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Showing Compound Epigallocatechin-(4beta->8)-epicatechin 3'-gallate (FDB016766)

Record Information
Version1.0
Creation date2010-04-08 22:12:38 UTC
Update date2019-11-26 03:13:45 UTC
Primary IDFDB016766
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEpigallocatechin-(4beta->8)-epicatechin 3'-gallate
DescriptionEpigallocatechin-(4beta->8)-epicatechin 3-O-gallate belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea. This could make epigallocatechin-(4beta->8)-epicatechin 3-O-gallate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate.
CAS Number126715-82-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Epigallocatechin-(4b->8)-epicatechin 3-O-gallateGenerator
Epigallocatechin-(4b->8)-epicatechin 3-O-gallic acidGenerator
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallic acidGenerator
Epigallocatechin-(4β->8)-epicatechin 3-O-gallateGenerator
Epigallocatechin-(4β->8)-epicatechin 3-O-gallic acidGenerator
Epigallocatechin(4b->8)epicatechin 3-O-gallateHMDB
Epigallocatechin-(4beta->8)-epicatechin-3-O-gallateHMDB
Epigallocatechin-(4beta->8)-epicatechin-3-O-gallate esterHMDB
Epigallocatechin-(4b->8)-epicatechin-3-O-gallate esterGenerator
Epigallocatechin-(4b->8)-epicatechin-3-O-gallic acid esterGenerator
Epigallocatechin-(4beta->8)-epicatechin-3-O-gallic acid esterGenerator
Epigallocatechin-(4β->8)-epicatechin-3-O-gallate esterGenerator
Epigallocatechin-(4β->8)-epicatechin-3-O-gallic acid esterGenerator
Epigallocatechin-(4b->8)-epicatechin 3'-gallateGenerator
Epigallocatechin-(4b->8)-epicatechin 3'-gallic acidGenerator
Epigallocatechin-(4beta->8)-epicatechin 3'-gallic acidGenerator
Epigallocatechin-(4β->8)-epicatechin 3'-gallateGenerator
Epigallocatechin-(4β->8)-epicatechin 3'-gallic acidGenerator
Epigallocatechin-(4beta->8)-epicatechin 3-gallatemanual
Epigallocatechin-(4beta->8)-epicatechin 3'-gallatemanual
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP3.21ALOGPS
logP4.4ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area307.75 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity184.25 m³·mol⁻¹ChemAxon
Polarizability71.24 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC37H30O17
IUPAC name(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C37H30O17/c38-15-8-20(42)28-26(9-15)52-35(13-4-22(44)31(48)23(45)5-13)33(50)30(28)29-21(43)11-18(40)16-10-27(53-37(51)14-6-24(46)32(49)25(47)7-14)34(54-36(16)29)12-1-2-17(39)19(41)3-12/h1-9,11,27,30,33-35,38-50H,10H2/t27-,30-,33-,34-,35-/m1/s1
InChI KeyLQQNPVZIFKLQPE-RGOYVLDUSA-N
Isomeric SMILESO[C@H]1[C@H](OC2=C([C@@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight746.63
Monoisotopic Molecular Weight746.148299506
Classification
Description Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative Parents
Substituents
  • B-type proanthocyanidin
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Catechin gallate
  • Epigallocatechin
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Pyrogallol derivative
  • Benzenetriol
  • Benzoic acid or derivatives
  • Benzoyl
  • Catechol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Polyol
  • Ether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.52%; H 4.05%; O 36.43%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D -71.8 (c, 1 in Me2CO)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpigallocatechin-(4beta->8)-epicatechin 3'-gallate, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002g-0500940600-f890cc25d2d93e71e4da2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kbr-0962621000-937983ab06b23bf69ae92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-0691000000-7502defb3d188a39fe242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0300111900-6c89ffa57f657fd3dffb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0914202200-36a55a42a503069c0e9c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0901000000-f39354ee36147f60cf682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0000070900-df0f0f53fd872f682c622021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fvj-0900038700-b81b0f6bdfaf188846c82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00p3-0911404300-9fdc79cc26555c4b36b42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0110344900-1d73ec93c53526d32c842021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ffw-0930416800-eced173636d46e985be52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-0720938200-f1e154215093e560de3b2021-09-24View Spectrum
NMRNot Available
ChemSpider ID391035
ChEMBL IDNot Available
KEGG Compound IDC10223
Pubchem Compound ID442678
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37650
CRC / DFC (Dictionary of Food Compounds) IDKTF13-L:KTF18-Q
EAFUS IDNot Available
Dr. Duke IDEPIGALLOCATECHIN-(4-BETA-8)-EPICATECHIN-3-O-GALLATE
BIGG IDNot Available
KNApSAcK IDC00002919
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 IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.