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E4268

(−)-Epigallocatechin gallate

Name: (−)-Epigallocatechin gallate
Brand: SIGMA

≥80% (HPLC), from green tea

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :

C₂₂H₁₈O₁₁

Numéro CAS:

989-51-5

Poids moléculaire :

458.37

NACRES:

NA.79

PubChem Substance ID:

57654159

UNSPSC Code:

12352205

MDL number:

MFCD00075940

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Propriétés

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.

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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

Classe de stockage

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c