Cicutoxin
Title: Cicutoxin
CAS Registry Number: 505-75-9
CAS Name: (8E,10E,12E,14R)-8,10,12-Heptadecatriene-4,6-diyne-1,14-diol
Molecular Formula: C17H22O2
Molecular Weight: 258.36
Percent Composition: C 79.03%, H 8.58%, O 12.39%
Literature 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°. [a]D15 -14.5° (c = 1.7 in ethanol). Sol in alc, chloroform, ether, hot water, alkali hydroxides. Practically insol in petr ether. Very toxic.
Melting point: mp 54°
Optical Rotation: [a]D15 -14.5° (c = 1.7 in ethanol)
 
Derivative Type: (±)-Form
Properties: Crystals from ether + petr ether, mp 67°. uv max (alc): 242, 252, 318.5, 335.5 nm (e ´ 10-3 14.6, 21.6, 50.6, 60.3).
Melting point: mp 67°
Absorption maximum: uv max (alc): 242, 252, 318.5, 335.5 nm (e ´ 10-3 14.6, 21.6, 50.6, 60.3)

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