Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2019-11-26 02:57:40 UTC
Primary IDFDB002594
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-p-Coumaric acid
DescriptionWidespread in plants, e.g. peel of black cherry (Prunus serotina), lentil seeds and from red clover (Trifolium pratense). Found by Bate-Smith in 48% of investigated dicotyledonous and 55% of monocotyledonous subspecies Coumaric 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. trans-p-Coumaric acid is found in many foods, some of which are common buckwheat, radish, sweet orange, and avocado.
CAS Number501-98-4
Structure
Thumb
Synonyms
SynonymSource
(2E)-3-(4-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(4-Hydroxyphenyl)-2-propenoic acidChEBI
(e)-p-Coumaric acidChEBI
(e)-p-Hydroxycinnamic acidChEBI
4'-HYDROXYCINNAMIC ACIDChEBI
Naringeninic acidChEBI
p-Coumaric acidChEBI
trans-p-Coumaric acidChEBI
trans-p-Coumarinic acidChEBI
trans-p-HydroxycinnamateChEBI
trans-p-Hydroxycinnamic acidChEBI
trans-4-HydroxycinnamateKegg
4-HydroxycinnamateKegg
(2E)-3-(4-Hydroxyphenyl)acrylateGenerator
(e)-3-(4-Hydroxyphenyl)-2-propenoateGenerator
(e)-p-CoumarateGenerator
(e)-p-HydroxycinnamateGenerator
4'-HYDROXYCINNAMateGenerator
NaringeninateGenerator
p-CoumarateGenerator
trans-p-CoumarateGenerator
trans-p-CoumarinateGenerator
trans-4-CoumarateHMDB
3-(4-Hydroxyphenyl)-2-propenoateHMDB
3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxyphenyl)acrylateHMDB
3-(4-Hydroxyphenyl)acrylic acidHMDB
4-CoumarateHMDB
4-Hydroxy cinnamateHMDB
4-Hydroxy cinnamic acidHMDB
4-HydroxyphenylpropenoateHMDB
4-Hydroxyphenylpropenoic acidHMDB
b-[4-Hydroxyphenyl]acrylateHMDB
b-[4-Hydroxyphenyl]acrylic acidHMDB
beta-[4-Hydroxyphenyl]acrylateHMDB
beta-[4-Hydroxyphenyl]acrylic acidHMDB
cis-p-CoumarateHMDB
HydroxycinnamateHMDB
Hydroxycinnamic acidHMDB
p-CumarateHMDB
p-Cumaric acidHMDB
p-HydroxycinnamateHMDB
p-Hydroxycinnamic acidHMDB
p-HydroxyphenylacrylateHMDB
p-Hydroxyphenylacrylic acidHMDB
Para coumarateHMDB
Para coumaric acidHMDB
Para-coumarateHMDB
Para-coumaric acidHMDB
4-Coumaric acid, (Z)-isomerHMDB
4-Coumaric acid, disodium saltHMDB
4-Coumaric acid, (e)-isomerHMDB
p-Coumaryl alcoholHMDB
trans-3-(4'-Hydroxyphenyl)-2-propenoic acidHMDB
trans-HPPAHMDB
(2E)-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acidHMDB
(e)-3-(4-Hydroxyphenyl)acrylic acidHMDB
(e)-4-Hydroxycinnamic acidHMDB
4’-hydroxycinnamic acidHMDB
p-Hydroxy-trans-cinnamic acidHMDB
p-trans-Coumaric acidHMDB
trans-3-(4-Hydroxyphenyl)-2-propenoic acidHMDB
trans-4-Coumaric acidHMDB
Β-[4-hydroxyphenyl]acrylic acidHMDB
4-Hydroxycinnamic acidChEBI
(E)-p-Coumaric acidbiospider
(E)-p-Hydroxycinnamic acidbiospider
2-Propenoic acid, 3-(4-hydroxyphenyl)-, (E)-biospider
Cinnamic acid, p-hydroxy-, (E)-biospider
p-Coumaric acid, transbiospider
trans-4-Hydroxycinnamic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.02 g/LALOGPS
logP1.74ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4ChemAxon
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
Polarizability16.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O3
IUPAC name(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
InChI KeyNGSWKAQJJWESNS-ZZXKWVIFSA-N
Isomeric SMILESOC(=O)\C=C\C1=CC=C(O)C=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-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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.85%; H 4.91%; O 29.24%DFC
Melting PointMp 210-213°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.79SANGSTER (1994)
Experimental pKapKa2 9.45 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data286 (e 19000) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03xr-6900000000-348f5c7c030570e0612fSpectrum
GC-MSp-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-014m-1981000000-e7648e85764a445a919cSpectrum
GC-MSp-Coumaric acid, 2 TMS, GC-MS Spectrumsplash10-066v-3791000000-a5712bbe8401ef499b5aSpectrum
GC-MSp-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-03di-8900000000-3bb023f80c1f54a16adcSpectrum
GC-MSp-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-03xr-5900000000-a364c62c9122c0fbe6deSpectrum
GC-MSp-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-014m-1981000000-e7648e85764a445a919cSpectrum
GC-MSp-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-066v-3791000000-a5712bbe8401ef499b5aSpectrum
GC-MSp-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-014m-1891000000-d8804981d3918cac534dSpectrum
Predicted GC-MSp-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014j-2900000000-7075c3e10f9df528109eSpectrum
Predicted GC-MSp-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-6390000000-3110f0f6eb462a38bb64Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-8900000000-3bb023f80c1f54a16adcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-b58aab08954c973df04eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-3ddb41572ba36a950e37Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-ccac7f071084bc660095Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-3900000000-5dc8af06da0120779cffSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9500000000-9187edc4498ab4345e5aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-3900000000-1118928776a5a6e213dbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3d831c6acd9d3188de2fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-fbb6439b7d012045f3a8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72bSpectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0900000000-c5faa58d353ca1466c3cSpectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0900000000-c45397049a7ba500b332Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-b58aab08954c973df04eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-3ddb41572ba36a950e37Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-ccac7f071084bc660095Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5dc8af06da0120779cffSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9500000000-9187edc4498ab4345e5aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3d831c6acd9d3188de2fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-fbb6439b7d012045f3a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-43c3377fad5f7488bea0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-2264676cffcfb3110cb8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdr-9600000000-9d441c7fc0720390be54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-2ce3562ddd5762384d09Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-f6c69044556dd2ca2134Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-f7e5cd9359ebf2ee51a6Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID498
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMP73-U:CMP74-V
EAFUS IDNot Available
Dr. Duke IDTRANS-P-COUMARIC-ACID|COUMARIC-ACID
BIGG IDNot Available
KNApSAcK IDC00000580
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID501-98-4
GoodScent IDrw1203781
SuperScent IDNot Available
Wikipedia IDCoumaric_acid
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
Flavours
FlavorCitations
balsamic
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.