(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one

(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one Basic information
Product Name:(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one
Synonyms:(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one;Corsevine;Korsevine
CAS:18209-21-7
MF:C28H45NO2
MW:427.6624
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Mol File:18209-21-7.mol
(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one Structure
(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one Chemical Properties
Melting point 169-170°C
Safety Information
MSDS Information
(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one Usage And Synthesis
DescriptionThe 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
ReferencesNuriddinov, Yunusov., Khim. Prir. Soedin., 3, 398 (1967)
(17ξ,20ξ,22ξ,25ξ)-3β-Hydroxy-28-methylveratraman-6(5H)-one Preparation Products And Raw materials
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