1-Methyl-10-(14,15-dihydroeburnamenine-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester

CAS No.
21851-24-1
Chemical Name:
1-Methyl-10-(14,15-dihydroeburnamenine-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester
Synonyms
Umbellamine;1-Methyl-10-(14,15-dihydroeburnamenin-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester;1-Methyl-10-(14,15-dihydroeburnamenine-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester;2H,12H-12a,2,7a-(Epoxyethanylylidene)indolo[2,3-a]quinolizine-15-carboxylic acid, 9-(14,15-dihydroeburnamenin-14-yl)-3-ethylidene-1,3,4,6,7,12b-hexahydro-10-hydroxy-12-methyl-, methyl ester, (2S,3E,7aS,12aS,12bS,15R)- (9CI)
CBNumber:
CB72268450
Molecular Formula:
C41H48N4O4
Molecular Weight:
660.84
MDL Number:
MOL File:
21851-24-1.mol

1-Methyl-10-(14,15-dihydroeburnamenine-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester Properties

Melting point 250°C (dec.).

1-Methyl-10-(14,15-dihydroeburnamenine-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester Chemical Properties,Uses,Production

Description

The root bark of Hunteria urnbellata (K. Schum) Hall yields this alkaloid which forms colourless needles from EtOH and has a specific rotation of [α]D - 217° (c 0.45, CHCl). The ultraviolet spectrum in EtOH has absorption maxima at 230-4, and 295 nm, shoulders at 276 and 299 nm and inflexions at 248 and 288 nm. The O-acetate gives an ultraviolet spectrum with absorption maxima at 230, 285, 289 and 293 nm with an inflexion at 251 nm. The base has also been characterized as the methyl ether, m.p. 250°C (dec.) when crystallized from MeOH-CHC13 , giving an ultraviolet spectrum in EtOH with absorption maxima at 230 and 294 nm and an inflexion at 250 nm. Thermolysis of the alkaloid furnishes eburnamenine.

References

Morita, Hesse, Schmid, Helv. Chirn. A eta, 52, 59 (1969)

1-Methyl-10-(14,15-dihydroeburnamenine-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester Preparation Products And Raw materials

Raw materials

Preparation Products

1-Methyl-10-(14,15-dihydroeburnamenine-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester Umbellamine 1-Methyl-10-(14,15-dihydroeburnamenin-14-yl)-11-hydroxy-1,2-dihydro-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester 2H,12H-12a,2,7a-(Epoxyethanylylidene)indolo[2,3-a]quinolizine-15-carboxylic acid, 9-(14,15-dihydroeburnamenin-14-yl)-3-ethylidene-1,3,4,6,7,12b-hexahydro-10-hydroxy-12-methyl-, methyl ester, (2S,3E,7aS,12aS,12bS,15R)- (9CI) 21851-24-1