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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.
"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]
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]
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.
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.
Sinigrin (the precursor to allyl isothiocyanate) broccoli family, brussels sprouts, black mustard. Glucotropaeolin (the precursor to benzyl isothiocyanate) Gluconasturtiin (the precursor to phenethyl isothiocyanate) Glucoraphanin (the precursor to sulforaphane) brassicas: broccoli, cauliflower, brussels sprouts, cabbages.
This page was last edited on 7 September 2024, at 08:40 (UTC).; Text is available under the Creative Commons Attribution-ShareAlike 4.0 License; additional terms may apply.
Mustard oil – (essential oil), containing a high percentage of allyl isothiocyanate or other isothiocyanates, depending on the species of mustard; Mustard oil (pressed) – used in India as a cooking oil. Also used as a massage oil. Mustard plant – Mustard seed –