Epicatechin-(4beta->8)-epigallocatechin 3,3'-digallate (CHEM032635)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:35:13 UTC
Update Date2016-11-09 01:20:45 UTC
Accession NumberCHEM032635
Identification
Common NameEpicatechin-(4beta->8)-epigallocatechin 3,3'-digallate
ClassSmall Molecule
DescriptionEpicatechin 3-O-gallate-(4beta->8)-epigallocatechin 3-O-gallate is found in tea. Epicatechin 3-O-gallate-(4beta->8)-epigallocatechin 3-O-gallate is isolated from commercial oolong tea (Camellia sinensis var. viridis).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epicatechin 3-O-gallate-(4b->8)-epigallocatechin 3-O-gallateGenerator
Epicatechin 3-O-gallate-(4β->8)-epigallocatechin 3-O-gallateGenerator
Epicatechin 3-O-gallic acid-(4b->8)-epigallocatechin 3-O-gallic acidGenerator
Epicatechin 3-O-gallic acid-(4beta->8)-epigallocatechin 3-O-gallic acidGenerator
Epicatechin 3-O-gallic acid-(4β->8)-epigallocatechin 3-O-gallic acidGenerator
3-O-Galloylepicatechin-(4beta->8)-epigallocatechin-3-O-gallateHMDB
Epicatechin 3-O-gallate(4b->8)epigallocatechin-3-O-gallateHMDB
(2R,3R)-8-[(2R,3R,4R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Epicatechin-(4b->8)-epigallocatechin 3,3'-digallateGenerator
Epicatechin-(4b->8)-epigallocatechin 3,3'-digallic acidGenerator
Epicatechin-(4beta->8)-epigallocatechin 3,3'-digallic acidGenerator
Epicatechin-(4β->8)-epigallocatechin 3,3'-digallateGenerator
Epicatechin-(4β->8)-epigallocatechin 3,3'-digallic acidGenerator
Chemical FormulaC44H34O21
Average Molecular Mass898.728 g/mol
Monoisotopic Mass898.159 g/mol
CAS Registry Number126715-90-0
IUPAC Name(2R,3R,4R)-4-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
Traditional Name(2R,3R,4R)-4-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
SMILESOC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C=C(O)C3=C2O[C@@H]([C@@H](C3)OC(=O)C2=CC(O)=C(O)C(O)=C2)C2=CC(O)=C(O)C(O)=C2)C(O)=C1
InChI IdentifierInChI=1S/C44H34O21/c45-18-10-23(49)33-31(11-18)62-40(14-1-2-20(46)22(48)3-14)42(65-44(61)17-8-29(55)38(59)30(56)9-17)35(33)34-24(50)13-21(47)19-12-32(63-43(60)16-6-27(53)37(58)28(54)7-16)39(64-41(19)34)15-4-25(51)36(57)26(52)5-15/h1-11,13,32,35,39-40,42,45-59H,12H2/t32-,35-,39-,40-,42-/m1/s1
InChI KeyFUNWNVWJOMCWIL-WZPNJOEPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthones
Alternative Parents
Substituents
  • Xanthone
  • Phenolic glycoside
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • Chromone
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • C-glycosyl compound
  • Glycosyl compound
  • Benzoate ester
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Benzoyl
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.17 g/LALOGPS
logP3.75ALOGPS
logP5.98ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area374.51 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity220.02 m³·mol⁻¹ChemAxon
Polarizability84.07 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0510190450-c8b3cb9cb2be88893f02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfu-0950341110-19781e50cd07b03c29dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0980110000-30004be43717cada09ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0300100390-c0d7cba70e9df31ef305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-0914300430-e43544d33d91d817390bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-0900000100-b261b6863f1f519616f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000890-b864c0861b6ed55485a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0400000890-beb2f1085074c959ed9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02bu-0401000190-975205984f3149c58effSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00c1-0100002950-9d3aa37ffcff3c16293eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbd-0200120980-f43bfe178e976ef6e2b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0035-0300220690-42ddaef32deaea45ba76Spectrum
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 IDHMDB0039304
FooDB IDFDB018850
Phenol Explorer IDNot Available
KNApSAcK IDC00009219
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9796831
ChEBI IDNot Available
PubChem Compound ID11622083
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.