E4143

(−)-Epigallocatechin gallate

≥95%

• Synonyme(s) : (−)-cis-2-(3,4,5-Trihydroxyphényl)-3,4-dihydro-1(2H)-benzopyrane-3,5,7-triol 3-gallate
• Formule empirique (notation de Hill) : C₂₂H₁₈O₁₁
• CAS Number: 989-51-5
• Poids moléculaire : 458.37
• Numéro MDL: MFCD00075940
• Code UNSPSC : 12352205
• ID de substance PubChem : 57654158
• Nomenclature NACRES : NA.25

Propriétés

• Niveau de qualité: 200
• Essai: ≥95%
• Solubilité: H₂O: ≥5 mg/mL, clear
• Application(s): metabolomics; vitamins, nutraceuticals, and natural products
• Température de stockage: 2-8°C
• Chaîne SMILES: 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
• Clé InChI: WMBWREPUVVBILR-WIYYLYMNSA-N
• Informations sur le gène: human ... CYP1A2(1544)

Description

Description générale

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

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
• induces cell death in acute myeloid leukaemia through death associated protein kinase-2 pathway analyzed through cell viability, cell cycle and apoptosis assay
• as an inhibitor of osteoclast differentiation in murine preosteoclast cell line RAW264.7
• to promote myogenic differentiation

Actions biochimiques/physiologiques

(-)-Epigallocatechin gallate (EGCG), an antioxidant polyphenol flavonoid exerts anti-tumor properties by inhibiting telomerase and DNA methyltransferase activity. EGCG inhibits the expression of matrix metalloproteinase-2 (MMP-2), MMP-9 and reduces the invasiveness. EGCG blocks the activation of epidermal growth factor (EGF) receptors and human epidermal growth factor receptor-2 (HER-2). 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. EGCG reduces skeletal muscle atrophy. EGCG has anti-aging property and increases myogenic differentiation. EGCG inhibits fatty acid synthase and glutamate dehydrogenase activity.

Informations sur la sécurité

• Pictogrammes: GHS07,GHS09
• Mention d'avertissement: Warning
• Mentions de danger: H302,H317,H319,H411
• Conseils de prudence: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 2
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)