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E4268

Sigma-Aldrich

(−)-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
MDL number:
MFCD00075940
UNSPSC Code:
12352205
PubChem Substance ID:
57654159
NACRES:
NA.79

biological source

green tea

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)

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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.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H317,H319,H411

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

E4268-100MG:
E4268-VAR:
E4268-BULK:
E4268-25MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tea polyphenols-their antioxidant properties and biological activity-a review
Gramza A, et al.,
Polish Journal of Food and Nutrition Sciences, 14(3), 219-219 (2005)
Xiaoqin Wang et al.
Journal of biomedical science, 23(1), 51-51 (2016-06-30)
Diastolic dysfunction refers to an impaired relaxation and an abnormality in a heart's filling during diastole while left ventricular systolic function is preserved. Diastolic dysfunction is commonly observed in patients with primary hypertension, diabetes and cardiomyopathies such as hypertrophic cardiomyopathy
Shounan Qi et al.
Molecular vision, 23, 171-178 (2017-05-02)
(-)-epigallocatechin-3-gallate (EGCG), a major catechin component of green tea, is reported to delay or prevent certain forms of cancer, arthritis, cardiovascular disease, and neurodegenerative disorders. In this study, we determined if systemically administered EGCG could protect the retina against light
Tia M Rains et al.
The Journal of nutritional biochemistry, 22(1), 1-7 (2010-12-01)
Green tea catechins (GTC) are polyphenolic compounds present in the unfermented dried leaves of the plant, Camellia sinensis. Results from a number of randomized, controlled intervention trials have shown that consumption of GTC (270 mg to 1200 mg/day) may reduce
Yoichi Kakuta et al.
Transplant international : official journal of the European Society for Organ Transplantation, 24(5), 514-522 (2011-02-05)
Epigallocatechin-3-gallate (EGCG) shows diverse chemical and biological activities. We investigated the effects of EGCG in a rat renal ischemia reperfusion (I/R) injury model. Sprague-Dawley rats received intraperitoneal injection of 50 mg/kg EGCG 48 h, 24 h, and 30 min prior
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