Structural Formula Vector Image
Title: Protoanemonin
CAS Registry Number: 108-28-1
CAS Name: 5-Methylene-2(5H)-furanone
Additional Names: 4-hydroxy-2,4-pentadienoic acid g-lactone; 5-methylene-2-oxodihydrofuran
Trademarks: Isomycin (Werfft)
Molecular Formula: C5H4O2
Molecular Weight: 96.08
Percent Composition: C 62.50%, H 4.20%, O 33.30%
Literature References: An antibacterial principle of Anemone pulsatilla L., Ranunculaceae: Seegal, Holden, Science 101, 413 (1945). Exists as a glucoside, ranunculin, in the intact plant, and is released by an enzymatic process on maceration of the plant tissue: R. Hill, R. van Heyningen, Biochem. J. 49, 332 (1951). Isoln: Asahina, Fujita, Acta Phytochim. 1, 1 (1922); Baer et al., J. Biol. Chem. 162, 65 (1946). Structure and synthesis: Asahina, Fujita, loc. cit.; Muskat et al., J. Am. Chem. Soc. 52, 326 (1930); Fox, Jr., Proc. Soc. Exp. Biol. 51, 102 (1942); Shaw, J. Am. Chem. Soc. 68, 2510 (1946). Industrial prepns: GB 759999 (1956 to Olin Mathieson), C.A. 51, 9678f (1957); Reicheneder et al., DE 1088047 (BASF), C.A. 56, 14086i (1962); Sakuma, Hirano, US 3203863 (1965 to Lion Dentifrice).
Properties: Pale yellow oil; volatile with steam. bp1.5 45°. Sol in ethylene dichloride, chloroform. Solubility in water ~1%. Stable in water. When pure the compd turns to a hard polymer which, when ground and extracted with boiling ethyl acetate, yields anemonin, q.v.
Boiling point: bp1.5 45°
Therap-Cat: Antibacterial.

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