Dhurrin

Title: Dhurrin
CAS Registry Number: 499-20-7
CAS Name: (aS)-a-(b-D-Glucopyranosyloxy)-4-hydroxybenzeneacetonitrile
Additional Names: p-hydroxymandelonitrile-b-D-glucoside; b-D-glucopyranosyloxy-L-p-hydroxymandelonitrile
Molecular Formula: C14H17NO7
Molecular Weight: 311.29
Percent Composition: C 54.02%, H 5.50%, N 4.50%, O 35.98%
Literature 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°. [a]D20 -65° (alc). uv max: 228 nm (e 13000). Sol in water, alcohol. Alkali labile.
Optical Rotation: [a]D20 -65° (alc)
Absorption maximum: uv max: 228 nm (e 13000)
Derivative Type: Pentaacetate
Molecular Formula: C24H27NO12
Molecular Weight: 521.47
Percent Composition: C 55.28%, H 5.22%, N 2.69%, O 36.82%
Properties: Needles from ethyl acetate + petr ether, mp 132-132.5°. [a]D20 -50.5° (c = 0.24 in alc).
Melting point: mp 132-132.5°
Optical Rotation: [a]D20 -50.5° (c = 0.24 in alc)
CAUTION: Yields HCN on hydrolysis.
Diaboline Diacerein Diacetazotol Diacetin Diacetonamine

Dhurrin
Dhurrin.svg
Identifiers
CAS number 499-20-7 YesY
PubChem 161355
ChemSpider 141737 N
Jmol-3D images Image 1
Properties
Molecular formula C14H17NO7
Molar mass 311.29 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Dhurrin is a cyanogenic glycoside occurring in plants. Its biosynthesis has been elucidated.[1][2] Dhurrin is hydrolyzed in the stomach of an insect into a carbohydrate and aglycone. The aglycone is unstable and releases hydrogen cyanide.