Record Information
Version1.0
Creation date2019-10-16 14:25:00 UTC
Update date2019-10-16 14:25:00 UTC
Primary IDFDB093704
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpigallocatechin-3-gallate
DescriptionEpigallocatechin gallate, also known as EGCG or catechin deriv., belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. Epigallocatechin gallate has been detected, but not quantified in, black tea and green tea. This could make epigallocatechin gallate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Epigallocatechin gallate.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(-)-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
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
Chemical FormulaC22H18O11
IUPAC name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
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
Isomeric SMILES[H][C@]1(CC2=C(O)C=C(O)C=C2O[C@]1([H])C1=CC(O)=C(O)C(O)=C1)OC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight458.3717
Monoisotopic Molecular Weight458.084911418
Classification
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
Ontology
Foods
  • Cocoa and cocoa products
  • Nuts and legumes:

    Fruits and vegetables:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MSEpigallocatechin-3-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ug0-0930000000-f01263ac8498e09a9b96Spectrum
    Predicted GC-MSEpigallocatechin-3-gallate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-1192005000-c1fb4fee1e85d6928c34Spectrum
    Predicted GC-MSEpigallocatechin-3-gallate, TBDMS_3_24, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEpigallocatechin-3-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSEpigallocatechin-3-gallate, "Epigallocatechin gallate,3TBDMS,#24" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0301900000-306bcb88a9db3b631447Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00or-0900000000-2209ff009c5d9cffaf40Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0aor-0000900008-24e0bb519bd4a4f909f0Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0912000000-3adc2bfa8656374fadffSpectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0900000000-421d0afdbaa8c277f57aSpectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0911000000-8cd4fb88571a263c38abSpectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0301900000-306bcb88a9db3b631447Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00or-0900000000-2209ff009c5d9cffaf40Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0aor-0000900008-24e0bb519bd4a4f909f0Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0912000000-3adc2bfa8656374fadffSpectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0900000000-421d0afdbaa8c277f57aSpectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0911000000-8cd4fb88571a263c38abSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0910000000-3ca87cd7e5536628266aSpectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0159-0917000000-0d7d5d2e8b3cd65a6134Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0159-0917000000-b1f0fb994ee815d3bc77Spectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-d3719d6cc341aafdd5caSpectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0901000000-bbef161918123e6de6a9Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0691000000-bf8635f20994642ca769Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0690000000-46717d45926c7c5d1a6dSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0920500000-a974f0f3117ff4b93e42Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-0910100000-a2be3929b160816f337aSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-c4f287a63df487615180Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0301900000-4bd59275b184970a157fSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0916400000-8e2c614db7634a27ffddSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900000000-236dc720968cdbf03811Spectrum
    NMRNot Available
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound IDNot Available
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDNot Available
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyFOBI:030489
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference