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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.
In organic chemistry, isothiocyanate is a functional group as found in compounds with the formula R−N=C=S. Isothiocyanates are the more common isomers of thiocyanates , which have the formula R−S−C≡N .
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 ...
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 .
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.
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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.
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