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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:13:22 UTC
Update Date2022-03-07 02:55:34 UTC
HMDB IDHMDB0037954
Secondary Accession Numbers
  • HMDB37954
Metabolite Identification
Common Name(+)-Epicatechin
Description(+)-Epicatechin, also known as ent-epicatechin, 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 (+)-Epicatechin is found, on average, in the highest concentration within pears (Pyrus communis) (+)-Epicatechin has also been detected, but not quantified in, several different foods, such as lettuces (Lactuca sativa), green tea, apples (Malus pumila), teas (Camellia sinensis), and common buckwheats (Fagopyrum esculentum). This could make (+)-epicatechin a potential biomarker for the consumption of these foods (+)-Epicatechin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on (+)-Epicatechin.
Structure
Thumb
Synonyms
ValueSource
(2S,3S)-3',4',5,7-Tetrahydroxyflavan-3-olChEBI
(2S,3S)-3,3',4',5,7-PentahydroxyflavanChEBI
ent-EpicatechinChEBI
(+)-cis-3,3',4',5,7-PentahydroxyflavanHMDB
(+)-EpicatecholHMDB
(2S,3S)-(+)-EpicatechinHMDB
(2S-cis)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triolHMDB
Catechin CHMDB
D-EpicatechinHMDB
Chemical FormulaC15H14O6
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
IUPAC Name(2S,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Namel-epicatechin
CAS Registry Number35323-91-2
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-/m0/s1
InChI KeyPFTAWBLQPZVEMU-ZFWWWQNUSA-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
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point235 - 237 °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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID147
FooDB IDFDB017126
KNApSAcK IDC00000957
Chemspider ID158494
KEGG Compound IDC09728
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound182232
PDB IDNot Available
ChEBI ID76125
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1680961
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .