4-Hydroxyphenylacetonitrile

4-Hydroxyphenylacetonitrile
Identifiers
CAS Number	14191-95-8;
ECHA InfoCard	100.034.572
PubChem CID	26548;
CompTox Dashboard (EPA)	DTXSID90161856 ;
Properties
Chemical formula	C8H7NO
Molar mass	133.15 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-Hydroxyphenylacetonitrile is a naturally occurring nitrile.

Occurrence

4-Hydroxyphenylacetonitrile occurs alongside 4-hydroxybenzylisothiocyanate as a degradation product of glucosinalbin, which is found in white mustard.^[1] The cabbage butterfly, which feeds on cruciferous plants containing glucosinalbin, among other things, can evade the toxicity of isothiocyanate by specifically breaking down glucosinalbin to 4-hydroxyphenylacetonitrile, which it can further metabolize.^[2] The horseradish tree contains niazirine, a glycoside of 4-hydroxyphenylacetonitrile.^[3]

The hydrogenation of 4-hydroxyphenylacetonitrile under palladium catalysis yields tyramine.^[4]

^ Vladimir Borek, Matthew J. Morra (2005-11-01), "Ionic Thiocyanate (SCN - ) Production from 4-Hydroxybenzyl Glucosinolate Contained in Sinapis alba Seed Meal", Journal of Agricultural and Food Chemistry, vol. 53, no. 22, pp. 8650–8654, doi:10.1021/jf051570r
^ Niels Agerbirk, Carl Erik Olsen, Henrik Bak Topbjerg, Jens Christian Sørensen (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, vol. 37, no. 11, pp. 1119–1130, doi:10.1016/j.ibmb.2007.06.009{{citation}}: CS1 maint: multiple names: authors list (link)
^ K Shanker, M Gupta, S Srivastava, D Bawankule, A Pal, S Khanuja (2007), "Determination of bioactive nitrile glycoside(s) in drumstick (Moringa oleifera) by reverse phase HPLC", Food Chemistry, vol. 105, no. 1, pp. 376–382, doi:10.1016/j.foodchem.2006.12.034{{citation}}: CS1 maint: multiple names: authors list (link)
^ Mairi I. McAllister, Cédric Boulho, Liam McMillan, Lauren F. Gilpin, Sandra Wiedbrauk, Colin Brennan, David Lennon (2018), "The production of tyramine via the selective hydrogenation of 4-hydroxybenzyl cyanide over a carbon-supported palladium catalyst", RSC Advances, vol. 8, no. 51, pp. 29392–29399, doi:10.1039/C8RA05654D, PMC 9084560, PMID 35548000{{citation}}: CS1 maint: multiple names: authors list (link)