Record Information
Version1.0
Creation date2010-04-08 22:05:47 UTC
Update date2020-02-24 19:10:45 UTC
Primary IDFDB003390
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-Isothiocyanatobutane
Description1-Isothiocyanatobutane, also known as BITC or N-butyl isothiocyanate, belongs to the class of organic compounds known as isothiocyanates. These are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S. 1-Isothiocyanatobutane is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Isothiocyanatobutane is a citrus, earthy, and fatty tasting compound. 1-Isothiocyanatobutane is found, on average, in the highest concentration within horseradish. 1-Isothiocyanatobutane has also been detected, but not quantified in, a few different foods, such as brassicas, cabbages, and cauliflowers. This could make 1-isothiocyanatobutane a potential biomarker for the consumption of these foods.
CAS Number592-82-5
Structure
Thumb
Synonyms
SynonymSource
BITCChEBI
BuNCSChEBI
Butyl mustard oilChEBI
ButylsenfoelChEBI
Isothiocyanic acid N-butyl esterChEBI
Isothiocyanic acid, butyl esterChEBI
N-Butyl isothiocyanateChEBI
Isothiocyanate N-butyl esterGenerator
Isothiocyanate, butyl esterGenerator
N-Butyl isothiocyanic acidGenerator
1-Isothiocyanato-butaneHMDB
Butyl isothiocyanateHMDB
Butyl isothiocyanate, 8ciHMDB
Tert-butyl isothiocyanateHMDB
TBITC CPDHMDB
Butyl isothiocyanic acidGenerator
Butane, 1-isothiocyanato-biospider
Butyl isothiocyanate, 8CIdb_source
Isothiocyanic acid n-butyl esterbiospider
N-butyl isothiocyanatebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.86ALOGPS
logP2.39ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.2 m³·mol⁻¹ChemAxon
Polarizability13.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H9NS
IUPAC name1-isothiocyanatobutane
InChI IdentifierInChI=1S/C5H9NS/c1-2-3-4-6-5-7/h2-4H2,1H3
InChI KeyLIMQQADUEULBSO-UHFFFAOYSA-N
Isomeric SMILESCCCCN=C=S
Average Molecular Weight115.197
Monoisotopic Molecular Weight115.045569983
Classification
Description belongs to the class of organic compounds known as isothiocyanates. These are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassIsothiocyanates
Sub ClassNot Available
Direct ParentIsothiocyanates
Alternative Parents
Substituents
  • Isothiocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.13%; H 7.87%; N 12.16%; S 27.84%DFC
Melting PointNot Available
Boiling PointBp9 58-59°DFC
Experimental Water SolubilityNot Available
Experimental logP2.92AUGUSTIN,S ET AL. (1987)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4980DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-560d0620f11fca8bf081JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4900000000-eb58ea6e66635e47ce26JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-fb596a2252e6005219fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-2eea33fc6554478f434cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-ac70a67f3404af2235e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-9500000000-aece654d61547421b82aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-02f332b3b3a55984d9a3JSpectraViewer
ChemSpider ID11124
ChEMBL IDCHEMBL1814588
KEGG Compound IDNot Available
Pubchem Compound ID11613
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31328
CRC / DFC (Dictionary of Food Compounds) IDCXG02-E:CXG02-E
EAFUS ID417
Dr. Duke IDBUTYLISOTHIOCYANATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID592-82-5
GoodScent IDrw1226161
SuperScent ID11613
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
Flavours
FlavorCitations
sulfur
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
pungent
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vegetable
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
herbaceous
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fatty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
spicy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
floral
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
citrus
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
woody
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
meaty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
wine_like
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
earthy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fruity
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
nutty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sulfury
  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).