Allyl isothiocyanate

Allyl isothiocyanate

Names
IUPAC name 3-Isothiocyanato-1-propene
Other names synthetic mustard oil
Identifiers
CAS Number	57-06-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:73224 N
ChEMBL	ChEMBL233248 Y
ChemSpider	21105854 Y
ECHA InfoCard	100.000.281
IUPHAR/BPS	2420
KEGG	D02818 Y
PubChem	5971
UNII	BN34FX42G3 Y
InChI InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2 Y Key: ZOJBYZNEUISWFT-UHFFFAOYSA-N Y 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/cm3
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).
N  (what is YN ?)
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. It is slightly soluble in water, but more soluble in most organic solvents.

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.

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

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 , and is used in certain cases for crop protection.