40163-56-2

Usage

Uses

Used in Pharmaceutical Applications:
EBURNAMENINE-14-CARBOXYLIC ACID, 14,15-DIHYDRO-14-HYDROXY-, ETHYL ESTER, (3A,14B,16A)is used as a pharmaceutical compound for its potential therapeutic effects. EBURNAMENINE-14-CARBOXYLIC ACID, 14,15-DIHYDRO-14-HYDROXY-, ETHYL ESTER, (3A,14B,16A)-'s unique structure and functional groups may allow it to interact with biological targets, such as enzymes or receptors, which could be beneficial in the treatment of various diseases or conditions.
Used in Chemical Research:
In the field of chemical research, EBURNAMENINE-14-CARBOXYLIC ACID, 14,15-DIHDRO-14-HYDROXY-, ETHYL ESTER, (3A,14B,16A)can be used as a starting material or intermediate in the synthesis of other complex organic molecules. Its unique structure and functional groups may provide new insights into chemical reactions and mechanisms, contributing to the advancement of chemical science.
Used in Drug Delivery Systems:
Similar to the application of gallotannin in drug delivery systems, EBURNAMENINE-14-CARBOXYLIC ACID, 14,15-DIHYDRO-14-HYDROXY-, ETHYL ESTER, (3A,14B,16A)could potentially be employed in the development of novel drug delivery systems. Its unique structure and functional groups may allow for targeted delivery of therapeutic agents, improving their bioavailability and therapeutic outcomes.

InChI:InChI=1/C22H28N2O3/c1-3-21-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(18(16)19(21)23)22(26,14-21)20(25)27-4-2/h5-6,8-9,19,26H,3-4,7,10-14H2,1-2H3/t19-,21+,22+/m1/s1

Upstream product

• 40163-56-2 Ethyl (+/-)-14-epivincaminate 
• 64-17-5 ethanol 
• 1617-90-9 vincamin 
• 42971-09-5 Vinpocetine 
• 64-67-5 diethyl sulfate 
• 28152-73-0 (3α,14β,16α)-14,15-dihydro-14-hydroxyeburnamenine-14-carboxylic acid 
• 105-58-8 Diethyl carbonate 
• 75-00-3 chloroethane 
• 74-96-4 ethyl bromide 
• 75-03-6 ethyl iodide 
• 43184-10-7 1α-ethyl-1-(2-hydroxy-2-ethoxycarbonylethyl)-1,2,3,4,6,7,12,12β-octahydroindolo-<2,3-a>quinolizine 
• 40163-56-2 (+/-)-3-epivincaminic acid ethyl ester 
• 43182-59-8 2-Acetoxy-3-((1S,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-propionic acid ethyl ester 
• 43184-10-7 3-((1S,12bS)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-hydroxy-propionic acid ethyl ester 

Downstream Products

• 40163-56-2 14,15-dihydro-14-(ethoxycarbonyl)-14-hydroxyeburnamenin(3α,14β,16α) 
• 42971-09-5 (+/-)-3-epi-apovincaminic acid ethyl ester 
• 40163-56-2 (+/-)-3-epi-14-epivincaminic acid ethyl ester 
• 42971-09-5 Vinpocetine 

Relevant academic research and scientific papers

A facile one-pot synthesis of vinpocetine

A one-pot synthesis of vinpocetine from vincamine was established. Lewis acids caused transesterification and/or dehydration of vincamine in EtOH. FeCl3 catalyzed both transesterification and dehydration while Ti(OEt)4 selectively catalyzed transesterification.

A CHANGCHUN amine ethyl ester preparation method

The invention discloses a preparation method of vincamine ethyl ester which is applied to the preparation field of a compound vinpocetine intermediate and impurities. The preparation method comprises the following steps: (1) in the presence of a first organic solvent and alkaline, enabling vincamine acid and an ethylation reagent to carry out ethylation reaction to obtain a reaction liquid, wherein the first organic solvent, the alkaline, the vincamine acid and the ethylation reagent are added into a reaction system by one step; (2) evaporating out the solvent from the reaction liquid obtained in the step (1) and then adding water to dissolve, washing an organic phase with a saline liquid after directly extracting by use of a second organic solvent to obtain an organic phase extracting liquid; (3) after dehydrating the organic phase extracting liquid obtained in the step (2) by a drying agent, filtering and concentrating to obtain a concentrated liquid; and (4) adding a third organic solvent into the concentrated liquid obtained in the step (3), separating out solids, filtering and drying the solids to obtain the vincamine ethyl ester. According to the preparation method of the vincamine ethyl ester, the raw materials are easily available and convenient to store, the reaction process is simple and convenient in operation, the safety is high, the cost is low, the yield of the vincamine ethyl ester is high, the quality of the vincamine ethyl ester is good, and needed reaction solvent and after-treatment solvent are little, and thus, the preparation method is suitable for the industrial production.

Kinetics and mechanisms of vinpocetine degradation in aqueous solutions

Under stressed conditions, vinpocetine (1; ethyl apovincamin-22-oate) equilibrates with vincaminic acid ethyl ester (2) and 14-epivincaminic acid ethyl ester (3), and hydrolyzes to apovincaminic acid (4). Sequentially, 2 is equilibrated with 14-epivincaminic acid ethyl ester (3) and hydrolyzes to vincaminic acid (5), which equilibrates with 4 and 14-epivincaminic acid (6). At acidic pH, the major route of degradation is 1?2→5. However, at neutral pH, the major route of degradation is 1→4?5. The kinetics for the degradation of 1 in the pH 1-3 region is represented by a consecutive reaction with a reversible step (second-order), but the degradation of 1 in the pH 3.5-6.0 region follows pseudo first-order kinetics. Significant buffer catalysis is observed with acetate and phosphate buffers. Reactions are dependent on the ionic strength, pH, and temperature. No oxygen effect on the degradation of vinpocetine is found.

Process for the preparation of vincaminic acid esters

The invention relates to a new process for the preparation of apovincaminic acid esters. More particularly, the invention concerns a process for preparing racemic and optionally active vincaminic acid esters of the formula (I) STR1 in which R1 and R2 independently stand for alkyl having from one to 6 carbon atoms, and 14-epimers thereof. According to the invention an octahydroindolo[2,3-a]quinolizine-oxime ester of the formula (II) STR2 in which R1 and R2 have the same meaning as defined above, is reacted with an aqueous solution of sulfurous acid or a salt thereof at a temperature of 80° to 110° C. and the 14-epimeric mixture obtained is epimerized or separated in a known manner and if desired, the racemic vincaminic acid esters are resolved. The valuable, pharmaceutically active compounds of the formula (I) can be prepared according to the invention in a considerably improved yield and the undesired side reactions can be suppressed and/or the by-products can easily be converted into other pharmaceutically active materials.