Allyl isothiocyanate

Allyl_isothiocyanate

• 

  2D skeletal structure of Allyl isothiocyanate

• 

  3D van der Waals model of Allyl isothiocyanate

Allyl isothiocyanate

Allyl isothiocyanate (AITC) is an organic compound with the formula CH_CHCH_NCS. It is a colorless oil with a pungent odor, commonly associated with mustard and horseradish. AITC is a member of the isothiocyanate family, which are compounds containing the functional group -N=C=S.

Chemical Properties

Allyl isothiocyanate is a volatile compound that is slightly soluble in water but more soluble in organic solvents. It is known for its ability to form thiourea derivatives when reacted with amines. The compound is stable under normal conditions but can decompose at elevated temperatures.

Natural Occurrence

AITC is naturally found in plants of the Brassicaceae family, such as mustard, horseradish, and wasabi. It is produced from the enzymatic hydrolysis of sinigrin, a glucosinolate, by the enzyme myrosinase. This reaction occurs when plant tissues are damaged, releasing the pungent compound as a defense mechanism against herbivores.

Uses

Allyl isothiocyanate is used as a flavoring agent in foods, imparting a spicy and pungent taste. It is also employed as a preservative due to its antimicrobial properties. In agriculture, AITC is used as a natural pesticide and fungicide.

In the laboratory, AITC is used as a reagent for the synthesis of other chemical compounds. It is also studied for its potential health benefits, including anti-cancer and anti-inflammatory properties.

Safety

Allyl isothiocyanate is an irritant to the skin, eyes, and respiratory system. Proper handling and protective equipment are recommended when working with this compound. Ingestion or inhalation of large amounts can be harmful.

Related Pages

• Isothiocyanate
• Glucosinolate
• Brassicaceae
• Mustard
• Horseradish