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.
| |
| Identifiers | |
|---|---|
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C8H7NOS | |
| 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).
| |
Occurrence
edit
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]
Production
editSimilar to its natural formation, 4-hydroxybenzyl isothiocyanate can be synthesized by reacting sinalbin with myrosinase.[4]
References
edit- ^ Kawakishi S, Muramatsu K (1966). "Studies on the Decomposition of Sinalbin". Agricultural and Biological Chemistry. 30 (7): 688–692. doi:10.1271/bbb1961.30.688.
- ^ a b Agerbirk N, Olsen CE, Topbjerg HB, Sørensen JC (November 2007). "Host plant-dependent metabolism of 4-hydroxybenzylglucosinolate in Pieris rapae: Substrate specificity and effects of genetic modification and plant nitrile hydratase". Insect Biochemistry and Molecular Biology. 37 (11): 1119–1130. Bibcode:2007IBMB...37.1119A. doi:10.1016/j.ibmb.2007.06.009. PMID 17916498.
- ^ a b Bell L, Oloyede OO, Lignou S, Wagstaff C, Methven L (September 2018). "Taste and Flavor Perceptions of Glucosinolates, Isothiocyanates, and Related Compounds" (PDF). Molecular Nutrition & Food Research. 62 (18): e1700990. doi:10.1002/mnfr.201700990. PMID 29578640.
- ^ Buskov S, Hasselstrøm J, Olsen CE, Sørensen H, Sørensen JC, Sørensen S (July 2000). "Supercritical fluid chromatography as a method of analysis for the determination of 4-hydroxybenzylglucosinolate degradation products". Journal of Biochemical and Biophysical Methods. 43 (1–3): 157–174. doi:10.1016/S0165-022X(00)00081-6. PMID 10869674.