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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:36:28 UTC
Update Date2021-10-13 06:35:54 UTC
HMDB IDHMDB0033833
Secondary Accession Numbers
  • HMDB33833
Metabolite Identification
Common NameMethyl cinnamate
DescriptionMethyl cinnamate is found in ceylan cinnamon. Methyl cinnamate occurs in essential oils e.g. from Ocimum and Alpinia species Also present in various fruits, e.g. guava, feijoa, strawberry. Methyl cinnamate is a 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.
Structure
Data?1563862468
Synonyms
ValueSource
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
Chemical FormulaC10H10O2
Average Molecular Weight162.1852
Monoisotopic Molecular Weight162.068079564
IUPAC Namemethyl (2Z)-3-phenylprop-2-enoate
Traditional Namemethyl (2Z)-3-phenylprop-2-enoate
CAS Registry Number103-26-4
SMILES
COC(=O)\C=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7-
InChI KeyCCRCUPLGCSFEDV-FPLPWBNLSA-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
  • 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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point36 °CNot Available
Boiling Point260.00 to 262.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility387.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.62Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP10(2.58) g/LALOGPS
logP10(2.52) g/LChemAxon
logS10(-2.9) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.51131661259
DarkChem[M-H]-133.34731661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methyl cinnamate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-2900000000-fa70434583f14596679d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl 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 - Methyl cinnamate 10V, Positive-QTOFsplash10-01q9-0900000000-14824eb7072537bd35302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 20V, Positive-QTOFsplash10-0gx0-2900000000-d9f3a46dc13424ed6d6b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 40V, Positive-QTOFsplash10-0udi-9700000000-786bab6ed4a26977fbf12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 10V, Negative-QTOFsplash10-03di-0900000000-ef3e4fba71ee6c0e61fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 20V, Negative-QTOFsplash10-03fr-0900000000-25c7a5be399d9bcc64812017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 40V, Negative-QTOFsplash10-0fb9-1900000000-fdff058008260fe95cbb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 10V, Negative-QTOFsplash10-03fr-0900000000-b6bdcd0fedc54834c9e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 20V, Negative-QTOFsplash10-0udi-0900000000-20d806534be8d5a510db2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 40V, Negative-QTOFsplash10-004i-9300000000-f637efaadb9d92581a8a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 10V, Positive-QTOFsplash10-001i-0900000000-3285e0b323d2266782ae2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 20V, Positive-QTOFsplash10-0udi-2900000000-abd0c0c325ee40da24cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl cinnamate 40V, Positive-QTOFsplash10-0fb9-9400000000-3c5a8c04f990bda446452021-09-24Wishart 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 IDFDB012001
KNApSAcK IDC00053486
Chemspider ID4933863
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl cinnamate
METLIN IDNot Available
PubChem Compound6428458
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1417571
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.. .