2958. Dhurrin
Nomenclature
CAS number: 499-20-7
(αS)-α-(β-d-Glucopyranosyloxy)-4-hydroxybenzeneacetonitrile; p-hydroxymandelonitrile-β-d-glucoside; β-d-glucopyranosyloxy-l-p-hydroxymandelonitrile. C14H17NO7; mol wt 311.29.
C 54.02%, H 5.50%, N 4.50%, O 35.98%.
Description and references
From the fruit of young Egyptian plants of Sorghum vulgare Pers., Gramineae: Dunstan, Henry, Chem. News 85, 301 (1902). Biosynthesis: Koukol et al., J. Biol. Chem. 237, 3223 (1962). Absolute configuration: Towers et al., Tetrahedron 20, 71 (1964). Allied to amygdalin, q.v. and the mandelonitrile glucosides.
Properties
Leaflets from water, prisms from alcohol, dec 200°. [α]D20 -65° (alc). uv max: 228 nm (ε 13000). Sol in water, alcohol. Alkali labile.Derivative
Pentaacetate.C24H27NO12; mol wt 521.47.
C 55.28%, H 5.22%, N 2.69%, O 36.82%.