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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:02:25 UTC
Update Date2023-02-21 17:24:04 UTC
HMDB IDHMDB0034236
Secondary Accession Numbers
  • HMDB34236
Metabolite Identification
Common NameBenzenepropanenitrile
DescriptionBenzenepropanenitrile, also known as 2-phenylethyl cyanide or (2-cyanoethyl)benzene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzenepropanenitrile has been detected, but not quantified in, several different foods, such as herbs and spices, cauliflowers (Brassica oleracea var. botrytis), cabbages (Brassica oleracea var. capitata), broccolis (Brassica oleracea var. italica), and brassicas. This could make benzenepropanenitrile a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Benzenepropanenitrile.
Structure
Data?1677000244
Synonyms
ValueSource
(2-Cyanoethyl)benzeneChEBI
1-Phenyl-2-cyanoethaneChEBI
2-Phenylethyl cyanideChEBI
3-PhenylpropiononitrileChEBI
BenzenepropionitrileChEBI
beta-Phenyl propionitrileChEBI
beta-Phenylethyl cyanideChEBI
Hydrocinnamique nitrileChEBI
HydrocinnamonitrileChEBI
PhenylpropanonitrileChEBI
PhenylpropionitrileChEBI
b-Phenyl propionitrileGenerator
Β-phenyl propionitrileGenerator
b-Phenylethyl cyanideGenerator
Β-phenylethyl cyanideGenerator
3-PhenylpropanonitrilMetaCyc, HMDB
1-cyano-2-PhenylethaneHMDB
3-PhenylpropanenitrileHMDB
3-PhenylpropionitrileHMDB
BenzenepropanitrileHMDB
beta-PhenylpropionitrileHMDB
Phenethyl cyanideHMDB
BenzenepropanenitrileChEBI
Chemical FormulaC9H9N
Average Molecular Weight131.1745
Monoisotopic Molecular Weight131.073499293
IUPAC Name3-phenylpropanenitrile
Traditional Namebenzylacetonitrile
CAS Registry Number645-59-0
SMILES
N#CCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H9N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7H2
InChI KeyACRWYXSKEHUQDB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-1 °CNot Available
Boiling Point261.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1679 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.72Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.15 g/LALOGPS
logP1.94ALOGPS
logP2.11ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.95 m³·mol⁻¹ChemAxon
Polarizability14.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.9131661259
DarkChem[M-H]-124.25831661259
DeepCCS[M+H]+126.01430932474
DeepCCS[M-H]-123.06730932474
DeepCCS[M-2H]-159.82130932474
DeepCCS[M+Na]+134.89530932474
AllCCS[M+H]+126.832859911
AllCCS[M+H-H2O]+122.232859911
AllCCS[M+NH4]+131.232859911
AllCCS[M+Na]+132.532859911
AllCCS[M-H]-127.532859911
AllCCS[M+Na-2H]-129.132859911
AllCCS[M+HCOO]-130.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzenepropanenitrileN#CCCC1=CC=CC=C12058.5Standard polar33892256
BenzenepropanenitrileN#CCCC1=CC=CC=C11190.2Standard non polar33892256
BenzenepropanenitrileN#CCCC1=CC=CC=C11239.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzenepropanenitrile EI-B (Non-derivatized)splash10-0006-9200000000-c15196ced049b8e3681a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzenepropanenitrile EI-B (Non-derivatized)splash10-0006-9200000000-c15196ced049b8e3681a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzenepropanenitrile GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-3f8b538083f03e684b1c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzenepropanenitrile GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 10V, Positive-QTOFsplash10-001i-0900000000-422476e232336cb1bc3b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 20V, Positive-QTOFsplash10-014i-1900000000-f25456149c249dad541c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 40V, Positive-QTOFsplash10-0uxu-9300000000-e6661cd33a9f8f3bed592016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 10V, Negative-QTOFsplash10-001i-0900000000-4076b2a2555b65c14bc42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 20V, Negative-QTOFsplash10-001i-1900000000-317c2d4de54973a867e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 40V, Negative-QTOFsplash10-0w4l-9700000000-45f7d73f62355efe43842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 10V, Positive-QTOFsplash10-001l-3900000000-f580aa6d0d3cb66199a22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 20V, Positive-QTOFsplash10-0a6r-9800000000-96778021816794d9dec32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 40V, Positive-QTOFsplash10-016u-9000000000-8e8a4a1f79e82cd94f852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 10V, Negative-QTOFsplash10-001i-0900000000-244a9c7ac26f199509262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 20V, Negative-QTOFsplash10-001i-0900000000-ead876da804cd98552cd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenepropanenitrile 40V, Negative-QTOFsplash10-004i-9200000000-30b5e7202812ed8f217a2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDFDB012548
KNApSAcK IDC00029809
Chemspider ID12061
KEGG Compound IDNot Available
BioCyc IDCPD-14673
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12581
PDB IDNot Available
ChEBI ID85426
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1058521
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.. .