61-1, 18449-76-8, 33509-64-7, 36793-06-3, 41897-31-8, 41897-32-9, 41897-33-0, 41897-34-1, 41897-37-4, 41897-38-5, 41897-39-6, 53448-52-5, 65137-86-2, 89615-04-3, 89615-05-4, 131233-91-5, 14703-09-4
methyl xyloside

C: 1128-40-1, 1198-82-9, 2592-55-4, 5155-43-1, 6340-52-9, 10503-91-0, 14009-07-5, 14687-15-1, 14917-55-6, 15814-59-2, 24332-98-7, 34299-65-5, 42214-00-6, 42214-11-9, 57783-34-3, 57783-36-5, 57783-38-7, 57783-40-1, 57783-42-3, 58525-46-5, 58525-47-6, 58525-48-7, 62182-01-8, 62182-02-9, 65310-00-1, 65941-62-0, 68069-80-7, 71116-57-9, 72274-54-5, 72274-55-6, 73036-22-3, 83198-64-5, 85505-15-3, 102517-74-8, 109718-80-1, 109718-81-2, 125280-09-3, 129172-95-8, 63864-94-8
methyl L-rhamnopyranoside

D: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride for 2.5h; Product distribution; Heating;	A n/a B n/a C n/a D 50.8%

...Expand

: 67-56-1
methanol

: trigoneoside VIIb

A: 97-30-3, 617-04-9, 709-50-2, 1824-94-8, 2152-78-5, 3396-99-4, 6819-48-3, 18469-06-2, 20550-04-3, 22277-65-2, 29411-57-2, 35437-40-2, 35437-43-5, 36191-11-4, 36191-12-5, 39598-79-3, 39598-80-6, 39598-89-5, 51023-63-3, 51223-62-2, 51224-38-5, 51224-39-6, 51224-40-9, 51224-41-0, 51819-81-9, 51819-82-0, 51819-83-1, 56688-81-4, 62279-53-2, 64281-79-4, 64281-80-7, 64912-19-2, 66101-73-3, 78184-90-4, 84368-39-8, 84368-40-1, 84368-41-2, 92142-37-5, 93302-26-2, 103421-28-9, 115794-08-6, 3149-68-6
methyl D-glucopyranoside

B: 91-09-8, 612-05-5, 1825-00-9, 2500-78-9, 3867-83-2, 3945-28-6, 5328-63-2, 6206-67-3, 6207-01-8, 6207-03-0, 7404-24-2, 17289-61-1, 18449-76-8, 33509-64-7, 36793-06-3, 41897-31-8, 41897-32-9, 41897-33-0, 41897-34-1, 41897-37-4, 41897-38-5, 41897-39-6, 53448-52-5, 65137-86-2, 89615-04-3, 89615-05-4, 131233-91-5, 14703-09-4
methyl xyloside

C: 1128-40-1, 1198-82-9, 2592-55-4, 5155-43-1, 6340-52-9, 10503-91-0, 14009-07-5, 14687-15-1, 14917-55-6, 15814-59-2, 24332-98-7, 34299-65-5, 42214-00-6, 42214-11-9, 57783-34-3, 57783-36-5, 57783-38-7, 57783-40-1, 57783-42-3, 58525-46-5, 58525-47-6, 58525-48-7, 62182-01-8, 62182-02-9, 65310-00-1, 65941-62-0, 68069-80-7, 71116-57-9, 72274-54-5, 72274-55-6, 73036-22-3, 83198-64-5, 85505-15-3, 102517-74-8, 109718-80-1, 109718-81-2, 125280-09-3, 129172-95-8, 63864-94-8
methyl L-rhamnopyranoside

D: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride for 2.5h; Product distribution; Heating;	A n/a B n/a C n/a D 50.6%

...Expand

: C27H44O4

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With silica gel	50%

: 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

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

Diosgenin 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.

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Diosgenin Synthetic route

Diosgenin Specification

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