| Identification | Back Directory | [Name]
stemmadenine | [CAS]
10012-73-4 | [Synonyms]
stemmadenine
15-epi-Stemmadenine
(19E)-2,7,19,20-Tetradehydro-17-hydroxy-3,7-secocuran-16-carboxylic acid methyl ester
(15β,19E)-2,7,19,20-Tetradehydro-17-hydroxy-3,7-secocuran-16-carboxylic acid methyl ester
1H-3,6-Ethanoazonino[5,4-b]indole-7-carboxylic acid, 5-ethylidene-2,4,5,6,7,8-hexahydro-7-(hydroxymethyl)-, methyl ester, (3S,5E,6S,7S)- | [Molecular Formula]
C21H26N2O3 | [MOL File]
10012-73-4.mol | [Molecular Weight]
354.44 |
| Hazard Information | Back Directory | [Description]
First isolated from various species of Stemmadenia, this alkaloid has subsequently
been found in DipZorrhynchus rondyZocarpon subsp. mossambiensis Benth. and
MeZodinus australis. The following specific rotations have been reported; [α]19D +
310° (c 0.527, pyridine), [α]20D~O + 329° (pyridine) and [α]25D~S + 324° (pyridine).
The alkaloid gives an ultraviolet spectrum exhibiting absorption maxima at 227,
284 and 292 m/J. with shoulders at 275 and 305 m/J.. One nitrogen atom is
tertiary, the other being part of the indole ring. The solution in concentrated
HN03 is a bright yellow. | [References]
Watts, Collera, Sandoval., Tetrahedron, 2, 173 (1958)
Stauffacher., HeZv. Chim. Acta, 44, 2006 (1961)
Sandoval et aZ., Tetrahedron Lett., 409 (1962)
Schumann, Schmid., HeZv. Chim. Acta., 46, 1996 (1963)
Linde., ibid, 48,1822 (1965) |
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