From Wikipedia, the free encyclopedia
Allyl isothiocyanate (AITC) is the organosulfur compound with the formula Allyl isothiocyanate
CH2 CHCH 2 NCS. 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. 
1 Biosynthesis and biological functions
2 Commercial and other applications
5 See also
Biosynthesis and biological functions
synthetic mustard oil
Allyl isothiocyanate comes from the seeds of black mustard (Brassica nigra) or
brown Indian mustard (Brassica juncea). When these mustard seeds are broken,
CAS number 57-06-7
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 UNII BN34FX42G3
harmful to the plant itself, it is stored in the harmless form of the glucosinolate, KEGG D02818
separate from the myrosinase enzyme. When an animal chews the plant, the allyl ChEMBL CHEMBL233248
isothiocyanate is released, repelling the animal. Jmol-3D Image 1
Commercial and other applications SMILES
Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and
CH2 =CHCH 2 Cl + KSCN → CH2 =CHCH 2 NCS + KCl. Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N
The product obtained in this fashion is sometimes known as synthetic mustard oil. InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
Allyl isothiocyanate can also be liberated by dry distillation of the seeds. The Key: ZOJBYZNEUISWFT-UHFFFAOYAS
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
Molecular C4 H5 NS
allyl isothiocyanate is used as an insecticide, bacteriocide  , and nematocide, formula
and is used in certain cases for crop protection. Molar mass 99.15 g mol−1
Hydrolysis of allyl isothiocyanate gives allyl amine. Density 1.013–1.020 g/cm3
Melting point −102 °C, 171 K, -152 °F
Safety Boiling point 148-154 °C, 421-427 K, 298-
Allyl isothiocyanate is fairly toxic with LD50 of 151 mg/kg and is a dangerous 309 °F
lachrymator. (verify) (what is: / ?)
Except where noted otherwise, data are given for
References materials in their standard state (at 25 °C,
1. ^ Everaerts, W.; Gees, M.; Alpizar, Y. A.; Farre, R.; Leten, C.; Apetrei, A.; Infobox references
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 .
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.2008.04.00 . 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
and 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. (2005), "Thiocyanates and Isothiocyanates, Organic", Ullmann's Encyclopedia of Industrial
Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a26_749
5. ^ 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 . edit
6. ^ Leffler, M. T. (1938), "Allylamine" , Org. Synth. 18: 5; Coll. Vol. 2: 24
Piperine, the active piquant chemical in black pepper
Capsaicin, the active piquant chemical in chili peppers
Allicin, the active piquant flavor chemical in raw garlic
via Allyl isothiocyanate