6835-99-0

Basic information

• Product Name: Eburnamenine-14-carboxylic acid,14,15-dihydro-14-hydroxy-,methyl ester,(3R,14R,16R)-
• CAS NO: 6835-99-0
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.449
• Mol File: 6835-99-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 508.9°Cat760mmHg
• Flash Point: 261.6°C
• Density: 1.36g/cm³
• CAS DataBase Reference: Eburnamenine-14-carboxylic acid,14,15-dihydro-14-hydroxy-,methyl ester,(3R,14R,16R)- (CAS DataBase Reference)
• NIST Chemistry Reference: Eburnamenine-14-carboxylic acid,14,15-dihydro-14-hydroxy-,methyl ester,(3R,14R,16R)- (6835-99-0)
• EPA Substance Registry System: Eburnamenine-14-carboxylic acid,14,15-dihydro-14-hydroxy-,methyl ester,(3R,14R,16R)- (6835-99-0)

Safety Data

• Hazardous Substances Data: 6835-99-0(Hazardous Substances Data)

Usage

General Description

Eburnamenine-14-carboxylic acid,14,15-dihydro-14-hydroxy-,methyl ester,(3R,14R,16R)- is a complex chemical compound with a molecular formula of C23H31NO5. It is classified as an alkaloid, which is a naturally occurring organic compound that contains basic nitrogen atoms. This particular alkaloid is derived from the Tabernaemontana genus of plants and has been the subject of research for its potential medicinal and pharmacological properties. The compound contains a methyl ester group and is structurally related to other bioactive alkaloids. Its exact biological activities and potential uses are still being explored by the scientific community.

Upstream product

• 30061-30-4 (-)-vincadifformine hydrochloride 
• 96861-85-7 O-methyl vincamine 
• 32790-10-6 14-epi-Δ¹⁷-vincamine 
• 66113-74-4 hydroxy-16 dehydro-1 vincadifformine 
• 1617-90-9 vincamin 
• 85588-92-7 (-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime 
• 83289-24-1 methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate 
• 3247-10-7 (-)-vincadifformine 
• 112965-87-4 (+)-15,15a-didehydro-15-formamido-D-homoeburnamin-14-one 
• 300661-83-0 diethyl 15aS-ethyl-2,3,6,11,15,15a-hexahydro-1H,5H-indolo[2,3-a]pyrano[3,2-i]quinolizine-14,14-(13H)-dicarboxylate 
• 135099-82-0 C₂₆H₃₄N₂O₅ 
• 135266-72-7 (1S,12bS)-1-(2,2'-diethoxycarbonylethyl)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine 
• 51152-47-7 (1R*,5S*,12bS*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde 
• 126218-04-0 dimethyl (2S,3R)-3-ethyl-1-(9-phenylfluoren-9-yl)hexahydroquinolinate 

Downstream Products

• 1617-90-9 vincamin 
• 4880-92-6 apovincamine 
• 4880-88-0 vinburnine 

Relevant articles and documents

Preparation methods for chiral impurities of vincamine

The invention relates to preparation methods for chiral impurities of vincamine. Through oriented synthesis method and the later column chromatography separation, high purity product of seven chiral impurities can be obtained, and the preparation methods can be used for the qualitative and quantitative analysis of impurities in the production of vincamine, so that the separation and confirmation of the seven chiral impurities in vincamine drugs can be realized, and the drug standard of the vincamine can be enhanced, and therefore, the vincamine with high purity can be obtained. Compared with existing preparation methods for the vincamine, the preparation methods relate to the preparation of seven chiral isomers, and are more complete and simpler in operation.

Syntheses and Cardiovascular Activity of Stereoisomers and Derivatives of Eburnane Alkaloids

The synthesis of all the possible isomers of the eburnamenine-vincamine type alkaloids 1b, 2a*, 3a and derivatives 4, 8, 9, 10 is described.Structures were determined by 1H- and 13C-NMR spectroscopy including special techniques such as DR, DEPT, DNOE, and 2D-HSC.In contrast to the known cerebrovascular effects of cis-(3S,16S) compounds, trans-(3S,16R) derivatives show a significant peripheral vasodilator effect. Key Word: Eburnanes / Alkaloids / Cardiovascular effects / Indoloquinolizines

SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS, XLIX. AROMATIC SUBSTITUENT EFFECTS IN THE C-14 EPIMERIZATION

Some A-ring substituted vincamine derivatives and their C-14 epimers have been prepared and the aromatic substituent effects on the epimeric equilibrium of these compounds investigated.