Epicatechin gallate

Epicatechin gallate
Names
	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
ChEBI	CHEBI:70255
ChEMBL	ChEMBL36327
ChemSpider	97034
Jmol 3D model	Interactive image
PubChem	107905
	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).
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	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]}

Epicatechin, as well as many other flavonoids, has been found to act as a non-selective antagonist of the opioid receptors, albeit with somewhat low affinity.^[4]

References

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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 (+)-Catechin 7-O-β-D-xylopyranoside Epicatechin-3′-O-glucoside Glochiflavanoside A, B, C D Polydine ((+)-catechin 7-0-α-L-arabinoside) Symplocoside (3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside)
Acetylated	Phylloflavan
Misc.	Thearubigins

Epicatechin gallate

References

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Names

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
ChEBI	CHEBI:70255^N
ChEMBL	ChEMBL36327^N
ChemSpider	97034^N
Jmol 3D model	Interactive image
PubChem	107905
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