1477. Bufotalin

Nomenclature

CAS number: 471-95-4
(3β,5β,16β)-16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide; 3β,14,16β-trihydroxy-5β-bufa-20,22-dienolide 16-acetate.
C26H36O6; mol wt 444.56.
C 70.24%, H 8.16%, O 21.59%.

Description and references

One of the genins found in the venom of the common European toad (Bufo vulgaris). Isoln and structure: Faust, Arch. Exp. Pathol. Pharmakol. 47, 279 (1902); 49, 1 (1902); Wieland, Weil, Ber. 46, 3315 (1913); Wieland, Weyland, Sitzungsber. Bayer. Akad. Wiss. (math.-physikal. Klasse) 1920, 329; Wieland et al., Ann. 524, 203 (1936); Meyer, Helv. Chim. Acta 32, 1993 (1949); Pettit et al., Chem. Commun. 1970, 1566. Synthesis: G. R. Pettit et al., J. Org. Chem. 52, 3573 (1987).

Chemical structure

Properties

Solvated crystals from alc. Sinters at 154°, dec 223°. Sublimes in high vacuum at 225-230°. uv max: 300 nm. [α]D20 +5.4° (c = 0.5 in chloroform). Sol in alcohol, chloroform.

Derivative

3-Acetate.

Properties

mp 269-272°.