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E4268

Sigma-Aldrich

(−)-Epigallocatechin gallate

≥80% (HPLC), from green tea

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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:
Molecular Weight:
458.37
MDL number:
PubChem Substance ID:
NACRES:
NA.79

biological source

green tea

Quality Level

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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This Item
E4143PHR1333324880
(−)-Epigallocatechin gallate ≥80% (HPLC), from green tea

E4268

(−)-Epigallocatechin gallate

(−)-Epigallocatechin gallate ≥95%

E4143

(−)-Epigallocatechin gallate

Epigallocatechin gallate Pharmaceutical Secondary Standard; Certified Reference Material

PHR1333

Epigallocatechin gallate

(–)-Epigallocatechin Gallate One of the main polyphenolic constituents of green tea that exhibits potent antitumor, anti-inflammatory, and antioxidant properties.

324880

(–)-Epigallocatechin Gallate

assay

≥80% (HPLC)

assay

≥95%

assay

-

assay

≥95% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

100

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

pharmaceutical (small molecule)

application(s)

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

Gene Information

human ... CYP1A2(1544)

Gene Information

human ... CYP1A2(1544)

Gene Information

-

Gene Information

-

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

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Customers Also Viewed

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1 of 8

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
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)
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
Xin Wang et al.
World journal of gastroenterology, 23(46), 8128-8139 (2018-01-02)
To investigate the effect of epigallocatechin gallate (EGCG) on structural changes of gut microbiota in colorectal carcinogenesis. An azoxymethane (AOM)/dextran sodium sulfate (DSS)-induced colitis mouse model was established. Forty-two female FVB/N mice were randomly divided into the following three groups:

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