E4268

(−)-Epigallocatechin gallate

≥80% (HPLC), from green tea

• 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
• NACRES: NA.79
• PubChem Substance ID: 57654159
• UNSPSC Code: 12352205
• MDL number: MFCD00075940

Properties

• biological source: green tea
• Quality Segment: 200
• assay: ≥80% (HPLC)
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• 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, is a bioactive component of green tea accounting for 50-80% of the total catechin content.

Application

(−)-Epigallocatechin gallate has been used as:

• a potential neuroprotective agent to test its protective effect against spinal cord injury and blood-spinal cord barrier (BSCB) leakage
• an effective antioxidant against light-induced photoreceptor degeneration in mice retina
• an antioxidant in retinitis pigmentosa (RP) and reduces oxidative damage and changes circadian rhythms in pigmented heterozygous P23H rat
• to test its reversal effect on Diastolic dysfunction in restrictive cardiomyopathy (RCM) mice
• an anti-cancer agent in colorectal cancer in mice

Biochem/physiol Actions

(−)-Epigallocatechin gallate (EGCG) comprises eight -hydroxyl (OH) groups that determine its high antioxidant property. Other than being an efficient free oxygen radical scavenger, it also acts as a good chelating agent and a modulator of important transcription factors, namely nuclear factor-kappa β (NF-kβ). EGEC is proven to be an efficient anti-obesity agent by increasing energy expenditure, fat oxidation, and lowering appetite in humans. EGCG also acts as an anti-inflammatory and neuroprotective agent in the initial stages of ischemia and spinal cord injury. It reduces caveolin-1 expression, maintaining blood-brain barrier integrity and downregulating pro-inflammatory cytokines.

Safety Information

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H302,H317,H319,H411
• pcodes: 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: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)