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Showing Compound 8-C-Ascorbylepigallocatechin 3-gallate (FDB018738)

Record Information
Version1.0
Creation date2010-04-08 22:13:54 UTC
Update date2019-11-26 03:16:36 UTC
Primary IDFDB018738
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8-C-Ascorbylepigallocatechin 3-gallate
Description8-C-Ascorbylepigallocatechin 3-gallate belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. 8-C-Ascorbylepigallocatechin 3-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 8-C-ascorbylepigallocatechin 3-gallate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 8-C-Ascorbylepigallocatechin 3-gallate.
CAS Number126715-87-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
8-C-Ascorbylepigallocatechin 3-gallic acidGenerator
8-C-Ascorbyl epigallocatechin 3-O-gallateHMDB
8-C-Ascorbylepigallocatechin 3-O-gallateHMDB
13-(1,2-Dihydroxyethyl)-8,12,16-trihydroxy-15-oxo-4-(3,4,5-trihydroxyphenyl)-3,11,14-trioxatetracyclo[8.6.0.0²,⁷.0¹²,¹⁶]hexadeca-1(10),2(7),8-trien-5-yl 3,4,5-trihydroxybenzoic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP0.93ALOGPS
logP0.63ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)7.98ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area293.59 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity142.73 m³·mol⁻¹ChemAxon
Polarizability57.49 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H24O17
IUPAC name13-(1,2-dihydroxyethyl)-8,12,16-trihydroxy-15-oxo-4-(3,4,5-trihydroxyphenyl)-3,11,14-trioxatetracyclo[8.6.0.0²,⁷.0¹²,¹⁶]hexadeca-1(10),2(7),8-trien-5-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C28H24O17/c29-7-16(35)24-28(41)27(40,26(39)44-24)19-17(45-28)6-11(30)10-5-18(42-25(38)9-3-14(33)21(37)15(34)4-9)22(43-23(10)19)8-1-12(31)20(36)13(32)2-8/h1-4,6,16,18,22,24,29-37,40-41H,5,7H2
InChI KeyDKFWYWRZDCPNOB-UHFFFAOYSA-N
Isomeric SMILESOCC(O)C1OC(=O)C2(O)C3=C(OC12O)C=C(O)C1=C3OC(C(C1)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight632.48
Monoisotopic Molecular Weight632.101349342
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
  • Epigallocatechin
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Galloyl ester
  • Gallic acid or derivatives
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Coumaran
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • Furofuran
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Gamma butyrolactone
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Tertiary alcohol
  • Tetrahydrofuran
  • Lactone
  • Hemiacetal
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.17%; H 3.82%; O 43.00%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]21D -215.1 (c, 1.0 in Me2CO)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0imi-9400063000-2a0c49d95e50fea2e6c3Spectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS8-C-Ascorbylepigallocatechin 3-gallate, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0j5i-1446719000-b06d418d1068e83972b82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ika-4391101000-e403c2d7028e0d247f8e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-6940000000-ac6c69205b7765c916ee2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-0200092000-c2b36126dd83839152fc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vi-9402102000-dbead45758a468a58bec2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-9611100000-a6b48a4399419e4907bc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00o0-0300926000-6388a8ed87264b0c75f72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0300390000-8c981c9e5c764a07effd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-3600490000-883fe4ccb03ba614f2a82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0000629000-15f4de368f707fa939e92021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0200489000-4bc7fe5ad2495b57652c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0505790000-792402b8a3e5e4c072652021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB39208
CRC / DFC (Dictionary of Food Compounds) IDLMN29-W:LMN29-W
EAFUS IDNot Available
Dr. Duke ID8-C-ASCORBYL-EPIGALLOCATECHIN-3-O-GALLATE
BIGG IDNot Available
KNApSAcK IDC00008969
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).