2-phenylbut-2-enal (YMDB01440)

Identification
YMDB IDYMDB01440
Name2-phenylbut-2-enal
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-phenylbut-2-enal belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 2-phenylbut-2-enal is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-phenylbut-2-enal may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2Z)-2-Phenyl-2-butenal
  • 2-Butenal, 2-phenyl
  • 2-Phenyl-2-buten-1-al
  • 2-phenyl-2-butenal
  • 2-Phenylacetaldehyde, alpha-ethylidene
  • 2-phenylcrotonaldehyde
  • alpha-ethylidenbenzeneacetaldehyde
  • alpha-ethylidene benzene acetaldehyde
  • alpha-Ethylidene-phenylacetaldehyde
  • Benzeneacetaldehyde, a-ethylidene-
CAS number4411-89-6
WeightAverage: 146.1858
Monoisotopic: 146.073164942
InChI KeyDYAOGZLLMZQVHY-XNWCZRBMSA-N
InChIInChI=1S/C10H10O/c1-2-9(8-11)10-6-4-3-5-7-10/h2-8H,1H3/b9-2+
IUPAC Name2-phenylbut-2-enal
Traditional IUPAC Name2-phenylbut-2-enal
Chemical FormulaC10H10O
SMILES[H]C(=O)C(=C([H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Styrene
  • 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
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP2.74ALOGPS
logP2.43ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.49 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BeanyNot Available
CocoaNot Available
CortexNot Available
HoneyNot Available
NarcissusNot Available
NuttyNot Available
RadishNot Available
SweetNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-c1ccc79271fc91dfd3e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-fcacddcba2fa79261f5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-2900000000-2d55ec5f0c3cd9cdaacfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9600000000-ba47697cec40b1ee8dd2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-cd79bb539d105536d8cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-0ee4c3daf24682a7ac9bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9400000000-3c0d3d5838245f22a585JSpectraViewer
References
References:
  • Mahadevan, K., Farmer, L. (2006). "Key odor impact compounds in three yeast extract pastes." J Agric Food Chem 54:7242-7250.16968089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID5363896
Kegg IDNot Available
ChemSpider ID19256
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available