943. Bakankosin

Nomenclature

CAS number: 1398-17-0
[3S-(3α,4β,4aα)]-4-Ethenyl-3-(β-d-glucopyranosyloxy)-3,4,4a,5,6,7-hexahydro-8H-pyrano[3,4-c]pyridin-8-one; bacancosin; Bakankoside.
C16H23NO8; mol wt 357.36.
C 53.78%, H 6.49%, N 3.92%, O 35.82%.

Description and 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).

Chemical structure

Derivative

Hydrate.

Properties

Bitter crystals, mp 157°; when anhydr mp 200°, also reported as mp 211-212°. [α]D 197°. uv max (alcohol): 235 nm (log ε 4.2). Freely sol in water, alc; slightly sol in ethyl acetate.