Title: Taxine
CAS Registry Number: 12607-93-1
Literature 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).
Properties: Granular amorphous powder, mp 121-124°. [a]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).
Melting point: mp 121-124°
Optical Rotation: [a]D17 +95.7° (c = 4.59 in ethanol)
Toxicity data: 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 Type: Taxine A
CAS Registry Number: 1361-49-5
CAS Name: (aR,bS)-b-(Dimethylamino)-a-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
Molecular Formula: C35H47NO10
Molecular Weight: 641.75
Percent Composition: C 65.50%, H 7.38%, N 2.18%, O 24.93%
Properties: mp 204-206°. [a]D -140° (CHCl3).
Melting point: mp 204-206°
Optical Rotation: [a]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. |