Record Information |
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Version | 2.0 |
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Creation Date | 2009-05-25 18:36:06 UTC |
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Update Date | 2014-12-24 20:22:49 UTC |
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Accession Number | T3D0778 |
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Identification |
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Common Name | Allyl isothiocyanate |
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Class | Small Molecule |
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Description | Allyl 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. (1, 2, 3, 4, 5). |
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Compound Type | - Cyanide Compound
- Food Toxin
- Household Toxin
- Industrial/Workplace Toxin
- Metabolite
- Organic Compound
- Pesticide
- Pollutant
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 2-Propenyl isothiocyanate | 3-Iso-Thiocyanatoprop-1-ene | 3-Isothiocyanato-1-propene | 3-Isothiocyanatoprop-1-ene | AITC | Allyl isosulfocyanate | Allyl isosulphocyanate | Allyl isothiocyanic acid | Allyl mustard oil | Allyl sevenolum | Allylsenevol | Allylsenfoel | Allylsevenolum | Allyspol | Artificial mustard oil | Carbospol | Isothiocyansaeureallylester | Mustard oil | Oil of mustard | Oleum sinapis | Redskin | Senfoel | Synthetic mustard oil | Volatile mustard oil | Volatile oil of mustard |
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Chemical Formula | C4H5NS |
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Average Molecular Mass | 99.154 g/mol |
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Monoisotopic Mass | 99.014 g/mol |
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CAS Registry Number | 57-06-7 |
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IUPAC Name | 3-isothiocyanatoprop-1-ene |
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Traditional Name | allyl isothiocyanate |
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SMILES | C=CCN=C=S |
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InChI Identifier | InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 |
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InChI Key | InChIKey=ZOJBYZNEUISWFT-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organosulfur compounds |
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Class | Isothiocyanates |
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Sub Class | Not Available |
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Direct Parent | Isothiocyanates |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Liquid |
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Appearance | Colorless oil. |
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Experimental Properties | Property | Value |
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Melting Point | -80°C | Boiling Point | Not Available | Solubility | 2 mg/mL at 20°C | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000e-9000000000-74e6764518eaef9083ea | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000e-9000000000-74e6764518eaef9083ea | 2018-05-18 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-e5da626a3f0a9112da7f | 2017-07-27 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0005-9000000000-52a42150ed565c57dd63 | 2012-07-25 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00kf-9000000000-f39db8b3315f05512c4e | 2012-07-25 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000l-9000000000-fd8f23ba9a99d3b95b60 | 2012-07-25 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-000e-9000000000-c10457306477602160fd | 2012-08-31 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-3900000000-6f00e6c8cbe246d39e05 | 2017-06-28 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9300000000-dc72ed6e7c7c177d9abf | 2017-06-28 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-ccb9e34efa3fbf3caebb | 2017-06-28 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-a31fab83b72890b37d9e | 2017-06-28 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052b-9000000000-ac309b871ff92649f3d1 | 2017-06-28 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-6a8f7896b2956a540af4 | 2017-06-28 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-6900000000-c391badfd4188e78a822 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9100000000-87228e1d22765d017b75 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4r-9000000000-605088af905285399996 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-9000000000-9aace16230ba7be259d5 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9000000000-286b63d3516de7d14a12 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-286b63d3516de7d14a12 | 2021-09-24 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-000e-9000000000-69a4920e3d464262cd5f | 2014-09-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Not Available | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Inhalation (7) ; oral (7) ; dermal (7)2) |
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Mechanism of Toxicity | Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (8) |
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Metabolism | Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (7) |
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Toxicity Values | LD50: 112 mg/kg (Oral, Rat) (10)
LD50: 88 mg/kg (Dermal, Rabbit (10)
LD50: 12 mg/kg (Intravenous, Rabbit) (10) |
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Lethal Dose | 200 to 300 milligrams for an adult human (cyanide salts). (6) |
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Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (11) |
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Uses/Sources | Synthetic allyl isothiocyanate is used as an insecticide, bacteriocide, and nematocide, and is used in certain cases for crop protection. (9) |
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Minimum Risk Level | Not Available |
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Health Effects | Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (7, 8) |
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Symptoms | Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (7, 8) |
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Treatment | EYES: irrigate opened eyes for several minutes under running water.
INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.
SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention.
INHALATION: supply fresh air. If required provide artificial respiration. |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB05843 |
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PubChem Compound ID | 5971 |
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ChEMBL ID | Not Available |
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ChemSpider ID | 21105854 |
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KEGG ID | C19317 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 494804 |
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BioCyc ID | Not Available |
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CTD ID | C004471 |
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Stitch ID | Allyl isothiocyanate |
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PDB ID | Not Available |
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ACToR ID | 47 |
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Wikipedia Link | Allyl isothiocyanate |
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References |
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Synthesis Reference | Not Available |
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MSDS | Link |
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General References | - Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [5556886 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Baselt RC and Cravey RH (1989). Disposition of Toxic Drugs and Chemicals in Man. 3rd ed. Chicago, IL.: Year Book Medical Publishers.
- ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. [Link]
- Wikipedia. Allyl isothiocyanate. Last Updated 20 May 2009. [Link]
- The Physical and Theoretical Chemistry Laboratory of Oxford University (2005). Material Safety Data Sheet (MSDS) for allyl isothiocyanate. [Link]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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Gene Regulation |
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Up-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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Down-Regulated Genes | Not Available |
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