Epicatechin gallate

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Epicatechin gallate

IUPAC name [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Other names ECG Epicatechin 3-gallate (-)-Epicatechin-3-O-gallate
Identifiers
CAS number	1257-08-5^Y
PubChem	107905
ChemSpider	97034^N
ChEBI	CHEBI:70255^N
ChEMBL	CHEMBL36327^N
Jmol-3D images	{{#if:O=C(O[C@@H]2Cc3c(O[C@@H]2c1ccc(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4\|Image 1
SMILES O=C(O[C@@H]2Cc3c(O[C@@H]2c1ccc(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4
InChI InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1^N Key: LSHVYAFMTMFKBA-TZIWHRDSSA-N^N InChI=1/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1 Key: LSHVYAFMTMFKBA-TZIWHRDSBY
Properties
Molecular formula	C₂₂H₁₈O₁₀
Molar mass	442.37 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Epicatechin gallate (ECG) is a flavan-3-ol, a type of flavonoid, present in green tea.^[1] It is also reported in buckwheat^[2] and in grape.^[3]

The tea component epicatechin gallate is being researched because in vitro experiments showed it can reverse methicillin resistance in bacteria like Staphylococcus aureus.^[1] If confirmed, this means the combined intake of a tea extract containing this component might also enhance the effectiveness of methicillin treatment against some resistant bacteria in vivo.^{[citation needed]}

References

↑ 1.0 1.1 Shiota, S; Shimizu, M; Mizushima, T; Ito, H; Hatano, T; Yoshida, T; Tsuchiya, T (1999). "Marked reduction in the minimum inhibitory concentration (MIC) of beta-lactams in methicillin-resistant Staphylococcus aureus produced by epicatechin gallate, an ingredient of green tea (Camellia sinensis)". Biological & pharmaceutical bulletin 22 (12): 1388–90. PMID 10746177.
↑ Danila, Ana-Maria; Kotani, Akira; Hakamata, Hideki; Kusu, Fumiyo (2007). "Determination of Rutin, Catechin, Epicatechin, and Epicatechin Gallate in BuckwheatFagopyrum esculentumMoench by Micro-High-Performance Liquid Chromatography with Electrochemical Detection". Journal of Agricultural and Food Chemistry 55 (4): 1139–43. doi:10.1021/jf062815i. PMID 17253718.
↑ Souquet, Jean-Marc; Cheynier, Véronique; Brossaud, Franck; Moutounet, Michel (1996). "Polymeric proanthocyanidins from grape skins". Phytochemistry 43 (2): 509. doi:10.1016/0031-9422(96)00301-9.

v t e Flavan-3-ols and their glycosides

Flavan-3-ols	Afzelechin Catechin (Epicatechin) Epicatechin gallate Epigallocatechin Epigallocatechin gallate Fisetinidol Gallocatechin Gallocatechin gallate Guibourtinidol Mesquitol Robinetinidol

O-methylated flavan-3ols	Meciadanol (3-O-methylcatechin) Ourateacatechin (4′-O-methyl-(−)-epigallocatechin)

Glycosides	Arthromerin A (Afzelechin-3-O-β-D-xylopyranoside) Arthromerin B (Afzelechin-3-O-β-D-glucopyranoside) Catechin-3-O-glucoside Catechin-3'-O-glucoside Catechin-4'-O-glucoside Catechin-5-O-glucoside Catechin-7-O-glucoside

Acetylated	Phylloflavan

Misc.	Thearubigins

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Epicatechin gallate

References

See also