Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2018-05-29 00:35:40 UTC
Primary IDFDB002593
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namep-Coumaric acid
Description4-Hydroxycinnamic acid, also known as trans-p-hydroxycinnamate or p-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. 4-Hydroxycinnamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxycinnamic acid exists in all living species, ranging from bacteria to humans. 4-Hydroxycinnamic acid is found, on average, in the highest concentration in a few different foods, such as pepper (c. frutescens), pineapples, and sunflowers and in a lower concentration in coffee, bog bilberries, and cucurbita (gourd). 4-Hydroxycinnamic acid has also been detected, but not quantified in, several different foods, such as flaxseeds, garden onions, black elderberries, black raspberries, and figs. This could make 4-hydroxycinnamic acid a potential biomarker for the consumption of these foods.
CAS Number7400-08-0
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-4-Hydroxycinnamic 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-Coumaric acidHMDB
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
4-Hydroxycinnamic acidChEBI
(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
(2e)-3-(4-Hydroxyphenyl)acrylateGenerator
(2e)-3-(4-Hydroxyphenyl)acrylic acidChEBI
(e)-P-CoumarateGenerator
(e)-P-HydroxycinnamateGenerator
p-Hydroxy-cinnamic acidbiospider
P-Hydroxycinnamic acidHMDB
p-Hydroxycinnamic acid, 8CIdb_source
para-Coumaratebiospider
para-Coumaric acidbiospider
trans-P-CoumarinateGenerator
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    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 Point211.5 oC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logP1.79SANGSTER (1994)
    Experimental pKa4.64
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919cJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-066v-3791000000-a5712bbe8401ef499b5aJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-3bb023f80c1f54a16adcJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-5900000000-a364c62c9122c0fbe6deJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919cJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066v-3791000000-a5712bbe8401ef499b5aJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1891000000-d8804981d3918cac534dJSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-7075c3e10f9df528109eJSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-6390000000-3110f0f6eb462a38bb64JSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-8900000000-3bb023f80c1f54a16adcJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-b58aab08954c973df04eJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-3ddb41572ba36a950e37JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-ccac7f071084bc660095JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-3900000000-5dc8af06da0120779cffJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9500000000-9187edc4498ab4345e5aJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-3900000000-1118928776a5a6e213dbJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3d831c6acd9d3188de2fJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-fbb6439b7d012045f3a8JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72bJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0900000000-c5faa58d353ca1466c3cJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0900000000-c45397049a7ba500b332JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-b58aab08954c973df04eJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-3ddb41572ba36a950e37JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-ccac7f071084bc660095JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5dc8af06da0120779cffJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9500000000-9187edc4498ab4345e5aJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3d831c6acd9d3188de2fJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-fbb6439b7d012045f3a8JSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-43c3377fad5f7488bea0JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-2264676cffcfb3110cb8JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdr-9600000000-9d441c7fc0720390be54JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-2ce3562ddd5762384d09JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-f6c69044556dd2ca2134JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-f7e5cd9359ebf2ee51a6JSpectraViewer
    MSMass Spectrum (Electron Ionization)splash10-03xr-6900000000-348f5c7c030570e0612fJSpectraViewer | MoNA
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
    ChemSpider ID553148
    ChEMBL IDCHEMBL66879
    KEGG Compound IDC00811
    Pubchem Compound ID637542
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID500
    DrugBank IDDB04066
    HMDB IDHMDB02035
    CRC / DFC (Dictionary of Food Compounds) IDCMP73-U:CMP73-U
    EAFUS IDNot Available
    Dr. Duke ID4-HYDROXYCINNAMIC-ACID|P-COUMARIC-ACID|P-HYDROXYCINNAMIC-ACID
    BIGG ID36077
    KNApSAcK IDC00000152
    HET IDHC4
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDCoumaric_acid
    Phenol-Explorer Metabolite ID454
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
    allelopathicDUKE
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti clastogenDUKE
    anti fertilityDUKE
    anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
    anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti nitrosaminicDUKE
    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.DUKE
    anti peroxidantDUKE
    anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    cholereticDUKE
    cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
    diaphoreticDUKE
    fungicide24127 A substance used to destroy fungal pests.DUKE
    lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.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
    prostaglandigenicDUKE
    prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
    tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    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.
    — 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.