(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one
- CAS No.
- 18209-21-7
- Chemical Name:
- (17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one
- Synonyms
- Korsevine;Corsevine;(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one
- CBNumber:
- CB62338448
- Molecular Formula:
- C28H45NO2
- Molecular Weight:
- 427.6624
- MDL Number:
- MOL File:
- 18209-21-7.mol
(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one Chemical Properties,Uses,Production
Description
The bulbs of Korolkowia sewerzowii also yield this steroidal alkaloid which is
precipitated by the addition of C6H6 to a petroleum ether extract of the mixed
alkaloids. The base has [α]D - 84° (c 0.9, CHC13) and forms crystalline salts,
e.g. the hydrobromide, m.p. 289-290°C; the perchlorate, m.p. 244-SoC; isothiocyanate, m.p. 264-SoC; oxime, m.p. 200-1 DC; methiodide, m.p. 244-SoC
and semicarbazone, m.p. 190°C after softening at 160°C. The O-acetyl derivative
forms a perchlorate, m.p. 178-9°C.
LiAIH4 or hydrogenation over Pt yields dihydrokorseving, m.p. 218-9°C;
[α]D - 87° (c 0.16, MeOH) which gives a diacetyl derivative, m.p. l33-4°C.
Chromic acid oxidation furnishes korsevinone forming a perchlorate, m.p. 240°C
after crystallization from H20. The structure of the alkaloid has been determined
from mass spectrometry, NMR, ultraviolet and infrared spectroscopy
References
Nuriddinov, Yunusov., Khim. Prir. Soedin., 3, 398 (1967)