9078. Taxine

Nomenclature

CAS number: 12607-93-1

Description and references

A mixture of alkaloids from needles and berries of the yew tree, Taxus baccata L., Taxaceae: Lucas, Arch. Pharm. 85, 145 (1856); Winterstein, Iatrides, Z. Physiol. Chem. 117, 240 (1921); Winterstein, Guyer, ibid. 128, 175 (1923); Callow et al., J. Chem. Soc. 1931, 2138. Structural studies of taxine-I: Baxter et al., ibid. 1962, 2964e; of taxine-II: Dukes et al., ibid. 1967, 448; Eyre et al., ibid. 452. Sepn of cryst taxine A and amorph taxine B from the amorph mixture: E. Graf, H. Bertholdt, Pharm. Zentralhalle 96, 385 (1957). Structure of taxine A: E. Graf et al., Ann. 1982, 376. Review: B. Lythgoe, The Alkaloids vol. X, R. H. F. Manske, Ed. (Academic Press, New York, 1968) pp 597-626. Toxicity data: Y. Tekol, Vet. Hum. Toxicol. 33, 337 (1991).

Chemical structure

Properties

Granular amorphous powder, mp 121-124°. [α]D17 +95.7° (c = 4.59 in ethanol). Sol in ether, chloroform, alcohol. Practically insol in water, petr ether. LD50 (as the sulfate salt) in mice (mg/kg): 19.72 orally, 21.88 i.p.; in rats (mg/kg): 20.18 s.c. (Tekol).

Derivative

Taxine A.

Nomenclature

CAS number: 1361-49-5
(αR,βS)-β-(Dimethylamino)-α-hydroxy benzenepropanoic acid (1S,2R,3E,5S,7S,8S,10R,13S)-2,13-bis(acetyloxy)-7,10-dihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.14,8]hexadeca-3,11-dien-5-yl ester.
C35H47NO10; mol wt 641.75.
C 65.50%, H 7.38%, N 2.18%, O 24.93%.

Properties

mp 204-206°. [α]D 140° (CHCl3).

Caution

Taxine is undoubtedly responsible for the poisonous properties of the yew. Fatalities among domestic animals due to yew poisoning are not uncommon. Human fatal symptoms are those of gastrointestinal irritation, cardiac and respiratory failure.