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4-Hydroxyphenylacetonitrile

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4-Hydroxyphenylacetonitrile
Identifiers
CAS Number
ECHA InfoCard 100.034.572 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
Properties
Chemical formula C8H7NO
Molar mass 133.15 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. 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. The horseradish tree contains niazirine, a glycoside of 4-hydroxyphenylacetonitrile.

Reactions

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

References

  1. 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
  2. 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)
  3. 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)
  4. 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)
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