Catechin (YMDB01653)

Identification
YMDB IDYMDB01653
NameCatechin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCatechin, also known as (2R,3S)-catechin or cianidanol, 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. Based on a literature review a significant number of articles have been published on Catechin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol
  • (+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol
  • (+)-Catechin hydrate
  • (+)-Catechol
  • (+)-Cyanidan-3-ol
  • (+)-Cyanidanol
  • (+)-Cyanidanol-3
  • (+/-)-catechin
  • (+/-)-catechin hydrate
  • (2R-trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
  • (2R,3S)-(+)-Catechin
  • (2R,3S)-Catechin
  • 3,3',4',5,7-Flavanpentol
  • Acid, catechinic
  • Acid, catechuic
  • Biocatechin
  • Catechin
  • Catechinate
  • Catechinic acid
  • Catechuate
  • Catechuic acid
  • Catergen
  • Cianidanol
  • Cianidanolum
  • Cianidol
  • Cyanidanol
  • Cyanidanol 3
  • Cyanidanol-3
  • D-(+)-Catechin
  • D-Catechin
  • Epicatechin
  • KB 53
  • KB-53
  • trans3,3,4,5,7 Pentahydroxyflavane
  • YK-85 light yellow powder 85
  • Zyma
  • (+)-Catechin
  • (-)-Epicatechin
  • (+)-(2R:3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol
  • (+)-(2R:3S)-5,7,3’,4’-Tetrahydroxyflavan-3-ol
  • (+)-3’,4’,5,7-Tetrahydroxy-2,3-trans-flavan-3-ol
  • (+)-Cianidanol
  • 3-Cyanidanol, (+)-
  • Cyanidol
  • Dexcyanidanol
  • trans-(+)-3,3',4',5,7-Flavanpentol
  • trans-(+)-3,3’,4’,5,7-Flavanpentol
CAS number154-23-4
WeightAverage: 290.2681
Monoisotopic: 290.07903818
InChI KeyPFTAWBLQPZVEMU-DZGCQCFKSA-N
InChIInChI=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
IUPAC Name(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional IUPAC Name(+)-catechol
Chemical FormulaC15H14O6
SMILESO[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C1
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
Physical Properties
StateSolid
Charge0
Melting point214 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP0.51 [PERRISSOUD,D & TESTA,B (1986)]PhysProp
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
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BitterFDB002571
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-3130069000-ca0968505fc89dd82640JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0920000000-5e84c0d9207a0a018ab4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4900000000-3e525d17e0b05647387aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-52e8123f5ed55bc47962JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0940000000-cfcd9b4e416f64a26916JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2910000000-be77474275eeee51824bJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15600
HMDB IDHMDB02780
Pubchem Compound ID9064
Kegg IDC06562
ChemSpider ID23170444
FOODB IDFDB002571
Wikipedia IDCatechin
BioCyc IDNot Available