8709. Solasodine

Nomenclature

CAS number: 126-17-0
(3β,22α,25R)-Spirosol-5-en-3-ol; solasod-5-en-3β-ol; Δ5-20βF,22αF,25αF,27-azaspirosten-3β-ol; solancarpidine; solanidine-S; purapuridine.
C27H43NO2; mol wt 413.64.
C 78.40%, H 10.48%, N 3.39%, O 7.74%.

Description and references

Steroidal alkaloid isolated from various Solanum species. By hydrolysis of solasonine: Rochelmeyer, Arch. Pharm. 277, 329 (1939). See also ref under Solasonine and Solanidine. Structure: Briggs et al., J. Chem. Soc. 1950, 3013. Synthesis: Uhle, J. Org. Chem. 27, 656 (1962); Schreiber, Rnsch, Tetrahedron 20, 1939 (1964); Kessar et al., ibid. 27, 2869 (1971). Comprehensive description: G. Indrayanto et al., Anal. Profiles Drug Subs. Excip. 24, 487-522 (1996).

Chemical structure

Properties

Hexagonal plates from methanol or by sublimation in high vacuum, mp 200-202°. [α]D25 98° (c = 0.14 in methanol); [α]D 113° (CHCl3). Alkaline reaction to litmus in alcoholic soln. pKb 6.30. uv max (methanol): 206 nm. Freely sol in benzene, pyridine, and chloroform. Practically insol in ether. Soly at 30° (mg/ml): methanol 9.5; 95% ethanol 5.0; acetone 3.5; n-hexane <1.0; water <1.0.

Use

Starting material for steroidal drugs.