CAS No 20831-76-9 , (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,
5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,
4-c]pyran-8-one

Title: Gentiopicrin
CAS Registry Number: 20831-76-9
CAS Name: (5R-trans)-5-Ethenyl-6-(b-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one
Synonyms: gentiopicroside
Molecular Formula: C16H20O9
Molecular Weight: 356.32
Percent Composition: C 53.93%, H 5.66%, O 40.41%
Literature 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°. [a]D20 -199° (ethanol). uv max (c = 0.0285 g/l methanol): 270 nm (log e 3.96).
Melting point: mp 191°
Optical Rotation: [a]D20 -199° (ethanol)
Absorption maximum: uv max (c = 0.0285 g/l methanol): 270 nm (log e 3.96)
 
Derivative Type: Hemihydrate
Properties: Crystals from 50% ethanol, mp 121°.
Melting point: mp 121°
 
Derivative Type: Tetraacetate
Molecular Formula: C24H28O13
Molecular Weight: 524.47
Percent Composition: 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 e 3.84).
Melting point: mp 138.5-139.5°
Absorption maximum: uv max (c = 0.0214 g/l methanol): 272 nm (log e 3.84)
 
Therap-Cat: Antimalarial.
Keywords: Antimalarial.