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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:09 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002780
Secondary Accession Numbers
  • HMDB02780
Metabolite Identification
Common NameCatechin
DescriptionCatechin, also known as cyanidanol or catechuic acid, 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 also belongs to the group of compounds known as flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids. Catechin is one of the 4 catechin known diastereoisomers. Two of the isomers are in trans configuration and are called catechin and the other two are in cis configuration and are called epicatechin. The most common catechin isomer is the (+)-catechin. The other stereoisomer is (-)-catechin or ent-catechin. The most common epicatechin isomer is (-)-epicatechin. Catechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Catechin is a bitter tasting compound and is associated with the bitterness in tea. Catechin is a plant 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. Catechin is an antioxidant flavonoid, occurring especially in woody plants as both Catechin and (-)-Catechin (cis) forms. Outside of the human body, Catechin is found, on average, in the highest concentration in foods, such as blackcurrants (Ribes nigrum), evergreen blackberries (Rubus laciniatus), and blackberries (Rubus) and in a lower concentration in dills (Anethum graveolens), hot chocolates, and medlars (Mespilus germanica). Catechin has also been detected, but not quantified in, several different foods, such as rice (Oryza sativa), apple ciders, peanuts (Arachis hypogaea), fruit juices, and red teas. This could make catechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Catechin.
Structure
Data?1582752256
Synonyms
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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling Point630.38 °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
LogP0.51PERRISSOUD,D & TESTA,B (1986)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker159.95530932474
[M+H]+Baker165.18330932474
[M-H]-Not Available159.955http://allccs.zhulab.cn/database/detail?ID=AllCCS00001934
[M+H]+Not Available165.183http://allccs.zhulab.cn/database/detail?ID=AllCCS00001934
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Bladder
  • Fibroblasts
  • Intestine
  • Platelet
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
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 IDNot Available
Good Scents IDrw1539671
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References