(-)-Epigallocatechin (CHEM021929)

Record Information
Version1.0
Creation Date2016-05-25 18:15:57 UTC
Update Date2026-05-14 17:54:43 UTC
Accession NumberCHEM021929
Identification
Common Name(-)-Epigallocatechin
ClassSmall Molecule
Description
A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-3,3',4',5,5',7-FlavanhexolChEBI
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triolChEBI
2,3-cis-EpigallocatechinChEBI
EpigallocatecholChEBI
L-EpigallocatechinChEBI
(-)-cis-3,3',4',5,5',7-HexahydroxyflavanHMDB
(-)-cis-3,3',4',5,5',7-HexahydroxyflavaneHMDB
(-)-EpigallocatecholHMDB
Antiscurvy factor C2HMDB
EGCHMDB
EpigallocatechinHMDB, MeSH
l-EpigallocatecholHMDB
Gallocatechol, (2R-trans)-isomerMeSH, HMDB
GallocatecholMeSH, HMDB
Gallocatechol, (2R-cis)-isomerMeSH, HMDB
GallocatechinMeSH, HMDB
(-)-3,3’,4’,5,5’,7-FlavanhexolHMDB
(-)-EpigallocatechinHMDB
(-)-epi-GallocatechinHMDB
(2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-trihydroxychromanHMDB
(2R,3R)-3,4-Dihydro-2-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran-3,5,7-triolHMDB
1-epi-3',4',5',5,7-Pentahydroxy-3-flavanolHMDB
1-epi-3’,4’,5’,5,7-Pentahydroxy-3-flavanolHMDB
3,3',4',5,5',7-FlavanhexolHMDB
3,3’,4’,5,5’,7-FlavanhexolHMDB
GalloepicatechinHMDB
epi-GallocatechinHMDB
Chemical FormulaC15H14O7
Average Molecular Mass306.268 g/mol
Monoisotopic Mass306.074 g/mol
CAS Registry Number970-74-1
IUPAC Name(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameepigallocatechin
SMILESO[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O
InChI IdentifierInChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15-/m1/s1
InChI KeyXMOCLSLCDHWDHP-IUODEOHRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentEpigallocatechins
Alternative Parents
Substituents
  • Epigallocatechin
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • 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 Solubility0.87 g/LALOGPS
logP0.71ALOGPS
logP1.49ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.73ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area130.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.98 m³·mol⁻¹ChemAxon
Polarizability29.14 ųChemAxon
Number of Rings3ChemAxon
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 IDDB03823
HMDB IDHMDB0038361
FooDB IDFDB017700
Phenol Explorer ID127
KNApSAcK IDC00008818
BiGG IDNot Available
BioCyc IDCPD-10411
METLIN IDNot Available
PDB IDEGT
Wikipedia LinkNot Available
Chemspider ID65231
ChEBI ID42255
PubChem Compound ID72277
Kegg Compound IDC12136
YMDB IDYMDB01682
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10775337
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19653629
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19937856
4. Cooper R, Morre DJ, Morre DM: Medicinal benefits of green tea: part II. review of anticancer properties. J Altern Complement Med. 2005 Aug;11(4):639-52.
5. Lin SC, Wang CP, Chen YM, Lu SY, Fann MJ, Liu CJ, Kao SY, Chang KW: Regulation of IGFBP-5 expression during tumourigenesis and differentiation of oral keratinocytes. J Pathol. 2002 Nov;198(3):317-25.
6. Davies SL, Bozzo J: Spotlight on tNOX: a tumor-selective target for cancer therapies. Drug News Perspect. 2006 May;19(4):223-5.
7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.