E4143

(−)-Epigallocatechin gallate

≥95%

• Synonym(s): (−)-cis-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol 3-gallate, (−)-cis-3,3′,4′,5,5′,7-Hexahydroxy-flavane-3-gallate, EGCG
• Empirical Formula (Hill Notation): C₂₂H₁₈O₁₁
• CAS Number: 989-51-5
• Molecular Weight: 458.37
• MDL number: MFCD00075940
• PubChem Substance ID: 57654158

Properties

• Quality Level: 200
• assay: ≥95%
• solubility: H₂O: ≥5 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c4cc(O)c(O)c(O)c4
• InChI: 1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1
• InChI key: WMBWREPUVVBILR-WIYYLYMNSA-N
• Gene Information: human ... CYP1A2(1544)

Description

General description

(−)-Epigallocatechin gallate from green tea is the prime bioactive component, accounting for 50-80% of the total catechin content.[1] It comprises a chemical structure similar to that of epicatechin gallate (ECG), an ester of gallic acid and epigallocatechin.[2]

Application

(-)-Epigallocatechin gallate has been used:

• as an anti-tumor agent on murine TRAMP metastatic prostate cell line by cell proliferation assay, apoptosis detection and modified Boyden-chamber assay[3]
• induces cell death in acute myeloid leukaemia through death associated protein kinase-2 pathway analyzed through cell viability, cell cycle and apoptosis assay[4]
• as an inhibitor of osteoclast differentiation in murine preosteoclast cell line RAW264.7[5]
• to promote myogenic differentiation[6]

Packaging

50 mg in poly bottle

Biochem/physiol Actions

(-)-Epigallocatechin gallate (EGCG), an antioxidant polyphenol flavonoid exerts anti-tumor properties by inhibiting telomerase and DNA methyltransferase activity.[1] EGCG inhibits the expression of matrix metalloproteinase-2 (MMP-2), MMP-9 and reduces the invasiveness.[3] EGCG blocks the activation of epidermal growth factor (EGF) receptors and human epidermal growth factor receptor-2 (HER-2).[1] EGCG increases bone mineral density and reduces bone resorption. EGCG inhibits osteoclastogenesis by inhibiting receptor activator of nuclear factor κ-B ligand (RANKL) induced nuclear factor κ B (NF-κB) transcriptional activity.[5] EGCG reduces skeletal muscle atrophy. EGCG has anti-aging property and increases myogenic differentiation.[6] EGCG inhibits fatty acid synthase and glutamate dehydrogenase activity.[7]

Safety Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H302 - H317 - H319 - H411
• Precautionary Statements: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves