10058. Xanthatin

Nomenclature

CAS number: 26791-73-1
[3aR-(3aα,7β,8aβ)]-3,3a,4,7,8,8a-Hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-2H-cyclohepta[b]furan-2-one.
C15H18O3; mol wt 246.30.
C 73.15%, H 7.37%, O 19.49%.

Description and 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).

Chemical structure

Properties

Flat needles from methanol or ethanol, mp 114.5-115°. uv max: 275, 213 nm (ε 22800, 7300). [α]D30 20° (ethanol). Sol in ether, acetone, alcohol; slightly sol in hot water (neutral pH). Practically insol in petr ether, 5% NaOH, 5% HCl.