Hecogenin supplier | CasNO.467-55-0

Name
Hecogenin
EINECS 207-392-4
CAS No. 467-55-0
Article Data24
CAS DataBase
Density 1.16 g/cm³
Solubility
Melting Point 268 °C
Formula C₂₇H₄₂O₄
Boiling Point 548.9 °C at 760 mmHg
Molecular Weight 430.628
Flash Point 177.8 °C
Transport Information
Appearance White solid.
Safety
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5a,25D-Spirostan-12-one, 3b-hydroxy- (7CI);5a-Spirostan-12-one, 3b-hydroxy-, (25R)- (8CI);(+)-Hecogenin;(25R)-3b-Hydroxy-5a-spirostan-12-one;(3b,5a,25R)-3-Hydroxyspirostan-12-one;12-Oxotigogenin;Gekogenin;Hocogenin;NSC 115921;
PSA 55.76000
LogP 4.97280

Synthetic route

: 915-35-5
hecogenin acetate

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With methanol; potassium hydroxide In dichloromethane at 20℃; for 18h;	99%
With methanol; potassium carbonate In tetrahydrofuran for 24h;	97%
With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 12h; Inert atmosphere;	95%

: (2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-8(2H)-one

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With sodium perborate tetrahydrate In tetrahydrofuran; water for 3h;	79%

: α-D-glucopyranosyl(1->4)α-D-glucopyranosyl(1->4)α-D-glucopyranosyl(1->3)hecogenin

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With sulfuric acid	44.8%

: 108747-55-3
12-methylenetigogenin

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With sodium periodate; potassium carbonate; tert-butyl alcohol Reagens 4: Kaliumpermanganat;

: 2137-20-4
3-oxo-5α-hecogenin

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With pyridine; sodium borate
With tetrahydrofuran; lithium aluminium tetrahydride; diethyl ether Behandeln des erhaltenen Reaktionsprodukts in Pyridin mit Bernsteinsaeure-anhydrid und mit Chrom(VI)-oxid und wss. Essigsaeure, danach mit methanol. Kalilauge;
Aspergillus niger;

: 4948-48-5
3β-acetoxy-(25R)-5α-spirostan-12-one

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride; ethanol

: 78179-47-2
(25R)-12α-(Aminomethyl)-5α-spirostan-3β,12β-diol

A: 72166-67-7
(25R)-3β-Hydroxy-C-homo-5α-spirostan-12-on

B: 72166-68-8
(25R)-3β-Hydroxy-C-homo-5α-spirostan-12-on

C: (25R)-12α-(Azidomethyl)-5α-spirostan-3β,12β-diol

D: 467-55-0
hecogenin

Conditions

Conditions	Yield
With sodium azide; sodium nitrite Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 3-O-<<β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 100℃; for 3.5h;

: 3-O-<<β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol

A: C39H62O14

B: C45H72O19

C: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride In butan-1-ol at 70℃; for 2.5h;	A 13.5 mg B 16.5 mg C 15 mg

...Expand

: 3-O-<<β-D-xylopyranosyl(1->4)-β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 100℃; for 3.5h;
Multi-step reaction with 2 steps 1: 20 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C 2: 2M HCl / ethanol / 3.5 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: 20 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C 2: 15 mg / 1M HCl / butan-1-ol / 2.5 h / 70 °C View Scheme

: 3-O-<<β-D-xylopyranosyl(1->4)-β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol

A: C39H62O14

B: C45H72O19

C: 3-O-<<β-D-glucopyranosyl(1->3)-β-D-glucopyranosyl(1->2> <β-D-xylopyranosyl(1->4)>-β-D-galactopyranosyl>-(25R)-5α-spirostan-12-one-3β-ol

D: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride In butan-1-ol at 70℃; for 2.5h;	A 10 mg B 13.5 mg C 20 mg D 10 mg

...Expand

: 168960-81-4
25(R)-5α-spirostan-3β-ol-12-one 3-O-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water for 2h; Heating;	4.9 mg

: (25R)-3β-[(O-β-D-glucopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-[O-α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one

A: 2280-44-6
D-Glucose

B: 10257-28-0
D-Galactose

C: 73-34-7
L-rhamnose

D: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 100℃; for 3h; Product distribution; Hydrolysis;	A 20.8 mg B 8.1 mg C 5.8 mg D 11.8 mg

...Expand

: 7647-01-0
hydrogenchloride

: 107492-88-6
20-isohecogenin

: 467-55-0
hecogenin

: 7647-01-0
hydrogenchloride

: 4948-48-5
3β-acetoxy-(25R)-5α-spirostan-12-one

: 467-55-0
hecogenin

cyclopseudohecogenin: cyclopseudohecogenin

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride; methanol

: 7647-01-0
hydrogenchloride

: 17990-60-2
(25R)-3β-hydroxy-5α-spirostan-12-one-(2,4-dinitro-phenylhydrazone)

tin (II)-chloride: tin (II)-chloride

: 467-55-0
hecogenin

...Expand

: (25R)-3β-[{O-β-D-xylopyranosyl-(1->3)-O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl}oxy]-5α-spirostan-12-one

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 98℃; for 2h;	3.4 mg

: (25R)-3β-hydroxy-5α-spirostan-12-one-3-O-β-xylopyranosyl(1->4)-[α-arabinopyranosyl(1->6)]-β-glucopyranoside

: 467-55-0
hecogenin

Conditions

Conditions	Yield
In ethanol; sulfuric acid at 100℃; for 6h;	2 mg

: 38673-31-3
(25R)-12-ethylenedioxy-5α-spirostan-3β-ol

: 467-55-0
hecogenin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Jones' reagent 2: Aspergillus niger View Scheme

: C31H48O6

: 467-55-0
hecogenin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. KOH 2: Jones' reagent 3: Aspergillus niger View Scheme

: 6875-60-1
25R-spirost-4-ene-3,12-dione

: 467-55-0
hecogenin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium/charcoal; dioxane; methanol. KOH-solution 2: sodium borate; pyridine View Scheme

: (23Ξ,25R)-23-bromo-spirost-4-ene-3,12-dione

: 467-55-0
hecogenin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; acetic acid; zinc-powder 2: palladium/charcoal; dioxane; methanol. KOH-solution 3: sodium borate; pyridine View Scheme

: (23Ξ,25R)-2α,4α,23-tribromo-5α-spirostan-3,12-dione

: 467-55-0
hecogenin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium iodide; acetone / Behandeln des Reaktionsprodukts in Aceton und Dioxan mit Chrom(II)-chlorid in wss. Salzsaeure 2: ethanol; acetic acid; zinc-powder 3: palladium/charcoal; dioxane; methanol. KOH-solution 4: sodium borate; pyridine View Scheme

: 467-55-0, 509-99-9, 545-78-8, 38676-82-3, 72203-53-3, 107492-88-6, 119008-59-2
(25S)-hecogenin

: 467-55-0
hecogenin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: ethanol; aqueous hydrochloric acid View Scheme

: 28180-63-4
(25R)-2α,3α-epoxy-5α-spirostan-12-one

: 467-55-0
hecogenin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene; diethyl ether; lithium alanate / Behandeln einer Loesung des Reaktionsprodukts in Essigsaeure mit Chrom(VI)-oxid und wss. Essigsaeure 2: tetrahydrofuran; lithium alanate; diethyl ether / Behandeln des erhaltenen Reaktionsprodukts in Pyridin mit Bernsteinsaeure-anhydrid und mit Chrom(VI)-oxid und wss. Essigsaeure, danach mit methanol. Kalilauge View Scheme

Yield

Multi-step reaction with 2 steps
1: benzene; diethyl ether; lithium alanate / Behandeln einer Loesung des Reaktionsprodukts in Essigsaeure mit Chrom(VI)-oxid und wss. Essigsaeure
2: tetrahydrofuran; lithium alanate; diethyl ether / Behandeln des erhaltenen Reaktionsprodukts in Pyridin mit Bernsteinsaeure-anhydrid und mit Chrom(VI)-oxid und wss. Essigsaeure, danach mit methanol. Kalilauge
View Scheme

: 1174898-06-6
(25R)-3β-[(O-β-D-glucopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one

: 467-55-0
hecogenin

Conditions

Conditions	Yield
With hydrogenchloride; water In 1,4-dioxane at 95℃; for 2h; Inert atmosphere;	1.2 mg

: 1499187-81-3
(25R)-3β-[(O-α-L-arabinopyranosyl-(1 → 2)-O-[β-D-xylopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-galactopyranosyl)oxy]-5α-spirostan-12-one

A: 58-86-6
D-xylose

B: 5328-37-0
L-arabinose

C: 3615-41-6
L-Rhamnose

D: 50-99-7
D-glucose

E: 59-23-4
D-Galactose

F: 467-55-0
hecogenin

Conditions

Conditions	Yield
With naringinase; potassium acetate; acetic acid In aq. buffer at 20℃; for 49h; pH=4.3; Enzymatic reaction;	A n/a B n/a C n/a D n/a E n/a F 3.1 mg

...Expand

: O-((2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-8-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)-1H-imidazole-1-carbothioate

: 467-55-0
hecogenin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / N,N-dimethyl acetamide; 1,4-dioxane / 48 h / Inert atmosphere; Schlenk technique; Irradiation 1.2: 2 h / Inert atmosphere; Schlenk technique; Irradiation 2.1: sodium perborate tetrahydrate / tetrahydrofuran; water / 3 h View Scheme

: 467-55-0
hecogenin

: 2137-20-4
3-oxo-5α-hecogenin

Conditions

Conditions	Yield
With Jones reagent In acetone at 20℃; for 0.333333h;	99%
Multi-step reaction with 4 steps 1: pyridine / Ambient temperature 2: BF3-Et2O / CH2Cl2 / Ambient temperature 3: aq. KOH 4: Jones' reagent View Scheme
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 3h;

: 108-24-7
acetic anhydride

: 467-55-0
hecogenin

: 915-35-5
hecogenin acetate

Conditions

Conditions	Yield
With pyridine at 20℃;	95%

: 467-55-0
hecogenin

: 545-77-7, 16653-52-4, 38673-26-6, 90375-72-7, 90457-38-8, 107297-25-6
3β,12β-dihydroxy-(25R)-5α-spirostane

Conditions

Conditions	Yield
With ammonia; lithium In tetrahydrofuran at -78 - -33℃; for 5h; Reduction;	95%
With diethyl ether; acetic acid; platinum Hydrogenation;
Stage #1: hecogenin With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water stereoselective reaction;

: 98-59-9
p-toluenesulfonyl chloride

: 467-55-0
hecogenin

: 60433-68-3
(25R)-12-oxo-5α-spirostan-3β-yl tosylate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 4℃; for 24h;	94%
With pyridine at 20℃;	93%
With pyridine
With pyridine

: 10000-20-1
1,2-bis(tert-butyldimethylsilyl)hydrazine

: 467-55-0
hecogenin

: 690275-05-9
C39H72N2O3Si2

Conditions

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In chloroform at 55℃; for 20h;	93%

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

: 467-55-0
hecogenin

: 1373440-74-4
hecogenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere; Molecular sieve;	91%

: 108-24-7
acetic anhydride

: 467-55-0
hecogenin

: 245124-65-6
(25R)-23-acetyl-22,26-epoxy-12-oxo-5α-cholesta-22-ene-3β,16β-diyl diacetate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 0.833333h; Ring cleavage; acetylation;	87%
With boron trifluoride diethyl etherate at 20℃; for 0.166667h;	87%

: 321125-08-0
2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

: 467-55-0
hecogenin

: hecogenin-3-yl 2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2-O-acetyl-3-O-triethylsilyl-α-L-arabinopyranoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS In dichloromethane at -20℃;	86%

: 108-24-7
acetic anhydride

: 467-55-0
hecogenin

: 1228298-02-9
(25R)-26-hydroxy-12,22-dioxo-5α-cholestan-3β,16β-diyl diacetate

Conditions

Conditions	Yield
Stage #1: acetic anhydride; hecogenin With boron trifluoride diethyl etherate In dichloromethane at 0℃; Stage #2: With water In dichloromethane Cooling with ice;	86%
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 0.25h;	86%
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 0.5h;

: 18162-48-6
tert-butyldimethylsilyl chloride

: 467-55-0
hecogenin

: 909880-00-8
(25R)-3β-(tert-butyl(dimethyl)silyloxy)-5α-spirostan-12-one

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 3h;	84%

: 20295-82-3
O-carboxymethylhydroxylamine hydrochloride

: 467-55-0
hecogenin

: (25R)-12E-[O-(carboxymethyl)oximino]-5α-spirostan-3β-ol

Conditions

Conditions	Yield
With pyridine at 20℃;	84%

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

: 467-55-0
hecogenin

: 869884-28-6
hecogenin 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;	82%

: 69739-34-0
t-butyldimethylsiyl triflate

: 467-55-0
hecogenin

: 1246949-40-5
C39H70O4Si2

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	80%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	80%

: 467-55-0
hecogenin

: 1432631-48-5
(25R)-3α-amino-5α-spirostan-12-one

Conditions

Conditions	Yield
Stage #1: hecogenin With methanesulfonyl chloride; triethylamine In dichloromethane Stage #2: With sodium azide In dimethyl sulfoxide at 70℃; Stage #3: With 10 wt% Pd(OH)2 on carbon; hydrogen	79%
Multi-step reaction with 3 steps 1: pyridine 2: sodium azide / 60 °C 3: triphenylphosphine; water / tetrahydrofuran / 20 °C View Scheme

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 467-55-0
hecogenin

: O-((2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-8-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)-1H-imidazole-1-carbothioate

Conditions

Conditions	Yield
With dmap In dichloromethane at 55℃; for 3h;	79%

: 5351-69-9
4-Phenyl-3-thiosemicarbazide

: 467-55-0
hecogenin

: 3β-hydroxy-5α,25R-spirostan-12-(phenyl thiosemicarbazone)

Conditions

Conditions	Yield
With pyridine at 20℃;	78%
In ethanol at 20℃;

: 38901-29-0
N-(2-(trifluoromethyl)phenyl)hydrazinecarbothioamide

: 467-55-0
hecogenin

: 3β-hydroxy-5α,25R-spirostan-12-(3'-trifluoromethylphenyl thiosemicarbazone)

Conditions

Conditions	Yield
With pyridine at 20℃;	75%

: 614-10-8
4-(2-methylphenyl)-3-thiosemicarbazide

: 467-55-0
hecogenin

: 3β-hydroxy-5α,25R-spirostan-12-(3'-methylphenyl thiosemicarbazone)

Conditions

Conditions	Yield
With pyridine at 20℃;	75%

: 73305-12-1
4-(2'-nitrophenyl)-3-thiosemicarbazide

: 467-55-0
hecogenin

: 3β-hydroxy-5α,25R-spirostan-12-(3'-nitrophenyl thiosemicarbazone)

Conditions

Conditions	Yield
With pyridine at 20℃;	72%

: 527-69-5
2-furancarbonyl chloride

: 467-55-0
hecogenin

: 3β-O-(furoyl)-5α,25R-spirostan-12-one

Conditions

Conditions	Yield
Stage #1: hecogenin With pyridine; dmap; triethylamine at 20℃; for 0.333333h; Stage #2: 2-furancarbonyl chloride	71%

: 21615-34-9
2-Methoxybenzoyl chloride

: 467-55-0
hecogenin

: 3β-O-(4'-chlorobenzoyl)-5α,25R-spirostan-12-one

Conditions

Conditions	Yield
Stage #1: hecogenin With pyridine; dmap; triethylamine at 20℃; for 0.333333h; Stage #2: 2-Methoxybenzoyl chloride	70%

: 593-56-6
N-methoxylamine hydrochloride

: 467-55-0
hecogenin

: 1033264-82-2
12-Z,E-methyloximehecogenin

Conditions

Conditions	Yield
With pyridine In toluene at 20 - 50℃;	69.5%

: 467-55-0
hecogenin

: 469-13-6
(25R)-C-homo-12a-oxa-3β-hydroxy-5α-spirostan-12-one

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 120h; Baeyer-Villiger oxidation; Darkness;	69%

: 467-55-0
hecogenin

: 10007-76-8
(25R)-5α-spirostan-3β,12β-diol diacetate

Conditions

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane; methanol at 10℃; for 0.5h;	68%
Multi-step reaction with 2 steps 1: 95 percent / liquid NH3; Li / tetrahydrofuran / 5 h / -78 - -33 °C 2: 90 percent / NEt3; DMAP / CH2Cl2 / 5.5 h View Scheme
Multi-step reaction with 2 steps 1: NaBH4 / dioxane; methanol / 0.5 h / 10 °C 2: 8.2 g / pyridine View Scheme
Multi-step reaction with 2 steps 1: platinum; acetic acid; diethyl ether / Hydrogenation View Scheme

: 6068-72-0
4-cyanobenzoyl chlorIde

: 467-55-0
hecogenin

: 3β-O-(5'-cyanobenzoyl)-5α,25R-spirostan-12-one

Conditions

Conditions	Yield
Stage #1: hecogenin With pyridine; dmap; triethylamine at 20℃; for 0.333333h; Stage #2: 4-cyanobenzoyl chlorIde	68%

: 42135-75-1
4-(2'-chlorophenyl)-3-thiosemicarbazide

: 467-55-0
hecogenin

: 3β-hydroxy-5α,25R-spirostan-12-(3'-chlorophenyl thiosemicarbazone)

Conditions

Conditions	Yield
With pyridine at 20℃;	65%

: ortho-iodophenyl chlorothionoformate

: 467-55-0
hecogenin

: C34H45IO5S

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃;	64%

: 122-04-3
4-nitro-benzoyl chloride

: 467-55-0
hecogenin

: 3β-O-(5'-nitrobenzoyl)-5α,25R-spirostan-12-one

Conditions

Conditions	Yield
Stage #1: hecogenin With pyridine; dmap; triethylamine at 20℃; for 0.333333h; Stage #2: 4-nitro-benzoyl chloride	63%

Hecogenin Specification

The Hecogenin, with the CAS registry number 467-55-0, is also known as (25R)-3b-Hydroxy-5a-spirostan-12-one. It belongs to the product categories of Steroids; Biochemistry; Steroids (Others). Its EINECS registry number is 207-392-4. This chemical's molecular formula is C₂₇H₄₂O₄ and molecular weight is 430.62. What's more, its systematic name is called (3β,5α,25R)-3-Hydroxyspirostan-12-one.

Physical properties about Hecogenin are: (1)ACD/LogP: 4.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.22; (4)ACD/LogD (pH 7.4): 4.22; (5)ACD/BCF (pH 5.5): 947.44; (6)ACD/BCF (pH 7.4): 947.44; (7)ACD/KOC (pH 5.5): 4701.29; (8)ACD/KOC (pH 7.4): 4701.29; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 44.76 Å²; (13)Index of Refraction: 1.558; (14)Molar Refractivity: 119.77 cm³; (15)Molar Volume: 371.1 cm³; (16)Surface Tension: 46.3 dyne/cm; (17)Density: 1.16 g/cm³; (18)Flash Point: 177.8 °C; (19)Enthalpy of Vaporization: 95.25 kJ/mol; (20)Boiling Point: 548.9 °C at 760 mmHg; (21)Vapour Pressure: 2.45E-14 mmHg at 25 °C.

Preparation of Hecogenin: this chemical can be prepared by a-D-Glucopyranosyl(1->4)a-D-glucopyranosyl(1->4)a-D-glucopyranosyl(1->3)hecogenin. This reaction needs reagent (NH₂)₂SO₄. The yield is 44.8 %.

Hecogenin can be prepared by a-D-Glucopyranosyl(1->4)a-D-glucopyranosyl(1->4)a-D-glucopyranosyl(1->3)hecogenin.

Uses of Hecogenin: (1) it is used in the preparation of steroidal hormones; (2) it is used to produce other chemicals. For example, it can produce 3b-Hydroxy-11b-bromo-12-oxo-(25R)-5a-spirostane. The reaction occurs with reagents Br₂, HCl and solvents methanol, CH₂Cl₂. The yield is 59 %.

Hecogenin can produce 3b-Hydroxy-11b-bromo-12-oxo-(25R)-5a-spirostane.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C2C[C@@H]1[C@@]6(C)CC[C@H](O)C[C@@H]6CC[C@H]1[C@H]5[C@]2([C@@H]4[C@@H](O[C@@]3(OC[C@@H](CC3)C)[C@H]4C)C5)C
(2) InChI: InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-22,24,28H,5-14H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22+,24+,25+,26-,27-/m1/s1
(3) InChIKey: QOLRLLFJMZLYQJ-LOBDNJQFSA-N

Product Name

Hecogenin

Synthetic route

Hecogenin Specification

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