4397. Gentiopicrin
Nomenclature
CAS number: 20831-76-9
(5R-trans)-5-Ethenyl-6-(β-d-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one; gentiopicroside. C16H20O9; mol wt 356.32.
C 53.93%, H 5.66%, O 40.41%.
Description and references
The principal bitter glucoside of common gentians, which was isolated in 1862 from Gentiana lutea, L., Gentianaceae: Canonica et al., Tetrahedron 16, 192 (1961). Isoln from roots of G. lutea: Korte, Ber. 87, 512 (1954); Korte et al., ibid. 91, 759 (1958). Structure: Canonica et al., Tetrahedron Lett. 1960(24), 7; Tetrahedron 16, 192 (1961). Revised structure: Inouye et al., Tetrahedron Lett. 1968, 4429. Absolute configuration: Manitto, Pagnoni, Gazz. Chim. Ital. 94, 229 (1964).
Properties
Crystals from anhydr ethyl acetate or abs alcohol, mp 191°. [α]D20 199° (ethanol). uv max (c = 0.0285 g/l methanol): 270 nm (log ε 3.96).Derivative
Hemihydrate.Properties
Crystals from 50% ethanol, mp 121°.Derivative
Tetraacetate.C24H28O13; mol wt 524.47.
C 54.96%, H 5.38%, O 39.66%.
Properties
Crystals from methanol. mp 138.5-139.5°. uv max (c = 0.0214 g/l methanol): 272 nm (log ε 3.84).Therapeutic Category
Antimalarial.
Keywords
Antimalarial