Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:57:53 UTC

Update Date

2023-02-21 17:23:59 UTC

HMDB ID

HMDB0034171

Secondary Accession Numbers

HMDB34171

Metabolite Identification

Common Name

Benzeneacetonitrile

Description

Benzeneacetonitrile, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(Cyanomethyl)benzene	ChEBI
2-Phenylacetonitrile	ChEBI
alpha-Cyanotoluene	ChEBI
alpha-Tolunitrile	ChEBI
Benzyl cyanide	ChEBI
Benzyl nitrile	ChEBI
a-Cyanotoluene	Generator
Α-cyanotoluene	Generator
a-Tolunitrile	Generator
Α-tolunitrile	Generator
.omega.-cyanotoluene	HMDB
Acetic acid, phenyl-nitrile	HMDB
alpha -Cyanotoluene	HMDB
alpha -Tolunitrile	HMDB
alpha-cyano-Toluene	HMDB
Benzeneacetonitrile, 9ci	HMDB
Benzylkyanid	HMDB
Benzylnitrile	HMDB
Cyanophenylmethane	HMDB
Enzylcyanide	HMDB
laquo omegaraquo -Cyanotoluene	HMDB
Omega-cyanotoluene	HMDB
Phenacetonitrile	HMDB
Phenyl acetyl nitrile	HMDB
Phenyl-acetonitrile	HMDB
Phenylacetonitrile	HMDB
Phenylacetonitrile, liquid	HMDB
Benzeneacetonitrile	ChEBI

Chemical Formula

C₈H₇N

Average Molecular Weight

117.1479

Monoisotopic Molecular Weight

117.057849229

IUPAC Name

2-phenylacetonitrile

Traditional Name

phenylacetonitrile

CAS Registry Number

140-29-4

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 Key

SUSQOBVLVYHIEX-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyl cyanides

Direct Parent

Benzyl cyanides

Alternative Parents

Substituents

Benzyl-cyanide
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nitrile (CHEBI:25979 )
benzenes (CHEBI:25979 )
a small molecule (PHENYLACETONITRILE )

Ontology

Physiological effect

Health effect

Observation

Breathing difficulties (HMDB: HMDB0034171)
Vomiting (HMDB: HMDB0034171)
Pain (HMDB: HMDB0034171)
Chest pain (HMDB: HMDB0034171)
Convulsion (HMDB: HMDB0034171)
Confusion (HMDB: HMDB0034171)
Vertigo (HMDB: HMDB0034171)
Apnea (HMDB: HMDB0034171)

Circulatory system disorder

Cardiac disorder

Cardiac arrest (HMDB: HMDB0034171)

Nervous system disorder

Coma (HMDB: HMDB0034171)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034171)
Cytoplasm (HMDB: HMDB0034171)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0034171)
Inhalation (HMDB: HMDB0034171)

Enteral

Ingestion (HMDB: HMDB0034171)

Source

Exogenous

Exogenous (HMDB: HMDB0034171)

Food

Food (HMDB: HMDB0034171)

Vegetable

Cabbage

Cauliflower (FooDB: FOOD00031)
Cabbage (FooDB: FOOD00851)

Leaf vegetable

Garden cress (FooDB: FOOD00099)
Green vegetables (FooDB: FOOD00872)

Root vegetable

Kohlrabi (FooDB: FOOD00033)

Fruit vegetable

Fruit

Tropical fruit

Papaya (FooDB: FOOD00041)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Endogenous

Plant

Plant (HMDB: HMDB0034171)

Process

Not Available

Role

Environmental role

Air pollutant (HMDB: HMDB0034171)

Biological role

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-23.8 °C	Not Available
Boiling Point	233.00 to 234.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.1 mg/mL at 25 °C	Not Available
LogP	1.56	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.85 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.67	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	14.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.79 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.34 m³·mol⁻¹	ChemAxon
Polarizability	12.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.162	31661259
DarkChem	[M-H]-	119.627	31661259
DeepCCS	[M+H]+	120.688	30932474
DeepCCS	[M-H]-	117.948	30932474
DeepCCS	[M-2H]-	154.427	30932474
DeepCCS	[M+Na]+	129.261	30932474
AllCCS	[M+H]+	123.1	32859911
AllCCS	[M+H-H2O]+	118.2	32859911
AllCCS	[M+NH4]+	127.6	32859911
AllCCS	[M+Na]+	128.9	32859911
AllCCS	[M-H]-	122.0	32859911
AllCCS	[M+Na-2H]-	124.0	32859911
AllCCS	[M+HCOO]-	126.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzeneacetonitrile	N#CCC1=CC=CC=C1	1921.0	Standard polar	33892256
Benzeneacetonitrile	N#CCC1=CC=CC=C1	1090.2	Standard non polar	33892256
Benzeneacetonitrile	N#CCC1=CC=CC=C1	1166.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)	splash10-014i-9700000000-aa951610ae3086079fc3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)	splash10-014i-6900000000-9fa568274538519d6221	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)	splash10-014i-4900000000-7fb420e2a4693843bcc6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)	splash10-014i-9700000000-44dc07c52f713661d49d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)	splash10-014i-9700000000-aa951610ae3086079fc3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)	splash10-014i-6900000000-9fa568274538519d6221	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)	splash10-014i-4900000000-7fb420e2a4693843bcc6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Benzeneacetonitrile EI-B (Non-derivatized)	splash10-014i-9700000000-44dc07c52f713661d49d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzeneacetonitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9600000000-3ff8c2a019af8041ccf5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzeneacetonitrile GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzeneacetonitrile GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-9600000000-bacbbfee69800587e876	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 10V, Positive-QTOF	splash10-014i-0900000000-26618186da25d2fb36a3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 20V, Positive-QTOF	splash10-014i-2900000000-36bcc9666d8d6f02be93	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 40V, Positive-QTOF	splash10-0006-9100000000-e64aaf4670bfdd42e5ec	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 10V, Negative-QTOF	splash10-014i-0900000000-c300e5c9a5a8fd9efed7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 20V, Negative-QTOF	splash10-014i-1900000000-62ae29742c669f0cbb48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 40V, Negative-QTOF	splash10-00kr-9400000000-a31fa80a0b41e8872dfd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 10V, Negative-QTOF	splash10-014i-0900000000-89c3f30c8225ba6d5d62	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 20V, Negative-QTOF	splash10-014i-0900000000-89c3f30c8225ba6d5d62	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 40V, Negative-QTOF	splash10-014i-7900000000-a5d53547c4ff1f8c5b08	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 10V, Positive-QTOF	splash10-00kf-9600000000-37eae74477faef6aa26e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 20V, Positive-QTOF	splash10-0006-9200000000-0ed055b02df43a8a2055	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzeneacetonitrile 40V, Positive-QTOF	splash10-00kf-9000000000-c6037f271472539420c4	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8794

PDB ID

Not Available

ChEBI ID

25979

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1049061

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Benzeneacetonitrile (HMDB0034171)

MOL for HMDB0034171 (Benzeneacetonitrile)

3D MOL for HMDB0034171 (Benzeneacetonitrile)

3D SDF for HMDB0034171 (Benzeneacetonitrile)

3D-SDF for HMDB0034171 (Benzeneacetonitrile)

PDB for HMDB0034171 (Benzeneacetonitrile)

3D PDB for HMDB0034171 (Benzeneacetonitrile)

SMILES for HMDB0034171 (Benzeneacetonitrile)

INCHI for HMDB0034171 (Benzeneacetonitrile)

Structure for HMDB0034171 (Benzeneacetonitrile)

3D Structure for HMDB0034171 (Benzeneacetonitrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra