Title: Picrotoxinin
CAS Registry Number: 17617-45-7
CAS Name: (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-Hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione
Molecular Formula: C15H16O6
Molecular Weight: 292.28
Percent Composition: C 61.64%, H 5.52%, O 32.84%
Literature References: Toxic component of picrotoxin, q.v. Prepn from picrotoxin: Horrmann, Ber. 45, 2090 (1912). Structure: Conroy, J. Am. Chem. Soc. 73, 1889 (1951); 79, 5550 (1957); Craven, Tetrahedron Lett. no. 19, 21 (1960). Total synthesis: E. J. Corey, H. L. Pearce, J. Am. Chem. Soc. 101, 5841 (1979). Structure-activity relationship: C. H. Jarboe et al., J. Med. Chem. 11, 729 (1968). Review: Porter, Chem. Rev. 67, 441 (1967).
Properties: Very bitter large prisms or small crystals contg water, mp 209.5°. [a]D17 +4.4° (c = 4.28 in abs alc), +3.49° (c = 7.57 in acetone). Soluble in hot common organic solvents, in cold alcohol and chloroform. LD50 i.p. in mice: 3 mg/kg (Jarboe).
Melting point: mp 209.5°
Optical Rotation: [a]D17 +4.4° (c = 4.28 in abs alc), +3.49° (c = 7.57 in acetone)
Toxicity data: LD50 i.p. in mice: 3 mg/kg (Jarboe) |