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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 11:52:29 UTC
Update Date2022-03-07 02:49:11 UTC
HMDB IDHMDB0001871
Secondary Accession Numbers
  • HMDB01871
Metabolite Identification
Common NameEpicatechin
DescriptionEpicatechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Catechin is a tannin peculiar to green and white tea because the black tea oxidation process reduces catechins in black tea. Catechin is a powerful, water soluble polyphenol and antioxidant that is easily oxidized. Several thousand types are available in the plant world. As many as two thousand are known to have a flavon structure and are called flavonoids. Catechin is one of them. Green tea is manufactured from fresh, unfermented tea leaves; the oxidation of catechins is minimal, and hence they are able to serve as antioxidants. Researchers believe that catechin is effective because it easily sticks to proteins, blocking bacteria from adhering to cell walls and disrupting their ability to destroy them. Viruses have hooks on their surfaces and can attach to cell walls. The catechin in green tea prevents viruses from adhering and causing harm. Catechin reacts with toxins created by harmful bacteria (many of which belong to the protein family) and harmful metals such as lead, mercury, chrome, and cadmium. From its NMR espectra, there is a doubt on 2 and 3 atoms configuration. It seems to be that they are in trans position.
Structure
Data?1601226709
Synonyms
ValueSource
(-)-EpicatechinHMDB
(-)-EpicatecholHMDB
(2R,3R)-(-)-EpicatechinHMDB
3,3',4',5,7-PentahydroxyflavaneHMDB
alpha-CatechinHMDB
EpicatecholHMDB
EpigallocatechinHMDB
L(-)-EpicatechinHMDB
L-AcacatechinHMDB
L-EpicatechinHMDB
L-EpicatecholHMDB
3,3',4',5,7-FlavanpentolHMDB
Cyanidanol 3HMDB
Cyanidanol-3HMDB
(+)-CatechinHMDB
(+)-CyanidanolHMDB
Acid, catechuicHMDB
CianidanolHMDB
Acid, catechinicHMDB
CatechinHMDB
Catechinic acidHMDB
Catechuic acidHMDB
CatergenHMDB
KB-53HMDB
ZymaHMDB
(+)-Cyanidanol-3HMDB
KB 53HMDB
Epi-catechinHMDB
EpicatechinPhytoBank
Chemical FormulaC15H14O6
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Nameent-epicatechin
CAS Registry Number490-46-0
SMILES
O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
InChI KeyPFTAWBLQPZVEMU-UKRRQHHQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point240 °CNot Available
Boiling Point630.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility63110 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.490 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP1.02ALOGPS
logP1.8ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74 m³·mol⁻¹ChemAxon
Polarizability28.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.88731661259
DarkChem[M-H]-164.03231661259
AllCCS[M+H]+168.38232859911
AllCCS[M-H]-167.25832859911
DeepCCS[M+H]+169.9230932474
DeepCCS[M-H]-167.56230932474
DeepCCS[M-2H]-201.3530932474
DeepCCS[M+Na]+176.57830932474
AllCCS[M+H]+168.432859911
AllCCS[M+H-H2O]+164.732859911
AllCCS[M+NH4]+171.832859911
AllCCS[M+Na]+172.832859911
AllCCS[M-H]-167.332859911
AllCCS[M+Na-2H]-166.832859911
AllCCS[M+HCOO]-166.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EpicatechinO[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C14436.3Standard polar33892256
EpicatechinO[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C13029.0Standard non polar33892256
EpicatechinO[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C13065.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epicatechin,1TMS,isomer #1C[Si](C)(C)O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C13049.8Semi standard non polar33892256
Epicatechin,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O23030.9Semi standard non polar33892256
Epicatechin,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C13091.6Semi standard non polar33892256
Epicatechin,1TMS,isomer #4C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C1O3082.9Semi standard non polar33892256
Epicatechin,1TMS,isomer #5C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1O3085.4Semi standard non polar33892256
Epicatechin,2TMS,isomer #1C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O[Si](C)(C)C)[C@@H](C1=CC=C(O)C(O)=C1)O22981.9Semi standard non polar33892256
Epicatechin,2TMS,isomer #10C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1O[Si](C)(C)C2976.2Semi standard non polar33892256
Epicatechin,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C12969.7Semi standard non polar33892256
Epicatechin,2TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C)C=C1O3009.1Semi standard non polar33892256
Epicatechin,2TMS,isomer #4C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O3012.0Semi standard non polar33892256
Epicatechin,2TMS,isomer #5C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C)=C12914.9Semi standard non polar33892256
Epicatechin,2TMS,isomer #6C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)C=C1O2956.2Semi standard non polar33892256
Epicatechin,2TMS,isomer #7C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)=CC=C1O2959.4Semi standard non polar33892256
Epicatechin,2TMS,isomer #8C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C12992.7Semi standard non polar33892256
Epicatechin,2TMS,isomer #9C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C12987.2Semi standard non polar33892256
Epicatechin,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C)=C12818.8Semi standard non polar33892256
Epicatechin,3TMS,isomer #10C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C12852.0Semi standard non polar33892256
Epicatechin,3TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)C=C1O2835.3Semi standard non polar33892256
Epicatechin,3TMS,isomer #3C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O2846.6Semi standard non polar33892256
Epicatechin,3TMS,isomer #4C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C12802.4Semi standard non polar33892256
Epicatechin,3TMS,isomer #5C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C12810.0Semi standard non polar33892256
Epicatechin,3TMS,isomer #6C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C2889.8Semi standard non polar33892256
Epicatechin,3TMS,isomer #7C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C)=C12879.4Semi standard non polar33892256
Epicatechin,3TMS,isomer #8C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C12882.9Semi standard non polar33892256
Epicatechin,3TMS,isomer #9C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)C=C1O[Si](C)(C)C2856.8Semi standard non polar33892256
Epicatechin,4TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C)=C12849.5Semi standard non polar33892256
Epicatechin,4TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C12852.9Semi standard non polar33892256
Epicatechin,4TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C2821.7Semi standard non polar33892256
Epicatechin,4TMS,isomer #4C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C12821.4Semi standard non polar33892256
Epicatechin,4TMS,isomer #5C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C12896.1Semi standard non polar33892256
Epicatechin,5TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C12897.5Semi standard non polar33892256
Epicatechin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C13359.0Semi standard non polar33892256
Epicatechin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O23331.0Semi standard non polar33892256
Epicatechin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C13363.2Semi standard non polar33892256
Epicatechin,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C1O3374.5Semi standard non polar33892256
Epicatechin,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1O3381.8Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C1=CC=C(O)C(O)=C1)O23518.1Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1O[Si](C)(C)C(C)(C)C3542.1Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C13500.6Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O3575.2Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O3559.2Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13450.5Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)C=C1O3498.3Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)=CC=C1O3472.3Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C13539.2Semi standard non polar33892256
Epicatechin,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13504.9Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13546.6Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13617.1Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O3600.4Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O3593.4Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C13583.6Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13584.1Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3623.8Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13659.0Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13627.1Semi standard non polar33892256
Epicatechin,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)C=C1O[Si](C)(C)C(C)(C)C3610.5Semi standard non polar33892256
Epicatechin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13761.3Semi standard non polar33892256
Epicatechin,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13742.8Semi standard non polar33892256
Epicatechin,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3723.2Semi standard non polar33892256
Epicatechin,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13725.7Semi standard non polar33892256
Epicatechin,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13782.0Semi standard non polar33892256
Epicatechin,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13906.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Epicatechin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0649000000-e7a2620a4d8b1c243de32014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epicatechin GC-EI-TOF (Non-derivatized)splash10-014i-0649000000-e7a2620a4d8b1c243de32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epicatechin GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-89375330724a4ecb82cf2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epicatechin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0940000000-3790a10ce8b93dcb92362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epicatechin GC-MS (5 TMS) - 70eV, Positivesplash10-000i-3130069000-ca0968505fc89dd826402017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epicatechin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000f-1690000000-16c536adc2a6e03c5b4f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-1910000000-92d64d3194a12735e5312012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014i-5900000000-1ec541b64eecd72f35512012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOFsplash10-0006-0090000000-53e575c7acf970449e842012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0079-0900000000-1c23cf9e8aa258a986ad2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-052r-1970000000-02212cd1c44e06d5add32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF , Negative-QTOFsplash10-002r-0090060010-fa16cfeadd4bc0a05e532017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF 20V, Negative-QTOFsplash10-05bk-0950000000-741428eb8454f83974a02017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF 10V, Negative-QTOFsplash10-000i-0090000000-6531ef6ba99afaf524252017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF , Negative-QTOFsplash10-000i-0090000000-6531ef6ba99afaf524252017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF , Negative-QTOFsplash10-002r-0090060010-fa16cfeadd4bc0a05e532017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF 20V, Negative-QTOFsplash10-05bk-0950000000-741428eb8454f83974a02017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF 10V, Negative-QTOFsplash10-000i-0090000000-6531ef6ba99afaf524252017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF 10V, Negative-QTOFsplash10-000i-0090000000-556ed7e0a7c3d19ecd862017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin ESI-TOF , Negative-QTOFsplash10-001l-0071900002-461eb0f7b0e90ba28a372017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin DI-ESI-qTof , Positive-QTOFsplash10-000i-0910000000-536acb5c7ec5ce972a4d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin DI-ESI-qTof , Negative-QTOFsplash10-0f9j-0970000000-6160314e88b9fecac1282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF , negative-QTOFsplash10-000i-0090000000-faedef1b08ce5b70459b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF , negative-QTOFsplash10-000j-0290000000-5e7b957db3c3dc34b50c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 10V, Positive-QTOFsplash10-0006-0590000000-aff1c3cc94786f87cacf2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 20V, Positive-QTOFsplash10-000i-0920000000-5e84c0d9207a0a018ab42017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 40V, Positive-QTOFsplash10-05fr-4900000000-3e525d17e0b05647387a2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 10V, Negative-QTOFsplash10-000i-0290000000-52e8123f5ed55bc479622017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 20V, Negative-QTOFsplash10-000i-0940000000-cfcd9b4e416f64a269162017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epicatechin 40V, Negative-QTOFsplash10-0a6r-2910000000-be77474275eeee51824b2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Intestine
  • Platelet
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.625 +/- 0.198 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 125 details
UrineDetected and Quantified0.13 +/- 0.20 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.014 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0207 +/- 0.0210 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified7.445 +/- 5.022 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified3.571 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB12039
Phenol Explorer Compound ID125
FooDB IDFDB003761
KNApSAcK IDC00000956
Chemspider ID65230
KEGG Compound IDC09727
BioCyc IDCPD-7630
BiGG IDNot Available
Wikipedia LinkCatechin
METLIN ID3420
PubChem Compound72276
PDB IDNot Available
ChEBI ID90
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1136801
References
Synthesis ReferenceLaw, Khoon Huat; Das, Nagaratnam P. Production of (-)-epicatechin by Uncaria elliptica callus cultures. Phytochemistry (1989), 28(4), 1099-100.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Li C, Meng X, Winnik B, Lee MJ, Lu H, Sheng S, Buckley B, Yang CS: Analysis of urinary metabolites of tea catechins by liquid chromatography/electrospray ionization mass spectrometry. Chem Res Toxicol. 2001 Jun;14(6):702-7. [PubMed:11409941 ]
  2. Yang CS, Lee MJ, Chen L: Human salivary tea catechin levels and catechin esterase activities: implication in human cancer prevention studies. Cancer Epidemiol Biomarkers Prev. 1999 Jan;8(1):83-9. [PubMed:9950244 ]
  3. Henning SM, Aronson W, Niu Y, Conde F, Lee NH, Seeram NP, Lee RP, Lu J, Harris DM, Moro A, Hong J, Pak-Shan L, Barnard RJ, Ziaee HG, Csathy G, Go VL, Wang H, Heber D: Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. J Nutr. 2006 Jul;136(7):1839-43. [PubMed:16772446 ]
  4. Lill G, Voit S, Schror K, Weber AA: Complex effects of different green tea catechins on human platelets. FEBS Lett. 2003 Jul 10;546(2-3):265-70. [PubMed:12832052 ]
  5. Murphy KJ, Chronopoulos AK, Singh I, Francis MA, Moriarty H, Pike MJ, Turner AH, Mann NJ, Sinclair AJ: Dietary flavanols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Am J Clin Nutr. 2003 Jun;77(6):1466-73. [PubMed:12791625 ]
  6. Meng X, Lee MJ, Li C, Sheng S, Zhu N, Sang S, Ho CT, Yang CS: Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans. Drug Metab Dispos. 2001 Jun;29(6):789-93. [PubMed:11353745 ]
  7. Sano A, Yamakoshi J, Tokutake S, Tobe K, Kubota Y, Kikuchi M: Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Biosci Biotechnol Biochem. 2003 May;67(5):1140-3. [PubMed:12834296 ]
  8. Babich H, Krupka ME, Nissim HA, Zuckerbraun HL: Differential in vitro cytotoxicity of (-)-epicatechin gallate (ECG) to cancer and normal cells from the human oral cavity. Toxicol In Vitro. 2005 Mar;19(2):231-42. [PubMed:15649637 ]
  9. Holt RR, Lazarus SA, Sullards MC, Zhu QY, Schramm DD, Hammerstone JF, Fraga CG, Schmitz HH, Keen CL: Procyanidin dimer B2 [epicatechin-(4beta-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa. Am J Clin Nutr. 2002 Oct;76(4):798-804. [PubMed:12324293 ]
  10. Spencer JP, Schroeter H, Crossthwaithe AJ, Kuhnle G, Williams RJ, Rice-Evans C: Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic Biol Med. 2001 Nov 1;31(9):1139-46. [PubMed:11677047 ]
  11. DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5. [PubMed:11823574 ]
  12. Vinson JA, Proch J, Bose P: MegaNatural((R)) Gold Grapeseed Extract: In Vitro Antioxidant and In Vivo Human Supplementation Studies. J Med Food. 2001 Spring;4(1):17-26. [PubMed:12639284 ]
  13. Lhoste EF, Ouriet V, Bruel S, Flinois JP, Brezillon C, Magdalou J, Cheze C, Nugon-Baudon L: The human colonic microflora influences the alterations of xenobiotic-metabolizing enzymes by catechins in male F344 rats. Food Chem Toxicol. 2003 May;41(5):695-702. [PubMed:12659723 ]
  14. Keen CL: Chocolate: food as medicine/medicine as food. J Am Coll Nutr. 2001 Oct;20(5 Suppl):436S-439S; discussion 440S-442S. [PubMed:11603654 ]