Title: Bufalin
CAS Registry Number: 465-21-4
CAS Name: (3b,5b)-3,14-Dihydroxybufa-20,22-dienolide
Molecular Formula: C24H34O4
Molecular Weight: 386.52
Percent Composition: C 74.58%, H 8.87%, O 16.56%
Literature 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).
Properties: Needles from methanol/chloroform, mp 242-243°. [a]D -20°. uv max (ethanol): 298 nm (log e 3.77).
Melting point: mp 242-243°
Optical Rotation: [a]D -20°
Absorption maximum: uv max (ethanol): 298 nm (log e 3.77)
Derivative Type: Sodium sulfate
Synonyms: Sodium bufalin-3-sulfate
Molecular Formula: C24H33NaO7S
Molecular Weight: 488.57
Percent Composition: 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°. [a]D23 -33.1° (c = 0.05 in methanol).
Melting point: mp 165.5-166.5°
Optical Rotation: [a]D23 -33.1° (c = 0.05 in methanol)
