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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:16 UTC
Update Date2023-02-21 17:20:20 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. 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
Data?1677000020
Synonyms
ValueSource
alpha-PentylcinnamaldehydeKegg
a-PentylcinnamaldehydeGenerator
Α-pentylcinnamaldehydeGenerator
a-AmylcinnamaldehydeHMDB
Α-amylcinnamaldehydeHMDB
alpha-Amylcinnamic aldehydeHMDB
2-PentylcinnamaldehydeHMDB
(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
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 Descriptors
Ontology
Physiological effect
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point80 °CNot Available
Boiling Point287.00 to 290.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility8.54 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.357 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.49931661259
DarkChem[M-H]-146.74531661259
DeepCCS[M+H]+153.73530932474
DeepCCS[M-H]-151.27430932474
DeepCCS[M-2H]-186.28630932474
DeepCCS[M+Na]+162.02830932474
AllCCS[M+H]+148.232859911
AllCCS[M+H-H2O]+144.232859911
AllCCS[M+NH4]+152.032859911
AllCCS[M+Na]+153.132859911
AllCCS[M-H]-153.632859911
AllCCS[M+Na-2H]-154.332859911
AllCCS[M+HCOO]-155.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Pentyl-3-phenyl-2-propenalCCCCC\C(C=O)=C\C1=CC=CC=C12204.4Standard polar33892256
2-Pentyl-3-phenyl-2-propenalCCCCC\C(C=O)=C\C1=CC=CC=C11613.4Standard non polar33892256
2-Pentyl-3-phenyl-2-propenalCCCCC\C(C=O)=C\C1=CC=CC=C11653.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Pentyl-3-phenyl-2-propenal EI-B (Non-derivatized)splash10-016u-6910000000-76423c557f3f4dd7528d2018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pentyl-3-phenyl-2-propenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-9810000000-5d50147550573496265f2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Pentyl-3-phenyl-2-propenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0gdi-4910000000-4ce2bc2a00dff2dc48e02014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 10V, Positive-QTOFsplash10-0udi-1390000000-ca55afbc23de86cbd2c42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 20V, Positive-QTOFsplash10-0zml-9620000000-1f4c1daee5177bed977e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 40V, Positive-QTOFsplash10-052f-9200000000-7ed528bae1e65bf013022017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 10V, Negative-QTOFsplash10-0udi-0090000000-aac6ad0789512ca03c132017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 20V, Negative-QTOFsplash10-0fk9-0950000000-e06e3c42a256d36ea1cd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 40V, Negative-QTOFsplash10-00di-4900000000-f5943dbfda6753242ead2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 10V, Negative-QTOFsplash10-0udi-1690000000-d3d5e2fec8076647fbda2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 20V, Negative-QTOFsplash10-0udi-5390000000-843a38d8d2580a4cccb32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 40V, Negative-QTOFsplash10-014l-6900000000-dd30a61af9f6506cb0162021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 10V, Positive-QTOFsplash10-0udi-2490000000-7f7af5c40156074155572021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 20V, Positive-QTOFsplash10-0006-9510000000-dbe3977208f978e698c02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Pentyl-3-phenyl-2-propenal 40V, Positive-QTOFsplash10-00mo-8900000000-e1178a4f97d239e6ecbe2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1361549
KEGG Compound IDC12288
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1712058
PDB IDNot Available
ChEBI ID32318
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001011
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]