Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2018-05-28 22:41:15 UTC
Primary IDFDB002571
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCatechin
DescriptionPresent in red wine. Widespread in plants; found in a variety of foodstuffs especies apricots, broad beans, cherries, chocolate, grapes, nectarines, red wine, rhubarb, strawberries and tea (+)-Catechin or Catechin is one of the 4 catechin diastereoisomers.
CAS Number154-23-4
Structure
Thumb
Synonyms
SynonymSource
(+)-(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
(+)-Cianidanolbiospider
(2R,3S)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triolbiospider
(2R,3S)-3,3',4',5,7-Flavanpentolbiospider
3,3',4',5,7-Pentahydroxyflavan; (+)-trans-formdb_source
Catechinbiospider
Catechol (8CI)manual
Cyanidoldb_source
D-Catecholbiospider
Dexcyanidanoldb_source
Drenoliverdb_source
trans-(+)-3,3',4',5,7-Flavanpentolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.65 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
Chemical FormulaC15H14O6
IUPAC name(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
InChI IdentifierInChI=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
Isomeric SMILESO[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 62.07%; H 4.86%; O 33.07%DFC
Melting PointMp 175-177° (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP0.51PERRISSOUD,D & TESTA,B (1986)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +17DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0749000000-e5b0b7512526810c1758View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0940000000-3790a10ce8b93dcb9236View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-3130069000-ca0968505fc89dd82640View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0190000000-0b55363090666c3a1f0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0ab9-0900000000-5dfb75ce17e0aea0642bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-003r-9000000000-ae956114187e6320ae3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0079-0900000000-dd93ef481c2fea84d4a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-0980000000-97f9a54412368150d277View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090010000-6ebf1de8cc1ea492a630View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052k-0960000000-77945100b7a1f6311aeaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-052k-0960000000-77945100b7a1f6311aeaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-05fr-0920000000-e829a07f24435afac743View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090010000-6ebf1de8cc1ea492a630View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-052k-0960000000-77945100b7a1f6311aeaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-25414078e505f0193624View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-05fr-0920000000-e829a07f24435afac743View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-000i-0910000000-a98df14e459446ae6ae2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0090000000-142161e341ec3ee68a3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0fga-0980000000-3406dfb006e610eb6fceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0090000000-466d29d8274d012f2ea3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0pds-0970000000-2631ce85b21e59412694View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05fr-1900000000-3424d3d2af180d7eabd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0590000000-aff1c3cc94786f87cacfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-5e84c0d9207a0a018ab4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-3e525d17e0b05647387aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-52e8123f5ed55bc47962View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0940000000-cfcd9b4e416f64a26916View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2910000000-be77474275eeee51824bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID8711
ChEMBL IDCHEMBL311498
KEGG Compound IDC06562
Pubchem Compound ID9064
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID124
DrugBank IDNot Available
HMDB IDHMDB02780
CRC / DFC (Dictionary of Food Compounds) IDCML31-M:CML34-P
EAFUS IDNot Available
Dr. Duke IDD-CATECHIN|(+)-CATECHIN|CATECHIN
BIGG IDNot Available
KNApSAcK IDC00000947
HET IDKXN
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCatechin
Phenol-Explorer Metabolite ID124
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
allelochemicDUKE
anti aggregantDUKE
anti alcoholic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti coagulant50249 An agent that prevents blood clotting.DUKE
anti complementaryDUKE
anti edemicDUKE
anti endotoxic50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti feedantDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hepatitic62868 Any compound that is able to prevent damage to the liver.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hyperlipidemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti lipoperoxidantDUKE
anti mutagenicDUKE
anti osteoticDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti periodontalDUKE
anti peroxidantDUKE
anti plaqueDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti radicularDUKE
anti sclerodermic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
astringent74783 A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.DUKE
beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
cAMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
catechol O-methyltransferase inhibitor48406 An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).DUKE
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
dermatitigenicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hemostatDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
neuroprotective63726 Any compound that can be used for the treatment of neurodegenerative disorders.DUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phagocytoticDUKE
propecicDUKE
vasoconstrictor50514 Drug used to cause constriction of the blood vessels.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).