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Identification
YMDB IDYMDB00498
Nametrans-4-Coumaric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionp-Coumaric acid is a hydroxycinnamic acid related to cinnamic acid, a type of polyphenol. It is an abundant phenolic phytochemical found in plant cell wall components. It is present in beer and wine. p-Coumaric acid is decarboxylated to 4-vinylphenol during wine fermentation by phenyl acrylic acid decarboxylase of certain strains yeast. Vinylphenols then spontaneously condensate with grape anthocyanins (mainly malvidin-3-O-glucoside) to form pigments important for the color of ageing wine. [PMID: 17303275]
Structure
Thumb
Synonyms
  • .beta.-[4-Hydroxyphenyl]acrylic acid
  • (2E)-3-(4-Hydroxyphenyl)-2-propenoic acid
  • (2E)-3-(4-hydroxyphenyl)acrylate
  • (2E)-3-(4-hydroxyphenyl)acrylic acid
  • (E)-3-(4-hydroxyphenyl)-2-propenoic acid
  • (E)-p-coumaric acid
  • (E)-p-hydroxycinnamic acid
  • 2-Propenoic acid, 3-(4-hydroxyphenyl)-
  • 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2E)-
  • 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (E)-
  • 3-(4-Hydroxyphenyl)-2-propenoate
  • 3-(4-Hydroxyphenyl)-2-propenoic acid
  • 3-(4-hydroxyphenyl)acrylate
  • 3-(4-hydroxyphenyl)acrylic acid
  • 4 - hydroxycinnamic acid
  • 4-coumarate
  • 4-Coumaric acid
  • 4-Hydroxy cinnamate
  • 4-Hydroxy cinnamic acid
  • 4-hydroxycinnamate
  • 4-hydroxycinnamic acid
  • 4-Hydroxyphenylpropenoate
  • 4-Hydroxyphenylpropenoic acid
  • 4'-Hydroxycinnamate
  • 4'-Hydroxycinnamic acid
  • b-[4-Hydroxyphenyl]acrylate
  • b-[4-Hydroxyphenyl]acrylic acid
  • beta-[4-Hydroxyphenyl]acrylate
  • beta-[4-Hydroxyphenyl]acrylic acid
  • Cinnamic acid, p-hydroxy-
  • Cinnamic acid, p-hydroxy-, (E)-
  • cis-p-Coumarate
  • hydroxycinnamate
  • hydroxycinnamic acid
  • naringeninic acid
  • p-Coumarate
  • p-coumaric acid
  • p-Coumaric acid,trans
  • p-Cumarate
  • p-Cumaric acid
  • p-Hydroxycinnamate
  • p-Hydroxycinnamic acid
  • p-Hydroxyphenylacrylate
  • p-Hydroxyphenylacrylic acid
  • Para coumarate
  • Para coumaric acid
  • Para-Coumarate
  • Para-Coumaric acid
  • trans-4-Hydroxycinnamate
  • trans-4-Hydroxycinnamic acid
  • trans-p-coumarate
  • trans-p-coumaric acid
  • trans-p-coumarinic acid
  • trans-p-Hydroxycinnamate
  • trans-p-hydroxycinnamic acid
  • (e)-3-(4-Hydroxyphenyl)-2-propenoate
  • (e)-p-Coumarate
  • (e)-p-Hydroxycinnamate
  • Naringeninate
  • trans-p-Coumarinate
  • trans-4-Coumarate
  • 4-Coumaric acid, (Z)-isomer
  • 4-Coumaric acid, disodium salt
  • 4-Coumaric acid, (e)-isomer
  • p-Coumaryl alcohol
  • trans-3-(4'-Hydroxyphenyl)-2-propenoic acid
  • trans-HPPA
  • (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid
  • (E)-3-(4-Hydroxyphenyl)acrylic acid
  • (E)-4-Hydroxycinnamic acid
  • 4’-Hydroxycinnamic acid
  • p-Hydroxy-trans-cinnamic acid
  • p-trans-Coumaric acid
  • trans-3-(4-Hydroxyphenyl)-2-propenoic acid
  • trans-4-Coumaric acid
  • β-[4-Hydroxyphenyl]acrylic acid
CAS number501-98-4
WeightAverage: 164.158
Monoisotopic: 164.047344122
InChI KeyNGSWKAQJJWESNS-ZZXKWVIFSA-N
InChIInChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
IUPAC Name(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional IUPAC Namecoumaric acid
Chemical FormulaC9H8O3
SMILESOC(=O)\C=C\C1=CC=C(O)C=C1
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-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
Physical Properties
StateSolid
Charge0
Melting point211.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP1.79 [SANGSTER (1994)]PhysProp
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
Biological Properties
Cellular Locations
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine metabolismec00360 Map00360
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB ReactionsNot Available
KEGG Reactions
3-(4-hydroxyphenyl)lactic acidwater + trans-4-Coumaric acid
Adenosine triphosphate + trans-4-Coumaric acid + Coenzyme AAdenosine monophosphate + Pyrophosphate + 4-Coumaroyl-CoA
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Ben-Bassat, Arie; Sariaslani, Fateme Sima; Huang, Lisa L.; Patnaik, Ranjan; Lowe, David J. Fermentative preparation of para-hydroxycinnamic acid and cinnamic acid at alkaline ph. U.S. Pat. Appl. Publ. (2005), 23 pp.
External Links:
ResourceLink
CHEBI ID32374
HMDB IDHMDB02035
Pubchem Compound ID322
Kegg IDC00811
ChemSpider ID553148
FOODB IDFDB002593
WikipediaCoumaric_acid
BioCyc IDCOUMARATE