2267. Cicutoxin

Nomenclature

CAS number: 505-75-9
(8E,10E,12E,14R)-8,10,12-Heptadecatriene-4,6-diyne-1,14-diol.
C17H22O2; mol wt 258.36.
C 79.03%, H 8.58%, O 12.39%.

Description and references

Poisonous principle of the water hemlock (Cicuta virosa L., Umbelliferae); naturally occurring as the (-)-form. Isoln: Jacobson, J. Am. Chem. Soc. 37, 916 (1915). Structure: Anet et al., J. Chem. Soc. 1953, 309. Synthesis of (±)-form: Hill et al., ibid. 1955, 1770. Antileukemic activity: T. Konoshima, K.-H. Lee, J. Nat. Prod. 49, 1117 (1986). Simple analytical method: R. A. Smith, D. Lewis, Vet. Hum. Toxicol. 29, 240 (1987).

Chemical structure

Properties

Prisms from ether + petr ether, transformed in air and light to yellow oily resin. mp 54°. [α]D15 -14.5° (c = 1.7 in ethanol). Sol in alc, chloroform, ether, hot water, alkali hydroxides. Practically insol in petr ether. Very toxic.

Derivative

(±)-Form.

Properties

Crystals from ether + petr ether, mp 67°. uv max (alc): 242, 252, 318.5, 335.5 nm (ε × 10-3 14.6, 21.6, 50.6, 60.3).