Title: Coriamyrtin
CAS Registry Number: 2571-86-0
CAS Name: (1aS,1bR,2S,2¢R,5S,6aR,7aR,8R)-Hexahydro-1b-hydroxy-6a-methyl-8-(1-methylethenyl)spiro[2,5-methano-7H-oxireno[3,4]cyclopent[1,2-d]oxepin-7,2¢-oxiran]-3(2H)-one
Molecular Formula: C15H18O5
Molecular Weight: 278.30
Percent Composition: C 64.74%, H 6.52%, O 28.74%
Literature References: Sesquiterpene of the picrotoxane group. Main toxic principle from leaves and fruit of Coraria myrtifolia L., Coriariaceae: M. J. Riban, C.R. Hebd. Seances Acad. Sci. 57, 798 (1863) and C. japonica A. Gray, Coriariaceae: Kariyone, Sato, J. Pharm. Soc. Jpn. 50, 106 (1930); Okuda, Pharm. Bull. 2, 185 (1954). Series of articles on structure, absolute configuration, stereochemistry and derivatives: T. Okuda, T. Yoshida, Chem. Pharm. Bull. 9, 379, 404 (1961); 15, 1687, 1697 (1967). Structural relationship to tutin, q.v.: eidem, Tetrahedron Lett. 1965, 439. Biosynthetic studies: M. Biollaz, D. Arigoni, Chem. Commun. 1969, 633. Synthetic studies: K. Tanaka et al., Chem. Pharm. Bull. 31, 1943, 1958, 1972 (1983). Pharmacology: E. E. Swanson, K. K. Chen, J. Pharmacol. Exp. Ther. 57, 410 (1936). Structure-activity relationship: C. H. Jarboe et al., J. Med. Chem. 11, 729 (1968).
Properties: Bitter, monoclinic prisms, mp 229-230°. [a]D14 +79°. Slightly sol in water, cold alc; freely sol in hot alc, in ether. LD50 i.p. in mice: 3 mg/kg (Jarboe).
Melting point: mp 229-230°
Optical Rotation: [a]D14 +79°
Toxicity data: LD50 i.p. in mice: 3 mg/kg (Jarboe) |