Epicatechin 3-gallate (CED0003737)

Record Information
Version1.0
Creation Date2016-05-26 02:35:48 UTC
Update Date2026-04-06 02:02:22 UTC
Accession NumberCHEM031366
Identification
Common NameEpicatechin 3-gallate
ClassSmall Molecule
Description
Epicatechin 3-gallate is an organic compound with the formula C22H18O10 and an average molecular weight of 442.38 g/mol. Epicatechin 3-gallate belongs to the flavans, a subclass of flavonoids within the organic compounds. Biologically, this compound serves as an antioxidant (PMC8253632). The compound is identified in 19 recorded sources across several sectors. Within the food, food processing and cookware sector, it is found in food packaging, the preparation of vinegar, the preparation of wort, the preparation of wine or sparkling wine, molasses and the treatment of molasses, and two other sources. It is present in electrical and electronic equipment, including batteries, capacitors, cell phones, printed circuit boards, wires and cables, and one additional source. In the healthcare, pharmaceuticals and veterinary products sector, it is associated with medical devices. It is found in lubricants used in energy, oil and gas as well as industrial manufacturing and chemical processing. Furthermore, it is recorded in synthetic textiles and carpets and rugs within the textiles, leather and furnishings sector, as well as one other sector. Recorded exposure routes for epicatechin 3-gallate include inhalation, oral, and touch.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallateChEBI
3-Gallate(-)-epicatecholChEBI
3-O-GalloylepicatechinChEBI
ECGChEBI
TeatanninChEBI
(-)-cis-3,3',4',5,7-Pentahydroxyflavane 3-gallic acidGenerator
3-Gallic acid(-)-epicatecholGenerator
(-)-Epicatechin 3-O-gallic acidGenerator
(-)-Epicatechin gallateHMDB
(-)-Epicatechin-3-gallateHMDB
(-)-Epicatechin-3-O-gallateHMDB
Epicatechin gallateHMDB, MeSH
Epicatechin gallate, (2R-cis)-isomerHMDB, MeSH
Epicatechol, gallateHMDB
L-Epicatechin gallateHMDB
Epicatechin-3-O-gallateMeSH, HMDB
Epicatechin-3-gallateMeSH, HMDB
Epicatechin-3-galloyl esterMeSH, HMDB
Epicatechin 3-gallic acidGenerator
Chemical FormulaC22H18O10
Average Molecular Mass442.376 g/mol
Monoisotopic Mass442.090 g/mol
CAS Registry Number1257-08-5
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(-)-epicatechin 3-O-gallate
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0umi-0920000000-718b2102383cc9dc533eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004l-1490224000-de77e2646c7aba3a8defNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0292000000-ece704ccdb047a088d28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0292000000-d89b96c676e7c3398d8fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0170-0950000000-685c095616785cc82303Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0940200000-84b58b678cc59833a025Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0290000000-440ff7c7a589e1c058b5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0290000000-8f606522637d9033c95fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0098500000-0c0b2ca06b9e49aa356bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0097500000-7a41879feecb968154e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0029600000-77ceea44aa3ce7f822f9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0029600000-7f271696d73430ee7463Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-21da01e01ba7fa12d6cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dr-0900000000-1b53eabb63f51dd0886fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-e435428b44afb21a7eeeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dr-0900000000-a3b08dd3f89619c2d4f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0930000000-19d10b8c4fe8d2256c14Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014u-0960500000-6417fae4919951138986Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0940000000-ce6989df78eb09b24d1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-cff394f106b307da1857Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-0920400000-e7005e91544f51f7efe1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-0910000000-a428a4e56e1884d5b86aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-2900000000-d86fe441a677946b2205Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0310900000-98e9c41598a749627127Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gdl-0913300000-af1ea1d6588fca8f1f9fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00or-0900000000-60192713dbf412058de2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0130900000-406473c14c03e2f28625Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fvi-0900100000-78d009c505a6dd4958f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-1907200000-63b0ac33d06fb57b24cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0096-0180900000-dc0551f2741ffaedb255Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00r6-0946800000-4458228f52cc84046fd1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fki-0944100000-80801cf04acf66c4f765Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3907.0Log mg/kg[2200:6900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
597ChemosterilantsAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureGlucose-6-phosphate 1-dehydrogenaseP11412Saccharomyces cerevisiae S288cPredicted (SEA)0.0778492
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)0.0778492
Beta-secretase 1 structureClick to view 3D structureBeta-secretase 1P56817HumansPredicted (SEA)0.0778492
Click to view 3D structureAlpha-(1,3)-fucosyltransferase 4P22083HumansPredicted (SEA)0.155698
Click to view 3D structure3-oxoacyl-(Acyl-carrier protein) reductaseQ8I2S7Plasmodium falciparum (isolate 3D7)Predicted (SEA)0.155698
Latent membrane protein 1 structureClick to view 3D structureLatent membrane protein 1P03230HHV-4Predicted (SEA)0.155698
Click to view 3D structureEnoyl-acyl-carrier protein reductaseQ965D5Plasmodium falciparumPredicted (SEA)0.0778492
Proteasome subunit beta type-5 structureClick to view 3D structureProteasome subunit beta type-5P28074HumansPredicted (SEA)0.0778492
Click to view 3D structureFatty acid synthaseQ965D7Plasmodium falciparumPredicted (SEA)0.0778492
Click to view 3D structure3-oxoacyl-acyl-carrier protein reductaseQ965D6Plasmodium falciparumPredicted (SEA)0.0778492
6-phosphogluconate dehydrogenase, decarboxylating structureClick to view 3D structure6-phosphogluconate dehydrogenase, decarboxylatingP52209HumansPredicted (SEA)0.0778492
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)0.0778492
DNA repair protein RAD52 homolog structureClick to view 3D structureDNA repair protein RAD52 homologP43351HumansPredicted (SEA)0.0778492
Pyruvate kinase PKM structureClick to view 3D structurePyruvate kinase PKMP14618HumansPredicted (SEA)0.0778492
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)7.00643
Apoptosis regulator Bcl-2 structureClick to view 3D structureApoptosis regulator Bcl-2P10415HumansPredicted (SEA)11.2103
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)0.700643
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)10.7432
Matrix metalloproteinase-14 structureClick to view 3D structureMatrix metalloproteinase-14P50281HumansPredicted (SEA)7.31783
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)0.778492
A disintegrin and metalloproteinase with thrombospondin motifs 4 structureClick to view 3D structureA disintegrin and metalloproteinase with thrombospondin motifs 4O75173HumansPredicted (SEA)4.98235
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)29.1156
NAD-dependent protein deacylase sirtuin-6 structureClick to view 3D structureNAD-dependent protein deacylase sirtuin-6Q8N6T7HumansPredicted (SEA)0.0778492
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI structureClick to view 3D structureEnoyl-[acyl-carrier-protein] reductase [NADH] FabIP0AEK4Escherichia coli (strain K12)Predicted (SEA)0.0778492
A disintegrin and metalloproteinase with thrombospondin motifs 5 structureClick to view 3D structureA disintegrin and metalloproteinase with thrombospondin motifs 5Q9UNA0HumansPredicted (SEA)5.60514
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0037944
FooDB IDFDB017114
Phenol Explorer IDNot Available
KNApSAcK IDC00008866
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEpicatechin_gallate
Chemspider ID97034
ChEBI ID70255
PubChem Compound ID107905
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18560275
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21080642
3.
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.