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Identification
YMDB IDYMDB01654
NameCinnamaldehyde
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCinnamaldehyde, also known as 3-fenylpropenal or 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. Cinnamaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Cinnamaldehyde is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (2E)-3-Phenyl-2-propenal
  • (2E)-3-Phenylacrylaldehyde
  • (e)-3-Phenyl-2-propenal
  • (e)-3-Phenyl-propenal
  • (e)-3-Phenylpropenal
  • (e)-Cinnamaldehyde
  • (e)-Cinnamic aldehyde
  • (e)-Phenylvinyl aldehyde
  • 3-Fenylpropenal
  • 3-Phenyl-2-propen-1-al
  • 3-Phenyl-2-propenaldehyde
  • 3-Phenylacrolein
  • 3-Phenylacrylaldehyde
  • 3-Phenylprop-2-enal
  • 3-Phenylprop-2-enaldehyde
  • 3-Phenylpropenal
  • Benzylideneacetaldehyde
  • beta-Phenylacrolein
  • beta-Phenylcrolein
  • Cinnamal
  • Cinnamic aldehyde
  • Cinnamic aldehyde, (e)-isomer
  • Cinnamyl aldehyde
  • Cinnamylaldehyde
  • Cinnemaldehyde
  • Supercinnamaldehyde
  • trans-3-Phenyl-2-propenal
  • trans-3-Phenylprop-2-enaldehyde
  • trans-Cinnamaldehyde
  • trans-Cinnamic aldehyde
  • trans-Cinnamylaldehyde
  • 2E)-3-Phenyl-2-propenal
  • (E)-3-Phenylacrolein
  • (E)-3-Phenylprop-2-en-1-al
  • (E)-3-Phenylprop-2-enal
  • (E)-3-Phenylprop-2-enone
  • E-Cinnamyl aldehyde
  • trans-3-Phenylpropenal
  • trans-Benzenepropenal
  • 3-Phenyl-2-propenal
  • 3-Phenyl-2-propene-1-al
CAS number104-55-2
WeightAverage: 132.1592
Monoisotopic: 132.057514878
InChI KeyKJPRLNWUNMBNBZ-QPJJXVBHSA-N
InChIInChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
IUPAC Name(2E)-3-phenylprop-2-enal
Traditional IUPAC Namecinnamal
Chemical FormulaC9H8O
SMILESO=C\C=C\C1=CC=CC=C1
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
  • Styrene
  • 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
Physical Properties
StateLiquid
Charge0
Melting point-7.5 °C
Experimental Properties
PropertyValueReference
Water Solubility1.42 mg/mL at 25 oC [VALVANI,SC et al. (1981)]PhysProp
LogP1.90 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP2ALOGPS
logP1.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.13 m³·mol⁻¹ChemAxon
Polarizability14.48 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
CinnamonFDB030727
CloveFDB030727
Red hotsFDB030727
SpiceFDB030727
SweetFDB030727
WarmFDB030727
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-3900000000-52db83b595237437ab08JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-5900000000-540c43f6893b35e8a105JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-5900000000-482f8b5c30c53689d8ebJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-3900000000-9d274f5e3981ab662650JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0900000000-4f0ad7748ac21b7320c9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-6900000000-ecaba4b9d657020c3f4cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-0900000000-c02b7869dea8f1113cb4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-2900000000-d89aa99ef7a6ae16b942JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ugi-8900000000-14f14e29c81360ebdd4bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-3900000000-52db83b595237437ab08JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-4900000000-e9eb0053986096f21c83JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a59-5900000000-a125425df0f09bb01129JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-056r-9300000000-043ea317ed08a1cbacfbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-39ab07ef5d737e851671JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0f89-5900000000-f27dd11a8900d729bd19JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0f89-5900000000-4e11cf955911f9ca7da2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-001i-3900000000-9d274f5e3981ab662650JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-001i-0900000000-4f0ad7748ac21b7320c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0f89-6900000000-e363e674a4ec6e092f26JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positivesplash10-001i-0900000000-c02b7869dea8f1113cb4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-001i-2900000000-7339e3ff66ab63ba3409JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0ugi-8900000000-1b72d0d216af15365444JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-067i-2900000000-76d2db81f3822a698f0aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-067i-2900000000-76d2db81f3822a698f0aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-4b1b083c8fdb2a27206bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-2900000000-eee6045375789bd7b511JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-ffef407879854d06bd7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-074611feed644fd89c07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-cbf5bec188b738c514afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p6-9600000000-5eb930cf87b199a5f449JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16731
HMDB IDHMDB03441
Pubchem Compound ID637511
Kegg IDC00903
ChemSpider ID553117
FOODB IDFDB030727
Wikipedia IDCinnamaldehyde
BioCyc IDNot Available