Mandelonitrile

 ( Cyanohydrins ) 

In organic chemistry, mandelonitrile is the nitrile of mandelic acid, or the cyanohydrin derivative of benzaldehyde. Small amounts of mandelonitrile occur in the Drupe of some fruits.

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Occurrence Mandelonitrile is the aglycone part of the cyanogenic glycosides prunasin and amygdalin. Prunasin can be hydrolyzed by the enyzme prunase into glucose and mandelonitrile (for example, when an appleseed is digested in a ruminant's stomach).

The naturally occurring ( R)-(+) enantiomer finds use as an intermediate in the preparation of optically active α-hydroxy carboxylic acids, α-hydroxy aldehydes, α-hydroxy ketones, and Amino alcohol.Kruse, C.G. In Collins, A.N. Sheldrake, G.N. Crosby, J., Eds. Chirality in Industry Chichester, UK, (1992), 279

Mandelonitrile can break down into cyanide and benzaldehyde, a reaction that can be catalysis by the enzyme mandelonitrile lyase.

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Preparation Racemic mandelonitrile may be prepared similar to many other cyanohydrins. In a one pot reaction, benzaldehyde is reacted with sodium bisulfite to give the corresponding adduct, which further reacts with aqueous sodium cyanide to give the racemic product:

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