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Epicatechin gallate
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Epicatechin gallate

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Epicatechin gallate
Chemical structure of epicatechin gallate
Chemical structure of 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.116.252
KEGG
PubChem CID
UNII
  • 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
  • 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
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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Epicatechin gallate (ECG) is a flavan-3-ol, a type of flavonoid, present in green tea. It is also reported in buckwheat and in grape.

The tea component epicatechin gallate is being researched because in vitro experiments showed it can reverse methicillin resistance in bacteria such as Staphylococcus aureus. Nevertheless, the compound is significantly degraded by steeping in boiling water, unlike related catechins.

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.

See also



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