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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:09 UTC
Update Date2019-05-24 17:48:48 UTC
HMDB IDHMDB0002780
Secondary Accession Numbers
  • HMDB02780
Metabolite Identification
Common NameCatechin
DescriptionCatechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. -- Pubchem.
Structure
Data?1558720128
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
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.51PERRISSOUD,D & TESTA,B (1986)
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0940000000-3790a10ce8b93dcb9236JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-3130069000-ca0968505fc89dd82640JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0190000000-0b55363090666c3a1f0fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0ab9-0900000000-5dfb75ce17e0aea0642bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-003r-9000000000-ae956114187e6320ae3aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0079-0900000000-dd93ef481c2fea84d4a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0980000000-97f9a54412368150d277JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090010000-6ebf1de8cc1ea492a630JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052k-0960000000-77945100b7a1f6311aeaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-052k-0960000000-77945100b7a1f6311aeaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-05fr-0920000000-e829a07f24435afac743JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090010000-6ebf1de8cc1ea492a630JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052k-0960000000-77945100b7a1f6311aeaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-25414078e505f0193624JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-05fr-0920000000-e829a07f24435afac743JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0910000000-a98df14e459446ae6ae2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0090000000-142161e341ec3ee68a3aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0fga-0980000000-3406dfb006e610eb6fceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-466d29d8274d012f2ea3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0pds-0970000000-2631ce85b21e59412694JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05fr-1900000000-3424d3d2af180d7eabd3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0590000000-aff1c3cc94786f87cacfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-5e84c0d9207a0a018ab4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-3e525d17e0b05647387aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-52e8123f5ed55bc47962JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0940000000-cfcd9b4e416f64a26916JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2910000000-be77474275eeee51824bJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Bladder
  • Fibroblasts
  • Intestine
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.650 +/- 0.009 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified1.223 +/- 0.147 uMAdult (>18 years old)Female
Normal
details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 124 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 124 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 124 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0058 +/- 0.011 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00667 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0125 +/- 0.0110 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>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
FoodDB 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9. [PubMed:16197573 ]
  8. Roura E, Andres-Lacueva C, Estruch R, Lamuela-Raventos RM: Total polyphenol intake estimated by a modified Folin-Ciocalteu assay of urine. Clin Chem. 2006 Apr;52(4):749-52. Epub 2006 Feb 9. [PubMed:16469857 ]
  9. Li C, Lee MJ, Sheng S, Meng X, Prabhu S, Winnik B, Huang B, Chung JY, Yan S, Ho CT, Yang CS: Structural identification of two metabolites of catechins and their kinetics in human urine and blood after tea ingestion. Chem Res Toxicol. 2000 Mar;13(3):177-84. [PubMed:10725114 ]
  10. Pignatelli P, Di Santo S, Buchetti B, Sanguigni V, Brunelli A, Violi F: Polyphenols enhance platelet nitric oxide by inhibiting protein kinase C-dependent NADPH oxidase activation: effect on platelet recruitment. FASEB J. 2006 Jun;20(8):1082-9. [PubMed:16770007 ]
  11. Tsuchiya H, Sato M, Kato H, Okubo T, Juneja LR, Kim M: Simultaneous determination of catechins in human saliva by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1997 Dec 5;703(1-2):253-8. [PubMed:9448083 ]
  12. Lotito SB, Fraga CG: Ascorbate protects (+)-catechin from oxidation both in a pure chemical system and human plasma. Biol Res. 2000;33(2):151-7. [PubMed:15693282 ]
  13. Filipe P, Silva JN, Haigle J, Freitas JP, Fernandes A, Santus R, Morliere P: Contrasting action of flavonoids on phototoxic effects induced in human skin fibroblasts by UVA alone or UVA plus cyamemazine, a phototoxic neuroleptic. Photochem Photobiol Sci. 2005 May;4(5):420-8. Epub 2005 Apr 5. [PubMed:15875075 ]
  14. Lotito SB, Fraga CG: (+)-Catechin as antioxidant: mechanisms preventing human plasma oxidation and activity in red wines. Biofactors. 1999;10(2-3):125-30. [PubMed:10609873 ]
  15. Farivar-Mohseni H, Kandzari SJ, Zaslau S, Riggs DR, Jackson BJ, McFadden DW: Synergistic effects of Cox-1 and -2 inhibition on bladder and prostate cancer in vitro. Am J Surg. 2004 Nov;188(5):505-10. [PubMed:15546559 ]