4-Hydroxybenzyl isothiocyanate

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Contents

4-Hydroxybenzyl isothiocyanate
Hydroxybenzyl isothiocyanate.svg
Names
Preferred IUPAC name
4-(Isothiocyanatomethyl)phenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C8H7NOS/c10-8-3-1-7(2-4-8)5-9-6-11/h1-4,10H,5H2
    Key: ATKWJXUJUNLTFU-UHFFFAOYSA-N
  • C1=CC(=CC=C1CN=C=S)O
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).

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

White mustard, Sinapis alba Sinapis alba 1.JPG
White mustard, Sinapis alba

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

Similar to its natural formation, 4-hydroxybenzyl isothiocyanate can be synthesized by reacting sinalbin with myrosinase. [4]

References

  1. ↑ 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 .
  2. 1 2 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.
  3. 1 2 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.
  4. ↑ 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.
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