Title: Bakankosin
CAS Registry Number: 1398-17-0
CAS Name: [3S-(3a,4b,4aa)]-4-Ethenyl-3-(b-D-glucopyranosyloxy)-3,4,4a,5,6,7-hexahydro-8H-pyrano[3,4-c]pyridin-8-one
Additional Names: bacancosin
Trademarks: Bakankoside
Molecular Formula: C16H23NO8
Molecular Weight: 357.36
Percent Composition: C 53.78%, H 6.49%, N 3.92%, O 35.82%
Literature References: Nitrogenous glucoside from seed of Strychnos vacacoua Baill., Loganiaceae. Ref: E. Bourquelot, H. Hérissey, Compt. Rend. 144, 575 (1907); 147, 750 (1908); Arch. Pharm. 247, 56 (1909); K. Balenovic et al., Helv. Chim. Acta 35, 2519 (1952). Proposed structure: G. Büchi, R. E. Manning, Tetrahedron Letters no. 26, 5 (1960); H. C. Beyerman et al., Bull. Soc. Chim. Fr. 1961, 1812; H. Inouye et al., Chem. Pharm. Bull. 24, 1406 (1976). Synthesis and structure: L. F. Tietze, Tetrahedron Lett. 29, 2535 (1976).
Derivative Type: Hydrate
Properties: Bitter crystals, mp 157°; when anhydr mp 200°, also reported as mp 211-212°. [a]D -197°. uv max (alcohol): 235 nm (log e 4.2). Freely sol in water, alc; slightly sol in ethyl acetate.
Melting point: mp 157°; mp 200°; mp 211-212°
Optical Rotation: [a]D -197°
Absorption maximum: uv max (alcohol): 235 nm (log e 4.2)
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