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(-)-epicatechin gallate (Synonyms: ECG)

Catalog No.GC10603

major catechin in green tea

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(-)-epicatechin gallate Chemical Structure

Cas No.: 1257-08-5

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10mM (in 1mL DMSO)
$69.00
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5mg
$45.00
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10mg
$63.00
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20mg
$135.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Protocol

Animal experiment:

Rats[2]Male Sprague-Dawley rats, obtained at 7 weeks of age (210-245 g) are used. Epicatechin gallate (ECG) is suspended in 0.5% w/v sodium carboxymethylcellulose at 12.5, 25.0 and 50.0 mg/10 mL for oral administration to rats at 10 mL/kg. For intravenous injection in rats at 1.0 mg/kg, an ethanolic solution of Epicatechin gallate is diluted with 10% w/v sodium citrate solution to 1.0 mg/mL; the final concentration of ethanol is 1% v/v[2].

References:

[1]. Waffo-Téguo P, et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer. 2001;40(2):173-9.
[2]. Takizawa Y, et al. Pharmacokinetics of (-)-epicatechin-3-O-gallate, an active component of Onpi-to, in rats. Biol Pharm Bull. 2003 May;26(5):608-12.

Background

(-)-epicatechin gallate is a major catechin component in green tea [1].

(-)-epicatechin gallate (ECG) plays an important role in cell growth inhibition, apoptosis and membrane transport system [1].

(-)-epicatechin gallate is a kind of catechin. In HCT-116 cells, ECG activated transcription factor 3 (ATF3), which played a critical role in pro-apoptosis. EGR-1 was involved in ECG-induced ATF3 expression. In HCT-116 cells, ECG (50 µM) increased NAG-1 and ATF3 expression in time- and dose-dependent way [1]. In carcinoma HSC-2 cells, ECG (50 µM) exhibited cytotoxicity with midpoint cytotoxicity (NR50) value of 67 µM. However, in normal HGF-2 fibroblasts, ECG exhibited cytotoxicity at concentrations up to 25 µM with NR50 value of 100 µM. In carcinoma HSC-2 cells, ECG (250 µM) induced nucleosomal DNA fragmentation and apoptosis. ECG (150 µM) significantly increased caspase-3 activity [2].

In rats, there were five metabolites of ECG: (-)-epicatechin gallate, 3’,4’’-di-O-methyl-(-)-epicatechin gallate, 4’’-O-methyl-(-)-epicatechin gallate, 4’-O-methyl-(-)-epicatechin gallate and 3’-O-methyl-(-)-epicatechin gallate, which were excreted in rat urine [3].

References:
[1].  Cho KN, Sukhthankar M, Lee SH, et al. Green tea catechin (-)-epicatechin gallate induces tumour suppressor protein ATF3 via EGR-1 activation. Eur J Cancer, 2007, 43(16): 2404-2412.
[2].  Babich H, Krupka ME, Nissim HA, et al. Differential in vitro cytotoxicity of (-)-epicatechin gallate (ECG) to cancer and normal cells from the human oral cavity. Toxicol In Vitro, 2005, 19(2): 231-242.
[3].  Kohri T, Suzuki M, Nanjo F. Identification of metabolites of (-)-epicatechin gallate and their metabolic fate in the rat. J Agric Food Chem, 2003, 51(18): 5561-5566.

Chemical Properties

Cas No. 1257-08-5 SDF
Synonyms ECG
Chemical Name (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate
Canonical SMILES OC1=CC(C(O[C@@H]2CC3=C(C=C(O)C=C3O)O[C@@H]2C4=CC=C(O)C(O)=C4)=O)=CC(O)=C1O
Formula C22H18O10 M.Wt 442.37
Solubility ≥ 22.1mg/mL in DMSO Storage 4°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 2.2606 mL 11.3028 mL 22.6055 mL
5 mM 0.4521 mL 2.2606 mL 4.5211 mL
10 mM 0.2261 mL 1.1303 mL 2.2606 mL
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