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global trader 471-53-4 Reliable quality of Enoxolone offer
Cas No: 471-53-4
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High purity Enoxolone (18-β-glycyrrhetinic acid) with high quality cas:471-53-4
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Glycyrrhetic Acid
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471-53-4 Usage

Uses

antitussive, antiinflammatory, antibacterial

Uses

The aglycone of the triterpenoid Glyccyrrhizic acid.

Definition

ChEBI: A pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30.

Chemical Properties

white or greyish-white crystalline powder

Uses

An anti-inflammatory (topical).
InChI:InChI=1/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

471-53-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (E0180500)  Enoxolone  European Pharmacopoeia (EP) Reference Standard 471-53-4 E0180500 1,880.19CNY Detail
Aldrich (G10105)  18β-Glycyrrhetinicacid  97% 471-53-4 G10105-25G 2,218.32CNY Detail
Aldrich (G10105)  18β-Glycyrrhetinicacid  97% 471-53-4 G10105-10G 1,247.22CNY Detail
TCI America (G0149)  Glycyrrhetic Acid  >97.0%(T) 471-53-4 25g 1,410.00CNY Detail
TCI America (G0149)  Glycyrrhetic Acid  >97.0%(T) 471-53-4 1g 185.00CNY Detail

471-53-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Enoxolone

1.2 Other means of identification

Product number -
Other names ENOLOXONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:471-53-4 SDS

471-53-4Synthetic route

glycyrrhizin
1405-86-3

glycyrrhizin

enoxolone
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

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

enoxolone
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
6',6''-dibenzyl-18β-glycyrrhizin
87918-97-6

6',6''-dibenzyl-18β-glycyrrhizin

enoxolone
471-53-4

enoxolone

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

β-glycyrrhizic acid monopotassium salt

enoxolone
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

3β-hydroxy-12-oxoolean-30-oic acid

B

enoxolone
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
methanol
67-56-1

methanol

apioglycyrrhizin
121709-66-8

apioglycyrrhizin

A

methyl glucoside of D-glucurono-6,3-lactone
135414-74-3

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

B

enoxolone
471-53-4

enoxolone

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

methanol

araboglycyrrhizin
121687-83-0

araboglycyrrhizin

A

methyl glucoside of D-glucurono-6,3-lactone
135414-74-3

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

B

enoxolone
471-53-4

enoxolone

C

methyl α,β-L-arabinopyranoside
449173-64-2

methyl α,β-L-arabinopyranoside

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

glycyrrhizin

A

enoxolone
471-53-4

enoxolone

B

D-glucuronyl-β-1,2-D-glucuronic acid

D-glucuronyl-β-1,2-D-glucuronic acid

Conditions
ConditionsYield
With glycyrrhizinic acid hydrolase at 40℃; pH 5.0, acetate buffer;
1-(18β-glycyrrhet-3-yl)-β-D-glucopyranuronic acid
34096-83-8

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

enoxolone
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

enoxolone
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

enoxolone
471-53-4

enoxolone

monoammonium salt of/the/ glycyrrhizinic acid

monoammonium salt of/the/ glycyrrhizinic acid

enoxolone
471-53-4

enoxolone

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

potassium salt of/the/ glycyrrhizinic acid

enoxolone
471-53-4

enoxolone

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

glycyrrhizic acid

enoxolone
471-53-4

enoxolone

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

glycyrrhizin

A

enoxolone
471-53-4

enoxolone

B

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

C38H49NO6

enoxolone
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%
enoxolone
471-53-4

enoxolone

O-benzyl-N,N'-dicyclohexylisourea
6738-17-6

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
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
enoxolone
471-53-4

enoxolone

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(3β)-3-[(methylsulfonyl)oxy]-11-oxo-olean-12-en-30-oic acid
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%
enoxolone
471-53-4

enoxolone

phenyl isocyanate
103-71-9

phenyl isocyanate

3-phenylcarbamoyl-18β-glycyrrhetinic acid

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%
enoxolone
471-53-4

enoxolone

3,11-dioxoolean-12-en-30-oic acid
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%
enoxolone
471-53-4

enoxolone

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

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

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

enoxolone

prenyl bromide
870-63-3

prenyl bromide

18β-glycyrrhetinic acid 30-prenyl ester

18β-glycyrrhetinic acid 30-prenyl ester

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

enoxolone

Chloroacetic anhydride
541-88-8

Chloroacetic anhydride

(3β)‐(2‐chloroacetyloxy)‐11‐oxo‐olean‐12‐en‐30‐oic acid
109278-66-2

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

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

enoxolone

oxymatrine

oxymatrine

C30H46O4*C15H24N2O2

C30H46O4*C15H24N2O2

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

enoxolone

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

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

C44H64O13

C44H64O13

Conditions
ConditionsYield
With Aliquat 336; potassium carbonate In dichloromethane; water for 48h; Ambient temperature;97%
3-bromo-4-fluoro-benzyl chloride
78239-72-2

3-bromo-4-fluoro-benzyl chloride

enoxolone
471-53-4

enoxolone

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

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%
enoxolone
471-53-4

enoxolone

1-Chloro-3-chloromethyl-benzene
620-20-2

1-Chloro-3-chloromethyl-benzene

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

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%
enoxolone
471-53-4

enoxolone

4-chlorophenacetyl chloride
25026-34-0

4-chlorophenacetyl chloride

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

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

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

enoxolone

chloroacetyl chloride
79-04-9

chloroacetyl chloride

(3β)‐(2‐chloroacetyloxy)‐11‐oxo‐olean‐12‐en‐30‐oic acid
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%
enoxolone
471-53-4

enoxolone

allyl bromide
106-95-6

allyl bromide

(3β,18β,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid allyl ester
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%
N-BOC-1,2-diaminoethane
57260-73-8

N-BOC-1,2-diaminoethane

enoxolone
471-53-4

enoxolone

N-[2-(tert-butoxycarbonylamino)ethyl]glycyrrhetinamide
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%
enoxolone
471-53-4

enoxolone

benzotriazol-1-ol
2592-95-2

benzotriazol-1-ol

1H‐benzo[d][1,2,3]triazol‐1‐yl‐3β‐hydroxy‐11‐oxo‐olean‐12‐en‐30‐oate
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℃;
enoxolone
471-53-4

enoxolone

benzotriazol-1-ol
2592-95-2

benzotriazol-1-ol

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

1H‐benzo[d][1,2,3]triazol‐1‐yl‐3β‐hydroxy‐11‐oxo‐olean‐12‐en‐30‐oate
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%
enoxolone
471-53-4

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
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℃;
enoxolone
471-53-4

enoxolone

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

(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;
enoxolone
471-53-4

enoxolone

4-Fluorobenzyl bromide
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

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%
enoxolone
471-53-4

enoxolone

methyllithium
917-54-4

methyllithium

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

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

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

1-bromo-butane

enoxolone
471-53-4

enoxolone

butyl 3β-hydroxy-11-oxo-olean-12-en-30-oate
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%
enoxolone
471-53-4

enoxolone

1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

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

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%
enoxolone
471-53-4

enoxolone

p-bromobenzyl chloride
589-17-3

p-bromobenzyl chloride

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

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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