Epigallocatechin gallate

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"EGCG" redirects here. For the software, see Extended GCG.
Epigallocatechin gallate
Structural formula of epigallocatechin gallate
Space-filling model of the epigallocatechin gallate molecule
Names
IUPAC name
[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate
Preferred IUPAC name
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Other names
(-)-Epigallocatechin gallate
Identifiers
989-51-5 N
ChEBI CHEBI:4806 YesY
ChEMBL ChEMBL297453 YesY
ChemSpider 58575 YesY
7002
Jmol 3D model Interactive image
MeSH Epigallocatechin+gallate
PubChem 65064
  • 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 YesY
    Key: WMBWREPUVVBILR-WIYYLYMNSA-N YesY
  • InChI=1/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
    Key: WMBWREPUVVBILR-WIYYLYMNBM
  • O=C(O[C@@H]2Cc3c(O[C@@H]2c1cc(O)c(O)c(O)c1)cc(O)cc3O)c4cc(O)c(O)c(O)c4
Properties
C22H18O11
Molar mass 458.372 g/mol
Appearance
soluble (33.3-100 g/L)[vague][1]
Solubility soluble in ethanol, DMSO, dimethyl formamide[1] at about 20 g/l[2]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Epigallocatechin gallate (EGCG), also known as epigallocatechin-3-gallate, is the ester of epigallocatechin and gallic acid, and is a type of catechin.

EGCG, the most abundant catechin in tea, is a polyphenol under basic research for its potential to affect human health and disease. EGCG is used in many dietary supplements.

Food sources

Tea

It is found in high content in the dried leaves of white tea (4245 mg per 100 g), green tea (7380 mg per 100 g) and, in smaller quantities, black tea.[3] During black tea production, the catechins are mostly converted to theaflavins and thearubigins.[4] via polyphenol oxidases.[which?]

Other

Trace amounts are found in apple skin, plums, onions, hazelnuts, pecans and carob powder (at 109 mg per 100 g).[3]

Bioavailability

When taken orally, EGCG has poor bioavailability even at such a high amount of daily intake equivalent to 8-16 cups of tea (800 mg), a dose causing mild adverse effects, such as nausea or heartburn.[5] After consumption, EGCG blood levels peak within 1.7 hours, then are excreted into the urine over 3-15 hours.[6]

Research on potential therapeutic uses

EGCG has been the subject of a number of basic and clinical research studies investigating its potential use as a therapeutic for a broad range of disorders.[7][8][9] As of 2015, however, these effects remain unsubstantiated in humans and there are no approved health claims for EGCG in the United States or Europe.[8][9] The US Food and Drug Administration has issued warning letters against marketers of products claiming that EGCG provides anti-disease effects or overall health benefits.[10][11]

See also

References

  1. ↑ 1.0 1.1 http://chemicalland21.com/lifescience/foco/%28-%29-EPIGALLOCATECHIN%20GALLATE.htm
  2. ↑ http://www.caymanchem.com/pdfs/70935.pdf
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ 8.0 8.1 Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ 9.0 9.1 Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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