9050. Tanacetin

Nomenclature

CAS number: 1401-54-3
[3aS-(3aα,5aβ,6β,9aα,9bβ)]-Decahydro-6,9a-dihydroxy-5a-methyl-3,9-bis(methylene)naphtho[1,2-b]furan-2(3H)-one; 1β,5α-dihydroxy-6β,7αH-selina-4(15),11(13)-dien-6,12-olide.
C15H20O4; mol wt 264.32.
C 68.16%, H 7.63%, O 24.21%.

Description and references

Isoln from seed, herb, and flowers of Tanacetum vulgare L., Compositae: Homolle, J. Pharm. Chim. 7, 57 (1845); Jaretzky, Kühne, Arch. Pharm. 271, 353 (1933); Suchy, Collect. Czech. Chem. Commun. 27, 1058 (1962). Structure and absolute config: Samek et al., ibid. 38, 1971 (1973).

Chemical structure

Properties

Crystals, mp 205°. [α]D22 +179.5° (c = 2.3 in ethanol).