2-acetyl-1-pyrroline (YMDB01451)

Identification
YMDB IDYMDB01451
Name2-acetyl-1-pyrroline
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-Acetyl-1-pyrroline, abbreviated 2AP is an aroma compound and flavor that gives white bread, jasmine rice and basmati rice, the spice pandan (Pandanus amaryllifolius), and bread flowers (Vallaris glabra) their typical smell. 2-Acetyl-1-pyrroline and its structural homolog, 6-acetyl-2,3,4,5-tetrahydropyridine of similar smell, can be formed by Maillard reactions during heating of food such as in baked bread. Both compounds have odor thresholds below 0.06 ng/l.[Wikipedia]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanone
  • 1-Pyrroline, 2-acetyl
  • 2-Acetyl-1-pyrolline
  • 2-Acetyl-4,5-dihydro-3H-pyrrole
  • 2AP
  • APR
  • 1-(3,4-dihydro-2H-Pyrrol-5-yl)ethanone, 9ci
  • 2-Acetyl-1-pyrroline
  • 2-Acetylpyrroline
CAS number99583-29-6
WeightAverage: 111.1418
Monoisotopic: 111.068413915
InChI KeyDQBQWWSFRPLIAX-UHFFFAOYSA-N
InChIInChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3
IUPAC Name1-(3,4-dihydro-2H-pyrrol-5-yl)ethan-1-one
Traditional IUPAC Name2-acetyl-1-pyrroline
Chemical FormulaC6H9NO
SMILES[H]C([H])([H])C(=O)C1=NC([H])([H])C([H])([H])C1([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolines
Sub ClassNot Available
Direct ParentPyrrolines
Alternative Parents
Substituents
  • Pyrroline
  • Ketimine
  • Ketone
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Imine
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.09 g/LALOGPS
logP0.19ALOGPS
logP0.86ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)18.44ChemAxon
pKa (Strongest Basic)3.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.39 m³·mol⁻¹ChemAxon
Polarizability12.01 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
HamFDB003364
NutFDB003364
NuttyFDB003364
RoastFDB003364
RoastedFDB003364
SweetFDB003364
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, Positivesplash10-014l-9000000000-b2ec2a5a737593af1876JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5900000000-ba7d8b3068bce1b47b39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9300000000-d40b8a0858de158c3dd1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-93e30e06cf0f3fac2e9eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-c99599e8eef94b8c0068JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3900000000-24d2c60642b551195027JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-a6046c2688bcfbb4c313JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-24735682b0a5560e64aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-9500000000-2e635455b88717ca2f97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-a0c8a0fe2acbc430c438JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-7cddab0b1712fe3943e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-9100000000-a2ea5be954e40e1ce67bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-efc17d3cfd9d54e8a0c4JSpectraViewer
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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 ID67125
HMDB IDHMDB0031308
Pubchem Compound ID522834
Kegg IDNot Available
ChemSpider ID456071
FOODB IDFDB003364
Wikipedia2-acetyl-1-pyrroline
BioCyc IDNot Available