Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2018-05-29 00:35:38 UTC
Primary IDFDB002590
Secondary Accession Numbers
  • FDB002591
Chemical Information
FooDB Namem-Coumaric acid
DescriptionCoumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. m-Coumaric acid is found in many foods, some of which are corn, garden tomato (variety), grape wine, and beer.
CAS Number588-30-7
Structure
Thumb
Synonyms
SynonymSource
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
3-Coumaric acidChEBI
m-Hydroxycinnamic acidChEBI
trans-3-HydroxycinnamateChEBI
trans-3-Hydroxycinnamic acidChEBI
(2E)-3-(3-Hydroxyphenyl)prop-2-enoateKegg
(2E)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
(2E)-3-(3-Hydroxyphenyl)acrylateGenerator
(e)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
3-CoumarateGenerator
m-HydroxycinnamateGenerator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acidGenerator
m-CoumarateGenerator
3'-HydroxycinnamateHMDB
3'-Hydroxycinnamic acidHMDB
3-(3-Hydroxyphenyl)-2-propenoateHMDB
3-(3-Hydroxyphenyl)-2-propenoic acidHMDB
3-(3-Hydroxyphenyl)acrylateHMDB
3-(3-Hydroxyphenyl)acrylic acidHMDB
3-(3-Hydroxyphenyl)acrylsaeureHMDB
3-(3-Hydroxyphenyl)prop-2-enoateHMDB
3-(3-Hydroxyphenyl)prop-2-enoic acidHMDB
3-HydroxycinnamateHMDB
3-Hydroxycinnamic acidHMDB
m-Hydroxy-cinnamateHMDB
m-Hydroxy-cinnamic acidHMDB
trans-3-Coumaric acidHMDB
3-Coumaric acid, (e)-isomerHMDB
Meta-coumaric acidHMDB
(E)-3-(3-Hydroxyphenyl)acrylic acidHMDB
(E)-3-Hydroxycinnamic acidHMDB
m-Coumaric acidHMDB
trans-3-(m-Hydroxyphenyl)-2-propenoic acidHMDB
trans-m-Coumaric acidHMDB
trans-m-Hydroxycinnamic acidHMDB
trans-3-CoumarateHMDB
(2e)-3-(3-Hydroxyphenyl)acrylateGenerator
m-Cumaric aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP1.71ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.37 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H8O3
IUPAC name(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+
InChI KeyKKSDGJDHHZEWEP-SNAWJCMRSA-N
Isomeric SMILESOC(=O)\C=C\C1=CC=CC(O)=C1
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
Classification
Description belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 65.85%; H 4.91%; O 29.24%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udl-1691000000-331053d0d0b85549ac0bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udl-1691000000-331053d0d0b85549ac0bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1891000000-049e1d80dd47b23e8c28View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-2900000000-91ffd4c10eaed6a17632View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-f1a30e2fb9cd1fb11341View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03xr-0900000000-4259219e89806dfe2602View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-4900000000-2157a17ec65ead35585eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00kf-9300000000-3325dd31a734dd4659bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-be33d196fbb525019f07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-d256885fb0f35d3d6680View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-be33d196fbb525019f07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-d256885fb0f35d3d6680View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-b5ad37fb931b464df7d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-c66c146ee9509bf8a413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9700000000-fcc332df0fcb818fe0e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-408ac0dd815354188750View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-146bae2da386ca2d4f1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-235b38f342376d1c9f90View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03xr-7900000000-61ee2ad0ad164a1f7550View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID553147
ChEMBL IDCHEMBL98521
KEGG Compound IDC12621
Pubchem Compound ID637541
Pubchem Substance IDNot Available
ChEBI ID47925
Phenol-Explorer ID463
DrugBank IDNot Available
HMDB IDHMDB01713
CRC / DFC (Dictionary of Food Compounds) IDCMP64-S:CMP64-S
EAFUS IDNot Available
Dr. Duke IDM-COUMARIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCoumaric_acid
Phenol-Explorer Metabolite ID463
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).