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Epicatechin 3-gallate (FDB017114)

Record Information
Version1.0
Creation date2010-04-08 22:12:51 UTC
Update date2019-11-26 03:14:13 UTC
Primary IDFDB017114
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpicatechin 3-gallate
Description(-)-Epicatechin 3-O-gallate, also known as 3-O-galloylepicatechin or ECG, belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin (-)-Epicatechin 3-O-gallate is a bitter tasting compound (-)-Epicatechin 3-O-gallate is found, on average, in the highest concentration within a few different foods, such as red tea, herbal tea, and green tea and in a lower concentration in peppermints (Mentha X piperita), common grapes (Vitis vinifera), and medlars (Mespilus germanica) (-)-Epicatechin 3-O-gallate has also been detected, but not quantified in, several different foods, such as kiwis (Actinidia chinensis), rubus (blackberry, raspberry), sweet oranges (Citrus sinensis), common wheats (Triticum aestivum), and pistachios (Pistacia vera). This could make (-)-epicatechin 3-O-gallate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (-)-Epicatechin 3-O-gallate.
CAS Number1257-08-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP2.55ALOGPS
logP3.38ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.76 m³·mol⁻¹ChemAxon
Polarizability41.64 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H18O10
IUPAC name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
InChI KeyLSHVYAFMTMFKBA-TZIWHRDSSA-N
Isomeric SMILESOC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC=C(O)C(O)=C1
Average Molecular Weight442.376
Monoisotopic Molecular Weight442.08999678
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
  • 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
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Catechol
  • Benzoyl
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.73%; H 4.10%; O 36.17%DFC
Melting PointMp 257-258° (253°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -160.6 (c, 0.22 in Me2CO)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEpicatechin 3-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0umi-0920000000-718b2102383cc9dc533eSpectrum
Predicted GC-MSEpicatechin 3-gallate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004l-1490224000-de77e2646c7aba3a8defSpectrum
Predicted GC-MSEpicatechin 3-gallate, TBDMS_3_23, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpicatechin 3-gallate, TBDMS_4_19, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpicatechin 3-gallate, TBDMS_4_25, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpicatechin 3-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpicatechin 3-gallate, "(-)-Epicatechin 3-O-gallate,3TBDMS,#23" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0292000000-ece704ccdb047a088d282017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0292000000-d89b96c676e7c3398d8f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0170-0950000000-685c095616785cc823032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0940200000-84b58b678cc59833a0252017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0290000000-440ff7c7a589e1c058b52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0290000000-8f606522637d9033c95f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0098500000-0c0b2ca06b9e49aa356b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0097500000-7a41879feecb968154e92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0029600000-77ceea44aa3ce7f822f92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0029600000-7f271696d73430ee74632017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0900000000-21da01e01ba7fa12d6cb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0900000000-1b53eabb63f51dd0886f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-e435428b44afb21a7eee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0900000000-a3b08dd3f89619c2d4f32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0930000000-19d10b8c4fe8d2256c142021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014u-0960500000-6417fae49199511389862021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0940000000-ce6989df78eb09b24d1f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-cff394f106b307da18572021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0920400000-e7005e91544f51f7efe12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0910000000-a428a4e56e1884d5b86a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-d86fe441a677946b22052016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0310900000-98e9c41598a7496271272016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdl-0913300000-af1ea1d6588fca8f1f9f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0900000000-60192713dbf412058de22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0130900000-406473c14c03e2f286252021-09-22View Spectrum
NMRNot Available
ChemSpider ID97034
ChEMBL IDCHEMBL36327
KEGG Compound IDNot Available
Pubchem Compound ID107905
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID128
DrugBank IDNot Available
HMDB IDHMDB37944
CRC / DFC (Dictionary of Food Compounds) IDCML31-M:KWF59-Y
EAFUS IDNot Available
Dr. Duke IDEPICATECHIN-GALLATE|(-)-EPICATECHIN-GALLATE|(-)-EPICATECHOL-GALLATE|1-EPICATECHIN-GALLATE|EPICATECHIN-3-O-GALLATE|EPICATECHOL-GALLATE|(-)-EPICATECHIN-3-O-GALLATE|(-)-EPICATECHIN-3-GALLATE|EPICATECHIN-3-GALLATE
BIGG IDNot Available
KNApSAcK IDC00008866
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID128
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
acetyl-CoA-carboxylase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
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 peroxidantDUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.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
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
glucosyl-transferase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.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
methyl-guanidine inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
mitogen52290 A chemical substance that encourages a cell to commence cell division, triggering mitosis.DUKE
nephroprotective76595 Any protective agent that is able to prevent damage to the kidney.DUKE
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
alpha-amylase inhibitor50627 An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-amylase (EC 3.2.1.1).CHEBI
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.
— 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).