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  • Ethyl gallate CAS 831-61-8 Ethyl 3,4,5-trihydroxybenzoate CAS no 831-61-8 3,4,5-Trihydroxybenzoic acid ethyl ester Gallic acid ethyl ester

    Cas No: 831-61-8

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831-61-8 Usage

Description

Ethyl gallate is a food additive with E number E313. It is the ethyl ester of gallic acid. Ethyl gallate is added to food as an antioxidant. Though found naturally in a variety of plant sources including walnuts Terminalia myriocarpa or chebulic myrobolan (Terminalia chebula). Ethyl gallate is produced from gallic acid and ethanol. It can be found in wine.

Chemical Properties

white to slightly beige fine powder

Uses

Ethyl Gallate is an apoptotic agent as a polyphenol compound. Antiproliferative.

Definition

ChEBI: A gallate ester obtained by the formal condensation of gallic acid with ethanol.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Purification Methods

Recrystallise the gallate from 1,2-dichloroethane, UV: max (neutral species) 275nm ( 10 000), (anion) 235nm ( 10 300), 279nm ( 11 400) and 324nm ( 8 500) [Campbell & Coppinger J Am Chem Soc 73 2708 1951]. [Beilstein 10 IV 2002.]

Check Digit Verification of cas no

The CAS Registry Mumber 831-61-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,3 and 1 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 831-61:
(5*8)+(4*3)+(3*1)+(2*6)+(1*1)=68
68 % 10 = 8
So 831-61-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O5/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,2H2,1H3

831-61-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A13733)  Ethyl 3,4,5-trihydroxybenzoate, 98%   

  • 831-61-8

  • 10g

  • 512.0CNY

  • Detail
  • Alfa Aesar

  • (A13733)  Ethyl 3,4,5-trihydroxybenzoate, 98%   

  • 831-61-8

  • 50g

  • 1232.0CNY

  • Detail

831-61-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl gallate

1.2 Other means of identification

Product number -
Other names N-ETHYLGALLATE

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:831-61-8 SDS

831-61-8Synthetic route

ethanol
64-17-5

ethanol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Ethyl gallate
831-61-8

Ethyl gallate

Conditions
ConditionsYield
With brominated modified sulfonic acid resin at 80℃; for 5h; Reagent/catalyst;98%
With toluene-4-sulfonic acid at 88℃; under 9308.91 Torr; for 0.133333h; Temperature; Wavelength; Time; Sealed tube; Microwave irradiation;96%
With sulfuric acid at 70℃;95%
ethyl 3,4,5-tribenzyloxybenzoate
100079-21-8

ethyl 3,4,5-tribenzyloxybenzoate

Ethyl gallate
831-61-8

Ethyl gallate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; atmospheric pressure;89%
diethyl sulfate
64-67-5

diethyl sulfate

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Ethyl gallate
831-61-8

Ethyl gallate

Conditions
ConditionsYield
With sodium hydrogencarbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 40℃; for 0.583333h;82%
ethyl 3,4,5-triacetoxybenzoate
73607-60-0

ethyl 3,4,5-triacetoxybenzoate

A

Ethyl gallate
831-61-8

Ethyl gallate

B

3,5-Diacetoxy-4-hydroxy-benzoic acid ethyl ester

3,5-Diacetoxy-4-hydroxy-benzoic acid ethyl ester

Conditions
ConditionsYield
With porcine pancreatic lipase In tetrahydrofuran; butan-1-ol at 28 - 30℃; for 120h;A 34%
B n/a
arsenic acid tris-(5-ethoxycarbonyl-2,3-dihydroxy-phenyl ester)

arsenic acid tris-(5-ethoxycarbonyl-2,3-dihydroxy-phenyl ester)

Ethyl gallate
831-61-8

Ethyl gallate

Conditions
ConditionsYield
With hydrogen sulfide
hydroquinone
123-31-9

hydroquinone

C9H9O5

C9H9O5

A

hydroquinone radical
3225-30-7

hydroquinone radical

B

Ethyl gallate
831-61-8

Ethyl gallate

Conditions
ConditionsYield
With potassium hydroxide In water Equilibrium constant; Irradiation;
ethanol
64-17-5

ethanol

3,4,5-tribenzyloxybenzoic acid
1486-48-2

3,4,5-tribenzyloxybenzoic acid

Ethyl gallate
831-61-8

Ethyl gallate

Conditions
ConditionsYield
With Acetyl bromide for 24h; Heating; Yield given;
tannin

tannin

Ethyl gallate
831-61-8

Ethyl gallate

Conditions
ConditionsYield
With hydrogenchloride; ethanol
sulfuric acid
7664-93-9

sulfuric acid

arsenic acid tris-(5-ethoxycarbonyl-2,3-dihydroxy-phenyl ester)

arsenic acid tris-(5-ethoxycarbonyl-2,3-dihydroxy-phenyl ester)

hydrogen sulfide
7783-06-4

hydrogen sulfide

Ethyl gallate
831-61-8

Ethyl gallate

3,4,5-tris-methoxycarbonyloxy-benzoic acid ethyl ester

3,4,5-tris-methoxycarbonyloxy-benzoic acid ethyl ester

aqueous-alcoholic NaOH-solution

aqueous-alcoholic NaOH-solution

Ethyl gallate
831-61-8

Ethyl gallate

water
7732-18-5

water

6-ethoxycarbonyl-2,3,4-trihydroxy-benzenediazonium-betaine

6-ethoxycarbonyl-2,3,4-trihydroxy-benzenediazonium-betaine

A

Ethyl gallate
831-61-8

Ethyl gallate

B

nitrogen

nitrogen

Conditions
ConditionsYield
at 220℃; im Einschmelzrohr;
Ethyl gallate
831-61-8

Ethyl gallate

benzene-1,2-diol
120-80-9

benzene-1,2-diol

ethyl 1,2,8-trihydroxy-9-oxo-9H-benzocycloheptene-6-carboxylate
54755-94-1

ethyl 1,2,8-trihydroxy-9-oxo-9H-benzocycloheptene-6-carboxylate

Conditions
ConditionsYield
With potassium iodate In water; acetone at 20℃; for 2.5h;99%
With potassium iodate In water
Ethyl gallate
831-61-8

Ethyl gallate

propargyl bromide
106-96-7

propargyl bromide

3,4,5-tris-prop-2-ynyloxybenzoic acid ethyl ester
1061204-68-9

3,4,5-tris-prop-2-ynyloxybenzoic acid ethyl ester

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In acetone Inert atmosphere; Reflux;98%
With 18-crown-6 ether; potassium carbonate In acetone for 24h; Reflux;83%
With potassium carbonate In acetone Reflux;
Ethyl gallate
831-61-8

Ethyl gallate

ethylenediamine
107-15-3

ethylenediamine

ethyl 8-hydroxy-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

ethyl 8-hydroxy-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

Conditions
ConditionsYield
In ethanol at 65℃; for 0.5h; Green chemistry;97%
Ethyl gallate
831-61-8

Ethyl gallate

4’-[(10-bromodecyl)oxy]-4-carbonitrile-[1,1’-biphenyl]
140713-89-9

4’-[(10-bromodecyl)oxy]-4-carbonitrile-[1,1’-biphenyl]

3,4,5-tris[6-(4'-cyanobiphenyl-4-yloxy)decyloxy]benzoic acid ethyl ester
618446-91-6

3,4,5-tris[6-(4'-cyanobiphenyl-4-yloxy)decyloxy]benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In butanone Heating;96%
Ethyl gallate
831-61-8

Ethyl gallate

methyl iodide
74-88-4

methyl iodide

ethyl 3,4,5-trimethoxybenzoate
6178-44-5

ethyl 3,4,5-trimethoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone at 25℃; Inert atmosphere;96%
Ethyl gallate
831-61-8

Ethyl gallate

1-dodecylbromide
143-15-7

1-dodecylbromide

ethyl 3,4,5-tri(dodecyloxy)benzoate
117241-30-2

ethyl 3,4,5-tri(dodecyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 6h;95%
With potassium carbonate; sodium iodide In acetonitrile at 105℃; for 48h;95%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;94%
1-bromo-1,1-dideuteriododecane
2159-25-3

1-bromo-1,1-dideuteriododecane

Ethyl gallate
831-61-8

Ethyl gallate

3,4,5-tris(1,1-dideuteriododecyloxy)benzoic acid ethyl ester
664340-96-9

3,4,5-tris(1,1-dideuteriododecyloxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;95%
Ethyl gallate
831-61-8

Ethyl gallate

1-Bromooctadecane
112-89-0

1-Bromooctadecane

C63H118O5
1268837-82-6

C63H118O5

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 12h; Inert atmosphere;95%
With potassium carbonate; potassium iodide In butanone for 72h; Inert atmosphere; Reflux;64%
With potassium carbonate; sodium iodide In acetone Reflux;
Ethyl gallate
831-61-8

Ethyl gallate

2-(2-Aminoethylamino)ethanol
111-41-1

2-(2-Aminoethylamino)ethanol

ethyl 8-hydroxy-4-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

ethyl 8-hydroxy-4-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

Conditions
ConditionsYield
In ethanol at 65℃; for 0.5h; Green chemistry;95%
octanol
111-87-5

octanol

Ethyl gallate
831-61-8

Ethyl gallate

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In toluene Reflux;94.1%
Ethyl gallate
831-61-8

Ethyl gallate

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

C13H15NO6

C13H15NO6

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;92.38%
Ethyl gallate
831-61-8

Ethyl gallate

1,5-diamino-3-azapentane
111-40-0

1,5-diamino-3-azapentane

ethyl 2,3,6,7-tetrahydro-1H,5H-pyrazino[1,2,3-de]quinoxaline-9-carboxylate

ethyl 2,3,6,7-tetrahydro-1H,5H-pyrazino[1,2,3-de]quinoxaline-9-carboxylate

Conditions
ConditionsYield
In ethanol at 65℃; for 0.5h; Green chemistry;92%
diiodomethane
75-11-6

diiodomethane

Ethyl gallate
831-61-8

Ethyl gallate

7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid ethyl ester

7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 120℃;91%
1-bromo-hexane
111-25-1

1-bromo-hexane

Ethyl gallate
831-61-8

Ethyl gallate

ethyl 3,4,5-tris(hexyloxy)benzoate

ethyl 3,4,5-tris(hexyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 12h; Inert atmosphere; Reflux;90%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 12h; Inert atmosphere;90%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Williamson Ether Synthesis;84%
pentadecyl bromide
629-72-1

pentadecyl bromide

Ethyl gallate
831-61-8

Ethyl gallate

ethyl 3,4,5-tris(pentadecyloxy)benzoate
1187649-66-6

ethyl 3,4,5-tris(pentadecyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere;89.6%
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; Inert atmosphere;89.6%
2-[2-(2-ethoxyethoxy)ethoxy]ethyl chloride
538371-55-0

2-[2-(2-ethoxyethoxy)ethoxy]ethyl chloride

Ethyl gallate
831-61-8

Ethyl gallate

ethyl-3,4,5-tri{2-[2-(2-ethoxyethoxy)ethoxy]ethoxy}benzoate

ethyl-3,4,5-tri{2-[2-(2-ethoxyethoxy)ethoxy]ethoxy}benzoate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone at 70℃; for 192h; Inert atmosphere;89%
1-bromo-octane
111-83-1

1-bromo-octane

Ethyl gallate
831-61-8

Ethyl gallate

ethyl 3,4,5-tris(octyloxy)benzoate
157980-10-4

ethyl 3,4,5-tris(octyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone for 120h; Heating;88%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Williamson Ether Synthesis;83%
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; Inert atmosphere;77.8%
1-iodo-10-undecene
7766-49-6

1-iodo-10-undecene

Ethyl gallate
831-61-8

Ethyl gallate

3,4,5-tris(10-undecenyloxy)benzoic acid ethyl ester
887914-56-9

3,4,5-tris(10-undecenyloxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;88%
1,5-difluoro-2,4-dinitrobenzene
327-92-4

1,5-difluoro-2,4-dinitrobenzene

Ethyl gallate
831-61-8

Ethyl gallate

C30H20N4O18

C30H20N4O18

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 25℃; for 0.25h;86%
Ethyl gallate
831-61-8

Ethyl gallate

2,6-dichloropyridine-3,5-dicarbonitrile
151229-84-4

2,6-dichloropyridine-3,5-dicarbonitrile

25,27-diaza-11,23-dicarboethoxy-4,6,16,18-tetracyano-26,28-dihydroxy-2,8,14,20-tetraoxacalix[4]arene

25,27-diaza-11,23-dicarboethoxy-4,6,16,18-tetracyano-26,28-dihydroxy-2,8,14,20-tetraoxacalix[4]arene

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 25℃; for 0.5h;86%
Ethyl gallate
831-61-8

Ethyl gallate

hexadecanyl bromide
112-82-3

hexadecanyl bromide

3,4,5-tris(hexadecyloxy)benzoesaeure-ethylester
138432-99-2

3,4,5-tris(hexadecyloxy)benzoesaeure-ethylester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 17h; Inert atmosphere;85%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 17h;84%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;75%
Ethyl gallate
831-61-8

Ethyl gallate

2,6-dichloro-4-ethylpyridine-3,5-dicarbonitrile
18520-07-5

2,6-dichloro-4-ethylpyridine-3,5-dicarbonitrile

25,27-diaza-11,23-dicarboethoxy-4,6,16,18-tetracyano-5,17-diethyl-26,28-dihydroxy-2,8,14,20-tetraoxacalix[4]arene

25,27-diaza-11,23-dicarboethoxy-4,6,16,18-tetracyano-5,17-diethyl-26,28-dihydroxy-2,8,14,20-tetraoxacalix[4]arene

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 25℃; for 1h;84%
1-bromo dodecane
112-29-8

1-bromo dodecane

Ethyl gallate
831-61-8

Ethyl gallate

ethyl 3,4,5-tri(decyloxy) benzoate

ethyl 3,4,5-tri(decyloxy) benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Williamson Ether Synthesis;82%
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; Inert atmosphere;70.3%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;70%
bis(phenyl) carbonate
102-09-0

bis(phenyl) carbonate

Ethyl gallate
831-61-8

Ethyl gallate

A

ethyl 3-hydroxy-4,5-carbonyldioxy-benzoate
107998-21-0

ethyl 3-hydroxy-4,5-carbonyldioxy-benzoate

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
A 82%
B n/a
1-undecen-11-ylbromide
7766-50-9

1-undecen-11-ylbromide

Ethyl gallate
831-61-8

Ethyl gallate

3,4,5-tris(10-undecenyloxy)benzoic acid ethyl ester
887914-56-9

3,4,5-tris(10-undecenyloxy)benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h;82%
With potassium carbonate In N,N-dimethyl-formamide for 48h;50%
1-Bromoheptane
629-04-9

1-Bromoheptane

Ethyl gallate
831-61-8

Ethyl gallate

ethyl 3,4,5-tris(heptyloxy)benzoate
1070380-33-4

ethyl 3,4,5-tris(heptyloxy)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Williamson Ether Synthesis;81%
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; Inert atmosphere;72.3%
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; Inert atmosphere;72.3%

831-61-8Relevant articles and documents

Biddle,Kelley

, p. 920 (1912)

The effect of solvent composition on grafting gallic acid onto chitosan via carbodiimide

Guo, Ping,Anderson, John D.,Bozell, Joseph J.,Zivanovic, Svetlana

, p. 171 - 180 (2016)

The primary antioxidant (AOX) activity of chitosan can be introduced by grafting of phenolic compound - gallic acid (GA) to its amino and/or hydroxyl groups. The objective of this study was to investigate the effect of ethanol (EtOH) concentration (0%, 25%, 50%, and 75% in water) on efficiency of grafting GA onto chitosan in the presence of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC)/N-hydroxysuccinimide (NHS). The grafting was confirmed by FTIR and the efficiency was quantified as Folin's total phenolics. When pure deionized water was used as a sole solvent (0% EtOH), GA was grafted to chitosan at the largest extent (285.9 mg GA/g chitosan). As the concentration of EtOH increased, the grafting efficiency proportionally decreased. NMR studies showed that EtOH inhibited grafting of GA by prohibiting the production of the intermediate - NHS ester. The results confirm that the concentration of EtOH in grafting solution significantly affects grafting efficiency of GA on chitosan.

-

Iljin

, p. 459 (1910)

-

Method for producing ester based on eco-friendly and high efficiency esterification by using base exchange of salt and the compound thereof

-

Paragraph 0099-0105; 0107, (2021/07/07)

The present invention relates to an esterification reaction-based eco-friendly and high efficiency ester compound using ion exchange and an ester compound thereof. The esterification generally proceeds by reverse reaction with water, resulting in poor yield of the ester. In order to avoid hydrolysis, the esterification reaction was environmentally or non-limited due to the continuous supply of hydrochloric acid gas or the use of chlorinated thionyl chloride as a noxious substance. To the present invention, a continuous hydrochloric acid gas is provided by ion exchange of a salt, and magnesium sulfate acts as a dehydrating agent to remove water generated in esterification. In addition, the reactants are cheap and the product is also low in harmfulness and easier to handle and thus more efficient reaction is possible.

Polyhydroxybenzoic acid derivatives as potential new antimalarial agents

Degotte, Gilles,Francotte, Pierre,Pirotte, Bernard,Frédérich, Michel

, (2021/08/07)

With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).

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