Nomenclature
CAS number: 505-75-9
(8
E,10
E,12
E,14
R)-8,10,12-Heptadecatriene-4,6-diyne-1,14-diol.
C
17H
22O
2; 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).
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).