Record Information
Version1.0
Creation date2010-04-08 22:09:33 UTC
Update date2019-11-26 03:04:44 UTC
Primary IDFDB011258
Secondary Accession Numbers
  • FDB002589
Chemical Information
FooDB Nameo-Coumaric acid
Description2-Hydroxycinnamic acid, also known as 2-coumarate or 2-coumaric acid, 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. 2-Hydroxycinnamic acid exists in all living organisms, ranging from bacteria to humans. 2-Hydroxycinnamic acid is found, on average, in the highest concentration within a few different foods, such as corns (Zea mays), hard wheats (Triticum durum), and olives (Olea europaea) and in a lower concentration in pears (Pyrus communis), grape wine, and dates (Phoenix dactylifera). 2-Hydroxycinnamic acid has also been detected, but not quantified in, several different foods, such as turmerics (Curcuma longa), sesames (Sesamum orientale), evening primroses (Oenothera biennis), common peas (Pisum sativum), and german camomiles (Matricaria recutita). This could make 2-hydroxycinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxycinnamic acid.
CAS Number583-17-5
Structure
Thumb
Synonyms
SynonymSource
(2E)-3-(2-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(2-HYDROXYPHENYL)acrylIC ACIDChEBI
(e)-2-Hydroxycinnamic acidChEBI
(e)-3-(2-Hydroxy-phenyl)-acrylic acidChEBI
(e)-3-(2-Hydroxyphenyl)-2-propenoic acidChEBI
(e)-O-Hydroxycinnamic acidChEBI
2-CoumarateChEBI
2-Coumaric acidChEBI
2-HydroxycinnamateChEBI
O-Coumaric acidChEBI
O-Hydroxy-trans-cinnamic acidChEBI
trans-2-HydroxycinnamateChEBI
trans-2-Hydroxycinnamic acidChEBI
trans-O-Hydroxycinnamic acidChEBI
(2E)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(2E)-3-(2-HYDROXYPHENYL)acrylateGenerator
(e)-2-HydroxycinnamateGenerator
(e)-3-(2-Hydroxy-phenyl)-acrylateGenerator
(e)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(e)-O-HydroxycinnamateGenerator
O-CoumarateGenerator
O-Hydroxy-trans-cinnamateGenerator
trans-O-HydroxycinnamateGenerator
2-Hydroxycinnamic acid, (e)-isomerMeSH
Ortho-hydroxycinnamic acidMeSH
2-Hydroxycinnamic acid, (Z)-isomerMeSH
3-(2-Hydroxyphenyl)prop-2-enoateHMDB
3-(2-Hydroxyphenyl)prop-2-enoic acidHMDB
O-HydroxycinnamateHMDB
O-Hydroxycinnamic acidHMDB
ortho-HydroxycinnamateHMDB
trans-O-CoumarateHMDB
trans-O-Coumaric acidHMDB
2-Hydroxycinnamic acidGenerator
trans-2-CoumarateGenerator, HMDB
(E)-3-(2-Hydroxyphenyl)acrylic acidHMDB
3-(2-Hydroxyphenyl)-2-propenoic acidHMDB
o-Hydroxycinnamic acidHMDB
trans-o-Coumaric acidHMDB
3-(2-Hydroxyphenyl)acrylic acidHMDB
trans-2-Coumaric acid HMDB
(2E)-3-(2-Hydroxyphenyl)prop-2-enoic acidHMDB
2'-Hydroxycinnamic acidHMDB
(2e)-3-(2-Hydroxyphenyl)-2-propenoateGenerator
(2e)-3-(2-HYDROXYPHENYL)acrylateGenerator
o-Coumaratebiospider
o-Coumaric aciddb_source
o-Cumaric aciddb_source
o-Hydroxycinnamatebiospider
o-Hydroxycinnamic acid, 8CIdb_source
ortho-Hydroxycinnamic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
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
Polarizability16.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O3
IUPAC name(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid
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-AATRIKPKSA-N
Isomeric SMILESOC(=O)\C=C\C1=CC=CC=C1O
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
Disposition

Route of exposure:

Source:

Role

Industrial application:

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 pKapKa1 3.7 (30°, 1.0M LiCl)DFC
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
EI-MSMass Spectrum (Electron Ionization)splash10-014j-8900000000-8e96a9ec1b9d035d3edbSpectrum
GC-MStrans-o-Coumaric acid, 2 TMS, GC-MS Spectrumsplash10-0002-0910000000-9e0bdbf6d6389288e318Spectrum
GC-MStrans-o-Coumaric acid, 2 TMS, GC-MS Spectrumsplash10-00dj-9710000000-829ded288e3ec8312160Spectrum
GC-MStrans-o-Coumaric acid, 2 TMS, GC-MS Spectrumsplash10-00dj-9710000000-8fb7bb39d916f7402980Spectrum
GC-MStrans-o-Coumaric acid, 2 TMS, GC-MS Spectrumsplash10-0296-2941000000-b85ebef8eb8c276f220fSpectrum
GC-MStrans-o-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-014i-9800000000-3650ee76a1293cba7523Spectrum
GC-MStrans-o-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-9e0bdbf6d6389288e318Spectrum
GC-MStrans-o-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-00dj-9710000000-829ded288e3ec8312160Spectrum
GC-MStrans-o-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-00dj-9710000000-8fb7bb39d916f7402980Spectrum
GC-MStrans-o-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-0296-2941000000-b85ebef8eb8c276f220fSpectrum
GC-MStrans-o-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-c783499d6f33717b71caSpectrum
Predicted GC-MStrans-o-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014j-2900000000-3a06c14b7e8999427ad9Spectrum
Predicted GC-MStrans-o-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00y3-6390000000-a82ff5bd6498e3c478eaSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-9e4823d321cfe6f5e5a4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-efd5de4e7fe4032816f6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-44e81c2c735a93efc7d7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014l-7900000000-977a2bb08508d16be531Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0fdn-4900000000-dcfe2b032cf6bbee16b3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-adbaf7b04487b18191e0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-d368e3c354c7b05a949fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-efd5de4e7fe4032816f6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-44e81c2c735a93efc7d7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014l-7900000000-a641b2c2528f829e8ac1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-adbaf7b04487b18191e0Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-2ca69c9285dedaa2f424Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-55078e8ec591840fb594Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fdn-4900000000-95f5386456c1c353a111Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-bf00664334bbd7d7d91dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-ba0915b2f87da989c92bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-fd2da9ac5865a50fc50cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdu-9300000000-3baee6b4124fba79677eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-69f05779283af436427dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1900000000-0bc76f24c2abf6670fc0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-a2981a5342a71b94ce69Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-972f865a96261dcb891aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0900000000-dfdb5072d39445a67f3aSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID553146
ChEMBL IDCHEMBL52564
KEGG Compound IDC01772
Pubchem Compound ID637540
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID462
DrugBank IDDB01650
HMDB IDHMDB02641
CRC / DFC (Dictionary of Food Compounds) IDGKS64-L:GKS64-L
EAFUS IDNot Available
Dr. Duke IDO-COUMARIC-ACID|2-HYDROXYCINNAMIC-ACID|O-HYDROXYCINNAMIC-ACID
BIGG IDNot Available
KNApSAcK IDC00002729
HET ID2HC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
allelopathicDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
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).
— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.