Mandelonitrile Glucoside
Structural Formula Vector Image
Title: Mandelonitrile Glucoside
CAS Registry Number: 138-53-4
CAS Name: a-(b-D-Glucopyranosyloxy)benzeneacetonitrile
Molecular Formula: C14H17NO6
Molecular Weight: 295.29
Percent Composition: C 56.94%, H 5.80%, N 4.74%, O 32.51%
Literature References: Prepn of d-form by action of yeast on amygdalin: Fischer, Ber. 28, 1508 (1895); Auld, J. Chem. Soc. 93, 1276 (1908). Isoln of d-form from Prunus serotina, Ehrk, P. macrophylla Sieb et Zucc., Rosaceae: Power, Moore, ibid. 95, 243 (1909); 97, 1099 (1910); Kariyone, Matsushima, J. Pharm. Soc. Jpn. No. 514, 1061 (1924); from Eucalyptus corynocalyx F.v.M., Myrtaceae: Finnemore et al., J. Proc. R. Soc. N.S.W. 69, 209 (1936); from Pteridium aquilinum (L.) Kühn, Polypodiaceae: Kofod, Eyjolfssen, Tetrahedron Lett. 1966, 1289. Isoln of dl-form from Prunus laurocerasus L. and Cotoneaster microphylla Wall., Rosaceae: Winkler, Simon, Ann. 31, 263 (1839); Hérissey, J. Pharm. Chim. 24, 537 (1906). Isoln of l-form from Sambucus nigra L., Caprifoliaceae: Guignart, Compt. Rend. 141, 16 (1905); Bourquelot, Danjot, ibid. 598 (1905). Prulaurasin is dl-mandelonitrile glucoside and sambunigrin is l-mandelonitrile glucoside: Caldwell, Courtauld, J. Chem. Soc. 91, 671 (1907). Biosynthesis of d-mandelonitrile glucoside: Mentzer, Favre-Bonvin, Compt. Rend. 253, 1072 (1961). Abs config of isomers: U. Schwarzmaier, Ber. 109, 3250 (1976).
Derivative Type: d-Form
Additional Names: Prunasin
Properties: Needles from chloroform, mp 147-148°. [a]D14 -29.94°. Soluble in water, alcohol, acetone. Converted by alkalies to prulaurasin.
Melting point: mp 147-148°
Optical Rotation: [a]D14 -29.94°
Derivative Type: dl-Form
Additional Names: Prulaurasin
Properties: Slightly bitter needles from ethyl acetate + ether, mp 123-125°. [a]D -54° (water). Soluble in water, alcohol. Practically insol in ether. On hydrolysis yields dl-mandelic acid.
Melting point: mp 123-125°
Optical Rotation: [a]D -54° (water)
Derivative Type: l-Form
Additional Names: Sambunigrin
Properties: Bitter needles from hot ethyl acetate, mp 151-152°. [a]D18 -75.1°. Soluble in water, alcohol, ethyl acetate. On hydrolysis yields l-mandelic acid.
Melting point: mp 151-152°
Optical Rotation: [a]D18 -75.1°

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