(-)-Epigallocatechin gallate (CHEM017303)

Record Information
Version1.0
Creation Date2016-05-22 04:13:51 UTC
Update Date2026-05-14 19:17:29 UTC
Accession NumberCHEM017303
Identification
Common Name(-)-Epigallocatechin gallate
ClassSmall Molecule
Description
A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-Epigallocatechin-3-O-gallateChEBI
[(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoateChEBI
EGCGChEBI
Epigallocatechin 3-gallateChEBI
(-)-Epigallocatechin-3-O-gallic acidGenerator
[(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoic acidGenerator
Epigallocatechin 3-gallic acidGenerator
Epigallocatechin gallic acidGenerator
(-)-Epigallocatechin gallatHMDB
(-)-Epigallocatechin gallateHMDB
(-)-Epigallocatechol gallateHMDB
(-)-Epigallocatehin gallateHMDB
Catechin deriv.HMDB
Epigallocatcchin gallateHMDB
EpigallocateHMDB
Epigallocic acidHMDB
Galloyl-L-epigallocatecholHMDB
Tea catechinHMDB
Epigallo-catechin gallateHMDB
Epigallocatechin-3-gallateHMDB
SunphenonHMDB
EGCG CPDHMDB
Epigallocatechin-3-O-gallateHMDB
Chemical FormulaC22H18O11
Average Molecular Mass458.372 g/mol
Monoisotopic Mass458.085 g/mol
CAS Registry Number989-51-5
IUPAC Name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(-)-epigallocatechin gallate
SMILESOC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(O)=C(O)C(O)=C1
InChI IdentifierInChI=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
InChI KeyWMBWREPUVVBILR-WIYYLYMNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechin gallates
Alternative Parents
Substituents
  • Catechin gallate
  • Epigallocatechin
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP2.38ALOGPS
logP3.08ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.99ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.75 m³·mol⁻¹ChemAxon
Polarizability43.27 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB12116
HMDB IDHMDB0003153
FooDB IDFDB093704
Phenol Explorer ID129
KNApSAcK IDC00000958
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3550
PDB IDNot Available
Wikipedia LinkEpigallocatechin_gallate
Chemspider ID58575
ChEBI ID4806
PubChem Compound ID65064
Kegg Compound IDC09731
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14633667
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15024383
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15950188
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17157668
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18665171
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18716169
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19113837
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19539611
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19784588
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19928918
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21080642
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21434603
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22300765
14. Liang, Huiling; Liang, Yuerong; Dong, Junjie; Lu, Jianliang. Tea extraction methods in relation to control of epimerization of tea catechins. Journal of the Science of Food and Agriculture (2007), 87(9), 1748-1752.
15. Uchida S, Ozaki M, Suzuki K, Shikita M: Radioprotective effects of (-)-epigallocatechin 3-O-gallate (green-tea tannin) in mice. Life Sci. 1992;50(2):147-52.
16. Dashwood WM, Carter O, Al-Fageeh M, Li Q, Dashwood RH: Lysosomal trafficking of beta-catenin induced by the tea polyphenol epigallocatechin-3-gallate. Mutat Res. 2005 Dec 11;591(1-2):161-72. Epub 2005 Jul 27.
17. Dorchies OM, Wagner S, Vuadens O, Waldhauser K, Buetler TM, Kucera P, Ruegg UT: Green tea extract and its major polyphenol (-)-epigallocatechin gallate improve muscle function in a mouse model for Duchenne muscular dystrophy. Am J Physiol Cell Physiol. 2006 Feb;290(2):C616-25.
18. Lill G, Voit S, Schror K, Weber AA: Complex effects of different green tea catechins on human platelets. FEBS Lett. 2003 Jul 10;546(2-3):265-70.
19. Henning SM, Aronson W, Niu Y, Conde F, Lee NH, Seeram NP, Lee RP, Lu J, Harris DM, Moro A, Hong J, Pak-Shan L, Barnard RJ, Ziaee HG, Csathy G, Go VL, Wang H, Heber D: Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. J Nutr. 2006 Jul;136(7):1839-43.
20. Suganuma M, Okabe S, Sueoka N, Sueoka E, Matsuyama S, Imai K, Nakachi K, Fujiki H: Green tea and cancer chemoprevention. Mutat Res. 1999 Jul 16;428(1-2):339-44.
21. Katiyar SK, Afaq F, Perez A, Mukhtar H: Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress. Carcinogenesis. 2001 Feb;22(2):287-94.
22. Meng X, Sang S, Zhu N, Lu H, Sheng S, Lee MJ, Ho CT, Yang CS: Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats. Chem Res Toxicol. 2002 Aug;15(8):1042-50.
23. Shirai T, Reshad K, Yoshitomi A, Chida K, Nakamura H, Taniguchi M: Green tea-induced asthma: relationship between immunological reactivity, specific and non-specific bronchial responsiveness. Clin Exp Allergy. 2003 Sep;33(9):1252-5.
24. Fujiki H, Suganuma M, Okabe S, Sueoka N, Komori A, Sueoka E, Kozu T, Tada Y, Suga K, Imai K, Nakachi K: Cancer inhibition by green tea. Mutat Res. 1998 Jun 18;402(1-2):307-10.
25. Wang YC, Bachrach U: The specific anti-cancer activity of green tea (-)-epigallocatechin-3-gallate (EGCG). Amino Acids. 2002;22(2):131-43.
26. Katiyar SK, Matsui MS, Elmets CA, Mukhtar H: Polyphenolic antioxidant (-)-epigallocatechin-3-gallate from green tea reduces UVB-induced inflammatory responses and infiltration of leukocytes in human skin. Photochem Photobiol. 1999 Feb;69(2):148-53.
27. Shirai T, Sato A, Chida K, Hayakawa H, Akiyama J, Iwata M, Taniguchi M, Reshad K, Hara Y: Epigallocatechin gallate-induced histamine release in patients with green tea-induced asthma. Ann Allergy Asthma Immunol. 1997 Jul;79(1):65-9.
28. Caporali A, Davalli P, Astancolle S, D'Arca D, Brausi M, Bettuzzi S, Corti A: The chemopreventive action of catechins in the TRAMP mouse model of prostate carcinogenesis is accompanied by clusterin over-expression. Carcinogenesis. 2004 Nov;25(11):2217-24. Epub 2004 Sep 9.
29. Ichihashi M, Ahmed NU, Budiyanto A, Wu A, Bito T, Ueda M, Osawa T: Preventive effect of antioxidant on ultraviolet-induced skin cancer in mice. J Dermatol Sci. 2000 Mar;23 Suppl 1:S45-50.
30. Dvorakova K, Dorr RT, Valcic S, Timmermann B, Alberts DS: Pharmacokinetics of the green tea derivative, EGCG, by the topical route of administration in mouse and human skin. Cancer Chemother Pharmacol. 1999;43(4):331-5.
31. Neuhaus T, Voit S, Lill G, Vetter H, Schror K, Weber AA: Platelet aggregation induced by the C-terminal peptide of thrombospondin-1 (4N1-1) is inhibited by epigallocatechin gallate but not by prostaglandin E1. Platelets. 2004 Nov;15(7):455-7.
32. Chen JJ, Ye ZQ, Koo MW: Growth inhibition and cell cycle arrest effects of epigallocatechin gallate in the NBT-II bladder tumour cell line. BJU Int. 2004 May;93(7):1082-6.
33. Kanadzu M, Lu Y, Morimoto K: Dual function of (--)-epigallocatechin gallate (EGCG) in healthy human lymphocytes. Cancer Lett. 2006 Sep 28;241(2):250-5. Epub 2005 Nov 21.
34. Rezai-Zadeh K, Shytle D, Sun N, Mori T, Hou H, Jeanniton D, Ehrhart J, Townsend K, Zeng J, Morgan D, Hardy J, Town T, Tan J: Green tea epigallocatechin-3-gallate (EGCG) modulates amyloid precursor protein cleavage and reduces cerebral amyloidosis in Alzheimer transgenic mice. J Neurosci. 2005 Sep 21;25(38):8807-14.