Back to Compounds

Showing Compound Pyrrole (FDB014718)

Record Information
Version1.0
Creation date2010-04-08 22:11:26 UTC
Update date2019-11-26 03:10:39 UTC
Primary IDFDB014718
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyrrole
DescriptionFlavouring ingredient Pyrrole has very low basicity compared to conventional amines and some other aromatic compounds like pyridine. This decreased basicity is attributed to the delocalization of the lone pair of electrons of the nitrogen atom in the aromatic ring. Pyrrole is a very weak base with a pKaH of about ?4. Protonation results in loss of aromaticity, and is, therefore, unfavorable.; Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. Substituted derivatives are also called pyrroles. For example, C4H4NCH3 is N-methylpyrrole. Porphobilinogen is a trisubstituted pyrrole, which is the biosynthetic precursor to many natural products.; The starting materials in the Piloty-Robinson pyrrole synthesis are 2 equivalents of an aldehyde and hydrazine. The product is a pyrrole with specific substituents in the 3 and 4 positions. The aldehyde reacts with the diamine to an intermediate di-imine (R?C=N?N=C?R), which, with added hydrochloric acid, gives ring-closure and loss of ammonia to the pyrrole. Pyrrole is found in tamarind and corn.
CAS Number109-97-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-Aza-2,4-cyclopentadieneChEBI
DivinyleneimineChEBI
DivinylenimineChEBI
ImidoleChEBI
MonopyrroleChEBI
PyrrolChEBI
1H-PyrroleHMDB
1H-Pyrrole, homopolymerHMDB
1H-Pyrrole, potassium saltHMDB
AzoleHMDB
FEMA 3386HMDB
IndoleHMDB
PolypyrroleHMDB, MeSH
PyrolleHMDB
PyrrholHMDB
PyrrolineHMDB
PyrroleChEBI
PyrrolesMeSH
Predicted Properties
PropertyValueSource
Water Solubility445 g/LALOGPS
logP0.76ALOGPS
logP1.05ChemAxon
logS0.82ALOGPS
pKa (Strongest Acidic)18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.82 m³·mol⁻¹ChemAxon
Polarizability7.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H5N
IUPAC name1H-pyrrole
InChI IdentifierInChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H
InChI KeyKAESVJOAVNADME-UHFFFAOYSA-N
Isomeric SMILESN1C=CC=C1
Average Molecular Weight67.0892
Monoisotopic Molecular Weight67.042199165
Classification
Description Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 71.61%; H 7.51%; N 20.88%DFC
Melting PointMp -24°DFC
Boiling PointBp761 130-131°DFC
Experimental Water Solubility45 mg/mL at 25 oCRIDDICK,JA et al. (1986)
Experimental logP0.75HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.97DFC
Refractive Indexn20D 1.5085DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00ko-9000000000-8908fc8793c6501dc2d02015-03-01View Spectrum
Predicted GC-MSPyrrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-9000000000-f644c5fdd4d5f9db3117Spectrum
Predicted GC-MSPyrrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9000000000-510c084e3c928fa514ae2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-150b960a1186c02653f72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-3bea04ffb045db51356d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9000000000-bb04398351cbc20c433b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-9b747cfdf2fe46d188ee2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-ac61df56d353d5acb48b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-8777c03f1c46a5fcce9d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-3f070060c5785123e18c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-3f070060c5785123e18c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02tc-9000000000-43982034e7a3a595201a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-e0673bc7e6a6226fb72e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-a3a7192ca6658a081b5b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-9000000000-972ac9fb6e8cbc34f0d32021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
ChemSpider ID7736
ChEMBL IDCHEMBL16225
KEGG Compound IDC19907
Pubchem Compound ID8027
Pubchem Substance IDNot Available
ChEBI ID19203
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35924
CRC / DFC (Dictionary of Food Compounds) IDJVF90-J:JVF90-J
EAFUS ID3266
Dr. Duke IDPYRROLE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1009261
SuperScent IDNot Available
Wikipedia IDPyrrole
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
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ethereal
  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).