Isothiocyanate

In organic chemistry, isothiocyanate is a functional group as found in compounds with the formula R−N=C=S.

Many isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates.

Cruciferous vegetables, such as bok choy, broccoli, cabbage, cauliflower, kale, and others, are rich sources of glucosinolate precursors of isothiocyanates.

[10]: 340 Isothiocyanates occur widely in nature and are of interest in food science and medical research.

[1] Vegetable foods with characteristic flavors due to isothiocyanates include bok choy, broccoli, cabbage, cauliflower, kale, wasabi, horseradish, mustard, radish, Brussels sprouts, watercress, papaya seeds, nasturtiums, and capers.

General structure of an isothiocyanate.
General structure of an isothiocyanate.
Synthesis of phenyl isothiocyanate
Synthesis of phenyl isothiocyanate
The reaction of acetophenone enolate with phenyl isothiocyanate. In this one-pot synthesis[9] the ultimate reaction product is a Thiazolidine. This reaction is stereoselective with the formation of the Z-isomer only.
The reaction of acetophenone enolate with phenyl isothiocyanate. In this one-pot synthesis [ 9 ] the ultimate reaction product is a Thiazolidine . This reaction is stereoselective with the formation of the Z-isomer only.