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Showing Compound Ethyl cinnamate (FDB012002)

Record Information
Version1.0
Creation date2010-04-08 22:09:56 UTC
Update date2019-11-26 03:05:56 UTC
Primary IDFDB012002
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 ceylon cinnamons (Cinnamomum verum), evergreen blackberries (Rubus laciniatus), tamarinds (Tamarindus indica), blackberries (Rubus), and tarragons (Artemisia dracunculus). 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.
CAS Number4192-77-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
(e)-ethyl cinnamatebiospider
2-Propenoic acid, 3-phenyl-, ethyl ester, (E)-biospider
Trans-ethyl cinnamatebiospider
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
Chemical FormulaC11H12O2
IUPAC nameethyl (2Z)-3-phenylprop-2-enoate
InChI IdentifierInChI=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
Isomeric SMILESCCOC(=O)\C=C/C1=CC=CC=C1
Average Molecular Weight176.2118
Monoisotopic Molecular Weight176.083729628
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 74.98%; H 6.86%; O 18.16%DFC
Melting PointMp 12°DFC
Boiling PointBp24 159°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd2525 1.05DFC
Refractive Indexn20D 1.5590DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEthyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fai-3900000000-a8d987a548c9fa6c7f2dSpectrum
Predicted GC-MSEthyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEthyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-061762de8ea8d97b5cfa2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4900000000-c561bd073358d027fd922017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-9500000000-f3a99db2bb06534a646b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-b7e60492dd7bc9500be12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-2240e17326bb0662c91c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fba-3900000000-0d609d9bc26a486298ca2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-ba8ba15dbd02ca4eec9e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-1900000000-935e6ce292933740c4932021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-6900000000-f309c938a129dc5470f62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-d4773b1f6c6f68c13fae2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-002df14c18a57d0f27a02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9500000000-502a9fa131a679c46ac92021-09-24View Spectrum
NMRNot Available
ChemSpider ID4447700
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5284656
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33834
CRC / DFC (Dictionary of Food Compounds) IDHCV54-E:HCL40-Z
EAFUS ID1162
Dr. Duke IDCINNAMIC-ACID-ETHYL-ESTER|ETHYL-CINNAMATE
BIGG IDNot Available
KNApSAcK IDC00035614
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID4192-77-2
GoodScent IDrw1014811
SuperScent ID637758
Wikipedia IDEthyl_cinnamate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
flower
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
honey
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
cinnamon
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
plum
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
berry
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).