Allyl isothiocyanate

Allyl isothiocyanate

Names
IUPAC name 3-Isothiocyanato-1-propene
Other names synthetic mustard oil
Identifiers
CAS Number	57-06-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:73224
ChEMBL	ChEMBL233248
ChemSpider	21105854
ECHA InfoCard	100.000.281
IUPHAR/BPS	2420
KEGG	D02818
PubChem	5971
UNII	BN34FX42G3
InChI InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N InChI=1/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 Key: ZOJBYZNEUISWFT-UHFFFAOYAS
SMILES C=CCN=C=S
Properties
Chemical formula	C4H5NS
Molar mass	99.15 g·mol^−1
Density	1.013–1.020 g/cm^3
Melting point	−102 °C (−152 °F; 171 K)
Boiling point	148 to 154 °C (298 to 309 °F; 421 to 427 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 is 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]

Biosynthesis and biological functions

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, 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:^[4]

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,^[5] and nematocide, and is used in certain cases for crop protection.^[4]

Hydrolysis of allyl isothiocyanate gives allylamine.^[6]

Safety

Allyl isothiocyanate has an LD₅₀ of 151 mg/kg and is a lachrymator.^[4]

Oncology

Based on in vitro experiments and animal models, allyl isothiocyanate exhibits many desirable attributes of a cancer chemopreventive agent.^[7]

See also

• Mustard Plaster, traditional home remedy
• 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

References

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.
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 and Medicinal Chemistry Letters. 21 (16): 4857–4859. doi:10.1016/j.bmcl.2011.06.035. PMID 21741838.
4. 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.
6. Leffler, M. T. (1938). "Allylamine". Org. Synth. 18: 5.; Coll. Vol., 2, p. 24
7. 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.