7414. Picrotin

Nomenclature

CAS number: 21416-53-5
(1aR,2aR,3S,6R,6aS,8aS,8bR,9S)-Hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-3,6-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione.
C15H18O7; mol wt 310.30.
C 58.06%, H 5.85%, O 36.09%.

Description and references

Nontoxic component of picrotoxin. Prepn from picrotoxin: Meyer, Bruges, Ber. 31, 2958 (1898). Structure studies: Bensted et al., J. Chem. Soc. 1952, 1042; Slater, Wilson, ibid. 1597; Holker et al., ibid. 1958, 2987. Total synthesis: E. J. Corey, H. L. Pearce, Tetrahedron Lett. 21, 1823 (1980). Toxicity data: C. H. Jarboe et al., J. Med. Chem. 11, 729 (1968). Review: Porter, Chem. Rev. 67, 441 (1967).

Chemical structure

Properties

Fine needles from water; thick, shiny prisms from aq alc soln, mp 248-250°. [α]D -64.7° (c = 2.31 in abs alc). Freely sol in abs alc, acetic acid, boiling water. Slightly sol in cold water. Practically insol in ether, chloroform, benzene. LD50 i.p. in mice: 135 mg/kg (Jarboe).