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Epigallocatechin (FDB017700)

Record Information
Version1.0
Creation date2010-04-08 22:13:15 UTC
Update date2019-11-26 03:15:04 UTC
Primary IDFDB017700
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpigallocatechin
Description(-)-Epigallocatechin, also known as epigallocatechol, 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 (-)-Epigallocatechin is a bitter tasting compound (-)-Epigallocatechin is found, on average, in the highest concentration within a few different foods, such as cocoa beans (Theobroma cacao), green tea, and black tea and in a lower concentration in herbal tea, peanuts (Arachis hypogaea), and pomegranates (Punica granatum) (-)-Epigallocatechin has also been detected, but not quantified in, several different foods, such as common beets (Beta vulgaris), pine nuts (Pinus), common mushrooms (Agaricus bisporus), red bell peppers (Capsicum annuum), and allia (Allium). This could make (-)-epigallocatechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (-)-Epigallocatechin.
CAS Number970-74-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
Chemical FormulaC15H14O7
IUPAC name(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
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
Isomeric SMILESO[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O)=C1)C=C(O)C=C2O
Average Molecular Weight306.2675
Monoisotopic Molecular Weight306.073952802
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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 CompositionC 58.83%; H 4.61%; O 36.57%DFC
    Melting PointMp 219-221° dec.DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical Rotation[a]D -60.3 (c, 0.3 in EtOH)DFC
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MSEpigallocatechin, non-derivatized, GC-MS Spectrumsplash10-0a4i-0978700000-567c7251027c80e91a01Spectrum
    GC-MSEpigallocatechin, non-derivatized, GC-MS Spectrumsplash10-0a4i-0967700000-febb7658ba2d5bd6d9b6Spectrum
    GC-MSEpigallocatechin, non-derivatized, GC-MS Spectrumsplash10-0a4i-0978700000-567c7251027c80e91a01Spectrum
    GC-MSEpigallocatechin, non-derivatized, GC-MS Spectrumsplash10-0a4i-0967700000-febb7658ba2d5bd6d9b6Spectrum
    Predicted GC-MSEpigallocatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0940000000-a9630fe8d1a042f59c2aSpectrum
    Predicted GC-MSEpigallocatechin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-3110049000-8b1040defcae8063c769Spectrum
    Predicted GC-MSEpigallocatechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f32017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f32017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714e2017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714e2017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f32017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-002r-0910000000-8dfe0ba4e2ec1225213f2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0pb9-0019003000-c4d2b02a82d1cf14714e2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-00p0-0951000000-95142c4b42b35c4bdac92017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0900000000-4e9ebbe814af2f8c284d2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-05r0-0913000000-be7d3c4d9b40f51414e72017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0529000000-0036b0386a7ade78fcac2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0690000000-702c5a1e065692895b3a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00vi-0690000000-7844ed1a917693a67b372017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0a4i-0029000000-82c2dfbbc69b748bc6f32017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-002r-0910000000-8dfe0ba4e2ec1225213f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00p0-0951000000-95142c4b42b35c4bdac92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c79003b472daf421e4922017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-f92cf1606a46a5b16f4f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-2026f33ac95d368b52682017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0729000000-fffbd456b9b51c7d02742016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-203a6a86214265bc09e42016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ds-2900000000-023b154fc2d731ecee102016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0219000000-db1826421845ecab14852016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05n0-0922000000-86fb5a0b2fc6608156042016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-2910000000-2375ce05cd5da757763c2016-08-03View Spectrum
    NMRNot Available
    ChemSpider ID65231
    ChEMBL IDCHEMBL47386
    KEGG Compound IDC12136
    Pubchem Compound ID72277
    Pubchem Substance IDNot Available
    ChEBI ID42255
    Phenol-Explorer ID127
    DrugBank IDNot Available
    HMDB IDHMDB38361
    CRC / DFC (Dictionary of Food Compounds) IDKZF28-J:KZF29-K
    EAFUS IDNot Available
    Dr. Duke IDEPIGALLOCATECHOL|(-)-EPI-GALLO-CATECHOL|(-)-EPIGALLOCATECHIN|EPIGALLOCATECHIN
    BIGG IDNot Available
    KNApSAcK IDC00008818
    HET IDEGT
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID127
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
    aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
    anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
    anti amebic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti caries52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti giardialDUKE
    anti mutagenicDUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti radicularDUKE
    anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
    beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
    catechol O-methyltransferase inhibitor48406 An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).DUKE
    lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
    neuroprotective63726 Any compound that can be used for the treatment of neurodegenerative disorders.DUKE
    peroxynitrite scavengerDUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    protisticideDUKE
    xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    bitter
    1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).