Record Information
Version1.0
Creation date2010-04-08 22:07:35 UTC
Update date2020-09-17 15:30:26 UTC
Primary IDFDB007401
Secondary Accession Numbers
  • FDB008290
Chemical Information
FooDB NameProlamine
DescriptionPyrrolidine, also known as azolidine, belongs to the class of organic compounds known as pyrrolidines which contain a pyrrolidine ring, a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. The pyrrolidine ring is the central structure of the amino acids, proline and hydroxyproline. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine and is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam). Pyrrolidine is a strong basic compound and is soluble in most organic solvents. Pyrrolidine is a clear liquid with an unpleasant ammoniacal, fishy, shellfish-like taste and seaweed-like odor ( http://www.thegoodscentscompany.com/data/rw1009391.html). Pyrrolidine is found naturally in the leaves of tobacco and carrot. Pyrrolidine is present in bread, milk, cheese, carrots, celery stalks, beer, spirits, coffee, caviar, and fatty fish. Pyrrolidine is a flavouring agent added in trace amounts to chewing gum, soft candy, and non-alcoholic beverages (RoutledgeHandbooks-9781439847503-chapter3.pdf). Pyrrolidine is widely distributed in foodstuffs in trace amounts, presumably as a bacterial decarboxylation product of proline Pyrrolidine is a metabolite of the gram-negative bacterium, Xenorhabdus (PMID: 19598185).
CAS Number123-75-1
Structure
Thumb
Synonyms
SynonymSource
AzolidineChEBI
TetrahydropyrroleChEBI
TetramethylenimineChEBI
1-AzacyclopentaneHMDB
AzacyclopentaneHMDB
FEMA 3523HMDB
Pyrrolidine hydrochlorideMeSH
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSProlamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-9000000000-0159c6ac6a2707c890fbSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00di-9000000000-b47872c22f260420fe4fSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-00di-9000000000-6703dc4e588e5b605dd2Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-00di-9000000000-1200244cbd952b0ff0e4Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-00di-9000000000-3e962c9c87606d1d4fb4Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-00di-9000000000-7aa207733141b620c612Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-00di-9000000000-cc43ed19d9780ad47907Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-00di-9000000000-6d604c6cb07d4b319fa7Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-00di-9000000000-201fcadb62ee720ec9e3Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-00dl-9000000000-2efe28538fd9387c1105Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-006x-9000000000-fe10abd985612deaee7bSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0006-9000000000-cc3a8f0b0eb43d64f2a4Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0006-9000000000-e5549871379e536221f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-50250fbde117c345f155Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-9a9bb68d33a6b556f753Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-4840aa812595ffd33b17Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-dc4555408f7b7029c1ecSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-d7dcf188af1b7f8ac9b4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-9000000000-0e5b8e3fe42b29779d06Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPROLAMINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDProlamin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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
Files
MSDSNot Available
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).