acrolein (YMDB00812)

Identification
YMDB IDYMDB00812
Nameacrolein
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAcrolein (propenal) is the simplest unsaturated aldehyde. It is produced widely but is most often immediately reacted with other products due to its instability and toxicity. Acrolein is a potent inhibitor of yeast alcohol dehydrogenase. It has a piercing, disagreeable, acrid smell similar to that of burning fat. It is responsible for cauliflower-like aromas as a result of bacterial spoilage. [PMID: 10092940]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Propen-1-one
  • 2-Propenal
  • 2-Propenaldehyde
  • Acquinite
  • Acraldehyde
  • Acraldehydeacroleina
  • Acrolein
  • Acroleina
  • Acroleine
  • Acrylaldehyd
  • Acrylaldehyde
  • Acrylic Aldehyde
  • Akrolein
  • Akroleina
  • Aldehyde acrylique
  • Aldeide acrilica
  • Allyl aldehyde
  • Aqualin
  • Aqualine
  • Biocide
  • Crolean
  • Ethylene aldehyde
  • Magnacide
  • Magnacide H
  • Prop-2-En-1-al
  • Propenal
  • Propylene aldehyde
  • Slimicide
  • trans-Acrolein
  • Aldehyde, acrylic
  • Aldehyde, allyl
  • Aldehyde, ethylene
  • CH2=chcho
  • Magnacide H and b
  • Papite
  • Prop-2-enal
  • Propenaldehyde
  • trans-Acrolein formylethylene
  • 2 Propenal
CAS number107-02-8
WeightAverage: 56.0633
Monoisotopic: 56.02621475
InChI KeyHGINCPLSRVDWNT-UHFFFAOYSA-N
InChIInChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2
IUPAC Nameprop-2-enal
Traditional IUPAC Nameacrolein
Chemical FormulaC3H4O
SMILES[H]C(=C)C([H])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Enal
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-87.7 °C
Experimental Properties
PropertyValueReference
Water Solubility212 mg/mL at 25 oC [SEIDELL,A (1941)]PhysProp
LogP-0.01 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility107 g/LALOGPS
logP0.18ALOGPS
logP0.37ChemAxon
logS0.28ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.37 m³·mol⁻¹ChemAxon
Polarizability5.58 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
AlmondFDB008307
CherryFDB008307
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 - EI-B (Non-derivatized)splash10-0a4i-9000000000-f6aba25388da7855f3ebJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-a667e77a9d666459b411JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-f6aba25388da7855f3ebJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-a667e77a9d666459b411JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-4a086c1c9c7836b7b307JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-cf50f66835baacbc5db4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-abefe6f7a672744326c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-32a4911454ef635f19edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-4740fe3b45257adba96aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-e578c9fb2097eb472d12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-c28d7e42ec75bd010f50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-af8a08e40e7604e1b105JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-a0d6dd919aed0acdb715JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-f12145ad941c7b169c50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-23a60e5f52ca732e0f56JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-23a60e5f52ca732e0f56JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-23a60e5f52ca732e0f56JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-34c0891db414206d2b40JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Kwolek-Mirek, M., Bednarska, S., Bartosz, G., Bilinski, T. (2009). "Acrolein toxicity involves oxidative stress caused by glutathione depletion in the yeast Saccharomyces cerevisiae." Cell Biol Toxicol 25:363-378.18563599
  • Ouyang, X., Tran, Q. T., Goodwin, S., Wible, R. S., Sutter, C. H., Sutter, T. R. (2011). "Yap1 activation by H2O2 or thiol-reactive chemicals elicits distinct adaptive gene responses." Free Radic Biol Med 50:1-13.20971184
  • Trotter, E. W., Collinson, E. J., Dawes, I. W., Grant, C. M. (2006). "Old yellow enzymes protect against acrolein toxicity in the yeast Saccharomyces cerevisiae." Appl Environ Microbiol 72:4885-4892.16820484
  • Wonisch, W., Schaur, R. J., Bilinski, T., Esterbauer, H. (1995). "Assessment of growth inhibition by aldehydic lipid peroxidation products and related aldehydes by Saccharomyces cerevisiae." Cell Biochem Funct 13:91-98.7758153
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15368
HMDB IDHMDB0041822
Pubchem Compound ID7847
Kegg IDC01471
ChemSpider ID7559
FOODB IDFDB008307
WikipediaAcrolein
BioCyc IDNot Available

Enzymes

Protein Details
1. NADPH dehydrogenase 2
General function:
Involved in catalytic activity
Specific function:
Oxidizes beta-NADH, beta-NADPH, and alpha-NADPH
Gene Name:
OYE2
Uniprot ID:
Q03558
Molecular weight:
45010.39844
Reactions
NADPH + acceptor → NADP(+) + reduced acceptor.
Protein Details
2. NADPH dehydrogenase 3
General function:
Involved in catalytic activity
Specific function:
Oxidizes beta-NADH, beta-NADPH, and alpha-NADPH
Gene Name:
OYE3
Uniprot ID:
P41816
Molecular weight:
44920.10156
Reactions
NADPH + acceptor → NADP(+) + reduced acceptor.