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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:14 UTC
Update Date2019-07-23 06:08:28 UTC
HMDB IDHMDB0031308
Secondary Accession Numbers
  • HMDB31308
Metabolite Identification
Common Name5-Acetyl-3,4-dihydro-2H-pyrrole
Description5-Acetyl-3,4-dihydro-2H-pyrrole, also known as 2AP or APR, 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. It is one of the key odourants of the crust of bread and considered to be responsible for the cracker-like odour properties. A pyrroline that is 1-pyrroline in which the hydrogen at position 2 is replaced by an acetyl group. 5-Acetyl-3,4-dihydro-2H-pyrrole is a strong basic compound (based on its pKa). 5-Acetyl-3,4-dihydro-2H-pyrrole is a sweet, ham, and nut tasting compound. Outside of the human body, 5-Acetyl-3,4-dihydro-2H-pyrrole has been detected, but not quantified in, cereals and cereal products and tortilla chips. This could make 5-acetyl-3,4-dihydro-2H-pyrrole a potential biomarker for the consumption of these foods. It is an aroma and flavour compound present in jasmine rice and basmati rice. It is responsible for the 'popcorn' aroma in a large variety of cereal and food products. In bread, it is primarily generated during baking but amounts are influenced by ingredient composition and fermentation conditions.
Structure
Data?1563862108
Synonyms
ValueSource
2-Acetyl-4,5-dihydro-3H-pyrroleChEBI
2APChEBI
APRChEBI
1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanoneHMDB
1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanone, 9ciHMDB
1-Pyrroline, 2-acetylHMDB
2-Acetyl-1-pyrollineHMDB
2-Acetyl-1-pyrrolineHMDB
2-AcetylpyrrolineHMDB
Chemical FormulaC6H9NO
Average Molecular Weight111.1418
Monoisotopic Molecular Weight111.068413915
IUPAC Name1-(3,4-dihydro-2H-pyrrol-5-yl)ethan-1-one
Traditional Name2-acetyl-1-pyrroline
CAS Registry Number85213-22-5
SMILES
CC(=O)C1=NCCC1
InChI Identifier
InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3
InChI KeyDQBQWWSFRPLIAX-UHFFFAOYSA-N
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9000000000-b2ec2a5a737593af1876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5900000000-ba7d8b3068bce1b47b39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9300000000-d40b8a0858de158c3dd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-93e30e06cf0f3fac2e9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-c99599e8eef94b8c0068Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3900000000-24d2c60642b551195027Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-a6046c2688bcfbb4c313Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003364
KNApSAcK IDNot Available
Chemspider ID456071
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Acetyl-1-pyrroline
METLIN IDNot Available
PubChem Compound522834
PDB IDNot Available
ChEBI ID67125
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .