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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

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About This Item

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
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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)

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.

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pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

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)

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