Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:08:00 UTC
Update date2018-05-29 18:27:17 UTC
Primary IDFDB008290
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyrrolidine
DescriptionPyrrolidine is a clear liquid with an unpleasant odor that is ammoniacal, fishy, shellfish-like and seaweed-like. Pyrrolidine is found naturally in the leaves of tobacco and carrot. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam). A pyrrolidine ring is the central structure of the amino acids proline and hydroxyproline (Wikipedia). Pyrrolidine is widely distributed in foods in trace amounts, presumably as bacterial decarboxylation product of proline. It is found in bread, milk, cheese, carrots, celery stalks, beer, spirits, coffee, caviar and fatty fish. It can also be used as a flavouring agent.
CAS Number123-75-1
Structure
Thumb
Synonyms
SynonymSource
AzolidineChEBI
TetrahydropyrroleChEBI
TetramethylenimineChEBI
1-AzacyclopentaneHMDB
AzacyclopentaneHMDB
FEMA 3523HMDB
Pyrrolidine hydrochlorideMeSH
3,4-dihydro-2H-PyrroleChEBI
δ(1)-pyrrolineGenerator
Predicted Properties
PropertyValueSource
Water Solubility291 g/LALOGPS
logP0.16ALOGPS
logP0.21ChemAxon
logS0.61ALOGPS
pKa (Strongest Basic)11.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.23 m³·mol⁻¹ChemAxon
Polarizability8.58 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H9N
IUPAC namepyrrolidine
InChI IdentifierInChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
InChI KeyRWRDLPDLKQPQOW-UHFFFAOYSA-N
Isomeric SMILESC1CCNC1
Average Molecular Weight71.121
Monoisotopic Molecular Weight71.073499293
Classification
Description belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassNot Available
Direct ParentPyrrolidines
Alternative Parents
Substituents
  • Pyrrolidine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.55%; H 12.75%; N 19.69%DFC
Melting PointFp -63°DFC
Boiling PointBp 88.5-89°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 11.31 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.86DFC
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-0159c6ac6a2707c890fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-50250fbde117c345f155View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-9a9bb68d33a6b556f753View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-4840aa812595ffd33b17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-dc4555408f7b7029c1ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-d7dcf188af1b7f8ac9b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-9000000000-0e5b8e3fe42b29779d06View in MoNA
ChemSpider ID29008
ChEMBL IDCHEMBL22830
KEGG Compound IDNot Available
Pubchem Compound ID31268
Pubchem Substance IDNot Available
ChEBI ID33135
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31641
CRC / DFC (Dictionary of Food Compounds) IDDFR12-Z:DFR12-Z
EAFUS ID3267
Dr. Duke IDPYRROLIDINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet ID123-75-1
GoodScent IDrw1009391
SuperScent ID31268
Wikipedia IDPyrrolidine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
alkaline
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
animal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ammoniacal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
egg
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
amine
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).