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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
Synonyms
  • 1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanone
  • 1-Pyrroline, 2-acetyl
  • 2-Acetyl-1-pyrolline
CAS number99583-29-6
WeightAverage: 111.1418
Monoisotopic: 111.068413915
InChI KeyInChIKey=DQBQWWSFRPLIAX-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
DescriptionThis compound belongs to the class of organic compounds known as pyrrolines. These 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
  • Ketone
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • 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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.39 m3·mol-1ChemAxon
Polarizability12.01 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
PathwaysNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
SpectraNot Available
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
Pubchem Compound ID:522834
ChemSpider ID:456071
Wikipedia:2-acetyl-1-pyrroline