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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:13:19 UTC
Update Date2020-09-28 06:37:33 UTC
HMDB IDHMDB0037953
Secondary Accession Numbers
  • HMDB37953
Metabolite Identification
Common Name(-)-Catechin
DescriptionCatechin, also known as cyanidanol or (2R,3S)-catechin, 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. Catechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Catechin is a bitter tasting compound. Outside of the human body, Catechin is found, on average, in the highest concentration within a few different foods, such as blackcurrants, evergreen blackberries, and rabbiteye blueberries and in a lower concentration in banana, common hazelnuts, and yellow bell peppers. Catechin has also been detected, but not quantified in, several different foods, such as tartary buckwheats, cocoa beans, sapodilla, wheat bread, and red bell peppers. This could make catechin a potential biomarker for the consumption of these foods. The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.
Structure
Data?1601229099
Synonyms
ValueSource
(+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-olChEBI
(+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-olChEBI
(+)-CatecholChEBI
(+)-Cyanidan-3-olChEBI
(2R,3S)-(+)-CatechinChEBI
(2R,3S)-CatechinChEBI
(2R-trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triolChEBI
Catechuic acidChEBI
CianidanolChEBI
CyanidanolChEBI
D-CatechinChEBI
CatechuateGenerator
(+)-CatechinHMDB
(+)-Catechin hydrateHMDB
(+)-CyanidanolHMDB
(+/-)-catechinHMDB
(+/-)-catechin hydrateHMDB
3,3',4',5,7-FlavanpentolHMDB
BiocatechinHMDB
CatechinateHMDB
Catechinic acidHMDB
CatergenHMDB
CianidanolumHMDB
CianidolHMDB
D-(+)-CatechinHMDB
trans3,3,4,5,7 PentahydroxyflavaneHMDB
YK-85 light yellow powder 85HMDB
Acid, catechinicHMDB
KB-53HMDB
ZymaHMDB
Cyanidanol 3HMDB
Cyanidanol-3HMDB
KB 53HMDB
Acid, catechuicHMDB
(+)-Cyanidanol-3HMDB
EpicatechinHMDB
(-)-EpicatechinHMDB
CatechinMeSH
(+)-(2R:3S)-5,7,3',4'-Tetrahydroxyflavan-3-olPhytoBank
(+)-(2R:3S)-5,7,3’,4’-Tetrahydroxyflavan-3-olPhytoBank
(+)-3’,4’,5,7-Tetrahydroxy-2,3-trans-flavan-3-olPhytoBank
(+)-CianidanolPhytoBank
3-Cyanidanol, (+)-PhytoBank
CyanidolPhytoBank
DexcyanidanolPhytoBank
trans-(+)-3,3',4',5,7-FlavanpentolPhytoBank
trans-(+)-3,3’,4’,5,7-FlavanpentolPhytoBank
Chemical FormulaC15H14O6
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
IUPAC Name(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name(+)-catechol
CAS Registry Number154-23-4
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-DZGCQCFKSA-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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175 - 176 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Polarizability27.89 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0940000000-3790a10ce8b93dcb9236Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-3130069000-ca0968505fc89dd82640Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0190000000-0b55363090666c3a1f0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0ab9-0900000000-5dfb75ce17e0aea0642bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-003r-9000000000-ae956114187e6320ae3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0079-0900000000-dd93ef481c2fea84d4a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0980000000-97f9a54412368150d277Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090010000-6ebf1de8cc1ea492a630Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052k-0960000000-77945100b7a1f6311aeaSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-052k-0960000000-77945100b7a1f6311aeaSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-05fr-0920000000-e829a07f24435afac743Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090010000-6ebf1de8cc1ea492a630Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052k-0960000000-77945100b7a1f6311aeaSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-25414078e505f0193624Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-05fr-0920000000-e829a07f24435afac743Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0910000000-a98df14e459446ae6ae2Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0090000000-142161e341ec3ee68a3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0fga-0980000000-3406dfb006e610eb6fceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-466d29d8274d012f2ea3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0pds-0970000000-2631ce85b21e59412694Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05fr-1900000000-3424d3d2af180d7eabd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0590000000-aff1c3cc94786f87cacfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-5e84c0d9207a0a018ab4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-3e525d17e0b05647387aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-52e8123f5ed55bc47962Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0940000000-cfcd9b4e416f64a26916Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2910000000-be77474275eeee51824bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 ID124
FooDB IDFDB002571
KNApSAcK IDC00000947
Chemspider ID8711
KEGG Compound IDC06562
BioCyc IDCPD-1961
BiGG IDNot Available
Wikipedia LinkCatechin
METLIN ID3419
PubChem Compound9064
PDB IDNot Available
ChEBI ID15600
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .