Title: Convallatoxin
CAS Registry Number: 508-75-8
CAS Name: (3b,5b)-3-[(6-Deoxy-a-L-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxocard-20(22)-enolide
Additional Names: strophanthidin a-L-rhamnoside
Trademarks: Convallaton; Corglykon; Korglykon
Molecular Formula: C29H42O10
Molecular Weight: 550.64
Percent Composition: C 63.26%, H 7.69%, O 29.06%
Literature References: From blossoms of lily of the valley (Convallaria majalis L., Liliaceae): Karrer, Helv. Chim. Acta 12, 506 (1929); from Ornithogalum umbellatum L., Liliaceae: Mrozik et al., ibid. 42, 683 (1959); from Antiaris toxicaria Lesch, Moraceae: Juslen et al., ibid. 46, 117 (1963). Structure: Tschesche, Haupt, Ber. 69, 459 (1936); Fieser, Jacobsen, J. Am. Chem. Soc. 59, 2335 (1937). Cleavage into L-rhamnose and strophanthidin: Reichstein, Katz, Pharm. Acta Helv. 18, 521 (1943); see also C.A. 38, 2046. Synthesis from strophanthidin and acetobromrhamnose: Reyle et al., Helv. Chim. Acta 33, 1541 (1950); Haede et al., DE 1933090 (1971 to Hoechst). Toxicity study: W. Förster et al., Arch. Int. Pharmacodyn. 155, 165 (1965).
Properties: Prisms from methanol + ether. mp 235-242°. [a]D22 -1.7 ± 3° (c = 0.65 in methanol); [a]D25 -9.4 ± 3° (c = 0.72 in dioxane). Sol in alcohol, acetone; slightly sol in chloroform, ethyl acetate, and water (1:2000). Practically insol in ether, petr ether. Gives Legal's reaction. LD50 in mice, rats (mg/kg): 10.0 i.p., 16.0 i.v. (Förster).
Melting point: mp 235-242°
Optical Rotation: [a]D22 -1.7 ± 3° (c = 0.65 in methanol); [a]D25 -9.4 ± 3° (c = 0.72 in dioxane)
Toxicity data: LD50 in mice, rats (mg/kg): 10.0 i.p., 16.0 i.v. (Förster)
Derivative Type: Tri-O-acetyl-convallatoxin
Molecular Formula: C35H48O13
Molecular Weight: 676.75
Percent Composition: C 62.12%, H 7.15%, O 30.73%
Properties: Needles from acetone + ether, mp 215-238°. [a]D25 -5.5 ± 2° (c = 0.962 in chloroform).
Melting point: mp 215-238°
Optical Rotation: [a]D25 -5.5 ± 2° (c = 0.962 in chloroform)
Therap-Cat: Cardiotonic.
Keywords: Cardiotonic. |