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Showing Compound 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
(-)-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
3,3',4',5,5',7-Hexahydroxyflavan; (-)-cis-formdb_source
L-Epigallocatecholbiospider
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
    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 agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
    Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
    Anti-acne50177 An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin.DUKE
    Anti-amebic33281 An agent that kills or inhibits the growth of amoebas, reducing infection and inflammation. Therapeutically, it's used to treat amoebic dysentery, amoebic liver abscess, and other intestinal infections, managing symptoms and preventing complications. Key medical uses include treating parasitic infections, such as those caused by Entamoeba histolytica.DUKE
    Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
    Anti carcinogenic35610 An agent that prevents or inhibits the formation of cancer, reducing tumor growth and proliferation. It plays a biological role in protecting cells from DNA damage and mutation. Therapeutically, it is used to prevent cancer development, with key medical applications in chemotherapy, radiation protection, and cancer prevention programs.DUKE
    Anti caries52217 An agent that prevents tooth decay, reducing bacterial acid production and promoting oral health. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing and treating dental caries. Key medical uses include toothpaste additives, mouthwashes, and dental varnishes to protect against tooth decay.DUKE
    Anti-giardialAn agent that treats intestinal infections caused by Giardia intestinalis, reducing symptoms and eliminating the parasite, commonly used in managing giardiasis.DUKE
    Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
    Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
    Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
    Anti-streptococcic33282 An agent that targets and combats Streptococcus bacteria, reducing infection and inflammation. Therapeutically, it is used to treat streptococcal infections, such as strep throat and skin infections, and to prevent complications like rheumatic fever.DUKE
    Beta-adrenergic receptor blocker37962 An agent that blocks beta-adrenergic receptors, reducing heart rate and blood pressure. Therapeutically, it manages hypertension, angina, and certain arrhythmias, while also being used to treat conditions like glaucoma, migraine headaches, and performance anxiety.DUKE
    Catechol O-methyltransferase inhibitor48406 An agent that blocks the activity of catechol O-methyltransferase, an enzyme involved in breaking down catecholamines. Therapeutically, it increases dopamine levels, commonly used in managing Parkinson's disease, depression, and anxiety disorders, as well as treating pain and fibromyalgia.DUKE
    Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.DUKE
    Neuroprotective63726 An agent that protects nerve cells from damage or degeneration, reducing the risk of neurodegenerative diseases. Therapeutically, it helps manage conditions like Alzheimer's, Parkinson's, and stroke, promoting neuronal survival and function.DUKE
    Peroxynitrite scavengerAn agent that binds to and removes peroxynitrite, a damaging oxidant. It plays a biological role in reducing oxidative stress and inflammation, with therapeutic applications in neurodegenerative and cardiovascular diseases, and key medical uses in treating conditions like stroke and atherosclerosis.DUKE
    Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
    ProtisticideAn agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections.DUKE
    Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.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).