4α,9-Epoxycevane-3β,4,7α,14,15α,16β,20-heptol 3-[(R)-2-methylbutanoate]

Description

According to Poethke, this base does not occur naturally but is formed by loss ofmethylethylglycollic acid from Germerine (q.v.) during the extraction process. Other workers, however, claim that it exists in Veratrum album and certain species of Zygadenus. It forms glancing prisms from C6H6 and has [α]²²_D - 9° (pyridine). It is only slightly soluble in most organic solvents. The hydrochloride crystallizes from EtOH, m.p. 247-2500 C (dec.); the platinichloride decomposes at 195-2000 C; picrate, yellow needles from Me2CO-Et20, decomposes at 244- 6°C and the triacetyl derivative has m.p. 242-4°C (dec.); [α]²⁷_D - 89° (pyridine). Alkaline hydrolysis furnishes germine and (-)-methylethylacetic acid. The base gives a cherry-red colour with H2S04 and a carmine-red colour with HCl, isobutyric acid being liberated from the latter mixture on heating.

References

Salzberger., Arch. Pharm., 228,462 (1890)
Poethke., ibid, 275,571 (1937)
Kupchan., J. Amer. Chem. Soc., 81, 1921 (1959)