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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:16 UTC
Update Date2018-05-19 23:38:27 UTC
HMDB IDHMDB0031313
Secondary Accession Numbers
  • HMDB0061830
  • HMDB31313
  • HMDB61830
Metabolite Identification
Common Name2-Pentyl-3-phenyl-2-propenal
Description2-Pentyl-3-phenyl-2-propenal, also known as alpha-amylcinnamaldehyde or pentylcinnamaldehyde, is a member of the class of compounds known as cinnamaldehydes. Cinnamaldehydes are organic aromatic compounds containing a cinnamaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. 2-Pentyl-3-phenyl-2-propenal is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Pentyl-3-phenyl-2-propenal is a flavouring agent and has a sweet, floral, and fruity taste. It is a non-carcinogenic (not listed by IARC) potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
alpha-PentylcinnamaldehydeKegg
a-PentylcinnamaldehydeGenerator
α-pentylcinnamaldehydeGenerator
a-AmylcinnamaldehydeGenerator
α-amylcinnamaldehydeGenerator
alpha-Amylcinnamic aldehydeMeSH
2-PentylcinnamaldehydeMeSH
(2Z)-2-BenzylideneheptanalHMDB
(2Z)-2-Pentyl-3-phenyl-2-propenalHMDB
2-(Phenylmethylene)-heptanalHMDB
2-(Phenylmethylene)heptanalHMDB
2-(Phenylmethylene)heptanal, 9ciHMDB
2-Benzylidene-heptanalHMDB
2-BenzylideneheptanalHMDB
2-Propenal, 3-phenyl-, monopentyl derivHMDB
a-Pentyl-b-phenylacroleinHMDB
a-Pentylcinnamaldehyde, 8ciHMDB
alpha-Amyl cinnamaldehydeHMDB
alpha-Amyl-alpha-amylcinnamaldehydeHMDB
alpha-Amyl-beta-phenylacroleinHMDB
alpha-AmylcinnamaldehydeHMDB
alpha-AmylcinnamicaldehydeHMDB
alpha-N-AmylcinnamaldehydeHMDB
alpha-N-Amylcinnamic aldehydeHMDB
alpha-Pentyl-beta-phenylacroleinHMDB
alpha-Pentyl-cinnamaldehydeHMDB
Amyl cinnamalHMDB
Amyl cinnamic aldehydeHMDB
AmylcinnamalHMDB
AmylcinnamaldehydeHMDB
Amylcinnamic acid aldehydeHMDB
Amylcinnamic aldehydeHMDB
FEMA 2061HMDB
FlomineHMDB
Heptanal, 2-(phenylmethylene)HMDB
JasmalHMDB
JasminalHMDB
JasminaldehydeHMDB
Jasmine aldehydeHMDB
PentylcinnamaldehydeHMDB
Pentyl cinnamaldehydeHMDB
Chemical FormulaC14H18O
Average Molecular Weight202.2921
Monoisotopic Molecular Weight202.135765198
IUPAC Name(2Z)-2-(phenylmethylidene)heptanal
Traditional Nameamyl cinnamic aldehyde
CAS Registry Number122-40-7
SMILES
CCCCC\C(C=O)=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H18O/c1-2-3-5-10-14(12-15)11-13-8-6-4-7-9-13/h4,6-9,11-12H,2-3,5,10H2,1H3/b14-11-
InChI KeyHMKKIXGYKWDQSV-KAMYIIQDSA-N
Chemical Taxonomy
DescriptionThis compound 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 Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point80 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP3.93ALOGPS
logP4.15ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity64.9 m³·mol⁻¹ChemAxon
Polarizability24.63 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-9810000000-5d50147550573496265fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1390000000-ca55afbc23de86cbd2c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zml-9620000000-1f4c1daee5177bed977eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-7ed528bae1e65bf01302View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-aac6ad0789512ca03c13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0950000000-e06e3c42a256d36ea1cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-f5943dbfda6753242eadView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0gdi-4910000000-4ce2bc2a00dff2dc48e0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC12288
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1712058
PDB IDNot Available
ChEBI ID32318
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Parhi R, Suresh P, Mondal S, Kumar PM: Novel penetration enhancers for skin applications: a review. Curr Drug Deliv. 2012 Mar;9(2):219-30. [PubMed:22023208 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  3. Wikipedia [Link]