Title: Artemisin
CAS Registry Number: 481-05-0
CAS Name: (3S,3aR,4S,5aS,9bS)-3a,5,5a,9b-Tetrahydro-4-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione
Additional Names: 6a,8a-dihydroxy-3-oxoeudesma-1,4-dien-12-oic acid 12,6-lactone; 8-hydroxysantonin
Molecular Formula: C15H18O4
Molecular Weight: 262.30
Percent Composition: C 68.68%, H 6.92%, O 24.40%
Literature References: From the closed, unexpanded flower heads of several Artemisia spp, especially Artemisia maritima L., and A. cina Berg., Compositae ("wormseed"). Found in the mother liquors from the extraction of santonin. Isoln: E. Merck, E. Merck's Jahresber. 1894, 3; Chem. Zentralbl. 1895, I, 436. Structure: Sumi, J. Am. Chem. Soc. 80, 4869 (1958); Cocker, McMurry, Tetrahedron 8, 181 (1960). Stereochemistry: Bolt et al., J. Chem. Soc. 1963, 5235. Synthesis of (+)-artemisin: Nakazaki, Naemura, Tetrahedron Lett. 1966, 2615.
Properties: Crystals from abs ethanol or ethyl acetate. Bitter taste. Turns yellow on exposure to light. mp 203°. bp0.1 260°. Sublimes760 170-175°. [a]D23 -84.9° (c = 3 in 95% ethanol). One gram dissolves in 60 ml boiling water, in 3 ml boiling alc. Sol in ethyl acetate. Practically insol in petr ether. Somewhat sol in chloroform.
Melting point: mp 203°
Boiling point: bp0.1 260°
Optical Rotation: [a]D23 -84.9° (c = 3 in 95% ethanol) |