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Allyl thiocyanate isomerizes to the isothiocyanate: [8] CH 2 =CHCH 2 SCN → CH 2 =CHCH 2 NCS. 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. It is used principally as a flavoring agent in foods.
Allyl thiocyanate isomerizes to the isothiocyanate: [4] CH 2 =CHCH 2 SCN → CH 2 =CHCH 2 NCS. Isothiocyanates can be prepared by treating organic dithiocarbamate salts with lead nitrate or tosyl chloride. [5] [6] Synthesis of phenyl isothiocyanate. Isothiocyanates may also be accessed by the fragmentation reactions of 1,4,2-oxathiazoles. [7]
Its pungent flavor is due to allyl isothiocyanate, a phytochemical of plants in the mustard family, Brassicaceae (for example, cabbage, horseradish or wasabi).. Mustard oil has about 60% monounsaturated fatty acids (42% erucic acid and 12% oleic acid); it has about 21% polyunsaturated fats (6% the omega-3 alpha-linolenic acid and 15% the omega-6 linoleic acid), and it has about 12% saturated fats.
"SN1-type" substrates (e.g., benzyl halides) tend to give the isothiocyanate derivatives. Some organic thiocyanates are generated by cyanation of some organosulfur compounds. Sulfenyl thiosulfates (RSSO 3 −) react with alkali metal cyanides to give thiocyanates with displacement of sulfite. This approach has been applied to allyl thiocyanate: [6]
The pungent feeling caused by allyl isothiocyanate, capsaicin, piperine, and allicin is caused by activation of the heat thermo- and chemosensitive TRP ion channels including TRPV1 and TRPA1 nociceptors. The pungency of chilies may be an adaptive response to microbial pathogens. [1]
Allyl isothiocyanate is the pungent ingredient in fresh horseradish sauce. The distinctive pungent taste of horseradish is from the compound allyl isothiocyanate . Upon crushing the flesh of horseradish, the enzyme myrosinase is released and acts on the glucosinolates sinigrin and gluconasturtiin , which are precursors to the allyl isothiocyanate.
For example, allylglucosinolate and allyl glucosinolate refer to the same compound: both versions are found in the literature. [5] Isothiocyanates are conventionally written as two words. [4] The following are some glucosinolates and their isothiocyanate products: [4] Allylglucosinolate is the precursor of allyl isothiocyanate
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