Allyl isothiocyanate

Allyl isothiocyanate (AITC) is the organosulfur compound with the formula CH2CHCH2NCS. This colorless oil is responsible for the pungent taste of mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated through the TRPA1 and TRPV1 ion channels.[1][2][3] It is slightly soluble in water, but more soluble in most organic solvents.[4]

Allyl isothiocyanate
Allyl isothiocyanate
Space-filling model of allyl isothiocyanate
Preferred IUPAC name
Other names
Synthetic mustard oil
3D model (JSmol)
ECHA InfoCard 100.000.281 Edit this at Wikidata
EC Number
  • 200-309-2
RTECS number
  • NX8225000
UN number 1545
  • InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 checkY
  • InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
  • C=CCN=C=S
Molar mass 99.15 g·mol−1
Density 1.013–1.020 g/cm3
Melting point −102 °C (−152 °F; 171 K)
Boiling point 148 to 154 °C (298 to 309 °F; 421 to 427 K)
GHS pictograms GHS02: FlammableGHS06: ToxicGHS07: HarmfulGHS09: Environmental hazard
GHS Signal word Danger
H226, H301, H310, H315, H319, H330, H335, H400, H410
P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P320, P321
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Biosynthesis and biological functionsEdit

Allyl isothiocyanate can be obtained 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[citation needed], 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. This chemical has recently been shown to strongly repel fire ants, (Solenopsis invicta)[5]

Commercial and other applicationsEdit

Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and potassium thiocyanate:[4]


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, as an anti-mold agent [6] bacteriocide,[7] and nematicide, and is used in certain cases for crop protection.[4]

Hydrolysis of allyl isothiocyanate gives allylamine.[8]


Allyl isothiocyanate has an LD50 of 151 mg/kg and is a lachrymator (similar to tear gas or mace).[4]


Based on in vitro experiments and animal models, allyl isothiocyanate exhibits many of the desirable attributes of a cancer chemopreventive agent.[9]

See alsoEdit


  1. ^ Everaerts, W.; Gees, M.; Alpizar, Y. A.; Farre, R.; Leten, C.; Apetrei, A.; Dewachter, I.; van Leuven, F.; et al. (2011). "The Capsaicin Receptor TRPV1 is a Crucial Mediator of the Noxious Effects of Mustard Oil". Current Biology. 21 (4): 316–321. doi:10.1016/j.cub.2011.01.031. PMID 21315593. S2CID 13151479.
  2. ^ Brône, B.; Peeters, P. J.; Marrannes, R.; Mercken, M.; Nuydens, R.; Meert, T.; Gijsen, H. J. (2008). "Tear gasses CN, CR, and CS are potent activators of the human TRPA1 receptor". Toxicology and Applied Pharmacology. 231 (2): 150–156. doi:10.1016/j.taap.2008.04.005. PMID 18501939.
  3. ^ Ryckmans, T.; Aubdool, A. A.; Bodkin, J. V.; Cox, P.; Brain, S. D.; Dupont, T.; Fairman, E.; Hashizume, Y.; Ishii, N.; et al. (2011). "Design and Pharmacological Evaluation of PF-4840154, a Non-Electrophilic Reference Agonist of the TrpA1 Channel". Bioorganic & Medicinal Chemistry Letters. 21 (16): 4857–4859. doi:10.1016/j.bmcl.2011.06.035. PMID 21741838.
  4. ^ a b c d Romanowski, F.; Klenk, H. "Thiocyanates and Isothiocyanates, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_749.
  5. ^ Hashimoto, Y., Yoshimura, M. & Huang, RN. Appl Entomol Zool (2019).
  6. ^ US Patent No. 8691042
  7. ^ Shin, I. S.; Masuda, H.; Naohide, K. (2004). "Bactericidal Activity of Wasabi (Wasabia japonica) against Helicobacter pylori". International Journal of Food Microbiology. 94 (3): 255–261. doi:10.1016/S0168-1605(03)00297-6. PMID 15246236.
  8. ^ Leffler, M. T. (1938). "Allylamine". Organic Syntheses. 18: 5.; Collective Volume, 2, p. 24
  9. ^ Zhang, Y (2010). "Allyl isothiocyanate as a cancer chemopreventive phytochemical". Molecular Nutrition & Food Research. 54 (1): 127–35. doi:10.1002/mnfr.200900323. PMC 2814364. PMID 19960458.