Epicatechin gallate

Epicatechin gallate
Names
	IUPAC name (2R,3R)-3′,4′,5,7-Tetrahydroxyflavan-3-yl 3,4,5-trihydroxybenzoate
	Systematic IUPAC name (2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
	Other names ECG; Epicatechin 3-gallate; (−)-Epicatechin-3-O-gallate
Identifiers
CAS Number	1257-08-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:70255 ;
ChEMBL	ChEMBL36327 ;
ChemSpider	97034 ;
ECHA InfoCard	100.116.252
KEGG	C22594;
PubChem CID	107905;
UNII	92587OVD8Z ;
CompTox Dashboard (EPA)	DTXSID70925231 ;
	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 Key: LSHVYAFMTMFKBA-TZIWHRDSSA-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;
	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;
Properties
Chemical formula	C22H18O10
Molar mass	442.37 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Epicatechin gallate (ECG, (−)-epicatechin-3-gallate) is a flavan-3-ol, a type of flavonoid, primarily found in green tea (Camellia sinensis), with smaller amounts in cocoa, grapes, and other plants. It is also reported in buckwheat and in grape.

As a polyphenolic catechin, ECG is formed by the esterification of epicatechin with gallic acid, contributing to antioxidant, antimicrobial, and potential anticancer properties. ECG is studied for its ability to reverse methicillin resistance in Staphylococcus aureus and inhibit inflammatory pathways, but its clinical use is limited by poor bioavailability and thermal instability in boiling water. Recent research highlights its potential in modulating SARS-CoV-2-related inflammation and bacterial virulence factors.

Epicatechin, as well as many other flavonoids, has been found to act as a nonselective antagonist of the opioid receptors, albeit with somewhat low affinity.

Names


IUPAC name (2R,3R)-3′,4′,5,7-Tetrahydroxyflavan-3-yl 3,4,5-trihydroxybenzoate
Systematic IUPAC name (2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Other names ECG Epicatechin 3-gallate (−)-Epicatechin-3-O-gallate
Identifiers
CAS Number	1257-08-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:70255^N
ChEMBL	ChEMBL36327^N
ChemSpider	97034^N
ECHA InfoCard	100.116.252
KEGG	C22594
PubChem CID	107905
UNII	92587OVD8Z^Y
CompTox Dashboard (EPA)	DTXSID70925231
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
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
Properties
Chemical formula	C₂₂H₁₈O₁₀
Molar mass	442.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references