Zygadenine

Title: Zygadenine
CAS Registry Number: 545-45-9
CAS Name: 4a,9-Epoxycevane-3b,4,14,15a,16b,20-hexol
Molecular Formula: C27H43NO7
Molecular Weight: 493.63
Percent Composition: C 65.69%, H 8.78%, N 2.84%, O 22.69%
Literature 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°. [a]D20 -48.4° (c = 1.26 in chloroform). Not precipitated by digitonin. Soluble in alcohol, benzene, chloroform.
Melting point: mp 214-216°
Optical Rotation: [a]D20 -48.4° (c = 1.26 in chloroform)
Derivative Type: Hydrochloride
Molecular Formula: C27H43NO7.HCl
Molecular Weight: 530.09
Percent Composition: C 61.18%, H 8.37%, N 2.64%, O 21.13%, Cl 6.69%
Properties: Crystals, dec 231-234°.
Derivative Type: Sulfate
Molecular Formula: 2(C27H43NO7).H2SO4
Molecular Weight: 1085.34
Percent Composition: 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.