You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:05 UTC
Update Date2019-07-23 06:09:01 UTC
HMDB IDHMDB0031566
Secondary Accession Numbers
  • HMDB31566
Metabolite Identification
Common Name2-Methyl-3-phenyl-2-propenal
Description2-Methyl-3-phenyl-2-propenal, also known as alpha-methyl cinnamaldehyde or 2-methyl-3-phenylacrolein, 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. 2-Methyl-3-phenyl-2-propenal is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methyl-3-phenyl-2-propenal is a sweet, cassia, and cinnamon tasting compound. Outside of the human body, 2-Methyl-3-phenyl-2-propenal is found, on average, in the highest concentration within peppermints. 2-Methyl-3-phenyl-2-propenal has also been detected, but not quantified in, herbs and spices. This could make 2-methyl-3-phenyl-2-propenal a potential biomarker for the consumption of these foods.
Structure
Data?1563862141
Synonyms
ValueSource
2-Methyl-3-phenylacroleinHMDB
2-Methyl-3-phenylacrylaldehydeHMDB
2-MethylcinnamaldehydeHMDB
3-Phenyl-2-methylacroleinHMDB
a-Methylcinnamaldehyde, 8ciHMDB
alpha-Methyl cinnamaldehydeHMDB
alpha-MethylcinnamaldehydeHMDB
alpha-Methylcinnamic aldehydeHMDB
FEMA 2697HMDB
Methyl cinnamic aldehydeHMDB
Chemical FormulaC10H10O
Average Molecular Weight146.1858
Monoisotopic Molecular Weight146.073164942
IUPAC Name(2Z)-2-methyl-3-phenylprop-2-enal
Traditional Name(2Z)-2-methyl-3-phenylprop-2-enal
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-CLFYSBASSA-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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
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
Polarizability16.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kg-6900000000-a06eb85c5a48ce4c78b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-89ab9e019921255893f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-8900000000-b4fddb38764c2c9112fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbl-9200000000-262050491995fee32332Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-221c71bf5191ae84a50eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0900000000-4be4c949046e9bb00c50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-8c03758b70ae4bf0c7e5Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008181
KNApSAcK IDNot Available
Chemspider ID4510994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5354896
PDB IDNot Available
ChEBI ID89992
Food Biomarker OntologyNot Available
VMH 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.. .