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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
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
  • trans-Cinnamic acid
  • β-Phenylacrylic 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
BalsamFDB008784
CinnamonFDB008784
HoneyFDB008784
StoraxFDB008784
SweetFDB008784
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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 IDFDB008784
WikipediaCinnamic_acid
BioCyc IDCPD-674