Diosgenin supplier | CasNO.512-04-9

Name
diosgenin
EINECS 208-134-3
CAS No. 512-04-9
Article Data52
CAS DataBase
Density 1.13 g/cm³
Solubility chloroform: 20 mg/mL, clear, slightly yellow
Melting Point 205-208 °C
Formula C₂₇H₄₂O₃
Boiling Point 527.1 °C at 760 mmHg
Molecular Weight 414.629
Flash Point 272.6 °C
Transport Information
Appearance Flaky or needle crystal
Safety 26-36/37
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 38.69000
LogP 5.71390

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%

...Expand

: 60478-68-4, 19057-60-4
dioscin

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water at 80℃;	1.82%
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;	8 mg
Multi-step reaction with 2 steps 1: 1 N H2SO4 / aq. ethanol 2: 1 N H2SO4 / aq. ethanol View Scheme

: 468-99-5
kryptogenin

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With aluminum isopropoxide; isopropyl alcohol
Multi-step reaction with 2 steps 1: pyridine 2: propanol-(2); sodium View Scheme
Multi-step reaction with 2 steps 1: pyridine 2: isopropyl alcohol; sodium View Scheme

: 7554-95-2
kryptogenin diacetate

A: (25R)-16ξ,23ξH-fesene-(5)-triol-(3β,22ξ,26)

B: 512-04-9
diosgenin

Conditions

Conditions	Yield
With sodium; isopropyl alcohol

: 64-17-5
ethanol

: (22Ξ:25R)-22.26-epoxy-cholestene-(5)-triol-(3β.16β.22)

: 64-19-7
acetic acid

: 512-04-9
diosgenin

...Expand

: 468-99-5
kryptogenin

: 555-31-7
aluminum isopropoxide

: 67-63-0
isopropyl alcohol

: 512-04-9
diosgenin

...Expand

: 512-06-1
yamogenin

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride; ethanol; water
Multi-step reaction with 2 steps 1: acetic acid anhydride 2: ethanol; HCl; water View Scheme

: 427-28-1
(25R)-3-β-hydroxyspirost-5-en-12-one

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With ethanol; sodium ethanolate; hydrazine hydrate
With alkali hydroxide; hydrazine hydrate; diethylene glycol

: 1180-12-7
Diosgeninmonoacetat

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride; ethanol; water

: 67-56-1
methanol

: C52H86O16

A: tetramethoxyarabinose

B: C35H56O8

C: 35939-73-2
Methyl-(6-desoxy-2,3,4-tri-O-methyl-α-L-mannopyranosid)

D: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride at 100℃; for 1h;

...Expand

: 53846-52-9, 99661-97-9, 55659-75-1
diosgenin 3-O-<α-L-rhamnopyranosyl(1<*>2)>-<β-D-glucopyranosyl(1<*>4)>-β-D-glucopyranoside

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;
Multi-step reaction with 3 steps 1: steroidal saponin-β-glucosidase from Aspergillus flavus / aq. buffer / 50 °C / pH 5 / Enzymatic reaction 2: steroidal saponin-α-1,2-rhamnosidase from C. lunata / aq. buffer / 50 °C / pH 5 / Enzymatic reaction 3: steroidal saponin-β-glucosidase from Aspergillus flavus / aq. buffer / 50 °C / pH 5 / Enzymatic reaction View Scheme

: 75055-90-2
(3β,25R)-spirost-5-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1->2)-[6-deoxy-α-L-mannopyranosyl-(1->3)]-β-D-glucopyranoside

A: 14144-06-0
trillin

B: 512-04-9
diosgenin

Conditions

Conditions	Yield
With sulfuric acid In methanol; water at 100℃; for 10h;	A 75 mg B 60 mg

: 50773-41-6
(3β,25R)-spirost-5-en-3-ol-3-O-α-L-arabinofuranosyl-(1->4)-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside

A: 14144-06-0
trillin

B: 19057-67-1
ophiopogonin C

C: 512-04-9
diosgenin

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane at 100℃; for 4h;
at 290℃; further temp.;

...Expand

: 94992-08-2
26-(O-β-D-glucopyranosyl)-3-β-[4-O-(β-D-glucopyranosyl)-2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-22,26-dihydroxyfurost-5-ene

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;

: 116481-33-5
diosgenin-3-O-α-L-rhamnopyranosyl-(1->2)-β-D-glucopyranoside

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With sulfuric acid In water for 3h; Heating;
Acid hydrolysis;

: 55972-80-0
26-O-β-D-glucopyranosyl-22-hydroxyfurost-5-ene-3β,26-diol 3-O-α-L-rhamnopyranosyl(1<*>2)-β-D-glucopyranoside

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 3h; Heating;

: 75050-63-4
permethylate of taccaoside

A: 24462-98-4
O4,O6-dimethyl-α-D-glucopyranose

B: 4348-77-0, 14187-51-0, 63122-28-1, 71049-57-5, 71049-59-7, 139628-30-1
2,3,4-tri-O-methyl-L-rhamnose

C: 512-04-9
diosgenin

Conditions

Conditions	Yield
With sulfuric acid In methanol; water at 100℃; for 10h;	A n/a B n/a C 16 mg

...Expand

: 19108-08-8
degalactototigonin

A: 14270-72-5
(25R)-5α-spirost-5-en-3β-ol 3-O-β-D-galactopyranoside

B: 55639-73-1, 60454-77-5, 74759-15-2, 99661-95-7, 104732-63-0, 108945-21-7, 111137-19-0, 144071-57-8
diosgenin 3-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside

C: 60454-78-6
(25R)-spirost-5-en-3β-ol 3-O-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside

D: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water for 1h; Heating;	A 120 mg B 170 mg C 320 mg D 140 mg

...Expand

: 94901-56-1
deltonin per-O-methylate

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;

: 50773-46-1
C61H102O20

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;

: 94898-69-8
rhapissaponin

: 512-04-9
diosgenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;	2 mg

: 98-59-9
p-toluenesulfonyl chloride

: 512-04-9
diosgenin

: 4965-78-0
(25R)-3β-O-(p-toluenesulfonyloxy)spirost-5-ene

Conditions

Conditions	Yield
With pyridine In dichloromethane for 3h; Darkness;	100%
With pyridine at 20℃; for 6h;	97.7%
With pyridine

: 149707-75-5
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

: 512-04-9
diosgenin

: 14144-06-0
trillin

Conditions

Conditions	Yield
Stage #1: 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate; diosgenin With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation; Stage #2: With sodium methylate Substitution;	100%

: C41H40Cl3NO16

: 512-04-9
diosgenin

: C39H62O12

Conditions

Conditions	Yield
Stage #1: C41H40Cl3NO16; diosgenin With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation; Stage #2: With sodium methylate Substitution;	100%

: 98-88-4
benzoyl chloride

: 512-04-9
diosgenin

: 4952-68-5
diosgenin benzoate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 12h;	100%

: 108-30-5
succinic acid anhydride

: 512-04-9
diosgenin

: 4965-84-8
4-(((25R)-spirost-5-ene-3β-yl)oxy)-4-oxobutanoic acid

Conditions

Conditions	Yield
With pyridine at 80℃;	100%
With dmap In toluene at 80℃;	99.2%
With dmap; triethylamine In dichloromethane at 80℃; for 72h;	94%

: 75-36-5
acetyl chloride

: 512-04-9
diosgenin

: (25R)-16,26-diacetoxy-4-cholesten-3,22-dione

Conditions

Conditions	Yield
With pyridine at 20℃; for 0.5h;	100%

: 32315-10-9
bis(trichloromethyl) carbonate

: 512-04-9
diosgenin

: 1337989-08-8
diosgenyl chloroformate

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; diosgenin In tetrahydrofuran at 20℃; Stage #2: With pyridine In tetrahydrofuran at 0℃; for 1h;	100%
In tetrahydrofuran at 0 - 20℃; for 6h;	70%
With pyridine In dichloromethane at 20℃; for 3h; Inert atmosphere;
In dichloromethane

: 108-24-7
acetic anhydride

: 512-04-9
diosgenin

: 1061-54-7
diosgenin acetate

Conditions

Conditions	Yield
With pyridine In dichloromethane	99%
With pyridine In dichloromethane at 20℃; for 6h;	97%
With pyridine In dichloromethane at 20℃; for 6h;	97%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 512-04-9
diosgenin

: 324740-29-6
3-O-(tert-butyldiphenylsilyl)diosgenin

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	99%
With 1H-imidazole In N,N-dimethyl-formamide	96%
With 1H-imidazole In dichloromethane at 20℃; for 12h;	93%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 512-04-9
diosgenin

: 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

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	99%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 50℃; for 0.5h;	99%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 50℃; for 0.5h;	98%

: 512-04-9
diosgenin

: 77-60-1
tigogenin

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In ethanol; dichloromethane	99%
With hydrogen; acetic acid; palladium on activated charcoal In ethanol; dichloromethane at 20℃; under 760 Torr; for 12h;	93%
With 5% Pd/C; hydrogen In ethyl acetate at 20℃; under 3750.38 Torr;
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 3h;

: 1221151-98-9
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

: 512-04-9
diosgenin

: 120969-06-4
diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside

Conditions

Conditions	Yield
trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) In dichloromethane at 20℃;	99%

: 7772-87-4
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

: 512-04-9
diosgenin

: 575458-79-6
diosgenin 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Conditions

Conditions	Yield
Stage #1: diosgenin With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 0.166667h; Molecular sieve; Inert atmosphere; Stage #2: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride In dichloromethane at 20℃; for 20h; Molecular sieve; Inert atmosphere;	99%

: 3,4,6-tri-O-benzyl-2-deoxy-2-(o-nitrobenzenesulfonylamino)-α-D-glucopyranosyl ortho-hexynylbenzoate

: 512-04-9
diosgenin

: diosgenyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2-dinitrobenzenesulfonylamino)-β-D-glucopyranoside

Conditions

Conditions	Yield
With (triphenyl phosphite)gold(I) chloride; silver tetrakis(pentafluorophenyl)borate In dichloromethane at 0℃; for 0.5h; Molecular sieve;	99%

: 108-24-7
acetic anhydride

: 512-04-9
diosgenin

: 2309-38-8
pseudodiosgenin diacetate

Conditions

Conditions	Yield
Stage #1: acetic anhydride With aluminum (III) chloride at 20℃; for 0.25h; Green chemistry; Stage #2: diosgenin at 140℃; for 3h; Reagent/catalyst; Green chemistry;	98%
With pyridine; ammonium chloride Reflux;	86%
Ring cleavage; acetylation; Heating;	56.3%

: 100-39-0
benzyl bromide

: 512-04-9
diosgenin

: 146333-24-6
3-O-benzyl diosgenin

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 90℃;	98%
Stage #1: diosgenin With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: benzyl bromide In tetrahydrofuran; N,N-dimethyl-formamide Heating; Further stages.;	97%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide Heating;	96%
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran for 16h; Heating;	90%
With sodium hydride

: 67124-60-1
3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

: 512-04-9
diosgenin

: 1028758-82-8
diosgenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy-carbonylamino)-β-D-glucopyranoside

Conditions

Conditions	Yield
Stage #1: diosgenin With silver trifluoromethanesulfonate In diethyl ether; dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide In diethyl ether; dichloromethane at 20℃; for 20h; Inert atmosphere;	98%

: 13139-16-7
N-(tert-butyloxycarbonyl)-L-isoleucine

: 512-04-9
diosgenin

: (25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-isoleucinate

Conditions

Conditions	Yield
Stage #1: N-(tert-butyloxycarbonyl)-L-isoleucine With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h; Stage #2: diosgenin In dichloromethane at 20℃; for 24h;	98%

: 13734-41-3
t-Boc-L-valine

: 512-04-9
diosgenin

: (25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-valinate

Conditions

Conditions	Yield
Stage #1: t-Boc-L-valine With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h; Stage #2: diosgenin In dichloromethane at 20℃; for 24h;	98%

: 2488-15-5
N-tert-butoxycarbonyl-L-methionine

: 512-04-9
diosgenin

: (25R)-spirost-5-en-3β-yl N-(t-butoxycarbonyl)-L-methioninate

Conditions

Conditions	Yield
Stage #1: N-tert-butoxycarbonyl-L-methionine With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h; Stage #2: diosgenin In dichloromethane at 20℃; for 24h;	98%

: 512-04-9
diosgenin

: 6877-70-9
(22R)-16β,22-epoxycholest-5-ene-3β,26-diol

Conditions

Conditions	Yield
With sodium cyanoborohydride In acetic acid for 2.5h; Ring cleavage;	97%
With sodium cyanoborohydride; propionic acid at 30℃; for 40h; Time; Inert atmosphere;	78%
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether	59%
Multi-step reaction with 2 steps 1: DMAP; Et3N 2: LiAlH4; AlCl3 View Scheme
Multi-step reaction with 4 steps 1: DMAP; Et3N 2: LiAlH4; AlCl3 3: pyridine 4: 32 percent / aq. tetrabutylammonium tetrafluoroborate / tetrahydrofuran / Electrochemical reaction View Scheme

: 1393471-65-2
2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl N-tosyl benzimidate

: 512-04-9
diosgenin

: 869884-32-2
diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnoside

Conditions

Conditions	Yield
Stage #1: 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl N-tosyl benzimidate; diosgenin In dichloromethane for 0.5h; Molecular sieve; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 2h; Molecular sieve; Inert atmosphere;	97%

: diosgen-3-yl ortho-hexynylbenzoate

: 512-04-9
diosgenin

: 3,3'-oxybis-(3β,25R)-(3'β,25'R)-spirost-5-ene

Conditions

Conditions	Yield
With (triphenyl phosphite)gold(I) chloride; silver tetrakis(pentafluorophenyl)borate at 80℃; Inert atmosphere; Molecular sieve; Darkness;	97%

: 3,4,6-tri-O-benzyl-2-deoxy-2-(p-nitrobenzenesulfonylamino)-α-D-glucopyranosyl ortho-hexynylbenzoate

: 512-04-9
diosgenin

: diosgenyl 3,4,6-tri-O-benzyl-2-deoxy-2-(p-nitrobenzenesulfonylamino)-β-D-glucopyranoside

Conditions

Conditions	Yield
With (triphenyl phosphite)gold(I) chloride; silver tetrakis(pentafluorophenyl)borate In dichloromethane at 0℃; for 0.5h; Molecular sieve;	97%

: 100-39-0
benzyl bromide

: 512-04-9
diosgenin

: diosgenin-3-benzyl ether

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 0.5h; Concentration;	96.2%

: 146728-55-4
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-(α/β)-D-glucopyranosyl trichloroacetimidate

: 512-04-9
diosgenin

: 575458-79-6
diosgenin 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -20℃; for 1h; Molecular sieve;	96%

: 108-24-7
acetic anhydride

: 512-04-9
diosgenin

: (25R)-23-acetyl-3,16-diacetoxy-22,23-pyran-cholesta-5,22-diene

Conditions

Conditions	Yield
With zinc(II) chloride at 20℃; for 72h;	96%

: 108-24-7
acetic anhydride

: 512-04-9
diosgenin

: 245124-64-5
(20S,25R)-23-acetyl-22,26-epoxycholesta-5,22-diene-3β,16β-diyl diacetate

Conditions

Conditions	Yield
With zinc(II) chloride at 20℃; for 40h;	95%
With boron trifluoride diethyl etherate at 20℃; for 0.833333h; Ring cleavage; acetylation;	85%
With boron trifluoride diethyl etherate at 20℃; for 0.166667h;	85%
With boron trifluoride diethyl etherate

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.

Product Name

diosgenin

Synthetic route

Diosgenin Specification

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