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471-53-4

Basic Information
CAS No.: 471-53-4
Name: Enoxolone
Molecular Structure:
Molecular Structure of 471-53-4 (Enoxolone)
Formula: C30H46O4
Molecular Weight: 470.68
Synonyms: Uralenic acid;(2S,4aR,6aS,6aS,6bR,8aS,10R,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate;Biosone;Hidermart;Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,20β)-;Glycyrrhetic acid;3-Glycyrrhetinic acid;Glycyrrhetinate;10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid;β-Glycyrrhetinic Acid;Hidermart (TN);Glycyrrhetin;r-Glycyrrhetinic acid;Glycyrrhetinic acid;Glycyrrhetinic acid (JAN);(3β)-3-Hydroxy-11-oxoolean-12-en-30-oic acid;
EINECS: 207-444-6
Density: 1.14 g/cm3
Melting Point: 292-295 °C(lit.)
Boiling Point: 588.3 °C at 760 mmHg
Flash Point: 323.7 °C
Solubility: Insoluble in water, but soluble in ethanol, chloroform, pyridine, acetic acid
Appearance: white or greyish-white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36
Safety: 22-24/25
Transport Information:
PSA: 74.60000
LogP: 6.41260
Synthetic route
1405-86-3

glycyrrhizin

471-53-4

enoxolone

Conditions
ConditionsYield
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;
Conditions
ConditionsYield
With hydrogenchloride In water85%
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%

(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-D-glucopyranosiduronic acid

471-53-4

enoxolone

Conditions
ConditionsYield
With hydrogenchloride In water; acetic acid at 100℃; for 1h;72%
With hydrogenchloride; water In chloroform for 6h; Reflux;13 mg
87918-97-6

6',6''-dibenzyl-18β-glycyrrhizin

471-53-4

enoxolone

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane for 4h;68.3%

β-glycyrrhizic acid monopotassium salt

471-53-4

enoxolone

Conditions
ConditionsYield
With sulfuric acid In water at 100℃; for 8h; Hydrolysis;68.3%
Conditions
ConditionsYield
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%

A

3β-hydroxy-12-oxoolean-30-oic acid

B

471-53-4

enoxolone

Conditions
ConditionsYield
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
Conditions
ConditionsYield
With potassium hydroxide
67-56-1

methanol

121709-66-8

apioglycyrrhizin

A

135414-74-3

methyl glucoside of D-glucurono-6,3-lactone

B

471-53-4

enoxolone

Conditions
ConditionsYield
With hydrogenchloride the structure was confirmed;
67-56-1

methanol

121687-83-0

araboglycyrrhizin

A

135414-74-3

methyl glucoside of D-glucurono-6,3-lactone

B

471-53-4

enoxolone

C

449173-64-2

methyl α,β-L-arabinopyranoside

Conditions
ConditionsYield
the structure was confirmed;
1405-86-3

glycyrrhizin

A

471-53-4

enoxolone

B

D-glucuronyl-β-1,2-D-glucuronic acid

Conditions
ConditionsYield
With glycyrrhizinic acid hydrolase at 40℃; pH 5.0, acetate buffer;
34096-83-8

1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid

471-53-4

enoxolone

Conditions
ConditionsYield
With luminal contents in rat colon In phosphate buffer at 37℃; pH=7.4; Kinetics; Hydrolysis;
ammonium salt of/the/ glycyrrhizinic acid

ammonium salt of/the/ glycyrrhizinic acid

471-53-4

enoxolone

Conditions
ConditionsYield
With sulfuric acid
With hydrogenchloride at 50℃;
With sulfuric acid at 130 - 155℃; unter Druck;
glycyrrhizinic acid

glycyrrhizinic acid

471-53-4

enoxolone

monoammonium salt of/the/ glycyrrhizinic acid

monoammonium salt of/the/ glycyrrhizinic acid

471-53-4

enoxolone

Conditions
ConditionsYield
With sulfuric acid
With β-glucuronidase
potassium salt of/the/ glycyrrhizinic acid

potassium salt of/the/ glycyrrhizinic acid

471-53-4

enoxolone

Conditions
ConditionsYield
With sulfuric acid
With hydrogenchloride at 50℃;
With sulfuric acid at 130 - 155℃; unter Druck;

glycyrrhizic acid

471-53-4

enoxolone

Conditions
ConditionsYield
With sulfuric acid In methanol Reflux;
1405-86-3

glycyrrhizin

A

471-53-4

enoxolone

B

34096-83-8

1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid

Conditions
ConditionsYield
With water at 100 - 140℃; under 52505.3 Torr; Kinetics; Thermodynamic data; Green chemistry;

C38H49NO6

471-53-4

enoxolone

Conditions
ConditionsYield
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;
Conditions
ConditionsYield
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%
471-53-4

enoxolone

6738-17-6

O-benzyl-N,N'-dicyclohexylisourea

51984-75-9

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
ConditionsYield
In chloroform for 5h; Heating;99%
Conditions
ConditionsYield
In methanol; diethyl ether at 0℃;99%
In tetrahydrofuran; diethyl ether for 0.833333h;89.7%
In diethyl ether; dichloromethane83%
Conditions
ConditionsYield
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
471-53-4

enoxolone

124-63-0

methanesulfonyl chloride

1326599-59-0

(3β)-3-[(methylsulfonyl)oxy]-11-oxo-olean-12-en-30-oic acid

Conditions
ConditionsYield
With pyridine at 20℃; for 70h;99%
With triethylamine In dichloromethane at 4℃; for 3h;65.7%
471-53-4

enoxolone

103-71-9

phenyl isocyanate

3-phenylcarbamoyl-18β-glycyrrhetinic acid

Conditions
ConditionsYield
With triethylamine In toluene at 110℃; for 2h;99%
Conditions
ConditionsYield
With pyridine at 20℃; for 16h;98%
With pyridine; dmap at 20℃; for 2h;98.2%
for 1.5h; Reflux;96.4%
471-53-4

enoxolone

6184-16-3, 7020-50-0, 146236-29-5

3,11-dioxoolean-12-en-30-oic acid

Conditions
ConditionsYield
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%
471-53-4

enoxolone

S-(1-butyn-3-yl)-O-methyl xanthate

Conditions
ConditionsYield
In toluene Heating;98%
471-53-4

enoxolone

870-63-3

prenyl bromide

18β-glycyrrhetinic acid 30-prenyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃; for 4h;98%
471-53-4

enoxolone

541-88-8

Chloroacetic anhydride

109278-66-2

(3β)‐(2‐chloroacetyloxy)‐11‐oxo‐olean‐12‐en‐30‐oic acid

Conditions
ConditionsYield
In ethyl acetate at 130℃; for 1h;98%
471-53-4

enoxolone

oxymatrine

C30H46O4*C15H24N2O2

Conditions
ConditionsYield
In ethanol at 50℃; Solvent; Temperature;97.8%
471-53-4

enoxolone

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

C44H64O13

Conditions
ConditionsYield
With Aliquat 336; potassium carbonate In dichloromethane; water for 48h; Ambient temperature;97%
78239-72-2

3-bromo-4-fluoro-benzyl chloride

471-53-4

enoxolone

3-(3-bromo-4-fluoro-benzyloxy)-11-oxoolean-12-ene-29-oic acid

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere;97%
471-53-4

enoxolone

620-20-2

1-Chloro-3-chloromethyl-benzene

3-(3-chloro-benzyloxy)-11-oxoolean-12-ene-29-oic acid

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere;97%
471-53-4

enoxolone

25026-34-0

4-chlorophenacetyl chloride

(3β)‐(2‐(4‐chlorophenyl)acetoxy)‐11‐oxo‐olean‐12‐en‐30‐oic acid

Conditions
ConditionsYield
With triethylamine In ethyl acetate for 24h; Reflux;97%
471-53-4

enoxolone

79-04-9

chloroacetyl chloride

109278-66-2

(3β)‐(2‐chloroacetyloxy)‐11‐oxo‐olean‐12‐en‐30‐oic acid

Conditions
ConditionsYield
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%
471-53-4

enoxolone

106-95-6

allyl bromide

31467-24-0

(3β,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid allyl ester

Conditions
ConditionsYield
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%
57260-73-8

N-BOC-1,2-diaminoethane

471-53-4

enoxolone

1334318-59-0

N-[2-(tert-butoxycarbonylamino)ethyl]glycyrrhetinamide

Conditions
ConditionsYield
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%
471-53-4

enoxolone

2592-95-2

benzotriazol-1-ol

1612838-71-7

1H‐benzo[d][1,2,3]triazol‐1‐yl‐3β‐hydroxy‐11‐oxo‐olean‐12‐en‐30‐oate

Conditions
ConditionsYield
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℃;
471-53-4

enoxolone

2592-95-2

benzotriazol-1-ol

57260-71-6

1-t-Butoxycarbonylpiperazine

1612838-71-7

1H‐benzo[d][1,2,3]triazol‐1‐yl‐3β‐hydroxy‐11‐oxo‐olean‐12‐en‐30‐oate

Conditions
ConditionsYield
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%
Conditions
ConditionsYield
With hydrogenchloride; zinc amalgam In 1,4-dioxane; water for 5h; Clemmensen Reduction; Cooling;95%
With hydrogenchloride; mercury dichloride; zinc In 1,4-dioxane; water90%
With platinum(IV) oxide; hydrogen In acetic acid87.6%
471-53-4

enoxolone

77397-93-4

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
ConditionsYield
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℃;
471-53-4

enoxolone

(3β,18β,20β)-3,11-dihydroxyoleana-12-en-29-oic acid

Conditions
ConditionsYield
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;
471-53-4

enoxolone

459-46-1

4-Fluorobenzyl bromide

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-eicosahydropicene-2-carboxylic acid 4-fluorobenzyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;95%
471-53-4

enoxolone

917-54-4

methyllithium

3β-hydroxy-11-methylene-18β-olean-12-en-30-oic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; diethyl ether at 20℃; for 1h;95%
109-65-9

1-bromo-butane

471-53-4

enoxolone

1375691-79-4

butyl 3β-hydroxy-11-oxo-olean-12-en-30-oate

Conditions
ConditionsYield
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%
471-53-4

enoxolone

104-83-6

1-Chloro-4-(chloromethyl)benzene

3-(4-chloro-benzyloxy)-11-oxoolean-12-ene-29-oic acid

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere;95%
471-53-4

enoxolone

589-17-3

p-bromobenzyl chloride

3-(4-bromo-benzyloxy)-11-oxoolean-12-ene-29-oic acid

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 8h; Inert atmosphere;95%
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    471-53-4

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    471-53-4

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Specification

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%.

Enoxolone can be prepared by b-glycyrrhizic acid monopotassium salt at the temperature of 100 °C

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%.

Enoxolone can be used to produce 3,11-dioxo-olean-12-en-30-oic acid at the temperature of 0 °C

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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