Cinnamic acid (YMDB01324)

Identification
YMDB IDYMDB01324
NameCinnamic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCinnamic acid is a hydroxycinnamic acid, a type of polyphenol. It is part of the biosynthetic shikimate and phenylpropanoid pathways. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine. Cinnamic acid has a honey-like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2E)-3-Phenyl-2-propenoic acid
  • (E)-3-phenyl-2-propenoate
  • (E)-3-phenyl-2-propenoic acid
  • 2-Propenoic acid, 3-phenyl-
  • 3-Phenyl-2-propenoate
  • 3-Phenyl-2-propenoic acid
  • 3-Phenyl-2-propenoic acid (cinnamic acid)
  • 3-phenyl-acrylate
  • 3-phenyl-acrylic acid
  • 3-Phenylacrylate
  • 3-Phenylacrylic acid
  • 3-phenylpropenoate
  • 3-phenylpropenoic acid
  • b-Phenylacrylic acid
  • Benzeneacrylic acid
  • Benzenepropenoate
  • Benzenepropenoic acid
  • benzylideneacetic acid
  • beta-Phenylacrylic acid
  • Cinnamate
  • Cinnamic acid
  • Cinnamylic acid
  • Kyselina skoricove
  • Phenylacrylate
  • Phenylacrylic acid
  • tert-beta-Phenylacrylic acid
  • (2E)-3-Phenylacrylic acid
  • (e)-Cinnamate
  • (e)-Cinnamic acid
  • PHENYLETHYLENECARBOXYLIC ACID
  • trans-3-Phenylacrylic acid
  • trans-beta-Carboxystyrene
  • trans-Cinnamate
  • trans-Zimtsaeure
  • (2E)-3-Phenyl-2-propenoate
  • (2E)-3-Phenylacrylate
  • Benzeneacrylate
  • PHENYLETHYLENECARBOXYLate
  • trans-3-Phenylacrylate
  • trans-b-Carboxystyrene
  • trans-Β-carboxystyrene
  • (2E)-2-Phenyl-2-propenoate
  • (2E)-2-Phenyl-2-propenoic acid
  • (e)-3-Phenylacrylate
  • (e)-3-Phenylacrylic acid
  • (e)-3-Phenylprop-2-enoate
  • (e)-3-Phenylprop-2-enoic acid
  • trans-3-Phenyl-2-propenoate
  • trans-3-Phenyl-2-propenoic acid
  • Cinnamic acid, 14C-labeled CPD
  • Cinnamic acid, 2-(14)C-labeled CPD
  • Cinnamic acid, 3-(14)C-labeled CPD
  • Cinnamic acid, (Z)-isomer
  • Cinnamic acid, 2-(13)C-labeled CPD
  • Cinnamic acid, 3H-labeled CPD (e)-isomer
  • Cinnamic acid, 3H-labeled CPD (Z)-isomer
  • Cinnamic acid, ion(1-)-(e)-isomer
  • Cinnamic acid, sodium salt
  • Cinnamic acid, sodium salt(e)-isomer
  • Cinnamic acid, sodium salt(Z)-isomer
  • Cinnamic acid, (trans)-(e)-isomer
  • Cinnamic acid, 14C-labeled CPD (e)-isomer
  • Cinnamic acid, ion(1-)
  • Cinnamic acid, nickel (+2) salt
  • Cinnamic acid, potassium salt
  • Cinnamic acid, zinc salt(e)-isomer
  • Cinnamic acid, 13C-labeled CPD
  • (2E)-3-Phenylprop-2-enoic acid
  • (2E)-Cinnamic acid
  • 3-Phenyl-(e)-2-propenoic acid
  • Β-phenylacrylic acid
  • trans-Cinnamic acid
CAS number621-82-9
WeightAverage: 148.1586
Monoisotopic: 148.0524295
InChI KeyWBYWAXJHAXSJNI-VOTSOKGWSA-N
InChIInChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
IUPAC Name(2E)-3-phenylprop-2-enoic acid
Traditional IUPAC Namecinnamic acid
Chemical FormulaC9H8O2
SMILESOC(=O)\C=C\C1=CC=CC=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point132-135 °C
Experimental Properties
PropertyValueReference
Water Solubility0.57 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP2.13 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.43 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
BalsamFDB012052
CinnamonFDB012052
HoneyFDB012052
StoraxFDB012052
SweetFDB012052
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
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) (1 TMS)splash10-0ue9-0910000000-4a7bcdfadd383bf577dcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0fb9-6920000000-727a2eb761e6e52fb47dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-117i-2920000000-f0d9ccc40786362ae4adJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ue9-0910000000-4a7bcdfadd383bf577dcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-6920000000-727a2eb761e6e52fb47dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-117i-2920000000-f0d9ccc40786362ae4adJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-2900000000-b105b3fcb63636d0d16fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-3107a2a1bec368528f82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ufr-6900000000-b0299d34fa9bb16b8258JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-4a879de8ea4f3acb0ae2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-88ad8c9c837a057bb2a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-18280fe18e43043d9e21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fb9-9600000000-04d36ba7639bc85e2023JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a8417274c4493c5b5871JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9100000000-d3712417826a69667981JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-37c486fa03918355413cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f6t-0900000000-218a5babf0ab7c31c498JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-88ad8c9c837a057bb2a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-e3a4fcaa911f14d3790dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-9600000000-04d36ba7639bc85e2023JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a8417274c4493c5b5871JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-d3712417826a69667981JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f6t-0900000000-218a5babf0ab7c31c498JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-f095c04fe81b2890cb1aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-1bb9599f57d5b1c1688bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-37c486fa03918355413cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-f5b771d960092fa83d2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-0900000000-58b4769b89ab3883fb05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6900000000-9f4710d90f0cafac6d7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-d015607beb5136324414JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-ff32add65ca52cbaae83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-3900000000-f2450299b70c3ec0faecJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0f6t-6900000000-77686ecc684f3b46bea6JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Okabe, Y., Katayama, N., Iwama, M., Watanabe, H., Ohgi, K., Irie, M., Nitta, K., Kawauchi, H., Takayanagi, Y., Oyama, F., et, a. l. .. (1991). "Comparative base specificity, stability, and lectin activity of two lectins from eggs of Rana catesbeiana and R. japonica and liver ribonuclease from R. catesbeiana." J Biochem 109:786-790.1917903
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:An, Hong; He, Xifeng; Fu, Jing. Synthesis of cinnamic acid. Huagong Shikan (2005), 19(7), 32-33, 41.
External Links:
ResourceLink
CHEBI ID27386
HMDB IDHMDB00567
Pubchem Compound ID444539
Kegg IDC10438
ChemSpider ID24532348
FOODB IDFDB012052
WikipediaCinnamic_acid
BioCyc IDCPD-674