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Record Information
Version3.6
Creation Date2007-04-12 15:38:43 UTC
Update Date2016-02-11 01:07:18 UTC
HMDB IDHMDB05843
Secondary Accession NumbersNone
Metabolite Identification
Common NameAllyl isothiocyanate
DescriptionAllyl isothiocyanate is a volatile organic compound. Allyl isothiocyanate (AITC) is a constituent of mustard, horseradish and wasabi and certain vegetables found in the human diet, mostly in cruciferous vegetables. AITC is a colorless to pale yellow liquid that is slightly soluble in water, but well soluble in most organic solvents. AITC possesses numerous biochemical and physiological activities. It is cytotoxic and tumorigenic at high doses and also is a modulator of enzymes involved in metabolism of xenobiotics, including carcinogens. It is plausible that the wide consumption of dietary AITC may have profound effects on human health. oxidative DNA damage may play important roles in carcinogenic processes induced by AITC. Allergic contact dermatitis from AICT is well known but infrequently reported. AITC is occasionally found as a volatile component of normal human biofluids. (PMID: 5556886 , 8222057 , 8000299 , 10754276 , 15373848 ).
Structure
Thumb
Synonyms
ValueSource
2-Propenyl isothiocyanateChEBI
3-isothiocyanato-1-PropeneChEBI
AITChEBI
AITCChEBI
Allyl isosulfocyanateChEBI
Allyl mustard oilChEBI
AllylsenfoelChEBI
Isothiocyanate d'allyleChEBI
Isothiocyanic acid allyl esterChEBI
Mustard oilChEBI
Oil OF mustardChEBI
Oleum sinapisChEBI
Senf oelChEBI
Volatile mustard oilChEBI
Volatile oil OF mustardChEBI
2-Propenyl isothiocyanic acidGenerator
Allyl isosulfocyanic acidGenerator
Allyl isosulphocyanateGenerator
Allyl isosulphocyanic acidGenerator
Isothiocyanic acid d'allyleGenerator
Isothiocyanate allyl esterGenerator
3-iso-Thiocyanatoprop-1-eneHMDB
Allyl isothiocyanate (natural)HMDB
Allyl isothiocyanateHMDB
Allyl isothiocyanate non-perfume gradeHMDB
Allyl sevenolumHMDB
AllylsenevolHMDB
AllylsevenolumHMDB
AllyspolHMDB
Artificial mustard oilHMDB
CarbospolHMDB
Caswell no. 027HMDB
FEMA no. 2034HMDB
IsothiocyansaeureallylesterHMDB
Oleum sinapis volatileHMDB
RedskinHMDB
SenfoelHMDB
Synthetic mustard oilHMDB
Chemical FormulaC4H5NS
Average Molecular Weight99.154
Monoisotopic Molecular Weight99.014269855
IUPAC Name3-isothiocyanatoprop-1-ene
Traditional Nameallyl isothiocyanate
CAS Registry Number57-06-7
SMILES
C=CCN=C=S
InChI Identifier
InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
InChI KeyInChIKey=ZOJBYZNEUISWFT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-80 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.32 mg/mLALOGPS
logP1.9ALOGPS
logP1.8ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.49 m3·mol-1ChemAxon
Polarizability10.51 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0005-9000000000-52a42150ed565c57dd63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9000000000-f39db8b3315f05512c4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000l-9000000000-fd8f23ba9a99d3b95b60View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-000e-9000000000-c10457306477602160fdView in MoNA
MSMass Spectrum (Electron Ionization)splash10-000e-9000000000-69a4920e3d464262cd5fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.14 +/- 0.098 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012440
KNApSAcK IDNot Available
Chemspider ID21105854
KEGG Compound IDC19317
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllyl isothiocyanate
NuGOwiki LinkHMDB05843
Metagene LinkHMDB05843
METLIN IDNot Available
PubChem Compound5971
PDB IDNot Available
ChEBI ID494804
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [5556886 ]
  2. Jiao D, Ho CT, Foiles P, Chung FL: Identification and quantification of the N-acetylcysteine conjugate of allyl isothiocyanate in human urine after ingestion of mustard. Cancer Epidemiol Biomarkers Prev. 1994 Sep;3(6):487-92. [8000299 ]
  3. Musk SR, Johnson IT: Allyl isothiocyanate is selectively toxic to transformed cells of the human colorectal tumour line HT29. Carcinogenesis. 1993 Oct;14(10):2079-83. [8222057 ]
  4. Murata M, Yamashita N, Inoue S, Kawanishi S: Mechanism of oxidative DNA damage induced by carcinogenic allyl isothiocyanate. Free Radic Biol Med. 2000 Mar 1;28(5):797-805. [10754276 ]
  5. Lerbaek A, Rastogi SC, Menne T: Allergic contact dermatitis from allyl isothiocyanate in a Danish cohort of 259 selected patients. Contact Dermatitis. 2004 Aug;51(2):79-83. [15373848 ]