324880

(–)-Epigallocatechin Gallate

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

• 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: 989-51-5
• Molecular Weight: 458.37
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00075940
• Assay: ≥95% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Properties

• description: Merck USA index - 14, 3526
• Quality Segment: 100
• 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
• SMILES string: O1[C@@H]([C@@H](Cc4c1cc(cc4O)O)OC(=O)c3cc(c(c(c3)O)O)O)c2cc(c(c(c2)O)O)O
• 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

Description

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.

Biochem/physiol Actions

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

Cell permeable: no

Packaging

Packaged under inert gas

Preparation Note

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

Disclaimer

Toxicity: Irritant (B)

Safety Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Codes: H302,H317,H319,H411
• Precautionary Statements: 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
• Storage Class: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable