Methyl gallate

Names

[ CAS No. ]:
99-24-1

[ Name ]:
Methyl gallate

[Synonym ]:
Methyl gallate
MFCD00002194
3,4,5-Trihydroxybenzoic acid methyl ester
Benzoic acid, 3,4,5-trihydroxy-, methyl ester
Methyl 3,4,5-trihydroxybenzoate
EINECS 202-741-7

Biological Activity

[Description]:

Methyl gallate is a plant phenolic with antioxidant, anticancer, and anti-inflammatory activities. Methyl gallate also shows bacterial inhibition activity.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Cardiovascular Disease

Research Areas >> Cancer

Research Areas >> Infection

Natural Products >> Phenols

[Target]

Bacterial[1]

[In Vitro]

The growth of A. viscosus is inhibited completely by a low dose of Methyl gallate (MIC=1 mg/mL). S. mutans and . sobrinus show intermediate sensitivity to Methyl gallate (MIC=2-4 mg/mL), whereas the growth of Lactobacillus spp. is inhibited completely at a relatively high concentration (MIC=8 mg/mL)[1]. Methyl gallate, in a concentration of 100 mM, could alleviate lipid peroxidation of the cells exposed to a short-term H2O2 treatment. In addition, Methyl gallate-treated cells could prevent intracellular glutathione (GSH) from being depleted following an exposure of H2O2 (8.0 mM) for a 3 h period[2]. Methyl gallate inhibits Treg cell-suppressive effects on effector CD4+ T cells and Treg migration toward tumor environment. Furthermore, forkhead box P3 (Foxp3) expression is also significantly decreased by methyl gallate[3].

[Cell Assay]

KB cells, a human mouth epithelial cell line, are treated with Methyl gallate (1-8 mg/mL) for 24 h. Cytotoxicity of Methyl gallate is assessed by a modified MTT assay[1].

[References]

[1]. Kang MS, et al. Inhibitory effect of methyl gallate and gallic acid on oral bacteria. J Microbiol. 2008 Dec;46(6):744-50.

[2]. Hsieh TJ, et al. Protective effect of methyl gallate from Toona sinensis (Meliaceae) against hydrogen peroxide-induced oxidative stress and DNA damage in MDCK cells. Food Chem Toxicol. 2004 May;42(5):843-50.

[3]. Lee H, et al. Methyl gallate exhibits potent antitumor activities by inhibiting tumor infiltration of CD4+CD25+ regulatory T cells. J Immunol. 2010 Dec 1;185(11):6698-705.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
450.1±40.0 °C at 760 mmHg

[ Melting Point ]:
201-204 °C

[ Molecular Formula ]:
C₈H₈O₅

[ Molecular Weight ]:
184.146

[ Flash Point ]:
190.8±20.8 °C

[ Exact Mass ]:
184.037170

[ PSA ]:
86.99000

[ LogP ]:
1.54

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.631

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
SOLUBLE IN HOT WATER

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LW8000000

CHEMICAL NAME :: Gallic acid, methyl ester

CAS REGISTRY NUMBER :: 99-24-1

BEILSTEIN REFERENCE NO. :: 2113180

LAST UPDATED :: 199701

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C8-H8-O5

MOLECULAR WEIGHT :: 184.16

WISWESSER LINE NOTATION :: QVR CQ DQ EQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),286,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 784 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),286,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 470 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),286,1982

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H317-H319-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R22;R36/37/38;R43

[ Safety Phrases ]:
S26-S36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LW8000000

[ HS Code ]:
2918290000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918290000

[ Summary ]:
HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

Articles

Antimicrobial activity of natural products from the flora of Northern Ontario, Canada.

Pharm. Biol. 53(6) , 800-6, (2015)

The number of multidrug resistant (MDR) microorganisms is increasing and the antimicrobial resistance expressed by these pathogens is generating a rising global health crisis. In fact, there are only ...

An Antioxidant Extract of the Insectivorous Plant Drosera burmannii Vahl. Alleviates Iron-Induced Oxidative Stress and Hepatic Injury in Mice.

PLoS ONE 10 , e0128221, (2015)

Free iron typically leads to the formation of excess free radicals, and additional iron deposition in the liver contributes to the oxidative pathologic processes of liver disease. Many pharmacological...

Characterization and storage stability of the extract of Thai mango (Mangifera indica Linn. Cultivar Chok-Anan) seed kernels.

J. Food Sci. Technol. 51(8) , 1453-62, (2014)

Qualitative analysis of hydrolysable extract from mango (Mangifera indica Linn. cultivar Chok-Anan) seed kernel was performed by means of reversed phase high-performance liquid chromatography coupled ...