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Record Information
Version1.0
Creation Date2014-09-11 05:21:20 UTC
Update Date2016-11-09 01:09:14 UTC
Accession NumberCHEM003853
Identification
Common NameBenzyl cinnamate
ClassSmall Molecule
DescriptionBenzyl cinnamate is found in cumin. Benzyl cinnamate is isolated from various plant species. Benzyl cinnamate is present in Sumatra and Penang benzoin, Peru and tolu balsams, main constituent of copaiba balsam. Benzyl cinnamate is a flavouring agent.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
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 Mass238.281 g/mol
Monoisotopic Mass238.099 g/mol
CAS Registry Number103-41-3
IUPAC Namebenzyl (2Z)-3-phenylprop-2-enoate
Traditional Namebenzyl (2Z)-3-phenylprop-2-enoate
SMILESO=C(OCC1=CC=CC=C1)\C=C/C1=CC=CC=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point37 - 39 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP4.03ALOGPS
logP4.24ChemAxon
logS-4.8ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0f6x-9600000000-b730105b1586b6466dfdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1590000000-d59e744cc0df894ea1e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2920000000-6c944a45122d144c5be2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9700000000-0cef35c32391ca819098View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-0890000000-0c8dd31dd420da8aaa72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004s-1910000000-475c63c855b416c3406cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3900000000-2e7d267ea7a7698e4165View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-4398f96ca62f3f4192eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-054x-7930000000-651e889cc06e8e51210cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-7920000000-7112ddc3c777a8c0212fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1390000000-66fcd7f42ef305268409View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-5920000000-11bd2d1f6032302ebf18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9600000000-78322ccdb4fc9f711f78View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0040286
FooDB IDFDB020007
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzyl cinnamate
Chemspider ID21391699
ChEBI IDNot Available
PubChem Compound ID15558051
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.