Title: Vicine
CAS Registry Number: 152-93-2
CAS Name: 2,6-Diamino-5-(b-D-glucopyranosyloxy)-4(1H)-pyrimidinone
Additional Names: 2,4-diamino-6-oxypyrimidine-5-(b-D-glucopyranoside); divicine 5-glucoside; vicioside; divicine-b-glucoside
Molecular Formula: C10H16N4O7
Molecular Weight: 304.26
Percent Composition: C 39.48%, H 5.30%, N 18.41%, O 36.81%
Literature References: Isoln from vetch seeds (Vicia sativa L., Leguminosae): Ritthausen, Ber. 9, 301 (1876); Levene, J. Biol. Chem. 18, 306 (1914); Levene, Senior, ibid. 25, 611 (1916); Herissey, Cheymol, Bull. Soc. Chim. Biol. 13, 29 (1931); Gmelin, Hasenmaier, Arzneim.-Forsch. 7, 755 (1957). Structure: Bendich, Trans. N.Y. Acad. Sci. 15, 58 (1952); Bendich, Clements, Biochim. Biophys. Acta 12, 462 (1953).
Properties: Needles from water, dec 243-244°. [a]D26 -11.7° (c = 3.9 in 0.2N NaOH). uv max (0.1N HCl): 274 nm (e 16400); (0.1N NaOH): 269, 248, 235, 230 nm (e 9520, 4360, 5180, 5090). One gram dissolves in about 100 ml water; slightly sol in alcohol; readily sol in dil acids and alkalies.
Optical Rotation: [a]D26 -11.7° (c = 3.9 in 0.2N NaOH)
Absorption maximum: uv max (0.1N HCl): 274 nm (e 16400)
NOTE: Another vicin, a rhamnosidoglucoside from vetch flowers, is described by Karrer, Widmer, Helv. Chim. Acta 10, 67 (1927). It has the formula: C21H21O12.2H2O. |