Enzymatic Synthesis of Acetoacetate Esters and Derivatives

• US 20100003730A1
• Filed: 07/03/2008
• Published: 01/07/2010
• Est. Priority Date: 07/03/2008
• Status: Active Grant

• Current Assignee: Cerecin, Inc.
• Original Assignee: Accela Incorporated (Piksel Incorporated)
• Inventors: Henderson, Samuel T.
• Granted Patent: US 8,105,809 B2
• Time in Patent Office: Days
• US Class Current: 435/135
• CPC Class Codes: C12P 7/62 Carboxylic acid esters
• CPC Class Codes: C12P 7/6454 by esterification

Abstract

In one embodiment, the present invention includes a method for the synthesis of an ester derivative of acetoacetate. The method includes providing a first ester of acetoacetate and providing an alcohol. The method further includes combining the first ester of acetoacetate and the alcohol in the presence of an enzyme capable of transesterification in a non-aqueous solvent to form the ester derivative of acetoacetate. The method results in the formation of the ester derivative of acetoacetate, which, in one embodiment, is monoacetoacetin.

Claims

1. A method for the synthesis of an ester derivative of acetoacetate, comprising providing a first ester of acetoacetate having of formula I:

2. The method of claim 1, wherein the ester derivative of acetoacetate is monoglyceride of acetoacetate.

3. The method of claim 1, wherein the first ester of acetoacetate is methylacetoacetate.

4. The method of claim 1, wherein the enzyme capable of transesterification in a non-aqueous solvent to form the ester derivative of acetoacetate is a lipase or an esterase.

5. The method of claim 1, wherein the enzyme is selected from the group consisting of Candida antarctica lipase, Aspergillus lipase, Thermoanaerobium brockii esterase, and Esterase E020.

6. The method of claim 1, wherein the non-aqueous solvent is selected from the group consisting of acetonitrile, MTBE, THF, acetone, and toluene.

7. The method of claim 6, wherein the non-aqueous solvent is acetonitrile.

8. The method of claim 1, further comprising purification of the ester derivative of acetoacetate.

9. The method of claim 1, wherein the alcohol is a polyol.

10. The method of claim 9, wherein the polyol is glycerol.

11. The method of claims 9, wherein the alcohol is glucose.