2513. Convicine

Nomenclature

CAS number: 19286-37-4
6-Amino-5-(β-d-glucopyranosyloxy)-2,4(1H,3H)-pyrimidinedione.
C10H15N3O8; mol wt 305.24.
C 39.35%, H 4.95%, N 13.77%, O 41.93%.

Description and references

From seeds of Vicia sativa L., Leguminosae: Ritthausen, J. Prakt. Chem. [2] 24, 202 (1881); Ber. 29, 894 (1896). Structure: Johnson, J. Am. Chem. Soc. 36, 337 (1914); Fisher, Johnson, ibid. 54, 2038 (1932); Bendick, Clements, Biochim. Biophys. Acta 12, 462 (1953); Bien et al., J. Chem. Soc. C 1968, 496. Synthesis: eidem, J. Chem. Soc. Perkin Trans. 1 1973, 1089.

Chemical structure

Properties

Leaflets from boiling water, dec without melting at 287°. uv max (pH 7): 245, 271 nm (log ε 3.43, 4.16). Sol in hot water, dil NaOH; slightly sol in cold water, alcohol. Practically insol in chloroform, glacial acetic acid.