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
DescriptionCoumaric 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. p-Coumaric acid is found in many foods, some of which are garden onion, turmeric, green bell pepper, and common thyme.
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
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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-066v-3791000000-a5712bbe8401ef499b5aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-3bb023f80c1f54a16adcView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-5900000000-a364c62c9122c0fbe6deView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1981000000-e7648e85764a445a919cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066v-3791000000-a5712bbe8401ef499b5aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1891000000-d8804981d3918cac534dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-2900000000-7075c3e10f9df528109eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-6390000000-3110f0f6eb462a38bb64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-03di-8900000000-3bb023f80c1f54a16adcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-b58aab08954c973df04eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-3ddb41572ba36a950e37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-ccac7f071084bc660095View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-3900000000-5dc8af06da0120779cffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9500000000-9187edc4498ab4345e5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00kb-3900000000-1118928776a5a6e213dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-3d831c6acd9d3188de2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-fbb6439b7d012045f3a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-9e18d43a8d86f9b9e72bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0900000000-c5faa58d353ca1466c3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0900000000-c45397049a7ba500b332View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-b58aab08954c973df04eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-3ddb41572ba36a950e37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-ccac7f071084bc660095View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-3900000000-5dc8af06da0120779cffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9500000000-9187edc4498ab4345e5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-3d831c6acd9d3188de2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-fbb6439b7d012045f3a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-43c3377fad5f7488bea0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-2264676cffcfb3110cb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdr-9600000000-9d441c7fc0720390be54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-2ce3562ddd5762384d09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-f6c69044556dd2ca2134View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-f7e5cd9359ebf2ee51a6View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03xr-6900000000-348f5c7c030570e0612fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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
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.