Epigallocatechin 3-cinnamate (CHEM032175)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:11:41 UTC
Update Date2016-11-09 01:19:25 UTC
Accession NumberCHEM032175
Identification
Common NameEpigallocatechin 3-cinnamate
ClassSmall Molecule
Description(-)-Epigallocatechin 3-cinnamate is found in tea. (-)-Epigallocatechin 3-cinnamate is isolated from Assam tea (Camellia sinensis var. assamica).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Epigallocatechin 3-cinnamic acidGenerator
(-)-Epigallocatechin 3-O-cinnamateHMDB
3-CinnamoylepigallocatechinHMDB
Epigallocatechin 3-cinnamateHMDB
Epigallocatechin 3-O-cinnamateHMDB
Epigallocatechin 3-O-cinnamic acidGenerator
Epigallocatechin 3-cinnamic acidGenerator
Chemical FormulaC24H20O8
Average Molecular Mass436.411 g/mol
Monoisotopic Mass436.116 g/mol
CAS Registry Number108907-46-6
IUPAC Name(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl (2E)-3-phenylprop-2-enoate
Traditional Nameepigallocatechin 3-O-cinnamate
SMILESOC1=CC2=C(C[C@@H](OC(=O)\C=C\C3=CC=CC=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1
InChI IdentifierInChI=1S/C24H20O8/c25-15-10-17(26)16-12-21(31-22(29)7-6-13-4-2-1-3-5-13)24(32-20(16)11-15)14-8-18(27)23(30)19(28)9-14/h1-11,21,24-28,30H,12H2/b7-6+/t21-,24-/m1/s1
InChI KeyGQGIIUWXMCBYIJ-UMMIVNDFSA-N
Chemical Taxonomy
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
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0099 g/LALOGPS
logP3.56ALOGPS
logP4.53ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.64ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity115.55 m³·mol⁻¹ChemAxon
Polarizability43.73 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-0930000000-9da718ce19fa91908b05Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-1900021000-34ff3208a73da7e09859Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0911300000-4a4766cd580830447497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a9-0911000000-e7e1f0cc332f64525e3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-2900000000-3bb436d3693de5997878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0404900000-9ad7afabf4353db7a946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-054t-1934200000-5028f06602c253be48abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-c9da52ca64335525165dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0301900000-e2350b74601510f86696Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0921200000-342a878854e0816d7272Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0911000000-6493bb28da78c61c6aadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0002900000-4c63e24e45e1f6cd31b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0932400000-26caae526e7d10ddcfffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-6944100000-e68ec6da2ae59b7b8c44Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0038831
FooDB IDFDB018264
Phenol Explorer IDNot Available
KNApSAcK IDC00008904
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10258687
ChEBI IDNot Available
PubChem Compound ID21629801
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.