4-Hydroxybenzyl isothiocyanate

4-Hydroxybenzyl isothiocyanate
Identifiers
CAS Number	2086-86-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:178135;
ChEMBL	ChEMBL3593946;
ChemSpider	141134;
PubChem CID	160611;
UNII	318HJ2034L;
CompTox Dashboard (EPA)	DTXSID20174974 ;
	InChI InChI=1S/C8H7NOS/c10-8-3-1-7(2-4-8)5-9-6-11/h1-4,10H,5H2 Key: ATKWJXUJUNLTFU-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1CN=C=S)O;
Properties
Chemical formula	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). Infobox references

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.

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.^[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

^ 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.

[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.

[:0-2] 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.

[Bell-3] 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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