Record Information
Version1.0
Creation date2010-04-08 22:09:58 UTC
Update date2019-11-26 03:06:04 UTC
Primary IDFDB012051
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Isothiocyanato-1-butene
Description4-Isothiocyanato-1-butene, also known as 1-butene 4-isothiocyanate or crotonyl mustard oil, 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. 4-Isothiocyanato-1-butene is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Isothiocyanato-1-butene is an aromatic and pungent tasting compound. 4-Isothiocyanato-1-butene has been detected, but not quantified in, several different foods, such as brassicas, cabbages, cauliflowers, horseradish, and white cabbages. This could make 4-isothiocyanato-1-butene a potential biomarker for the consumption of these foods.
CAS Number3386-97-8
Structure
Thumb
Synonyms
SynonymSource
1-Butene 4-isothiocyanateHMDB
1-Butene-4-isothiocyanateHMDB
3-Butenyl isothiocyanateHMDB
But-3-enyl isothiocyanateHMDB
Crotonyl mustard oilHMDB
Crotyl mustard oilHMDB
Isothiocyanic acid, 3-butenyl esterHMDB
BylITCHMDB
ButenylisothiocyanateHMDB
1-butene 4-isothiocyanatebiospider
1-Butene, 4-isothiocyanato-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.41ALOGPS
logP2.09ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.25 m³·mol⁻¹ChemAxon
Polarizability12.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H7NS
IUPAC name4-isothiocyanatobut-1-ene
InChI IdentifierInChI=1S/C5H7NS/c1-2-3-4-6-5-7/h2H,1,3-4H2
InChI KeySKIHGKNFJKJXPX-UHFFFAOYSA-N
Isomeric SMILESC=CCCN=C=S
Average Molecular Weight113.181
Monoisotopic Molecular Weight113.029919919
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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.06%; H 6.23%; N 12.38%; S 28.33%DFC
Melting PointNot Available
Boiling PointBp11.5 57.5-58.5°DFC
Experimental Water Solubility0.46 mg/mL at 20 oCBEILSTEIN
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-9200000000-1a40200ada4e3470682dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fr-9200000000-1a40200ada4e3470682dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-9000000000-8f560f490ac3ff773e2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5900000000-6b5a0c36ac97abfbfafdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-107fe6a8c4c497549b8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a06462555fc1d0881d1cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-2fd61d6aae4db1e2552bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-9400000000-b269adb37f1cf3ae532bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ab47c48091b0e907f16eJSpectraViewer
ChemSpider ID69373
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID76922
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33867
CRC / DFC (Dictionary of Food Compounds) IDHCV39-D:HCV39-D
EAFUS ID386
Dr. Duke ID3-BUTENYL-ISOTHIOCYANATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1586801
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
anti mutagenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
aromatic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent
  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).