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Benzyl isothiocyanate, and other isothiocyanates in general, were found to be protective against pancreatic carcinogenesis in vitro [3] via expression of the p21/WAF1 gene. [4] A recent published study showed its restraining impact on obesity, fatty liver, and insulin resistance in diet-induced obesity mouse model.
Glucotropaeolin or benzyl glucosinolate is a glucosinolate found in cruciferous vegetables, particularly garden cress. [1] Upon enzymatic activity, it is transformed into benzyl isothiocyanate , which contributes to the characteristic flavor of these brassicas .
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] This methodology has been applied to a polymer-supported synthesis of isothiocyanates. [8]
The standard product of the reaction is the isothiocyanate (mustard oil); the other two products mainly occur in the presence of specialised plant proteins that alter the outcome of the reaction. [12] A mustard oil glycoside 1 is converted to an isothiocyanate 3 (mustard oil). Glucose 2 is liberated as well, only the β-form is shown
The isothiocyanate further decomposes into hydroxybenzyl alcohols with the release of thiocyanates. [1] [2] [3] In the presence of a nitrile-specifier protein, the less toxic 4-hydroxyphenylacetonitrile is formed from the mustard oil glycoside instead. The cabbage butterfly exploits this mechanism to avoid the toxic effects of the ...
The main complication with this route is the competing formation of alkyisothiocyanates. "SN1-type" substrates (e.g., benzyl halides) tend to give the isothiocyanate derivatives. Some organic thiocyanates are generated by cyanation of some organosulfur compounds.
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.
Hence, this enzyme has one substrate, benzyl isothiocyanate, and one product, benzyl thiocyanate. This enzyme belongs to the family of isomerases, specifically those other isomerases sole sub-subclass for isomerases that do not belong in the other subclasses. The systematic name of this enzyme class is benzyl-thiocyanate isomerase.