Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2020-02-24 19:11:08 UTC
Primary IDFDB000258
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namep-Coumaric acid ethyl ester
DescriptionEthyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is a member of the class of compounds known as coumaric acid esters. Coumaric acid esters are aromatic compounds containing an ester derivative of coumaric acid. Ethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Ethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate can be found in vinegar, which makes ethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Ethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acidGenerator
Ethyl coumarateMeSH
p-Coumarate ethyl esterGenerator
Predicted Properties
PropertyValueSource
Water Solubility1.08 g/LALOGPS
logP3.07ALOGPS
logP2.57ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.56 m³·mol⁻¹ChemAxon
Polarizability20.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H12O3
IUPAC nameethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C11H12O3/c1-2-14-11(13)8-5-9-3-6-10(12)7-4-9/h3-8,12H,2H2,1H3/b8-5+
InChI KeyZOQCEVXVQCPESC-VMPITWQZSA-N
Isomeric SMILES[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)OCC
Average Molecular Weight192.2112
Monoisotopic Molecular Weight192.07864425
Classification
Description Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acid esters
Alternative Parents
Substituents
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSp-Coumaric acid ethyl ester, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002b-3900000000-adeb64c5ef3917249416Spectrum
Predicted GC-MSp-Coumaric acid ethyl ester, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00bc-7960000000-7a906d9d886340ad9026Spectrum
Predicted GC-MSp-Coumaric acid ethyl ester, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-fa98aa825e98d5e4dbe0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2900000000-9046f3c5b644285fdd44Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r1-9600000000-68ca4019875cfb123b7eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-1900000000-0eda5713cb09121815eeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-e08e0cf47402b48a970bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-5900000000-89c5425dc2ad882fd806Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-0900000000-6d5286b080594008431cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-701fc2056fa56c7fa89dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-e87789e612d0edbed0f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ke-0900000000-eb4a4b2c6555ec34eb36Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-2900000000-567d29746d4742e6f585Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-9500000000-9381a300a2bac955422aSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID491
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
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
MSDSNot Available
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.