Allyl isothiocyanate

Chembox new
Name = Allyl isothiocyanate
ImageFile = Allyl-isothiocyanate-2D-skeletal.png ImageName = Allyl isothiocyanate
ImageFile1 = Allyl-isothiocyanate-3D-vdW.png ImageName1 = Space-filling model of allyl isothiocyanate
IUPACName = 3-isothiocyanato-1-propene
OtherNames = synthetic mustard oil
Section1 = Chembox Identifiers
CASNo = 57-06-7
SMILES = C=CCN=C=S
Section2 = Chembox Properties
Formula = C₄H₅NS
MolarMass = 99.15 g/mol
Density = 1.013-1.020 g/cm³
MeltingPt = -102 °C
BoilingPt = 148-154 °C

Allyl isothiocyanate is the organosulfur compound with the formula CH₂CHCH₂NCS. This colourless oil is responsible for the pungent taste of mustard, horseradish, and wasabi. It is slightly soluble in water, but well soluble in most organic solvents.F. Romanowski, H. Klenk "Thiocyanates and Isothiocyanates, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim.]

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.

Commericial and other applications

Allyl isothiocyanate is produced commercially by the reaction of allyl chloride and potassium thiocyanate::CH₂=CHCH₂Cl + KSCN → CH₂=CHCH₂NCS + KClThe product obtained in this fashion is sometimes known as "synthetic mustard oil." Allyl isothiocyanate can also be liberated by drydistillation 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, bacterialcide, and nematocide, and is used in certain cases for crop protection.

Hydrolysis of allyl isothiocyanate gives allyl amine. [OrgSynth | author = M. T. Leffler | title = Allylamine | collvol = 2 | collvolpages = 24 | year = 1943 | prep = CV2P0024]

afety

Allyl isothiocyanate is mildly toxic with ld₅₀ of 151 mg/kg but is a dangerous lachrymator.

References

ee also

* Piperine, the active piquant chemical in black pepper
* Capsaicin, the active piquant chemical in chile peppers
* Allicin, the active piquant flavor chemical in uncooked garlic and onions (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)
* List of phytochemicals in food