m-Coumaric acid (CHEM021806)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:12:59 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021806
Identification
Common Namem-Coumaric acid
ClassSmall Molecule
DescriptionA 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
m-Hydroxycinnamic acidChEBI
trans-3-HydroxycinnamateChEBI
trans-3-Hydroxycinnamic acidChEBI
(2E)-3-(3-Hydroxyphenyl)prop-2-enoateKegg
(2E)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
(2E)-3-(3-Hydroxyphenyl)acrylateGenerator
(e)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
3-CoumarateGenerator
m-HydroxycinnamateGenerator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acidGenerator
m-CoumarateGenerator
3'-HydroxycinnamateHMDB
3'-Hydroxycinnamic acidHMDB
3-(3-Hydroxyphenyl)-2-propenoateHMDB
3-(3-Hydroxyphenyl)-2-propenoic acidHMDB
3-(3-Hydroxyphenyl)acrylateHMDB
3-(3-Hydroxyphenyl)acrylsaeureHMDB
3-(3-Hydroxyphenyl)prop-2-enoateHMDB
3-(3-Hydroxyphenyl)prop-2-enoic acidHMDB
3-HydroxycinnamateHMDB
3-Hydroxycinnamic acidHMDB
m-Hydroxy-cinnamateHMDB
m-Hydroxy-cinnamic acidHMDB
3-Coumaric acid, (e)-isomerMeSH, HMDB
Meta-coumaric acidMeSH, HMDB
(E)-3-(3-Hydroxyphenyl)acrylic acidHMDB
(E)-3-Hydroxycinnamic acidHMDB
trans-3-(m-Hydroxyphenyl)-2-propenoic acidHMDB
trans-m-Coumaric acidHMDB
trans-m-Hydroxycinnamic acidHMDB
trans-3-CoumarateHMDB
Chemical FormulaC9H8O3
Average Molecular Mass164.158 g/mol
Monoisotopic Mass164.047 g/mol
CAS Registry Number588-30-7
IUPAC Name(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
Traditional Namem-coumaric acid
SMILESOC(=O)\C=C\C1=CC=CC(O)=C1
InChI IdentifierInChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+
InChI KeyKKSDGJDHHZEWEP-SNAWJCMRSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP1.71ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
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
Polarizability16.37 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udl-1691000000-331053d0d0b85549ac0bSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udl-1691000000-331053d0d0b85549ac0bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1891000000-049e1d80dd47b23e8c28Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-2900000000-91ffd4c10eaed6a17632Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-f1a30e2fb9cd1fb11341Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03xr-0900000000-4259219e89806dfe2602Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-4900000000-2157a17ec65ead35585eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00kf-9300000000-3325dd31a734dd4659bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-be33d196fbb525019f07Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-d256885fb0f35d3d6680Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-be33d196fbb525019f07Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-d256885fb0f35d3d6680Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-87be0242c9f5b426f6b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-9e4128fa078e73e71cbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0900000000-d256885fb0f35d3d6680Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9100000000-1865c168df491277a4d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9000000000-296d14129321002679a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9700000000-6d29cdde66b32806de5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-9da76da83e0462c48acfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-bf33c5b8f5901c60b332Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-2900000000-11ae76e2fe36da1dfbe6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-b6bf0b46b2fa8324cf71Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kb-0900000000-1065251e7cf92f343533Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-9000000000-0a87c81608b3fbcee7c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-b5ad37fb931b464df7d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-c66c146ee9509bf8a413Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9700000000-fcc332df0fcb818fe0e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-408ac0dd815354188750Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-146bae2da386ca2d4f1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-235b38f342376d1c9f90Spectrum
MSMass Spectrum (Electron Ionization)splash10-03xr-7900000000-61ee2ad0ad164a1f7550Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001713
FooDB IDFDB002590
Phenol Explorer ID463
KNApSAcK IDC00052344
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID305
PDB IDNot Available
Wikipedia LinkM-coumaric_acid
Chemspider ID553147
ChEBI ID32357
PubChem Compound ID637541
Kegg Compound IDC12621
YMDB IDNot Available
ECMDB IDECMDB21171
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15120569
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22014177
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
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5. Neish, A. C. Formation of m- and p-coumaric acids by enzymic deamination of the corresponding isomers of tyrosine. Phytochemistry (Elsevier) (1961), 1 1-24.
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14. Funk C, Braune A, Grabber JH, Steinhart H, Bunzel M: Moderate ferulate and diferulate levels do not impede maize cell wall degradation by human intestinal microbiota. J Agric Food Chem. 2007 Mar 21;55(6):2418-23. Epub 2007 Feb 24.
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17. Efdi M, Itoh T, Akao Y, Nozawa Y, Koketsu M, Ishihara H: The isolation of secondary metabolites and in vitro potent anti-cancer activity of clerodermic acid from Enicosanthum membranifolium. Bioorg Med Chem. 2007 Jun 1;15(11):3667-71. Epub 2007 Mar 18.
18. Azzini E, Bugianesi R, Romano F, Di Venere D, Miccadei S, Durazzo A, Foddai MS, Catasta G, Linsalata V, Maiani G: Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads of Cynara scolymus L. (cultivar Violetto di Provenza) in human subjects: a pilot study. Br J Nutr. 2007 May;97(5):963-9.
19. Appiah-Opong R, Commandeur JN, van Vugt-Lussenburg B, Vermeulen NP: Inhibition of human recombinant cytochrome P450s by curcumin and curcumin decomposition products. Toxicology. 2007 Jun 3;235(1-2):83-91. Epub 2007 Mar 15.
20. Wang Q, Morris ME: The role of monocarboxylate transporter 2 and 4 in the transport of gamma-hydroxybutyric acid in mammalian cells. Drug Metab Dispos. 2007 Aug;35(8):1393-9. Epub 2007 May 14.
21. Keyhanian S, Stahl-Biskup E: Phenolic constituents in dried flowers of aloe vera (Aloe barbadensis) and their in vitro antioxidative capacity. Planta Med. 2007 Jun;73(6):599-602. Epub 2007 May 22.
22. Kosanam H, Prakash PK, Yates CR, Miller DD, Ramagiri S: Rapid screening of doping agents in human urine by vacuum MALDI-linear ion trap mass spectrometry. Anal Chem. 2007 Aug 1;79(15):6020-6. Epub 2007 Jun 30.
23. Rakotondramanana DL, Delomenede M, Baltas M, Duran H, Bedos-Belval F, Rasoanaivo P, Negre-Salvayre A, Gornitzka H: Synthesis of ferulic ester dimers, functionalisation and biological evaluation as potential antiatherogenic and antiplasmodial agents. Bioorg Med Chem. 2007 Sep 15;15(18):6018-26. Epub 2007 Jun 29.
24. Gomez-Ruiz JA, Leake DS, Ames JM: In vitro antioxidant activity of coffee compounds and their metabolites. J Agric Food Chem. 2007 Aug 22;55(17):6962-9. Epub 2007 Jul 27.
25. Wu CI, Tsai CC, Lu CC, Wu PC, Wu DC, Lin SY, Shiea J: Diagnosis of occult blood in human feces using matrix-assisted laser desorption ionization/time-of-flight mass spectrometry. Clin Chim Acta. 2007 Sep;384(1-2):86-92. Epub 2007 Jun 26.
26. Henry BL, Monien BH, Bock PE, Desai UR: A novel allosteric pathway of thrombin inhibition: Exosite II mediated potent inhibition of thrombin by chemo-enzymatic, sulfated dehydropolymers of 4-hydroxycinnamic acids. J Biol Chem. 2007 Nov 2;282(44):31891-9. Epub 2007 Sep 5.
27. Qin J, Chen D, Hu H, Qiao M, Zhao X, Chen B: Body distributioin of RGD-mediated liposome in brain-targeting drug delivery. Yakugaku Zasshi. 2007 Sep;127(9):1497-501.
28. Monteiro M, Farah A, Perrone D, Trugo LC, Donangelo C: Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J Nutr. 2007 Oct;137(10):2196-201.
29. Mennen LI, Sapinho D, Ito H, Bertrais S, Galan P, Hercberg S, Scalbert A: Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. Br J Nutr. 2006 Jul;96(1):191-8.
30. Konishi Y, Kobayashi S: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2004 Oct 20;52(21):6418-24.
31. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510