8307. Ryanodine

Nomenclature

CAS number: 15662-33-6
Ryanodol 3-(1H-pyrrole-2-carboxylate).
C25H35NO9; mol wt 493.55.
C 60.84%, H 7.15%, N 2.84%, O 29.18%.

Description and references

Insecticidal principle isolated from Ryania speciosa Vahl., Flacourtiaceae: E. F. Rogers et al., J. Am. Chem. Soc. 70, 3086 (1948); R. B. Kelly et al., Can. J. Chem. 29, 905 (1951). Structure: D. R. Babin et al., Experientia 21, 425 (1965); J. Santroch et al., ibid. 21, 730 (1965); K. Wiesner et al., Tetrahedron Lett. 1967, 221; K. Wiesner, Adv. Org. Chem. 8, 295 (1972). Crystal structure: S. N. Srivastava, M. Przybylska, Can. J. Chem. 46, 795 (1968). 1H-NMR: A. L. Waterhouse et al., Chem. Commun. 1984, 1265. Synthetic studies: P. Deslongchamps, Pure Appl. Chem. 49, 1329 (1977). Effect on calcium ion uptake by cardiac sarcoplasmic reticulum vesicles: L. R. Jones et al., J. Pharmacol. Exp. Ther. 209, 48 (1979); L. R. Jones, S. E. Cala, J. Biol. Chem. 256, 11809 (1981).

Chemical structure

Properties

Crystals, dec 219-220°. [α]D25 +26° (methanol). uv max (alc): 268.5 nm (log ε 4.18). Sol in water, alcohol, acetone, ether, chloroform. Practically insol in benzene, petr ether.

Use

Insecticide.