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Allyl isothiocyanate

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Allyl isothiocyanate
Allyl isothiocyanate
Space-filling model of allyl isothiocyanate
Names
IUPAC name 3-Isothiocyanato-1-propene
Other names synthetic mustard oil
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.281 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N
  • InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2Key: ZOJBYZNEUISWFT-UHFFFAOYAS
SMILES
  • C=CCN=C=S
Properties
Chemical formula C4H5NS
Molar mass 99.15 g·mol
Density 1.013–1.020 g/cm
Melting point −102 °C (−152 °F; 171 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Allyl isothiocyanate (AITC) is the organosulfur compound with the formula CH2CHCH2NCS. This colorless oil is responsible for the pungent taste of mustard, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC is mediated through the TRPA1 and TRPV1 ion channels. It is slightly soluble in water, but well soluble in most organic solvents.

Biosynthesis and biological functions

Allyl isothiocyanate comes from the seeds of black mustard (Brassica nigra) or brown Indian mustard (Brassica juncea). When these mustard seeds are broken, the enzyme myrosinase is released and acts on a glucosinolate known as sinigrin to give allyl isothiocyanate.

Allyl isothiocyanate serves the plant as a defense against herbivores; since it is harmful to the plant itself, it is stored in the harmless form of the glucosinolate, separate from the myrosinase enzyme. When an animal chews the plant, the allyl isothiocyanate is released, repelling the animal.

Commercial and other applications

Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and potassium thiocyanate:

CH2=CHCH2Cl + KSCN → CH2=CHCH2NCS + KCl.

The product obtained in this fashion is sometimes known as synthetic mustard oil. Allyl isothiocyanate can also be liberated by dry distillation of the seeds. The product obtained in this fashion is known as volatile oil of mustard and is usually around 92% pure. It is used principally as a flavoring agent in foods. Synthetic allyl isothiocyanate is used as an insecticide, bacteriocide, and nematocide, and is used in certain cases for crop protection.

Hydrolysis of allyl isothiocyanate gives allyl amine.

Safety

Allyl isothiocyanate is fairly toxic with LD50 of 151 mg/kg and is a dangerous lachrymator.

References

  1. . doi:10.1016/j.cub.2011.01.031. PMID 21315593. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
  2. Brône B, Peeters PJ, Marrannes R, Mercken M, Nuydens R, Meert T, Gijsen HJ (2008). "Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor". Toxicol. Appl. Pharmacol. 231 (2): 150–6. doi:10.1016/j.taap.2008.04.00. PMID 18501939. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. Ryckmans T, Aubdool A A, Bodkin J V, Cox P, Brain S D, Dupont T, Fairman E, Hashizume Y, Ishii N, Kato T, Kitching L, Newman J, Omoto K, Rawson D and Strover J (2011). "Design and pharmacological evaluation of PF-4840154, a non-electrophilic reference agonist of the TrpA1 channel". Bioorganic. Med. Chem. Lett. doi:10.1016/j.bmcl.2011.06.035. PMID 21741838. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ F. Romanowski, H. Klenk "Thiocyanates and Isothiocyanates, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim.
  5. M. T. Leffler (1943). "Allylamine". Organic Syntheses; Collected Volumes, vol. 2, p. 24.

See also

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