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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:49:12 UTC
Update Date2021-10-13 08:25:55 UTC
HMDB IDHMDB0040286
Secondary Accession Numbers
  • HMDB40286
Metabolite Identification
Common NameBenzyl cinnamate
DescriptionBenzyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Benzyl cinnamate is a sweet, apricot, and balsam tasting compound. Benzyl cinnamate is found, on average, in the highest concentration within cumins (Cuminum cyminum). This could make benzyl cinnamate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzyl cinnamate.
Structure
Data?1563863518
Synonyms
ValueSource
Benzyl cinnamic acidGenerator
2-Propenoic acid, 3-phenyl-, phenylmethyl esterHMDB
3-Phenyl-2-propenoic acid phenylmethyl esterHMDB
Benzyl (2E)-3-phenyl-2-propenoateHMDB
Benzyl 3-phenylpropenoateHMDB
Benzyl alcohol cinnamic esterHMDB
Benzyl alcohol, cinnamateHMDB
Benzyl laquo gammaraquo -phenylacrylateHMDB
BenzylcinnamateHMDB
Benzylester kyseliny skoricoveHMDB
CinnameinHMDB
Cinnamic acid, benzyl esterHMDB
FEMA 2142HMDB
trans-Cinnamic acid benzyl esterHMDB
Benzyl (2Z)-3-phenylprop-2-enoic acidGenerator
Benzyl cinnamateMeSH
Chemical FormulaC16H14O2
Average Molecular Weight238.2812
Monoisotopic Molecular Weight238.099379692
IUPAC Namebenzyl (2Z)-3-phenylprop-2-enoate
Traditional Namebenzyl (2Z)-3-phenylprop-2-enoate
CAS Registry Number103-41-3
SMILES
O=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11-
InChI KeyNGHOLYJTSCBCGC-QXMHVHEDSA-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
  • Benzyloxycarbonyl
  • Styrene
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point37 - 39 °CNot Available
Boiling Point195.00 to 200.00 °C. @ 5.00 mm HgThe Good Scents Company Information System
Water Solubility9.27 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.060The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP10(4.03) g/LALOGPS
logP10(4.24) g/LChemAxon
logS10(-4.8) g/LALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity72.44 m³·mol⁻¹ChemAxon
Polarizability26.73 ųChemAxon
Number of Rings2ChemAxon
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]+158.92831661259
DarkChem[M-H]-155.6931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzyl cinnamateO=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C13024.2Standard polar33892256
Benzyl cinnamateO=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C11982.7Standard non polar33892256
Benzyl cinnamateO=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C12099.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl cinnamate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9600000000-b730105b1586b6466dfd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl cinnamate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl 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 - Benzyl cinnamate 10V, Positive-QTOFsplash10-000i-1590000000-d59e744cc0df894ea1e32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 20V, Positive-QTOFsplash10-001i-2920000000-6c944a45122d144c5be22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 40V, Positive-QTOFsplash10-0006-9700000000-0cef35c32391ca8190982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 10V, Negative-QTOFsplash10-002r-0890000000-0c8dd31dd420da8aaa722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 20V, Negative-QTOFsplash10-004s-1910000000-475c63c855b416c3406c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 40V, Negative-QTOFsplash10-004i-3900000000-2e7d267ea7a7698e41652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 10V, Negative-QTOFsplash10-000i-0090000000-4398f96ca62f3f4192ee2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 20V, Negative-QTOFsplash10-054x-7930000000-651e889cc06e8e51210c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 40V, Negative-QTOFsplash10-0a6u-7920000000-7112ddc3c777a8c0212f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 10V, Positive-QTOFsplash10-000i-1390000000-66fcd7f42ef3052684092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 20V, Positive-QTOFsplash10-000x-5920000000-11bd2d1f6032302ebf182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl cinnamate 40V, Positive-QTOFsplash10-0006-9600000000-78322ccdb4fc9f711f782021-09-23Wishart 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 IDFDB020007
KNApSAcK IDNot Available
Chemspider ID21391699
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzyl cinnamate
METLIN IDNot Available
PubChem Compound15558051
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1014311
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.. .