A fast and efficient process for the preparation of n-retinylidene-n-retinylethanolamine (a2e)
AssigneesPurdue Research Foundation, Comell University Center for Technology Licensing at Cornell University (CTL)
InventorsDavid H. Thompson, Giulia Murbach De Oliveira, Marcelo M. Nociari
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Abstract
A process for the preparation of high quality N-retinylidene-N-retinylethanolamine (A2E) using a continuous flow reaction system is described, wherein the process first provides a mixing point for one equivalent of ATR and about ten equivalents of ethanolamine, followed by later introduction of about twelve equivalents of acetic acid into the stream of the continuous reaction flow at about 25° C. using DMSO as the solvent. The products obtained by this process are also described. A rapid method to access the purity of a sample of A2E is described.
Claims27
A process for the production of N-retinylidene-N-retinylethanolamine (A2E), which is substantially free of impurities, from ethanolamine and all-trans-retinal (ATR) in the presence of acetic acid, the process comprising the steps of:
- a) preparing a first solution consisting essentially of ATR in a first solvent;
- b) preparing a second solution consisting essentially of ethanolamine in a second solvent;
- c) preparing a third solution consisting essentially of acetic acid in a third solvent;
- d) introducing the first, second and third solutions into a continuous flow reactor at a constant flow rate and a constant temperature to yield a fourth solution containing A2E exiting the continuous flow reactor after a residence time in the continuous flow reactor (TR);
- and
- e) purifying the A2E from the fourth solution to yield A2E that is substantially free of impurities.
A rapid method to access the purity of a sample of A2E, the method comprising the steps of:
- a) dissolving the sample of A2E in alcohol to yield a solution;
- b) measuring ultraviolet absorbances of the A2E solution in alcohol at 439 nm and 339 nm;
- c) determining the ratio of the absorbance at 439 nm divided by the absorbance at 339 nm;
- and
- wherein a ratio of about 1.39 indicates the sample of A2E is substantially free of impurities
Dependencies are inferred from the claim text.