alpha-Santonin

Title: a-Santonin
CAS Registry Number: 481-06-1
CAS Name: [3S-(3a,3aa,5ab,9bb)]-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione
Additional Names: 1,2,3,4,4a,7-hexahydro-1-hydroxy-a,4a,8-trimethyl-7-oxo-2-naphthaleneacetic acid g-lactone; l-santonin
Molecular Formula: C15H18O3
Molecular Weight: 246.30
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature 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 Type: (-)-Form
Properties: Tabular crystals, orthorhombic sphenoidal, mp 170-173°. Almost tasteless with bitter aftertaste. [a]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.
Melting point: mp 170-173°
Optical Rotation: [a]D25 -170 to -175° (c = 2 in alc)
Density: d 1.187
Derivative Type: (±)-Form
Properties: Colorless plates from methanol, mp 181°. uv max (ethanol): 241 nm (log e 4.10).
Melting point: mp 181°
Absorption maximum: uv max (ethanol): 241 nm (log e 4.10)
Derivative Type: (+)-Form
Properties: Colorless plates from methanol, mp 172°. [a]D20 +165.9° (c = 1.92 in ethanol).
Melting point: mp 172°
Optical Rotation: [a]D20 +165.9° (c = 1.92 in ethanol)
Derivative Type: 4-Hydroxysantonin see Artemisin
Therap-Cat: Anthelmintic (Nematodes).
Therap-Cat-Vet: Has been used as an anthelmintic.
Keywords: Anthelmintic (Nematodes).
alpha-Spinasterol alpha-Terpineol alpha-Terthienyl alpha-Tocotrienol alpha-Yohimbine