Record Information
Version1.0
Creation date2010-04-08 22:10:17 UTC
Update date2018-01-23 19:24:22 UTC
Primary IDFDB012644
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePiperidine
DescriptionPresent in black pepper (Piper nigrum). Flavouring agent Piperidine (Azinane after the Hantzsch?Widman nomenclature) is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom. It is a colorless fuming liquid with an odor described as ammoniacal, pepper-like; the name comes from the genus name Piper, which is the Latin word for pepper. Piperidine is a widely used building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals.; Piperidine is a widely used secondary amine. It is widely used to convert ketones to enamines. Enamines derived from piperidine can be used in the Stork enamine alkylation reaction.; Piperidine is used as a solvent and as a base. The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents. Piperidine is found in many foods, some of which are pepper (c. annuum), red bell pepper, herbs and spices, and soy bean.
CAS Number110-89-4
Structure
Thumb
Synonyms
SynonymSource
AzacyclohexaneChEBI
AzinaneChEBI
CyclopentimineChEBI
HexahydropyridineChEBI
PentamethyleneamineChEBI
PentamethyleneimineChEBI
PentamethylenimineChEBI
pipChEBI
CypentilHMDB
FEMA 2908HMDB
Hexahydro-pyridineHMDB
HexazaneHMDB
PerhydropyridineHMDB
PiperidinHMDB
Piperidine ON rasta resinHMDB
hexahydro-PyridineHMDB
PIPbiospider
Piperidine [UN2401] [Corrosive]biospider
Piperidine on rasta resinbiospider
Pyridine, hexahydro-biospider
Predicted Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP0.97ALOGPS
logP0.66ChemAxon
logS0.16ALOGPS
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.84 m³·mol⁻¹ChemAxon
Polarizability10.43 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H11N
IUPAC namepiperidine
InChI IdentifierInChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
InChI KeyNQRYJNQNLNOLGT-UHFFFAOYSA-N
Isomeric SMILESC1CCNCC1
Average Molecular Weight85.1475
Monoisotopic Molecular Weight85.089149357
Classification
Description belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassNot Available
Direct ParentPiperidines
Alternative Parents
Substituents
  • Piperidine
  • 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 stateLiquid
Physical DescriptionNot Available
Mass CompositionC 70.53%; H 13.02%; N 16.45%DFC
Melting PointMp -9°DFC
Boiling PointBp20 17.7°DFC
Experimental Water Solubility1000 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.84HANSCH,C ET AL. (1995)
Experimental pKapKa 11.12 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.86DFC
Refractive Indexn20D 1.4534DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0543-9000000000-6b1887859e5474352d6eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053u-9000000000-507e3f9eabf271f642f3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0563-9000000000-c08d3d67e81c397678d2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0543-9000000000-6b1887859e5474352d6eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053u-9000000000-507e3f9eabf271f642f3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0563-9000000000-c08d3d67e81c397678d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052u-9000000000-95f068cd42017a2e7446View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-a76c8bf8d69f5f3e831aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-fe1ffe6a62bbbfa35a46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-c57e3de57c466c728f49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-9000000000-7936721ae1a323f2cd83View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-9000000000-6bcb90141de97851b0ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9000000000-155786c0621c522e75a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-646cb2a227fa351da3dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-32222dc7a0d132edf443View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-646cb2a227fa351da3dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-071a5573608ae27993d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-80fe3a58dda39ff48e6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-1a5edb15988820bf46f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-79404da79119ad6ba660View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-f83e1ccbb9745637eb97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-348e151611d5b46f3a33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-8c4547384f2bc29d797bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-bd6d487d25b0e623403eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-d9b236846b0611684014View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9000000000-508b10b77d98c3915247View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-b616957223f2d18551fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-a2e05ca3b5d63ce6a366View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015c-9000000000-49c805d2b27473cc8f88View in MoNA
MSMass Spectrum (Electron Ionization)splash10-053u-9000000000-9b296a6ad56d186eee6fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID7791
ChEMBL IDCHEMBL15487
KEGG Compound IDC01746
Pubchem Compound ID8082
Pubchem Substance IDNot Available
ChEBI ID18049
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34301
CRC / DFC (Dictionary of Food Compounds) IDHJM94-U:HJM94-U
EAFUS ID3053
Dr. Duke IDPIPERIDINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDPIP
Flavornet IDNot Available
GoodScent IDrw1009201
SuperScent ID8082
Wikipedia IDPiperidine
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
anti enzymaticDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
diaphoreticDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hepatotropicDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
spinoconvulsantDUKE
urate-solventDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
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.
heavy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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).