Methyl gallate Chemical Properties

Melting point:

201-204 °C

Boiling point:

278.08°C (rough estimate)

Density 

1.3840 (rough estimate)

refractive index 

1.5690 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

ethanol: 50 mg/mL, clear

form 

Crystalline Powder

pka

8.04±0.23(Predicted)

color 

White to slightly beige

Water Solubility 

SOLUBLE IN HOT WATER

Merck 

14,4345

BRN 

2113180

InChIKey

FBSFWRHWHYMIOG-UHFFFAOYSA-N

LogP

0.860

CAS DataBase Reference

99-24-1(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 3,4,5-trihydroxy-, methyl ester (99-24-1)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36/37-24/25

WGK Germany 

3

RTECS 

LW8000000

TSCA 

Yes

HS Code 

29182900

MSDS

• Language:English Provider:Methyl gallate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl gallate Usage And Synthesis

Description

Methyl gallate is a phenolic compound found in Terminalia myriocarpa and Geranium niveum. It is also found in wine.
It is the methyl ester of gallic acid.

Description

Methyl gallate is a phenol that has been found in Meliaceae and has diverse biological activities. It reduces adipogenic hormonal stimulation-induced lipid accumulation in 3T3-L1 cells when used at a concentration of 50 μM. Methyl gallate is active against V. cholerae in vitro (MIC = 32 μg/ml) and reduces V. cholerae-induced intestinal fluid accumulation in suckling mice when administered at doses of 50, 100, and 200 mg/kg. It reduces tumor growth and decreases the number of intratumor CD25⁺Foxp3^high regulatory T cells (Tregs) in an EL-4 model of murine lymphoma. Methyl gallate (0.7, 7, and 70 mg/kg) reduces knee joint edema and leukocyte, neutrophil, and mononuclear cell infiltration in a mouse model of zymosan-induced arthritis.

Chemical Properties

white to slightly beige crystalline powder

Uses

Methyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.

Uses

Methyl 3,4,5-trihydroxybenzoate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.

Uses

The gallate ester methyl gallate is used as an antioxidant. A ease was reported using a reprography paper.

Definition

ChEBI: Methyl 3,4,5-trihydroxybenzoate is a gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties. It has a role as a plant metabolite, an anti-inflammatory agent and an antioxidant.

Contact allergens

This ester of gallic acid is used as an antioxidant agent. A case was reported by using a reprography paper.

Purification Methods

Methyl gallate [99-24-1] M 184.2, m 202o. Crystallise the gallate ester from MeOH. [Beilstein 10 IV 1998.]

References

[1] MISO JEON  Yong S K  Naimur Rahman. Wnt/β-catenin signaling plays a distinct role in methyl gallate–mediated inhibition of adipogenesis[J]. Biochemical and biophysical research communications, 2016, 479 1: Pages 22-27. DOI: 10.1016/j.bbrc.2016.08.178
[2] PRASANTA K. BAG . In vivo fluid accumulation-inhibitory, anticolonization and anti-inflammatory and in vitro biofilm-inhibitory activities of methyl gallate isolated from Terminalia chebula against fluoroquinolones resistant Vibrio cholerae[J]. Microbial pathogenesis, 2019, 128: Pages 41-46. DOI: 10.1016/j.micpath.2018.12.037
[3] HEEKYUNG LEE. Methyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells.[J]. Journal of immunology, 2010: 6698-6705. DOI: 10.4049/jimmunol.1001373
[4] LUANA BARBOSA CORREA. Anti-inflammatory Effect of Methyl Gallate on Experimental Arthritis: Inhibition of Neutrophil Recruitment, Production of Inflammatory Mediators, and Activation of Macrophages[J]. Journal of Natural Products , 2016, 79 6: 1554-1566. DOI: 10.1021/acs.jnatprod.5b01115

Methyl gallate(99-24-1)Related Product Information

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