E3768

(−)-Epigallocatechin

≥95% (HPLC), from green tea

• Synonym(s): (−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxyflavane
• Empirical Formula (Hill Notation): C₁₅H₁₄O₇
• CAS Number: 970-74-1
• Molecular Weight: 306.27
• MDL number: MFCD00075939
• UNSPSC Code: 12352205
• PubChem Substance ID: 24894529
• NACRES: NA.21

Properties

• biological source: green tea
• Quality Level: 200
• Assay: ≥95% (HPLC)
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c3cc(O)c(O)c(O)c3
• InChI: 1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1
• InChI key: XMOCLSLCDHWDHP-IUODEOHRSA-N
• Gene Information: human ... CYP1A2(1544)

Description

General description

(−)-Epigallocatechin is one of the main catechin compounds found in green tea and the most abundant one (~20%), with antioxidant properties.

Application

(−)-Epigallocatechin (EGC) has been used:

• as a reference standard in high-performance liquid chromatography (HPLC) analysis
• to analyze its inhibitory effect on α-amylase and α-glucosidase activity to control postprandial hyperglycemia in Diabetes mellitus
• in cell viability assays to check its efficacy and protection against ferroptosis and iron toxicity in murine pancreatic β-cells
• to evaluate its potential anti-inflammatory effects on long-term acute and chronic Pristen-induced arthritis
• to treat pregnant and nursing mice, on in vitro angiogenesis, proliferation, and movement of endothelial cells
• to evaluate its effect on pregnant and nursing mice spleen based on the number and localization of CD4⁺ (cluster of differentiation 4) and CD8⁺ cluster of differentiation 8) cells

Biochem/physiol Actions

(−)-Epigallocatechin (EGC) has proven to be an anti-cancer agent by its inhibitory effects on heregulin-b1 (HRG)-induced migration/invasion in MCF-7 human breast carcinoma cells. It has also shown strong antiviral activity against the herpes simplex virus.

Green tea polyphenol. Anticancer agent. Lower antioxidant activity than EGCG.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves