A phenol with diverse biological activities
Related Products
Isomer(s)
24962(−)-Gallocatechin Gallate
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(−)-Epigallocatechin Gallate

Item No. 70935

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4-dihydro-5,7-dihydroxy-2R-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3R-yl-3,4,5-trihydroxy-benzoate
CAS Number
989-51-5
Synonyms
  • EGCG
Molecular Formula
C22H18O11
Formula Weight
458.4
Purity
≥96%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 25 mg/ml
λmax
276 nm
SMILES
Oc1cc(O)c2C[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@H](Oc2c1)c1cc(O)c(O)c(O)c1
InChi Code
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
Origin
Plant/Folium camelliae
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    (–)-Epigallocatechin gallate (EGCG) is a phenol that has been found in green and black tea plants and has diverse biological activities.1,2,3,4,5,6,7 It is lytic against T. cruzi amastigotes, with a 50% bactericidal concentration (MBC50) value of 0.53 pM.1 EGCG decreases deoxyguanosine oxidation and tyrosine nitration (IC50s = 0.25 and 0.11 mM, respectively) and inhibits macrophage-mediated LDL oxidation in vitro.2,3 EGCG increases LDL receptor binding activity and lowers cholesterol levels in HepG2 cells via increased cholesterol efflux.4 It inhibits heregulin-β1-induced activation of ErbB2 and ErbB3, as well as migration and invasion of MCF-7 breast cancer cells.5 In vivo, EGCG reduces food intake and body weight, serum levels of insulin, leptin, testosterone, and growth hormone, and the size of the ventral prostate, testis, liver, and spleen in male Sprague Dawley, lean Zucker, and obese Zucker rats when administered at doses of 82, 81, and 92 mg/kg, respectively.6 It also reduces increases in hepatic steatosis, inflammatory cell infiltration, and injury in a mouse model of non-alcoholic steatohepatitis (NASH) induced by a methionine- and choline-deficient diet when administered at doses of 50 and 100 mg/kg.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Paveto, C., Güida, M.C., Esteva, M.I., et al. Anti-Trypanosoma cruzi activity of green tea (Camellia sinensis) catechins. Antimicrob. Agents Chemother. 48(1), 69-74 (2004).

    2. Fiala, E.S., Sodum, R.S., Bhattacharya, M., et al. (−)-Epigallacatechin gallate, a polyphenolic tea antioxidant, inhibits peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine. Experientia 52, 922-926 (1996).

    3. Yoshida, H., Ishikawa, T., Hosoai, H., et al. Inhibitory effect of tea flavonoids on the ability of cells to oxidize low density lipoprotein. Biochem. Pharmacol. 58, 1695-1703 (1999).

    4. Bursill, C.A., and Roach, P.D. Modulation of cholesterol metabolism by the green tea polyphenol (−)-epigallocatechin gallate in cultured human liver (HepG2) cells. J. Agric. Food Chem. 54, 1621-1626 (2006).

    5. Kushima, Y., Iida, K., Nagaoka, Y., et al. Inhibitory effect of (‒)-epigallocatechin and (−)-epigallocatechin gallate against heregulin β1-induced migration/invasion of the MCF-7 breast carcinoma cell line. Biol. Pharm. Bull. 32(5), 899-904 (2009).

    6. Kao, Y.H., Hiipakka, R.A., and Liao, S. Modulation of endocrine systems and food intake by green tea epigallocatechin gallate. Endocrinology 141(3), 980-987 (2000).

    7. Ding, Y., Sun, X., Chen, Y., et al. Epigallocatechin gallate attenuated non-alcoholic steatohepatitis induced by methionine- and choline-deficient diet. Eur. J. Pharmacol. 761, 405-412 (2015).