12-10329. Zygadenine [Archived]
Nomenclature
CAS number: 545-45-9
4α,9-Epoxycevane-3β,4,14,15α,16β,20-hexol. C27H43NO7; mol wt 493.63.
C 65.69%, H 8.78%, N 2.84%, O 22.69%.
Description and references
Occurs together with germine in various species of Zygadenus (death camas) and Veratrum (Liliaceae): Heyl et al., J. Am. Chem. Soc. 35, 258 (1913); Heyl, Herr, ibid. 71, 1751 (1949); Kupchan, Deliwala, ibid. 75, 1025 (1953); Klohs et al., ibid. 4925; Stoll, Seebeck, Helv. Chim. Acta 36, 1570 (1953); Kupchan et al., J. Am. Chem. Soc. 77, 689, 755 (1955). Structure: Kupchan, ibid. 78, 3546 (1956); 81, 1925 (1959).
Properties
Fine needles from benzene. mp 214-216°. [α]D20 48.4° (c = 1.26 in chloroform). Not precipitated by digitonin. Soluble in alcohol, benzene, chloroform.Derivative
Hydrochloride.C27H43NO7.HCl; mol wt 530.09.
C 61.18%, H 8.37%, N 2.64%, O 21.13%, Cl 6.69%.
Properties
Crystals, dec 231-234°.Derivative
Sulfate.2(C27H43NO7).H2SO4; mol wt 1085.34.
C 59.76%, H 8.17%, N 2.58%, O 26.53%, S 2.95%.
Properties
Crystals, dec 237-242°.Status
This monograph has been retired and is no longer subject to revision or update.