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Sigma-Aldrich

(–)-Epigallocatechin Gallate

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

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Synonym(s):
(–)-Epigallocatechin Gallate, EGCG, (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol-3-(3,4,5-trihydroxybenzoate), HAT Inhibitor X, Histone Acetyltransferase Inhibitor X, p300/CBP Inhibitor VIII, PCAF Inhibitor V, DNA MTase Inhibitor IV, DNA Methyltransferase Inhibitor IV
Empirical Formula (Hill Notation):
C22H18O11
CAS Number:
Molecular Weight:
458.37
MDL number:

Quality Level

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

faint pink

solubility

water: 5 mg/mL
DMSO: soluble

shipped in

ambient

storage temp.

−20°C

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

General description

One of the main polyphenolic constituents of green tea that exhibits potent antitumor, anti-inflammatory, and antioxidant properties. Arrests cell cycling at G0/G1 phase and induces apoptosis in a dose-dependent manner. Shown to inhibit PMA-induced skin thickening and to activate of protein kinase C. Also activates ornithine decarboxylase and interleukin-1α mRNA and protein expression. Acts as an inhibitor of inducible nitric oxide synthase (iNOS) gene expression and enzyme activity. Also blocks peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine. Strongly and directly inhibits telomerase in cell-free systems and in cancer cell lines. An inhibitor of Dnmt1 (IC50 = 210-470 nM). Acts as a selective and noncompetitive inhibitor of HAT activities (IC50 = 30, 50, 60 and 70 µM for p300, CBP, PCAF and TIP60) with minimal effects on HDAC, SIRT and HMTase.
One of the main polyphenolic constituents of green tea that possesses potent antitumor, anti-inflammatory, and antioxidant properties. EGCG has been shown to inhibit PMA-induced skin thickening, activation of protein kinase C, activation of ornithine decarboxylase, and activation of interleukin-1α mRNA and protein expression. Has also been shown to inhibit inducible nitric oxide synthase (iNOS) gene expression and enzyme activity and to inhibit the peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine. Also strongly and directly inhibits telomerase. Acts as a selective and noncompetitive inhibitor of HAT activities (IC50 = 30, 50, 60 and 70 µM for p300, CBP, PCAF and TIP60) with minimal effects on HDAC, SIRT and HMTase.

Biochem/physiol Actions

Cell permeable: no
Primary Target
PMA-induced skin thickening
Product does not compete with ATP.
Reversible: no
Target IC50: 210-470 nM against Dnmt1; 30, 50, 60 and 70 µM for p300, CBP, PCAF and TIP60

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution, aliquot and freeze at -20°C. DMSO stock solutions are stable for up to 3 months at -20°C.

Other Notes

Choi, K.C., et al. 2009. Cancer Res.69, 583.
Dell′Aicia, I., et al. 2004. EMBO reports 5, 1.
Tachibana, H., et al. 2004. Nat. Struct. Mol. Biol.11, 380.
Naasami, I., et al. 1998. Biochem. Biophys. Res. Commun. 249, 391.
Ahmad, N., et al. 1997. J. Natl. Cancer89, 1881.
Chan, M.M.-Y., et al. 1997. Biochem. Pharmacol. 54, 1281.
Lin, Y.-L., and Lin, J.-K. 1997. Mol. Pharmacol. 52, 465.
Fiala, E.S., et al. 1996. Experientia 52, 922.
Katiyar, S.K., et al. 1995. J. Invest. Dermatol. 105, 394.
Liao, S., et al. 1995. Cancer Lett. 96, 239.
Yamane, T., et al. 1995. Cancer Res. 55, 2081.
Huang, M.T., et al. 1992. Carcinogenesis 13, 947.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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


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