Coumaric acid (CHEM022456)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:35:34 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022456
Identification
Common NameCoumaric acid
ClassSmall Molecule
DescriptionThe cis-isomer of 2-coumaric acid.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2Z)-3-(2-Hydroxyphenyl)acrylic acidChEBI
2-CoumarinateChEBI
cis-2-Hydroxy cinnamateChEBI
cis-2-Hydroxycinnamic acidChEBI
(2Z)-3-(2-Hydroxyphenyl)acrylateGenerator
2-Coumarinic acidGenerator
cis-2-Hydroxy cinnamic acidGenerator
cis-2-HydroxycinnamateGenerator
CoumarinateGenerator
CoumarateGenerator, HMDB
(Z)-FormHMDB
3-(2-Hydroxyphenyl)-(2Z)-2-propenoic acidHMDB
3-(2-Hydroxyphenyl)-(Z)-2-propenoic acidHMDB
3-(2-Hydroxyphenyl)-2-propenoic acid, 9ciHMDB
Cinnamic acid, O-hydroxy-, (Z)- (8ci)HMDB
cis-O-Coumaric acidHMDB
cis-O-Hydroxycinnamic acidHMDB
Coumarinic acidHMDB
cis-2-CoumarateGenerator, HMDB
(2Z)-3-(2-Hydroxyphenyl)-2-propenoic acidHMDB
(Z)-2-Hydroxycinnamic acidHMDB
(Z)-3-(2-Hydroxyphenyl)acrylic acidHMDB
(Z)-o-Hydroxycinnamic acidHMDB
2-Coumaric acidHMDB
2-Hydroxycinnamic acidHMDB
3-(2-Hydroxyphenyl)-2-propenoic acidHMDB
cis-o-Coumaric acidHMDB
cis-o-Hydroxycinnamic acidHMDB
o-Coumaric acidHMDB
o-Hydroxy-cis-cinnamic acidHMDB
o-Hydroxycinnamic acidHMDB
Chemical FormulaC9H8O3
Average Molecular Mass164.158 g/mol
Monoisotopic Mass164.047 g/mol
CAS Registry Number495-79-4
IUPAC Name(2Z)-3-(2-hydroxyphenyl)prop-2-enoic acid
Traditional Name2-coumarinate
SMILESOC(=O)\C=C/C1=CC=CC=C1O
InChI IdentifierInChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5-
InChI KeyPMOWTIHVNWZYFI-WAYWQWQTSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
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
Polarizability16.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-01ox-1941000000-85dd77bfea7f6b8125b7Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-01ox-1941000000-85dd77bfea7f6b8125b7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-73438ba0cdf6f364fa48Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-6663bcef745d1f3aa724Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-a82ff5bd6498e3c478eaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-ba0915b2f87da989c92bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-fd2da9ac5865a50fc50cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdu-9300000000-3baee6b4124fba79677eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-69f05779283af436427dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1900000000-0bc76f24c2abf6670fc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-a2981a5342a71b94ce69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-d75d91b3944a2cbb443cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-4cc760aa4a932aabf83eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ftf-9300000000-3a6e7e80a1f918c0bb34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-972f865a96261dcb891aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0900000000-dfdb5072d39445a67f3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-8900000000-badf365b10d631e59196Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041592
FooDB IDFDB021703
Phenol Explorer IDNot Available
KNApSAcK IDC00019207
BiGG IDNot Available
BioCyc IDCPD-7418
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCoumaric acid
Chemspider ID4444389
ChEBI ID28873
PubChem Compound ID5280841
Kegg Compound IDC05838
YMDB IDNot Available
ECMDB IDM2MDB004460
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.