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Showing Compound Methyl cinnamate (FDB012001)

Record Information
Version1.0
Creation date2010-04-08 22:09:56 UTC
Update date2019-11-26 03:05:55 UTC
Primary IDFDB012001
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyl cinnamate
DescriptionOccurs in essential oils e.g. from Ocimum and Alpinia subspecies Also present in various fruits, e.g. guava, feijoa, strawberry. Flavouring agent Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. It is found naturally in a variety of plants, including in fruits, like strawberry, and some culinary spices, such as Sichuan pepper and some varieties of basil. Eucalyptus olida has the highest known concentrations of methyl cinnamate (98%) with a 2-6% fresh weight yield in the leaf and twigs. Methyl cinnamate is found in many foods, some of which are chinese cinnamon, fruits, herbs and spices, and sweet basil.
CAS Number103-26-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Methyl cinnamic acidGenerator
3-Phenyl-methyl ester(2E)-2-propenoic acidHMDB
3-Phenyl-methyl ester(e)-2-propenoic acidHMDB
Cinnamic acid,methyl ester (trans)HMDB
FEMA 2698HMDB
Methyl (2E)-3-phenyl-2-propenoateHMDB
Methyl (2E)-3-phenylacrylateHMDB
Methyl (e)-cinnamateHMDB
Methyl cinnamate, (e)HMDB
Methyl ester(e)-cinnamic acidHMDB
Methyl trans-cinnamateHMDB
trans-Methyl cinnamateHMDB
Methyl (2Z)-3-phenylprop-2-enoic acidGenerator
2-propenoic acid, 3-phenyl-, methyl ester, (2E)-biospider
2-Propenoic acid, 3-phenyl-, methyl ester, (E)-biospider
3-Phenyl-methyl ester(2e)-2-propenoic acidHMDB
Cinnamic acid, methyl ester, (e)-biospider
Trans-methyl cinnamatebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP2.58ALOGPS
logP2.52ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.83 m³·mol⁻¹ChemAxon
Polarizability17.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H10O2
IUPAC namemethyl (2Z)-3-phenylprop-2-enoate
InChI IdentifierInChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7-
InChI KeyCCRCUPLGCSFEDV-FPLPWBNLSA-N
Isomeric SMILESCOC(=O)\C=C/C1=CC=CC=C1
Average Molecular Weight162.1852
Monoisotopic Molecular Weight162.068079564
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
  • Fatty acyl
  • Benzenoid
  • Methyl ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 74.06%; H 6.21%; O 19.73%DFC
Melting PointMp 36°DFC
Boiling PointBp 263°DFC
Experimental Water SolubilityNot Available
Experimental logP2.62HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMethyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ue9-2900000000-fa70434583f14596679dSpectrum
Predicted GC-MSMethyl cinnamate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-14824eb7072537bd35302017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gx0-2900000000-d9f3a46dc13424ed6d6b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9700000000-786bab6ed4a26977fbf12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ef3e4fba71ee6c0e61fa2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-0900000000-25c7a5be399d9bcc64812017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-1900000000-fdff058008260fe95cbb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-0900000000-b6bdcd0fedc54834c9e62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-20d806534be8d5a510db2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-f637efaadb9d92581a8a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-3285e0b323d2266782ae2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2900000000-abd0c0c325ee40da24cb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9400000000-3c5a8c04f990bda446452021-09-24View Spectrum
NMRNot Available
ChemSpider ID4933863
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6428458
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33833
CRC / DFC (Dictionary of Food Compounds) IDHCV54-E:HCL39-F
EAFUS ID2290
Dr. Duke IDCINNAMIC-ACID-METHYL-ESTER|METHYL-CINNAMATE|(E)-METHYL-CINNAMATETRANS-CINNAMIC-ACID-METHYL-ESTER
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID103-26-4
GoodScent IDrw1417571
SuperScent IDNot Available
Wikipedia IDMethyl_cinnamate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
strawberry
  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. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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. 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.
cherry
  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).