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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:53 UTC
Update Date2021-10-13 06:39:18 UTC
HMDB IDHMDB0034171
Secondary Accession Numbers
  • HMDB34171
Metabolite Identification
Common NameBenzeneacetonitrile
DescriptionBenzeneacetonitrile, also known as alpha-cyanotoluene or alpha-tolunitrile, belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group. Benzeneacetonitrile exists in all living organisms, ranging from bacteria to humans. Benzeneacetonitrile is found, on average, in the highest concentration within kohlrabis (Brassica oleracea var. gongylodes) and peppermints (Mentha X piperita). Benzeneacetonitrile has also been detected, but not quantified in, several different foods, such as garden tomato (var.), blackberries (Rubus), garden tomatoes (Solanum lycopersicum), cherry tomatoes (Solanum lycopersicum var. cerasiforme), and cauliflowers (Brassica oleracea var. botrytis). This could make benzeneacetonitrile a potential biomarker for the consumption of these foods. Benzeneacetonitrile is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Benzeneacetonitrile.
Structure
Data?1563862522
Synonyms
ValueSource
(Cyanomethyl)benzeneChEBI
2-PhenylacetonitrileChEBI
alpha-CyanotolueneChEBI
alpha-TolunitrileChEBI
Benzyl cyanideChEBI
Benzyl nitrileChEBI
a-CyanotolueneGenerator
Α-cyanotolueneGenerator
a-TolunitrileGenerator
Α-tolunitrileGenerator
.omega.-cyanotolueneHMDB
Acetic acid, phenyl-nitrileHMDB
alpha -CyanotolueneHMDB
alpha -TolunitrileHMDB
alpha-cyano-TolueneHMDB
Benzeneacetonitrile, 9ciHMDB
BenzylkyanidHMDB
BenzylnitrileHMDB
CyanophenylmethaneHMDB
EnzylcyanideHMDB
laquo omegaraquo -CyanotolueneHMDB
Omega-cyanotolueneHMDB
PhenacetonitrileHMDB
Phenyl acetyl nitrileHMDB
Phenyl-acetonitrileHMDB
PhenylacetonitrileHMDB
Phenylacetonitrile, liquidHMDB
BenzeneacetonitrileChEBI
Chemical FormulaC8H7N
Average Molecular Weight117.1479
Monoisotopic Molecular Weight117.057849229
IUPAC Name2-phenylacetonitrile
Traditional Namephenylacetonitrile
CAS Registry Number140-29-4
SMILES
N#CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
InChI KeySUSQOBVLVYHIEX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl cyanides
Direct ParentBenzyl cyanides
Alternative Parents
Substituents
  • Benzyl-cyanide
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-23.8 °CNot Available
Boiling Point233.00 to 234.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.1 mg/mL at 25 °CNot Available
LogP1.56Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.85 g/LALOGPS
logP10(1.42) g/LALOGPS
logP10(1.67) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Acidic)14.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.34 m³·mol⁻¹ChemAxon
Polarizability12.75 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]+123.16231661259
DarkChem[M-H]-119.62731661259
DeepCCS[M+H]+120.68830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzeneacetonitrileN#CCC1=CC=CC=C11921.0Standard polar33892256
BenzeneacetonitrileN#CCC1=CC=CC=C11090.2Standard non polar33892256
BenzeneacetonitrileN#CCC1=CC=CC=C11166.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)splash10-014i-9700000000-aa951610ae3086079fc32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)splash10-014i-6900000000-9fa568274538519d62212017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)splash10-014i-4900000000-7fb420e2a4693843bcc62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)splash10-014i-9700000000-44dc07c52f713661d49d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)splash10-014i-9700000000-aa951610ae3086079fc32018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)splash10-014i-6900000000-9fa568274538519d62212018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)splash10-014i-4900000000-7fb420e2a4693843bcc62018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)splash10-014i-9700000000-44dc07c52f713661d49d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzeneacetonitrile GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9600000000-3ff8c2a019af8041ccf52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzeneacetonitrile GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzeneacetonitrile GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-9600000000-bacbbfee69800587e8762014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 10V, Positive-QTOFsplash10-014i-0900000000-26618186da25d2fb36a32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 20V, Positive-QTOFsplash10-014i-2900000000-36bcc9666d8d6f02be932016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 40V, Positive-QTOFsplash10-0006-9100000000-e64aaf4670bfdd42e5ec2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 10V, Negative-QTOFsplash10-014i-0900000000-c300e5c9a5a8fd9efed72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 20V, Negative-QTOFsplash10-014i-1900000000-62ae29742c669f0cbb482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 40V, Negative-QTOFsplash10-00kr-9400000000-a31fa80a0b41e8872dfd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 10V, Negative-QTOFsplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 20V, Negative-QTOFsplash10-014i-0900000000-89c3f30c8225ba6d5d622021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 40V, Negative-QTOFsplash10-014i-7900000000-a5d53547c4ff1f8c5b082021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 10V, Positive-QTOFsplash10-00kf-9600000000-37eae74477faef6aa26e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 20V, Positive-QTOFsplash10-0006-9200000000-0ed055b02df43a8a20552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzeneacetonitrile 40V, Positive-QTOFsplash10-00kf-9000000000-c6037f271472539420c42021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB012457
KNApSAcK IDC00007674
Chemspider ID13839308
KEGG Compound IDC16074
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8794
PDB IDNot Available
ChEBI ID25979
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1049061
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Huang L, Liu Y, Xie F, Hu Y: An organic molecule modulated chemoselective cyclization of alkynyl nitriles tethered to 2-alkyl substituted chromones with multireactive sites. Org Lett. 2012 Dec 21;14(24):6122-5. doi: 10.1021/ol302964x. Epub 2012 Dec 4. [PubMed:23210678 ]
  2. Rao CN, Hoz S: Photostimulated reduction of nitriles by SmI2. J Org Chem. 2012 Apr 20;77(8):4029-34. doi: 10.1021/jo300383r. Epub 2012 Apr 11. [PubMed:22468753 ]
  3. Petrickova A, Vesela AB, Kaplan O, Kubac D, Uhnakova B, Malandra A, Felsberg J, Rinagelova A, Weyrauch P, Kren V, Bezouska K, Martinkova L: Purification and characterization of heterologously expressed nitrilases from filamentous fungi. Appl Microbiol Biotechnol. 2012 Feb;93(4):1553-61. doi: 10.1007/s00253-011-3525-7. Epub 2011 Sep 3. [PubMed:21892598 ]
  4. Amwayi PW, Masiga DK, Govender P, Teal PE, Torto B: Mass spectral determination of phenylacetonitrile (PAN) levels in body tissues of adult desert locust, Schistocerca gregaria. J Insect Physiol. 2012 Aug;58(8):1037-41. doi: 10.1016/j.jinsphys.2012.03.012. Epub 2012 May 17. [PubMed:22609420 ]
  5. Noge K, Abe M, Tamogami S: Phenylacetonitrile from the giant knotweed, Fallopia sachalinensis, infested by the Japanese beetle, Popillia japonica, is induced by exogenous methyl jasmonate. Molecules. 2011 Aug 3;16(8):6481-8. doi: 10.3390/molecules16086481. [PubMed:21814160 ]
  6. Strzalko T, Wartski L, Corset J, Castella-Ventura M, Froment F: Study of the lithiated phenylacetonitrile monoanions and dianions formed according to the lithiated base used (LHMDS, LDA, or n-BuLi). 2. Alkylation and deuteriation mechanism study by vibrational and NMR spectroscopy and quantum chemistry calculations. J Org Chem. 2012 Aug 3;77(15):6431-42. doi: 10.1021/jo300758g. Epub 2012 Jul 23. [PubMed:22742856 ]
  7. Tang YB, Zhang CM, Fang C, Hu C, Huang L, Chen CH, Xiao ZY: [Design, synthesis and evaluation of novel 2H-1, 4-benzodiazepine-2-ones as inhibitors of HIV-1 transcription]. Yao Xue Xue Bao. 2011 Jun;46(6):688-94. [PubMed:21882530 ]
  8. Mei L, Hai ZJ, Jie S, Ming ZS, Hao Y, Liang HK: Modular synthesis of oxazolines and their derivatives. J Comb Chem. 2009 Mar 9;11(2):220-7. doi: 10.1021/cc8001537. [PubMed:19138088 ]
  9. de Oliveira JR, Mizuno CM, Seleghim MH, Javaroti DC, Rezende MO, Landgraf MD, Sette LD, Porto AL: Biotransformation of phenylacetonitrile to 2-hydroxyphenylacetic acid by marine fungi. Mar Biotechnol (NY). 2013 Feb;15(1):97-103. doi: 10.1007/s10126-012-9464-1. Epub 2012 Jul 12. [PubMed:22790719 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .