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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:36:31 UTC
Update Date2022-03-07 02:53:52 UTC
HMDB IDHMDB0033834
Secondary Accession Numbers
  • HMDB33834
Metabolite Identification
Common NameEthyl cinnamate
DescriptionEthyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Ethyl cinnamate is a sweet, balsam, and berry tasting compound. Ethyl cinnamate is found, on average, in the highest concentration within red wine. Ethyl cinnamate has also been detected, but not quantified in, several different foods, such as tamarinds (Tamarindus indica), prickly pears (Opuntia), chinese cinnamons (Cinnamomum aromaticum), tarragons (Artemisia dracunculus), and fruits. This could make ethyl cinnamate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Ethyl cinnamate.
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

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point12 °CNot Available
Boiling Point269.00 to 270.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility160.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.708 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.46931661259
DarkChem[M-H]-137.73931661259
DeepCCS[M+H]+137.81530932474
DeepCCS[M-H]-135.14330932474
DeepCCS[M-2H]-171.12630932474
DeepCCS[M+Na]+146.66530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl cinnamateCCOC(=O)\C=C/C1=CC=CC=C12121.1Standard polar33892256
Ethyl cinnamateCCOC(=O)\C=C/C1=CC=CC=C11401.5Standard non polar33892256
Ethyl cinnamateCCOC(=O)\C=C/C1=CC=CC=C11507.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl cinnamate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fai-3900000000-a8d987a548c9fa6c7f2d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl cinnamate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl cinnamate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 10V, Positive-QTOFsplash10-004i-0900000000-061762de8ea8d97b5cfa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 20V, Positive-QTOFsplash10-001i-4900000000-c561bd073358d027fd922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 40V, Positive-QTOFsplash10-0ufu-9500000000-f3a99db2bb06534a646b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 10V, Negative-QTOFsplash10-004i-0900000000-b7e60492dd7bc9500be12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 20V, Negative-QTOFsplash10-004i-2900000000-2240e17326bb0662c91c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 40V, Negative-QTOFsplash10-0fba-3900000000-0d609d9bc26a486298ca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 10V, Positive-QTOFsplash10-001i-0900000000-ba8ba15dbd02ca4eec9e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 20V, Positive-QTOFsplash10-0ue9-1900000000-935e6ce292933740c4932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 40V, Positive-QTOFsplash10-0ufr-6900000000-f309c938a129dc5470f62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 10V, Negative-QTOFsplash10-004i-0900000000-d4773b1f6c6f68c13fae2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 20V, Negative-QTOFsplash10-0udi-1900000000-002df14c18a57d0f27a02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl cinnamate 40V, Negative-QTOFsplash10-0fb9-9500000000-502a9fa131a679c46ac92021-09-24Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1551521
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.. .