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Record Information
Version3.6
Creation Date2006-05-22 15:12:36 UTC
Update Date2016-02-11 01:06:04 UTC
HMDB IDHMDB03153
Secondary Accession NumbersNone
Metabolite Identification
Common NameEpigallocatechin gallate
DescriptionEpigallocatechin gallate (EGCG) is the principal catechin in tea from Camellia sinensis, the most consumed beverage worldwide (after water). Depending on brew time and temperature, a single cup of green tea may contain 100-200 mg EGCG. To control the dose of EGCG administered in experimental studies, green tea solids (GTS) or capsules of green tea extract standardized to EGCG content are often employed. However, there is considerable variability in the EGCG content of commercially available dietary supplements, ranging from 12-143% of the tablet or capsule weight. While standardizing tea preparations to EGCG or using highly purified EGCG for research presents an important strategy for the conduct of precise studies as well as the ability to replicate experiments, it is worth noting this approach limits the potential contributions and possible synergy with other bioactive tea ingredients, including caffeine and other flavonoids. Human studies of the bioavailability of green tea catechins reveal these compounds to be poorly absorbed, with <0.1% of ingested catechins appearing in blood. Most ingested EGCG is rapidly cleared from blood with an elimination half-life of {approx}3 h and preferentially excreted via bile to the colon. The growing interest in the role of EGCG in health promotion and disease prevention is reflected by an exponential growth of research publications in this field. (J Am Coll Nutr. 2007 Aug;26(4):362S-365S).
Structure
Thumb
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
(-)-Epigallocatechin 3-gallic acidGenerator
(-)-Epigallocatechin gallatHMDB
(-)-Epigallocatechin gallateHMDB
(-)-Epigallocatechol gallateHMDB
(-)-Epigallocatehin gallateHMDB
Catechin deriv.HMDB
Epigallocatcchin gallateHMDB
EpigallocateHMDB
Epigallocic acidHMDB
Galloyl-L-epigallocatecholHMDB
Tea catechinHMDB
Chemical FormulaC22H18O11
Average Molecular Weight458.3717
Monoisotopic Molecular Weight458.084911418
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
CAS Registry Number989-51-5
SMILES
OC1=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 Identifier
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
InChI KeyInChIKey=WMBWREPUVVBILR-WIYYLYMNSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Benzoate ester
  • Pyrogallol derivative
  • Benzylether
  • Benzoic acid or derivatives
  • Benzenetriol
  • Resorcinol
  • 1,2-diphenol
  • Benzoyl
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Polyol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 - 142 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.073 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.75 m3·mol-1ChemAxon
Polarizability43.27 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Kidney
  • Liver
  • Muscle
  • Neuron
  • Platelet
  • Prostate
  • Skin
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 129
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 129
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 129
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 129
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 129
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 129
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 129
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 129
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID129
Phenol Explorer Metabolite ID129
FoodDB IDFDB017702
KNApSAcK IDC00000958
Chemspider ID58575
KEGG Compound IDC09731
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpigallocatechin gallate
NuGOwiki LinkHMDB03153
Metagene LinkHMDB03153
METLIN ID3550
PubChem Compound65064
PDB IDEGG
ChEBI ID4806
References
Synthesis ReferenceLiang, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [16772446 ]
  2. 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. [12832052 ]
  3. 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. [1731169 ]
  4. 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. [16054165 ]
  5. 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. [16403950 ]
  6. 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. [10518005 ]
  7. 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. [11181450 ]
  8. 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. [12184788 ]
  9. 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. [12956747 ]
  10. 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. [9675322 ]
  11. Wang YC, Bachrach U: The specific anti-cancer activity of green tea (-)-epigallocatechin-3-gallate (EGCG). Amino Acids. 2002;22(2):131-43. [12395181 ]
  12. 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. [10048310 ]
  13. 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. [9236503 ]
  14. 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. [15358631 ]
  15. 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. [10764992 ]
  16. 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. [10071985 ]
  17. 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. [15745318 ]
  18. 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. [15142168 ]
  19. 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. [16303244 ]
  20. 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. [16177050 ]