1479. Bufotoxin

Nomenclature

CAS number: 464-81-3
(3β,5β,16β)-16-(Acetyloxy)-3-[[8-[[(1S)-4-[(aminoiminomethyl)amino]-1-carboxybutyl]amino]-1,8-dioxooctyl]oxy]-14-hydroxybufa-20,22-dienolide; vulgarobufotoxin; bufotalin 3-suberoylarginine ester.
C40H60N4O10; mol wt 756.93.
C 63.47%, H 7.99%, N 7.40%, O 21.14%.

Description and references

Principal toxin of the venom of the common European toad, Bufo vulgaris. Isoln and structure: Wieland, Alles, Ber. 55, 1789 (1922); Wieland et al., Ann. 524, 203 (1936); Meyer, Helv. Chim. Acta 32, 1993 (1949); Urscheler et al., ibid. 38, 883 (1955). Alternate structure: Kamano et al., Tetrahedron Lett. 1968, 5673; Linde-Tempel, Helv. Chim. Acta 53, 2188 (1970). Partial synthesis: Pettit, Kamano, Chem. Commun. 1972, 45.

Chemical structure

Properties

Monohydrate, bitter needles from alc, dec 205°. uv max: 295 nm (log ε 3.74). Freely sol in methanol, pyridine, sparingly sol in abs alc. Practically insol in water, ether, acetone, chloroform, petr ether.