Showing Compound Card for alpha-Methylcinnamaldehyde (CDB000556)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:43:31 UTC
Updated at2020-11-18 16:35:16 UTC
CannabisDB IDCDB000556
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Methylcinnamaldehyde
Descriptionα-Methylcinnamaldehyde belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. α-Methylcinnamaldehyde has a cinnamon, balsamic odor with a spicy, sweet and woody taste. α-Methylcinnamaldehyde is a methylated, more stable, derivative of cinnamaldehyde. Cinnamaldehyde is a pale yellow, viscous liquid which occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90 % cinnamaldehyde. Cinnamaldehyde was first isolated from cinnamon essential oil in 1834 and was first synthesized in the laboratory by the Italian chemist Luigi Chiozza in 1854. α-Methylcinnamaldehyde has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 )
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC10H10O
Average Molecular Weight146.19
Monoisotopic Molecular Weight146.0732
IUPAC Name(2E)-2-methyl-3-phenylprop-2-enal
Traditional Name2-propenal, 2-methyl-3-phenyl-
CAS Registry Number101-39-3
SMILES
C\C(C=O)=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H10O/c1-9(8-11)7-10-5-3-2-4-6-10/h2-8H,1H3/b9-7+
InChI KeyVLUMOWNVWOXZAU-VQHVLOKHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamaldehydes
Sub ClassNot Available
Direct ParentCinnamaldehydes
Alternative Parents
Substituents
  • Cinnamaldehyde
  • Benzenoid
  • Monocyclic benzene moiety
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.31ALOGPS
logP2.37ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.49 m³·mol⁻¹ChemAxon
Polarizability16.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-3c372336f298738d45382016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4900000000-e0cbf725690742892c092016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9400000000-0941a9778032f54434b72016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-852f0c2718c7833d3c7b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-2281c62f8802f3de7cfc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar9-9700000000-667d30b1499448d092c12016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5372813
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]