Conditions | Yield |
---|---|
With methanol; thionyl chloride at 0 - 20℃; for 9h; Reagent/catalyst; Inert atmosphere; | 90% |
With hydrogenchloride; water In methanol at 90℃; for 20h; | |
With hydrogenchloride In water at 100℃; for 20h; | |
With sulfuric acid In methanol Reflux; | 250 mg |
With methanol; sulfuric acid at 90℃; for 24h; |
enoxolone
Conditions | Yield |
---|---|
With hydrogenchloride In water | 85% |
Multi-step reaction with 2 steps 1: 18.4 percent / CHCl3; dimethylformamide / 72 h / Ambient temperature 2: 68.3 percent / 20percent H2SO4 / dioxane / 4 h View Scheme | |
With hydrogenchloride In ethanol; water at 30 - 35℃; for 48h; | 0.53% |
enoxolone
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetic acid at 100℃; for 1h; | 72% |
With hydrogenchloride; water In chloroform for 6h; Reflux; | 13 mg |
B
enoxolone
C
11-deoxyglycyrrhetinic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water at 100℃; for 8h; Hydrolysis; | A n/a B 69.9% C 1.1% |
6',6''-dibenzyl-18β-glycyrrhizin
enoxolone
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane for 4h; | 68.3% |
enoxolone
Conditions | Yield |
---|---|
With sulfuric acid In water at 100℃; for 8h; Hydrolysis; | 68.3% |
Ammonium glycyrrhizate
enoxolone
Conditions | Yield |
---|---|
at 40℃; for 3h; 15percent aq. solution of β-glucuronidase, acetate buffer 4.6; | 48% |
With β-glucuronidase In water at 40℃; for 3h; Rate constant; Kinetics; Product distribution; acetate buffer 4.6; other temp., other pH, other time; | 48.08% |
B
enoxolone
Conditions | Yield |
---|---|
With β-glucuronidase In acetate buffer at 37℃; for 144h; pH=5.2; Hydrolysis; Enzymatic reaction; | A n/a B 45.9% |
11-deoxyglycyrrhetinic acid
B
enoxolone
Conditions | Yield |
---|---|
Stage #1: 11-deoxyglycyrrhetinic acid With ozone In methanol; dichloromethane at -60℃; Stage #2: With acetic acid; zinc In methanol; dichloromethane at 0℃; for 1h; Further stages.; | A 42% B n/a |
acetoxolone
enoxolone
Conditions | Yield |
---|---|
With potassium hydroxide |
methanol
apioglycyrrhizin
A
methyl glucoside of D-glucurono-6,3-lactone
B
enoxolone
C
methyl D-apiofuranoside
Conditions | Yield |
---|---|
With hydrogenchloride the structure was confirmed; |
methanol
araboglycyrrhizin
A
methyl glucoside of D-glucurono-6,3-lactone
B
enoxolone
C
methyl α,β-L-arabinopyranoside
Conditions | Yield |
---|---|
the structure was confirmed; |
Conditions | Yield |
---|---|
With glycyrrhizinic acid hydrolase at 40℃; pH 5.0, acetate buffer; |
1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid
enoxolone
Conditions | Yield |
---|---|
With luminal contents in rat colon In phosphate buffer at 37℃; pH=7.4; Kinetics; Hydrolysis; |
enoxolone
Conditions | Yield |
---|---|
With sulfuric acid | |
With hydrogenchloride at 50℃; | |
With sulfuric acid at 130 - 155℃; unter Druck; |
enoxolone
enoxolone
Conditions | Yield |
---|---|
With sulfuric acid | |
With β-glucuronidase |
enoxolone
Conditions | Yield |
---|---|
With sulfuric acid | |
With hydrogenchloride at 50℃; | |
With sulfuric acid at 130 - 155℃; unter Druck; |
enoxolone
Conditions | Yield |
---|---|
With sulfuric acid In methanol Reflux; |
glycyrrhizin
A
enoxolone
B
1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid
Conditions | Yield |
---|---|
With water at 100 - 140℃; under 52505.3 Torr; Kinetics; Thermodynamic data; Green chemistry; |
enoxolone
Conditions | Yield |
---|---|
With nickel(II) bromide dimethoxyethane; manganese; 2.9-dimethyl-1,10-phenanthroline; carbon dioxide In N,N-dimethyl-formamide at 20℃; under 2585.81 Torr; for 20h; Sealed tube; chemoselective reaction; |
enoxolone
methyl iodide
methyl glycyrrhetinate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 24h; | 100% |
With potassium carbonate In acetone at 20℃; for 12h; | 95% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; | 94% |
enoxolone
O-benzyl-N,N'-dicyclohexylisourea
benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate
Conditions | Yield |
---|---|
In chloroform for 5h; Heating; | 99% |
diazomethane
enoxolone
methyl glycyrrhetinate
Conditions | Yield |
---|---|
In methanol; diethyl ether at 0℃; | 99% |
In tetrahydrofuran; diethyl ether for 0.833333h; | 89.7% |
In diethyl ether; dichloromethane | 83% |
enoxolone
diazomethyl-trimethyl-silane
methyl glycyrrhetinate
Conditions | Yield |
---|---|
In methanol; diethyl ether at 0 - 20℃; for 2h; | 99% |
In diethyl ether at 20℃; for 1h; | 98% |
In methanol; hexane; toluene at 20℃; for 0.5h; | 91% |
In methanol; diethyl ether |
enoxolone
methanesulfonyl chloride
(3β)-3-[(methylsulfonyl)oxy]-11-oxo-olean-12-en-30-oic acid
Conditions | Yield |
---|---|
With pyridine at 20℃; for 70h; | 99% |
With triethylamine In dichloromethane at 4℃; for 3h; | 65.7% |
Conditions | Yield |
---|---|
With triethylamine In toluene at 110℃; for 2h; | 99% |
enoxolone
acetic anhydride
acetoxolone
Conditions | Yield |
---|---|
With pyridine at 20℃; for 16h; | 98% |
With pyridine; dmap at 20℃; for 2h; | 98.2% |
for 1.5h; Reflux; | 96.4% |
enoxolone
3,11-dioxoolean-12-en-30-oic acid
Conditions | Yield |
---|---|
With chromium(VI) oxide; sulfuric acid In acetone at 0℃; for 1h; | 98% |
With Jones reagent In acetone at 0℃; for 1.5h; | 96.25% |
With Jones reagent In acetone at 0℃; for 2h; | 96% |
enoxolone
Methyl ester of glycyrrhetic acid
Conditions | Yield |
---|---|
In toluene Heating; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50℃; for 4h; | 98% |
enoxolone
Chloroacetic anhydride
(3β)‐(2‐chloroacetyloxy)‐11‐oxo‐olean‐12‐en‐30‐oic acid
Conditions | Yield |
---|---|
In ethyl acetate at 130℃; for 1h; | 98% |
enoxolone
Conditions | Yield |
---|---|
In ethanol at 50℃; Solvent; Temperature; | 97.8% |
Conditions | Yield |
---|---|
In ethanol at 50℃; Solvent; Temperature; | 97.8% |
Conditions | Yield |
---|---|
With Aliquat 336; potassium carbonate In dichloromethane; water for 48h; Ambient temperature; | 97% |
3-bromo-4-fluoro-benzyl chloride
enoxolone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere; | 97% |
enoxolone
4-chlorophenacetyl chloride
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate for 24h; Reflux; | 97% |
enoxolone
chloroacetyl chloride
(3β)‐(2‐chloroacetyloxy)‐11‐oxo‐olean‐12‐en‐30‐oic acid
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 20℃; for 4h; | 96.2% |
Stage #1: enoxolone; chloroacetyl chloride With triethylamine In tetrahydrofuran at 25℃; for 12h; Stage #2: With hydrogenchloride In dichloromethane; water | 45.3% |
enoxolone
allyl bromide
(3β,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid allyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50℃; for 4h; | 96% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 84.2% |
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 24.1667h; | 69% |
N-BOC-1,2-diaminoethane
enoxolone
N-[2-(tert-butoxycarbonylamino)ethyl]glycyrrhetinamide
Conditions | Yield |
---|---|
Stage #1: enoxolone With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: N-BOC-1,2-diaminoethane In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 96% |
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 10h; | 90% |
Stage #1: enoxolone With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N-BOC-1,2-diaminoethane In N,N-dimethyl-formamide at 0 - 20℃; | 64% |
enoxolone
benzotriazol-1-ol
1H‐benzo[d][1,2,3]triazol‐1‐yl‐3β‐hydroxy‐11‐oxo‐olean‐12‐en‐30‐oate
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile for 0.333333h; Reflux; | 95.8% |
With hydrogenchloride In water for 3.5h; Reflux; | 90% |
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; | 27% |
With piperazine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; |
enoxolone
benzotriazol-1-ol
1-t-Butoxycarbonylpiperazine
1H‐benzo[d][1,2,3]triazol‐1‐yl‐3β‐hydroxy‐11‐oxo‐olean‐12‐en‐30‐oate
Conditions | Yield |
---|---|
Stage #1: enoxolone; benzotriazol-1-ol With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 0.333333h; Stage #2: 1-t-Butoxycarbonylpiperazine In dichloromethane for 24h; Reflux; | 95.8% |
enoxolone
11-deoxyglycyrrhetinic acid
Conditions | Yield |
---|---|
With hydrogenchloride; zinc amalgam In 1,4-dioxane; water for 5h; Clemmensen Reduction; Cooling; | 95% |
With hydrogenchloride; mercury dichloride; zinc In 1,4-dioxane; water | 90% |
With platinum(IV) oxide; hydrogen In acetic acid | 87.6% |
enoxolone
11-hydroxymethyl-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydro-picene-3,14-diol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 60 - 70℃; for 4h; | 95% |
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran at 0 - 20℃; | 63% |
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran | |
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; |
enoxolone
Conditions | Yield |
---|---|
With sodium tetrahydroborate; sodium hydroxide In tetrahydrofuran; water for 24h; Reflux; | 95% |
With sodium tetrahydroborate; sodium hydroxide In tetrahydrofuran; water for 4h; Reflux; | 80% |
With sodium hydroxide; sodium tetrahydroborate In tetrahydrofuran; water for 4h; Reduction; Heating; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; diethyl ether at 20℃; for 1h; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h; | 95% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 85.8% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere; | 95% |
The Enoxolone, with the CAS registry number 471-53-4, is also known as 18-beta-Glycyrrhetinic acid. It belongs to the product categories of Pentacyclic Triterpenes; Tri-Terpenoids; Miscellaneous; Biochemistry; Terpenes; Terpenes (Others); Natural Plant Extract; Cosmetic Ingredients & Chemicals; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS number is 207-444-6. This chemical's molecular formula is C30H46O4 and molecular weight is 470.68. What's more, its systematic name is (3β)-3-hydroxy-11-oxoolean-12-en-30-oic acid. Its classification code is Anti-Inflammatory Agents. It can be used as edible flavoring and sauces. It should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides. It is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice. It is used in flavoring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties.
Physical properties of Enoxolone are: (1)ACD/LogP: 6.57; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.73; (4)ACD/LogD (pH 7.4): 3.93; (5)ACD/BCF (pH 5.5): 8289; (6)ACD/BCF (pH 7.4): 131.57; (7)ACD/KOC (pH 5.5): 12748.06; (8)ACD/KOC (pH 7.4): 202.35; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 52.6 Å2; (13)Index of Refraction: 1.562; (14)Molar Refractivity: 133.69 cm3; (15)Molar Volume: 411.6 cm3; (16)Polarizability: 52.99×10-24cm3; (17)Surface Tension: 47.7 dyne/cm; (18)Density: 1.14 g/cm3; (19)Flash Point: 323.7 °C; (20)Enthalpy of Vaporization: 100.81 kJ/mol; (21)Boiling Point: 588.3 °C at 760 mmHg; (22)Vapour Pressure: 2.71E-16 mmHg at 25°C.
Preparation: this chemical can be prepared by b-glycyrrhizic acid monopotassium salt at the temperature of 100 °C. This reaction will need reagent H2SO4 and solvent H2O with the reaction time of 8 hours. The yield is about 68.3%.
Uses of Enoxolone: it can be used to produce 3,11-dioxo-olean-12-en-30-oic acid at the temperature of 0 °C. It will need reagents CrO3, H2SO4 and solvent acetone with the reaction time of 1 hour. The yield is about 98%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and is irritating to eyes. You should not breathe dust. When using it, you must avoid contact with eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@]5(C)C[C@H]4/C3=C/C(=O)[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC[C@@]4(C)CC5
(2)Std. InChI: InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,
(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
(3)Std. InChIKey: MPDGHEJMBKOTSU-YKLVYJNSSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 308mg/kg (308mg/kg) | Drugs in Japan Vol. -, Pg. 319, 1990. | |
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02067, | |
mouse | LD50 | subcutaneous | 518mg/kg (518mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 5, Pg. 98, 1963. |
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