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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:36:28 UTC
Update Date2019-07-23 06:14:28 UTC
HMDB IDHMDB0033833
Secondary Accession Numbers
  • HMDB33833
Metabolite Identification
Common NameMethyl cinnamate
DescriptionMethyl cinnamate, also known as fema 2698, belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Methyl cinnamate is an extremely weak basic (essentially neutral) compound (based on its pKa). Methyl cinnamate is a sweet, balsam, and cherry tasting compound. Outside of the human body, Methyl cinnamate is found, on average, in the highest concentration within a few different foods, such as sweet basils, cumins, and safflowers. Methyl cinnamate has also been detected, but not quantified in, several different foods, such as pepper (spice), fruits, peppermints, chinese cinnamons, and sweet bay. This could make methyl cinnamate a potential biomarker for the consumption of these foods. It is known to attract males of various orchid bees, such as Aglae caerulea. The oral LD50 for rats is 2610 mg/kg. Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. White Ruffle (Crespa blanca)Stanhopea embreei, an orchidVanillaModerately toxic by ingestion. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry. Purple Lovingly (Querendona Morada)Ocimum americanum cv.
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

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point36 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.62Not Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available138.51131661259
DarkChem[M-H]-PredictedNot Available133.34731661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-2900000000-fa70434583f14596679d2017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-14824eb7072537bd35302017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gx0-2900000000-d9f3a46dc13424ed6d6b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9700000000-786bab6ed4a26977fbf12017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ef3e4fba71ee6c0e61fa2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-0900000000-25c7a5be399d9bcc64812017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-1900000000-fdff058008260fe95cbb2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-0900000000-b6bdcd0fedc54834c9e62021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-20d806534be8d5a510db2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-f637efaadb9d92581a8a2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-3285e0b323d2266782ae2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2900000000-abd0c0c325ee40da24cb2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9400000000-3c5a8c04f990bda446452021-09-08View 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 IDNot Available
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
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.. .