8175. Rheadine

Nomenclature

CAS number: 2718-25-4
(8β)-8-methoxy-16-methyl-2,3:10,11-bis[methylenebis(oxy)]rheadan; rhoeadine.
C21H21NO6; mol wt 383.39.
C 65.79%, H 5.52%, N 3.65%, O 25.04%.

Description and references

Isoln from the seed capsules of corn poppy (Papaver rhoeas L., Papaveraceae): Hesse, Ann. 140, 145 (1866); Arch. Pharm. 228, 7 (1890); Awe, ibid. 274, 439 (1936); Awe, Winkler, ibid. 290, 367 (1957); Nemecková, Santavy, Collect. Czech. Chem. Commun. 27, 1210 (1962). Structure and stereochemistry: Santavy et al., ibid. 30, 3479 (1965); 32, 4452 (1967). Total synthesis: Klotzer et al., Helv. Chim. Acta 54, 2057 (1971); 55, 2228 (1972); Irie et al., J. Chem. Soc. Perkin Trans. 1 1972, 2986.

Chemical structure

Properties

Crystals from ethanol, mp 252-254°. [α]D23 +235° (c = 1.01 in chloroform); [α]D22 +174° (c = 0.69 in pyridine). uv max (ethanol): 239, 290 nm (ε 9150, 9180). Slightly sol in ethyl acetate, methylene chloride. Practically insol in water, alcohol, chloroform, ether, benzene.