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Skeletal formula
Ball-and-stick model
IUPAC name
Other names
532-28-5 YesY
ChEBI CHEBI:16910 YesY
ChemSpider 10304 YesY
Jmol interactive 3D Image
KEGG C00561 YesY
PubChem 10758
Molar mass 133.15 g mol−1
Density 1.117 g/mL at 25 °C
Melting point 28 to 30 °C (82 to 86 °F; 301 to 303 K)
Boiling point 17 to 0 °C (63 to 32 °F; 290 to 273 K)
Main hazards toxic
R-phrases R23/24/25 R36/37/38 R41
S-phrases S22 S26 S36/37/39 S45
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related compounds
mandelic acid, phenylacetonitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the pits of some fruits.


Mandelonitrile is the aglycone part of the cyanogenic glycosides prunasin and amygdalin.

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 2-amino alcohols.[2]

Mandelonitrile is broken down into cyanide and benzaldehyde by the enzyme mandelonitrile lyase.


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:[3]

Preparation of mandelonitrile.png


  1. ^ Sigma-Aldrich product page
  2. ^ Kruse, C.G. In Collins, A.N. Sheldrake, G.N. Crosby, J., Eds. Chirality in Industry Chichester, UK , (1992), 279
  3. ^ Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941). "Mandelic Acid". Org. Synth. ; Coll. Vol. 1, p. 336