(-)-Epigallocatechin gallate
[CAS# 989-51-5]

Identification

• Classification: Biochemical >> Plant extracts
• Name: (-)-Epigallocatechin gallate
• Synonyms: (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-(3,4,5-trihydroxybenzoate); EGCG
• Molecular Formula: C₂₂H₁₈O₁₁
• Molecular Weight: 458.38
• CAS Registry Number: 989-51-5
• EC Number: 619-381-5
• SMILES: C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

Properties

• Solubility: 10 m (water), 100 mM (DMSO, ethamol)
• Density: 1.9±0.1 g/cm³, Calc.^*
• Melting point: 222-224 °C
• Index of Refraction: 1.857, Calc.^*
• alpha: -179
• Boiling Point: 909.1±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 320.0±27.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H312-H317-H319-H401-H411
• Safety Statements: P261-P264-P264+P265-P270-P272-P273-P280-P301+P317-P302+P352-P305+P351+P338-P317-P321-P330-P333+P317-P337+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin sensitization	Skin Sens.	1A	H317
Skin sensitization	Skin Sens.	1	H317
Acute hazardous to the aquatic environment	Aquatic Acute	2	H401
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

(-)-Epigallocatechin gallate (EGCG) is a prominent polyphenol found in green tea, recognized for its numerous health benefits and potential therapeutic applications. It belongs to the class of catechins, which are natural antioxidants known for their ability to scavenge free radicals and mitigate oxidative stress. The discovery of EGCG can be traced back to the early 20th century, with the compound being isolated in the 1930s by Japanese scientists studying the components of green tea.

The interest in EGCG surged in the latter half of the 20th century as researchers began to uncover its beneficial properties. Numerous studies have reported its role in promoting health and preventing various diseases, particularly cardiovascular diseases, cancer, and metabolic disorders. EGCG accounts for a significant portion of the total catechin content in green tea, making it a key focus of nutritional and pharmaceutical research.

EGCG's applications are vast and diverse. One of the primary areas of interest is its potential in cancer prevention and treatment. Research has demonstrated that EGCG can inhibit tumor growth, induce apoptosis in cancer cells, and prevent metastasis. These effects are attributed to its ability to modulate various signaling pathways involved in cell proliferation and survival, making it a candidate for incorporation into cancer therapies.

In addition to its anti-cancer properties, EGCG is recognized for its cardiovascular benefits. Studies have shown that it can help lower blood pressure, reduce cholesterol levels, and improve endothelial function, contributing to overall heart health. The antioxidant properties of EGCG play a crucial role in these protective effects, reducing oxidative damage to blood vessels and promoting better circulation.

EGCG also exhibits potential neuroprotective effects, with research suggesting its ability to protect neuronal cells from damage and reduce the risk of neurodegenerative diseases such as Alzheimer's and Parkinson's. Its anti-inflammatory and antioxidant properties are believed to contribute to these neuroprotective effects, highlighting the compound's versatility in promoting health.

The food and beverage industry has also embraced EGCG due to its functional properties. As a natural antioxidant, it is utilized in food preservation and enhancing the nutritional profile of various products. Furthermore, the popularity of green tea as a health drink has led to increased interest in EGCG supplements, which are marketed for their health benefits and weight management properties.

In recent years, advancements in formulation technologies have allowed for the development of more bioavailable forms of EGCG, enhancing its absorption and efficacy in the human body. These innovations pave the way for the potential therapeutic use of EGCG in clinical settings.

In conclusion, (-)-Epigallocatechin gallate is a valuable chemical substance with a significant impact on health and wellness. From its discovery in green tea to its diverse applications in cancer prevention, cardiovascular health, and neuroprotection, EGCG continues to be a subject of extensive research. Its integration into dietary supplements and food products further emphasizes its importance as a natural compound with the potential to improve health outcomes.

References

1997. Absorption and distribution of tea catechin, (-)-epigallocatechin-3-gallate, in the rat. Journal of Nutritional Science and Vitaminology, 43(6).
DOI: 10.3177/jnsv.43.679

2005. The Acid-Promoted Reaction of the Green Tea Polyphenol Epigallocatechin Gallate with Nitrite Ions. Chemical Research in Toxicology, 18(3).
DOI: 10.1021/tx0496486

2005. EGCG, a major component of green tea, inhibits VEGF production by swine granulosa cells. BioFactors (Oxford, England), 23(1).
DOI: 10.1002/biof.5520230104