8361. α-Santonin
Nomenclature
Description and references
Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima L., sens. lat., Compositae [Levant wormseed] and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region. Structure: Clemo et al., J. Chem. Soc. 1930, 1110; Ruzicka, Steiner, Helv. Chim. Acta 17, 614 (1934). Stereochemistry: Corey, J. Am. Chem. Soc. 77, 1044 (1955); Cocker, McMurry, Tetrahedron 8, 181 (1960); Asher, Sim, Proc. Chem. Soc. London 1962, 111, 335; Nakazaki, Arakawa, Bull. Chem. Soc. Jpn. 37, 464 (1964); Pregosin et al., J. Chem. Soc. Perkin Trans. 1 1972, 299. Total synthesis: Abe et al., Proc. Jpn. Acad. 30, 116 (1954); J. Am. Chem. Soc. 78, 1422 (1956); US 2836604 (1958 to Takeda); J. A. Marshall, P. G. M. Wuts, J. Org. Chem. 43, 1086 (1978). Mass spectral studies of the santonins and derivs: Woseda et al., Tetrahedron 23, 4623 (1967). Review: C. H. Heathcock in The Total Synthesis of Natural Products vol. 2, J. W. ApSimon, Ed. (Wiley, New York, 1973) pp 315-324.
Derivative
(-)-Form.Properties
Tabular crystals, orthorhombic sphenoidal, mp 170-173°. Almost tasteless with bitter aftertaste. [α]D25 -170 to -175° (c = 2 in alc). Becomes yellow on exposure to light. Irritating to mucous membranes. d 1.187. One part dissolves in 5000 parts of cold water, in 250 parts of boiling water, in 280 parts of 50% alcohol at 17°, in 10 parts of boiling 50% alcohol, in 44 parts of cold 90% alcohol, in 3 parts of boiling 90% alcohol, in 125 parts of cold ether, in 72 parts of boiling ether, in 4.3 parts of cold chloroform.Derivative
(±)-Form.Properties
Colorless plates from methanol, mp 181°. uv max (ethanol): 241 nm (log ε 4.10).Derivative
(+)-Form.Properties
Colorless plates from methanol, mp 172°. [α]D20 +165.9° (c = 1.92 in ethanol).Derivative
4-Hydroxysantonin see Artemisin.Therapeutic Category
Anthelmintic (Nematodes).
Therapeutic Category (Veterinary)
Has been used as an anthelmintic.Keywords
Anthelmintic (Nematodes)