Title: Xanthatin
CAS Registry Number: 26791-73-1
CAS Name: [3aR-(3aa,7b,8ab)]-3,3a,4,7,8,8a-Hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-2H-cyclohepta[b]furan-2-one
Molecular Formula: C15H18O3
Molecular Weight: 246.30
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature References: Antimicrobial agent from Xanthium strumarium L., sens. lat.; X. pennsylvanicum Wallr., Compositae; X. riparium. Isoln: J. E. Little et al., Arch. Biochem. 27, 247 (1950); T. A. Geissman et al., J. Am. Chem. Soc. 76, 685 (1954). Structure: P. G. Deuel, T. A. Geissman, ibid. 79, 3778 (1957). Evaluation as repellent of blue mussel: A. Harada et al., Agric. Biol. Chem. 49, 1887 (1985).
Properties: Flat needles from methanol or ethanol, mp 114.5-115°. uv max: 275, 213 nm (e 22800, 7300). [a]D30 -20° (ethanol). Sol in ether, acetone, alcohol; slightly sol in hot water (neutral pH). Practically insol in petr ether, 5% NaOH, 5% HCl.
Melting point: mp 114.5-115°
Optical Rotation: [a]D30 -20° (ethanol)
Absorption maximum: uv max: 275, 213 nm (e 22800, 7300) |