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Chemical compound From Wikipedia, the free encyclopedia
4-Hydroxybenzyl isothiocyanate is a naturally occurring isothiocyanate. It is formed as a degradation product of sinalbin from white mustard and is responsible for the pungent taste of mustard seeds.
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Molar mass | 165.21 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[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 isothiocyanate.[2] Similar to other isothiocyanates found in cruciferous vegetables, this compound contributes to the pungent flavor of mustard.[3]
Similar to its natural formation, 4-hydroxybenzyl isothiocyanate can be synthesized by reacting sinalbin with myrosinase.[4]
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