Back to Compounds

Showing Compound trans-o-Coumaric acid (FDB002589)

Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2020-04-21 18:02:21 UTC
Primary IDFDB002589
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-o-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 Number614-60-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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)acrylic acidbiospider
(E)-2-Hydroxycinnamic acidbiospider
(E)-3-(2-Hydroxyphenyl)-2-propenoic aciddb_source
(E)-3-(2-Hydroxyphenyl)prop-2-enoic acidbiospider
(E)-o-Hydroxycinnamic acidbiospider
2-Propenoic acid, 3-(2-hydroxyphenyl)-, (2E)-biospider
2-Propenoic acid, 3-(2-hydroxyphenyl)-, (E)- (9CI)biospider
Cinnamic acid, o-hydroxy-, (E)-biospider
o-Hydroxy-trans-cinnamatebiospider
o-Hydroxy-trans-cinnamic acidbiospider
trans-2-Coumaric acidbiospider
trans-o-Coumaratebiospider
trans-o-Hydroxycinnamatebiospider
trans-o-Hydroxycinnamic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.15 g/LALOGPS
logP1.9ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
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
Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionC 65.85%; H 4.91%; O 29.24%DFC
    Melting PointMp 207-208° dec.DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKapKa 4.61DFC
    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-8900000000-8e96a9ec1b9d035d3edb2015-03-01View Spectrum
    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
    Predicted GC-MStrans-o-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-9e4823d321cfe6f5e5a42012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-efd5de4e7fe4032816f62012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-44e81c2c735a93efc7d72012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014l-7900000000-977a2bb08508d16be5312012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb52012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0fdn-4900000000-dcfe2b032cf6bbee16b32012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-adbaf7b04487b18191e02012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-d368e3c354c7b05a949f2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-efd5de4e7fe4032816f62017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-44e81c2c735a93efc7d72017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014l-7900000000-a641b2c2528f829e8ac12017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9300000000-fe9b4a0aa3b23d5c2eb52017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-adbaf7b04487b18191e02017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-2ca69c9285dedaa2f4242017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-55078e8ec591840fb5942017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0fdn-4900000000-95f5386456c1c353a1112017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-bf00664334bbd7d7d91d2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-ba0915b2f87da989c92b2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-fd2da9ac5865a50fc50c2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdu-9300000000-3baee6b4124fba79677e2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-69f05779283af436427d2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1900000000-0bc76f24c2abf6670fc02017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-a2981a5342a71b94ce692017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-972f865a96261dcb891a2021-09-22View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0900000000-dfdb5072d39445a67f3a2021-09-22View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)Spectrum
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound IDNot Available
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDNot Available
    CRC / DFC (Dictionary of Food Compounds) IDGKS64-L:CMP58-T
    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 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
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference