Title: Mandelonitrile
CAS Registry Number: 532-28-5
CAS Name: a-Hydroxybenzeneacetonitrile
Additional Names: mandelic acid nitrile; benzaldehyde cyanohydrin
Molecular Formula: C8H7NO
Molecular Weight: 133.15
Percent Composition: C 72.16%, H 5.30%, N 10.52%, O 12.02%
Literature References: Isoln of d-form from peach flower buds: Jones, Enzie, Science 134, 284 (1961). Prepn of d-form by hydrolysis of amygdalin: Auld, J. Chem. Soc. 95, 927 (1909); Smith, Ber. 64, 427 (1931). Resolution of dl-form: Feist, Arch. Pharm. 247, 226 (1909). Synthesis of l-form using cotton fibers: Bredig, Gerstner, Biochem. Z. 250, 414 (1932). Asymmetric synthesis: Krieble, Wieland, J. Am. Chem. Soc. 43, 164 (1921); Prelog, Wilhelm, Helv. Chim. Acta 37, 1634 (1954); Tsuboyama, Bull. Chem. Soc. Jpn. 35, 1004 (1962). It has been suggested that mandelonitrile may be responsible for the alleged anticancer activity of Laetrile, q.v.: see Culliton, Science 182, 1000 (1973). Metabolism study: P. D. A. Singh et al., Biochem. Pharmacol. 34, 2207 (1985).
Derivative Type: dl-Form
Properties: Yellow, oily liquid, mp -10°. Decomp at 170°. d 1.115-1.120. Almost insol in water. Freely sol in alcohol, chloroform, ether.
Melting point: mp -10°
Density: d 1.115-1.120
Derivative Type: d-Form
Properties: [a]D25 +43.75° (c = 5.006 in benzene).
Optical Rotation: [a]D25 +43.75° (c = 5.006 in benzene)
Use: Preparing bitter almond water, by mixing 11 g with 500 g alc and 1489 g water; the mixture contains 0.1% HCN. |