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Ethylcinnamate (YMDB01689)

Identification
YMDB IDYMDB01689
NameEthylcinnamate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthylcinnamate 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. Ethylcinnamate is a weakly acidic compound (based on its pKa). Ethylcinnamate may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Propenoic acid, 3-phenyl-, ethyl ester
  • 3-Phenylpropenoic acid ethyl
  • Cinnamic acid ethyl ester
  • Cinnamic acid, ethyl ester
  • Ethyl (2E)-3-phenyl-2-propenoate
  • Ethyl 3-phenyl-2-propenoate
  • Ethyl 3-phenylacrylate
  • Ethyl 3-phenylpropenoate
  • Ethyl beta-phenylacrylate
  • Ethyl cinnamate
  • Ethyl trans-cinnamate
  • Ethylcinnamic acid
CAS number103-36-6
WeightAverage: 175.2038
Monoisotopic: 175.075904596
InChI KeyPPDRIRGALQZEPP-BQYQJAHWSA-M
InChIInChI=1S/C11H12O2/c1-2-9-5-3-4-6-10(9)7-8-11(12)13/h3-8H,2H2,1H3,(H,12,13)/p-1/b8-7+
IUPAC Name(2E)-3-(2-ethylphenyl)prop-2-enoate
Traditional IUPAC Name(2E)-3-(2-ethylphenyl)prop-2-enoate
Chemical FormulaC11H11O2
SMILESCCC1=CC=CC=C1\C=C\C([O-])=O
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
  • Organic anion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateLiquid
Charge-1
Melting point7.0 °C
Experimental Properties
PropertyValueReference
Water Solubility0.178 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP2.99 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP3.34ALOGPS
logP3.09ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.54 m³·mol⁻¹ChemAxon
Polarizability18.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-195f5e512d6eed18790aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0900000000-82bf4ffc975988474e91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbl-1900000000-562515f3d51805558bc7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-add430840f9e1f42caf4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-7582f38d2428080338bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-1900000000-bd55f67983b3968adac2JSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID17841636
Kegg IDC06359
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available