Record Information
Version1.0
Creation date2010-04-08 22:10:02 UTC
Update date2018-05-28 23:34:57 UTC
Primary IDFDB012199
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBenzyl isothiocyanate
DescriptionIsolated from Tropaeolum majus (garden nasturtium) and Lepidium sativum (garden cress), also in other plants especies in the Cruciferae. Potential nutriceutical. Benzyl isothiocyanate is found in many foods, some of which are horseradish tree, garden cress, papaya, and cabbage.
CAS Number622-78-6
Structure
Thumb
Synonyms
SynonymSource
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
(isothiocyanatomethyl)benzenebiospider
(Isothiocyanatomethyl)benzene, 9CIdb_source
AB 2 (VAN)biospider
Alpha-isothiocyanatotoluenebiospider
Benzene, (isothiocyanatomethyl)-biospider
Benzylsenfoel (german)biospider
Toluene, α-isothiocyanato-biospider
Toluene, alpha-isothiocyanato-biospider
α-isothiocyanatotolueneGenerator
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H7NS
IUPAC name(isothiocyanatomethyl)benzene
InChI IdentifierInChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
InChI KeyMDKCFLQDBWCQCV-UHFFFAOYSA-N
Isomeric SMILESS=C=NCC1=CC=CC=C1
Average Molecular Weight149.213
Monoisotopic Molecular Weight149.029919919
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.40%; H 4.73%; N 9.39%; S 21.49%DFC
Melting PointMp 41°DFC
Boiling PointBp12 125-126°DFC
Experimental Water Solubility0.109 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP3.16HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-29b203aa3cc9f04c2fdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-c83b146c4b125e3d9b83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-e7980a61941ab132ea80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-33afb787a500e9b4e0dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-6755d456251a0541ed94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-2fcb3ba0537189b628deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-4900000000-52000359d56b4bbd3d79View in MoNA
ChemSpider ID2256
ChEMBL IDCHEMBL55285
KEGG Compound IDC03098
Pubchem Compound ID2346
Pubchem Substance IDNot Available
ChEBI ID17484
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33969
CRC / DFC (Dictionary of Food Compounds) IDHFB54-D:HFB54-D
EAFUS ID324
Dr. Duke IDBENZYL-ISOTHIOCYANATE
BIGG IDNot Available
KNApSAcK IDC00032761
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1012031
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 / Bioactivities
DescriptorIDDefinitionReference
albuminurigenicDUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti asthmatic49167 A drug used to treat asthma.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
antibiotic22582 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti mutagenicDUKE
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti nitrosaminicDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
flatulentDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
viristatDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
watercress
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dusty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
horseradish
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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).