Methyl gallate
[CAS# 99-24-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Methyl gallate
• Synonyms: Methyl 3,4,5-trihydroxybenzoate
• Molecular Formula: C₈H₈O₅
• Molecular Weight: 184.15
• CAS Registry Number: 99-24-1
• EC Number: 202-741-7
• SMILES: COC(=O)C1=CC(=C(C(=C1)O)O)O

Properties

• Solubility: Soluble (hot water)
• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 199-203 °C
• Index of Refraction: 1.631, Calc.^*
• Boiling Point: 450.1±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 190.8±20.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Methyl gallate, an ester of gallic acid, is a naturally occurring compound widely recognized for its various biological activities. The molecular formula of methyl gallate is C₇H₈O₅, and it features a gallate moiety with a methoxy group, which contributes to its chemical properties. Methyl gallate is primarily found in several plant sources, including gallnuts, tea leaves, and some fruits, where it serves as a secondary metabolite.

The discovery of methyl gallate can be traced back to the early investigations of gallotannins and their hydrolysis products in the 19th century. Researchers found that methyl gallate could be synthesized through the methylation of gallic acid, a process that involves the introduction of a methoxy group into the carboxylic acid functional group of gallic acid. This synthetic route has facilitated the study of methyl gallate and its derivatives, leading to a better understanding of its potential applications.

One of the most notable aspects of methyl gallate is its antioxidant properties. Studies have demonstrated that methyl gallate can effectively scavenge free radicals, which are unstable molecules that can cause cellular damage and contribute to various diseases, including cancer and neurodegenerative disorders. This ability to inhibit oxidative stress has garnered interest in its use as a dietary supplement and natural preservative in food and cosmetics.

In addition to its antioxidant capacity, methyl gallate exhibits antimicrobial and anti-inflammatory properties. Research has shown that it can inhibit the growth of various pathogens, including bacteria and fungi, making it a potential candidate for developing natural antimicrobial agents. Its anti-inflammatory effects have also been investigated, with studies indicating that methyl gallate may modulate inflammatory pathways, providing a basis for its use in treating inflammatory diseases.

Methyl gallate has also been explored for its potential therapeutic applications in the field of cancer research. Some studies have indicated that it can induce apoptosis in cancer cells, promoting cell death and inhibiting tumor growth. This has led to interest in its use as an adjunct therapy in cancer treatment, particularly in combination with conventional chemotherapeutic agents.

In the realm of agriculture, methyl gallate has been studied for its potential as a natural pesticide. Its ability to repel pests and inhibit fungal growth positions it as a viable alternative to synthetic agrochemicals, aligning with the growing demand for sustainable and environmentally friendly agricultural practices.

Overall, methyl gallate is a compound with a rich history of discovery and diverse applications across various fields, including food science, medicine, and agriculture. Its antioxidant, antimicrobial, anti-inflammatory, and potential anticancer properties highlight its importance as a subject of ongoing research and innovation in the quest for natural and effective solutions in health and industry.

References

2024. Chemical Constituents from the Leaves of Dracontomelon duperreanum. Chemistry of Natural Compounds, 60(5).
DOI: 10.1007/s10600-024-04479-0

2024. Spectroscopic Studies on Plant Extract Mediated ZnO Nanoparticles as a Potential Cytotoxic Agent. Journal of Applied Spectroscopy, 91(4).
DOI: 10.1007/s10812-024-01799-5

2024. Exploring the medicinal potential of Senna siamea roots: an integrated study of antibacterial and antioxidant activities, phytochemical analysis, ADMET profiling, and molecular docking insights. Applied Biological Chemistry, 67(1).
DOI: 10.1186/s13765-024-00899-2