ignavine
- CAS No.
- 1357-76-2
- Chemical Name:
- ignavine
- Synonyms
- ignavine;Hetisan-2α,3β,9,15β-tetrol 2-benzoate;Hetisan-2,3,9,15-tetrol, 2-benzoate, (2α,3β,15β)- (9CI)
- CBNumber:
- CB71342456
- Molecular Formula:
- C27H31NO5
- Molecular Weight:
- 449.54
- MDL Number:
- MOL File:
- 1357-76-2.mol
ignavine Chemical Properties,Uses,Production
Description
This aconitine alkaloid is present in several A conitum species indigenous to Japan, e.g. Aconitum calliantum Koidzumi, A. grossedentatum, Nakai, A. hakusanense Nakai, A. kamtschaticum Willd. et Reichb., A. lucidusculum Nakai, A. senanense Nakai, A. subcuneatum Nakai, A. tortuosum Willd. and A. Zuccarini Nakai. It yields clusters of colourless needles when crystallized from Me2COMeOH and gives a form, m.p. 172-4 °c in addition to the one having the above melting point. It is dextrorotatory with [α]29D~} + 85.27° (MeOH), or [α]14D + 92.98°. Crystalline salts of the alkaloid have been prepared, e.g. the hydrochloride, m.p. 245-6°C (dec.); hydrobromide, m.p. 260-2°C (dec.) and the nitrate which crystallizes as the monohydrate, m.p. 220-2°C (dec. dry). Alkaline hydrolysis furnishes benzoic acid and hydroignavinol, C20H2S04N, m.p. 302°C.
References
Ochiai et al., J. Pharm. Soc., Japan, 72, 816 (1952) Ochiai et al., ibid, 76, 550 (1956) Ochiai", Okamoto, Sasaki., ibid, 75,545 (1955) Ochiai et al., Chem. Pharm. Bull., 6,327 (1958) Ochiai et al., ibid, 8, 976 (1960) Pelletier., Tetrahedron, 14,103 (1961)