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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:36:31 UTC
Update Date2019-07-23 06:14:28 UTC
HMDB IDHMDB0033834
Secondary Accession Numbers
  • HMDB33834
Metabolite Identification
Common NameEthyl cinnamate
DescriptionEthyl cinnamate, also known as fema 2430, belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. The p-methoxy derivative is reported to be a monoamine oxidase inhibitor. It can be synthesized by the esterification reaction involving ethanol and cinnamic acid in the presence of sulfuric acid. Ethyl cinnamate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl cinnamate is a sweet, balsam, and berry tasting compound. Outside of the human body, Ethyl cinnamate has been detected, but not quantified in, several different foods, such as tarragons, tamarinds, evergreen blackberries, corns, and ceylon cinnamons. This could make ethyl cinnamate a potential biomarker for the consumption of these foods. Pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note". Ethyl cinnamate is the ester of cinnamic acid and ethanol. It is present in the essential oil of cinnamon.
Structure
Data?1563862468
Synonyms
ValueSource
Ethyl cinnamic acidGenerator
(e)-Ethyl cinnamateHMDB
3-Phenyl-ethyl ester(e)-2-propenoic acidHMDB
Ethyl (2E)-3-phenyl-2-propenoateHMDB
Ethyl (2E)-3-phenylacrylateHMDB
Ethyl (e)-cinnamateHMDB
Ethyl cinnamate, transHMDB
Ethyl trans-cinnamateHMDB
FEMA 2430HMDB
trans-Ethyl cinnamateHMDB
Ethyl (2Z)-3-phenylprop-2-enoic acidGenerator
Chemical FormulaC11H12O2
Average Molecular Weight176.2118
Monoisotopic Molecular Weight176.083729628
IUPAC Nameethyl (2Z)-3-phenylprop-2-enoate
Traditional Nameethyl (2Z)-3-phenylprop-2-enoate
CAS Registry Number4192-77-2
SMILES
CCOC(=O)\C=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8-
InChI KeyKBEBGUQPQBELIU-HJWRWDBZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acid esters
Direct ParentCinnamic acid esters
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Styrene
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point12 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP3.1ALOGPS
logP2.87ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.58 m³·mol⁻¹ChemAxon
Polarizability19.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fai-3900000000-a8d987a548c9fa6c7f2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-061762de8ea8d97b5cfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4900000000-c561bd073358d027fd92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-9500000000-f3a99db2bb06534a646bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-b7e60492dd7bc9500be1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-2240e17326bb0662c91cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fba-3900000000-0d609d9bc26a486298caSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012002
KNApSAcK IDC00035614
Chemspider ID4447700
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl cinnamate
METLIN IDNot Available
PubChem Compound5284656
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .