4-Hydroxybenzyl isothiocyanate
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4-Hydroxybenzyl isothiocyanate is a naturally occurring isothiocyanate. It is formed as a degradation product of sinalbin from white mustard and contributes to the pungent taste of mustard seeds.
Occurrence
4-hydroxybenzyl isothiocyanate occurs as a degradation product of sinalbin or glucosinalbin in white mustard. This compound is broken down as a mustard oil glycoside by myrosinase, releasing the isothiocyanate. The isothiocyanate further decomposes into hydroxybenzyl alcohols with the release of thiocyanates. 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 isothiocyanate. Similar to other isothiocyanates found in cruciferous vegetables, this compound contributes to the pungent flavor of mustard.
Production
Similar to its natural formation, 4-hydroxybenzyl isothiocyanate can be synthesized by reacting sinalbin with myrosinase.