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

InChI

1S/C8H8O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2-3,9-11H,1H3

InChIKey

FBSFWRHWHYMIOG-UHFFFAOYSA-N

SMILES

COC(=O)c1cc(O)c(O)c(O)c1

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 

TSCA listed

HS Code 

29182900

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

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.

Biological Activity

A large number of cell and animal experiments have shown that MG has good therapeutic effects, such as anti-tumor, anti-inflammatory, anti-oxidation, anti-microbial, anti-malarial and so on^[5].

Contact allergens

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

Source

Methyl gallate is widely found in natural plants, such as Juglans mandshurica, Galla chinensis, Paeonia anomala, Phyllanthus emblica, Mangifera indica, Plicosepalus acacia, Carica papaya Linn, and Maple (Genus Acer)^[5].

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
[5] Liang, H., Huang, Q., Zou, L., Wei, P., Lu, J., Zhang, Y. (2023). Methyl gallate: Review of pharmacological activity. Pharmacological Research, 194, Article 106849. https://doi.org/10.1016/j.phrs.2023.106849

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