1471. Bufalin

Nomenclature

CAS number: 465-21-4
(3β,5β)-3,14-Dihydroxybufa-20,22-dienolide.
C24H34O4; mol wt 386.52.
C 74.58%, H 8.87%, O 16.56%.

Description and references

Cardiotonic steroid constituent of Ch'an Su (also called Senso), a galenical preparation of the dried venom of the Chinese toad, Bufo bufo gargarizans. Isoln and characterization: M. Kotake, K. Kuwada, Sci. Papers Inst. Phys. Chem. Res. Jpn. 36, 106 (1939), C.A. 33, 73049 (1939); K. Meyer, Helv. Chim. Acta 32, 1238 (1949). Structure: K. Kuwada, J. Chem. Soc. Jpn. 60, 335 (1939), C.A. 35, 511239 (1941). Prepn from resibufogenin, q.v.: H. Kondo, S. Ohno, US 3134772 (1964); from digitoxigenin, q.v.: G. R. Pettit et al., US 3687944 (1972). Total synthesis: F. Sondheimer et al., J. Am. Chem. Soc. 91, 1228 (1969). Additional syntheses: G. R. Pettit et al., J. Org. Chem. 35, 2895 (1970); Y. Kamano, G. R. Pettit, ibid. 38, 222 (1973); E. Yoshii et al., Chem. Pharm. Bull. 25, 2249 (1977); K. Wiesner et al., Helv. Chim. Acta 66, 2632 (1983). Pharmacology: S. Yoshida, T. Sakai, Jpn. J. Pharmacol. 23, 859 (1973); 24, 97 (1974).

Chemical structure

Properties

Needles from methanol/chloroform, mp 242-243°. [α]D 20°. uv max (ethanol): 298 nm (log ε 3.77).

Derivative

Sodium sulfate.

Nomenclature

Sodium bufalin-3-sulfate.
C24H33NaO7S; mol wt 488.57.
C 59.00%, H 6.81%, Na 4.71%, O 22.92%, S 6.56%.

Properties

Isoln from Japanese toad Bufo vulgaris formosus: K. Shimada et al., Tetrahedron Lett. 1974, 2767. Colorless amorphous solid, mp 165.5-166.5°. [α]D23 33.1° (c = 0.05 in methanol).