4-Hydroxyphenylacetonitrile

4-Hydroxyphenylacetonitrile
Names
	Preferred IUPAC name 4-(Hydroxyphenyl)acetonitrile
Identifiers
CAS Number	14191-95-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16667;
ChemSpider	24729;
ECHA InfoCard	100.034.572
EC Number	238-046-0;
KEGG	C03766;
PubChem CID	26548;
UNII	18Q5J224RM;
CompTox Dashboard (EPA)	DTXSID90161856 ;
	InChI InChI=1S/C8H7NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5H2 Key: AYKYOOPFBCOXSL-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1CC#N)O;
Properties
Chemical formula	C8H7NO
Molar mass	133.15 g·mol−1
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	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]

Reactions

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

References

^ 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, Bibcode:2005JAFC...53.8650B, doi:10.1021/jf051570r, PMID 16248567
^ 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, Bibcode:2007IBMB...37.1119A, 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, Bibcode:2018RSCAd...829392M, doi:10.1039/C8RA05654D, PMC 9084560, PMID 35548000{{citation}}: CS1 maint: multiple names: authors list (link)

[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, Bibcode:2005JAFC...53.8650B, doi:10.1021/jf051570r, PMID 16248567

[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, Bibcode:2007IBMB...37.1119A, 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, Bibcode:2018RSCAd...829392M, doi:10.1039/C8RA05654D, PMC 9084560, PMID 35548000{{citation}}: CS1 maint: multiple names: authors list (link)

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