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Showing Compound 2-Phenethyl isothiocyanate (FDB004307)

Record Information
Version1.0
Creation date2010-04-08 22:06:11 UTC
Update date2019-11-26 02:59:57 UTC
Primary IDFDB004307
Secondary Accession Numbers
  • FDB017803
Chemical Information
FooDB Name2-Phenethyl isothiocyanate
DescriptionPhenethyl isothiocyanate, also known as peitc or beta-phenylethyl isothiocyanic acid, belongs to benzene and substituted derivatives class of compounds. Those are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenethyl isothiocyanate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Phenethyl isothiocyanate is a bitter, gooseberry, and green tasting compound and can be found in a number of food items such as herbs and spices, brassicas, horseradish, and cabbage, which makes phenethyl isothiocyanate a potential biomarker for the consumption of these food products. Phenethyl isothiocyanate (PEITC) is a naturally occurring isothiocyanate whose precursor, gluconasturtiin is found in some cruciferous vegetables, especially watercress .
CAS Number2257-09-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2-Isothiocyanatoethyl)benzeneChEBI
2-Phenylethyl isothiocyanateChEBI
beta-Phenethyl isothiocyanateChEBI
beta-Phenylethyl isothiocyanateChEBI
PEITCChEBI
Phenethyl mustard oilChEBI
PhenylaethylsenfoelChEBI
Phenylethyl isothiocyanateChEBI
2-Phenylethyl isothiocyanic acidGenerator
b-Phenethyl isothiocyanateGenerator
b-Phenethyl isothiocyanic acidGenerator
beta-Phenethyl isothiocyanic acidGenerator
Β-phenethyl isothiocyanateGenerator
Β-phenethyl isothiocyanic acidGenerator
b-Phenylethyl isothiocyanateGenerator
b-Phenylethyl isothiocyanic acidGenerator
beta-Phenylethyl isothiocyanic acidGenerator
Β-phenylethyl isothiocyanateGenerator
Β-phenylethyl isothiocyanic acidGenerator
Phenylethyl isothiocyanic acidGenerator
(2-Isothiocyanatoethyl)benzene, 9ciHMDB
Phenethyl isothiocyanateHMDB
PhenethylisothiocyanateHMDB
PEITC compoundHMDB
Phenethyl isothiocyanic acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP3.41ALOGPS
logP3.08ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.7 m³·mol⁻¹ChemAxon
Polarizability18.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H9NS
IUPAC name(2-isothiocyanatoethyl)benzene
InChI IdentifierInChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
InChI KeyIZJDOKYDEWTZSO-UHFFFAOYSA-N
Isomeric SMILESS=C=NCCC1=CC=CC=C1
Average Molecular Weight163.239
Monoisotopic Molecular Weight163.045569983
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9400000000-89e2793dff2133a5d1962015-03-01View Spectrum
GC-MS2-Phenethyl isothiocyanate, non-derivatized, GC-MS Spectrumsplash10-0lxx-9600000000-1487c40cb717ac50d540Spectrum
GC-MS2-Phenethyl isothiocyanate, non-derivatized, GC-MS Spectrumsplash10-0006-9300000000-dce10ef46bd36fa88995Spectrum
GC-MS2-Phenethyl isothiocyanate, non-derivatized, GC-MS Spectrumsplash10-0lxx-9600000000-1487c40cb717ac50d540Spectrum
GC-MS2-Phenethyl isothiocyanate, non-derivatized, GC-MS Spectrumsplash10-0006-9300000000-dce10ef46bd36fa88995Spectrum
Predicted GC-MS2-Phenethyl isothiocyanate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9300000000-8ba905c1a81fe91b0bffSpectrum
Predicted GC-MS2-Phenethyl isothiocyanate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Phenethyl isothiocyanate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-eb29097e9abb6d0a69b62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-be2e5f6b10478c76d7a62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-8900000000-0665aea5aa041d7a38bc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-8cdabbdaddb353bffc802016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-8900000000-ec5fdeb8c6a63b0341dd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-eae0633f4737c22d4ec32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-d4c3b06d47f3ec6e00712021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-7900000000-e5f90967fb5289ac63ab2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9100000000-5c511cf6c615d97e03b32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-cd84ea46dbb46a75690a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID2-PHENETHYL-ISOTHIOCYANATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).