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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:44:35 UTC
Update Date2022-03-07 02:53:56 UTC
HMDB IDHMDB0033969
Secondary Accession Numbers
  • HMDB33969
Metabolite Identification
Common NameBenzyl isothiocyanate
DescriptionBenzyl isothiocyanate, also known as benzylsenfoel or a-isothiocyanatotoluene, 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. Benzyl isothiocyanate has been detected, but not quantified in, garden cresses (Lepidium sativum) and horseradishes (Armoracia rusticana). This could make benzyl isothiocyanate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Benzyl isothiocyanate.
Structure
Data?1563862488
Synonyms
ValueSource
alpha-IsothiocyanatotolueneChEBI
BenzylsenfoelChEBI
Isothiocyanic acid, benzyl esterChEBI
a-IsothiocyanatotolueneGenerator
Α-isothiocyanatotolueneGenerator
Isothiocyanate, benzyl esterGenerator
Benzyl isothiocyanic acidGenerator
(Isothiocyanatomethyl)-benzeneHMDB
(Isothiocyanatomethyl)benzeneHMDB
(Isothiocyanatomethyl)benzene, 9ciHMDB
AB 2HMDB
alpha-Isothiocyanato-tolueneHMDB
Benzyl isothio cyanateHMDB
Benzyl mustard oilHMDB
Benzyl-isothiocyanateHMDB
BenzylisothiocyanateHMDB
Isothiocyanato-methyl-benzeneHMDB
Isothiocyanic acid benzyl esterHMDB
IsothiocyanotaomethylbenzeneHMDB
Phenylmethyl isothiocyanateHMDB
Pmitc CPDHMDB
TromacapsHMDB
TromalytHMDB
Tromalyt active substanceHMDB
TromocapsHMDB
UrogranHMDB
3-Benzylisothiocyanic acidHMDB
Chemical FormulaC8H7NS
Average Molecular Weight149.213
Monoisotopic Molecular Weight149.029919919
IUPAC Name(isothiocyanatomethyl)benzene
Traditional Namebenzyl isothiocyanate
CAS Registry Number622-78-6
SMILES
S=C=NCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
InChI KeyMDKCFLQDBWCQCV-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
  • Isothiocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point41 °CNot Available
Boiling Point242.00 to 243.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.11 mg/mL at 25 °CNot Available
LogP3.16Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.057 g/LALOGPS
logP3.22ALOGPS
logP2.79ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.94 m³·mol⁻¹ChemAxon
Polarizability16.16 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]+131.62131661259
DarkChem[M-H]-125.88831661259
DeepCCS[M+H]+126.58930932474
DeepCCS[M-H]-123.50130932474
DeepCCS[M-2H]-160.33630932474
DeepCCS[M+Na]+135.47430932474
AllCCS[M+H]+129.832859911
AllCCS[M+H-H2O]+125.232859911
AllCCS[M+NH4]+134.032859911
AllCCS[M+Na]+135.232859911
AllCCS[M-H]-129.632859911
AllCCS[M+Na-2H]-131.332859911
AllCCS[M+HCOO]-133.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzyl isothiocyanateS=C=NCC1=CC=CC=C12134.6Standard polar33892256
Benzyl isothiocyanateS=C=NCC1=CC=CC=C11332.5Standard non polar33892256
Benzyl isothiocyanateS=C=NCC1=CC=CC=C11364.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl isothiocyanate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-29b203aa3cc9f04c2fda2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl isothiocyanate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzyl isothiocyanate 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 - Benzyl isothiocyanate 10V, Positive-QTOFsplash10-0udi-0900000000-c83b146c4b125e3d9b832015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 20V, Positive-QTOFsplash10-0udi-0900000000-e7980a61941ab132ea802015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 40V, Positive-QTOFsplash10-0udi-5900000000-33afb787a500e9b4e0db2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 10V, Negative-QTOFsplash10-0002-0900000000-6755d456251a0541ed942015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 20V, Negative-QTOFsplash10-0002-0900000000-2fcb3ba0537189b628de2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 40V, Negative-QTOFsplash10-0udj-4900000000-52000359d56b4bbd3d792015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 10V, Positive-QTOFsplash10-0006-9300000000-36e2dbdd7dd78a8f2f102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 20V, Positive-QTOFsplash10-0006-9000000000-9428f84221678a6add2d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 40V, Positive-QTOFsplash10-00kf-9100000000-3969a1ae3b90f0b703962021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 10V, Negative-QTOFsplash10-0002-0900000000-3562640e821f8add3ef42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 20V, Negative-QTOFsplash10-0002-3900000000-6055c25e29b6bc71605a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzyl isothiocyanate 40V, Negative-QTOFsplash10-0a4i-9200000000-b4350e1294364ff09ad02021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB004133
KNApSAcK IDC00007675
Chemspider ID2256
KEGG Compound IDC03098
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzyl isothiocyanate
METLIN IDNot Available
PubChem Compound2346
PDB IDNot Available
ChEBI ID17484
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012031
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.. .