Esters of O-substituted hydroxy carboxylic acids and preparations thereof

摘要

Esters of O-substituted hydroxy carboxylic acids are provided having Formula 1, or 2, or both Formulas 1 and 2:;
wherein R and R1 are independently selected from the group consisting of substituted and unsubstituted, branched- and straight-chain, saturated, unsaturated, and polyunsaturated C1-C22 alkyl, substituted and unsubstituted C3-C8 cycloalkyl, substituted and unsubstituted C6-C20 carbocyclic aryl, and substituted and unsubstituted C4-C20 heterocyclic; wherein the heteroatoms are selected from sulfur, nitrogen, and oxygen; and wherein n is 1-6. Process of producing esters of O-substituted hydroxy carboxylic acids are also provided.

主权项

1. A process for producing an ester of O-substituted hydroxy carboxylic acids having Formula 1:wherein
R is retinyl; and R1 is selected from the group consisting of branched- and straight-chain, saturated, unsaturated, and polyunsaturated C1-C22 alkyl; C3-C8 cycloalkyl; C6-C20 carbocyclic aryl; and C4-C20 heterocyclic group; the heterocyclic group comprises sulfur, nitrogen, or oxygen; and n is 1-6, wherein R1 is optionally substituted with a group selected from C1-C6-alkoxy, C1-C15 aminocarbonyl, C1-C15 amido, cyano, C2-C6-alkoxycarbonyl, C2-C6-alkanoyloxy, hydroxy, aryl, heteroaryl, thioether, and C3-C15 trialkylammonium;the process comprising:
(a) contacting an alcohol having Formula 3:
R—OH  3with a terminal halogen-substituted straight-chain carboxylic acid having Formula 4 or a short-chain ester having Formula 5:
X(CH2)nCOOH  4 X(CH2)nCOOR5  5in the presence of an enzyme to produce an intermediate having Formula 6:wherein
R and n are as defined above; R5 is a straight or branched C1-C4 alkyl or alkenyl; and X is a halogen atom; and (b) reacting said intermediate with a carboxylic acid optionally in the presence of a base and optionally in the presence of a catalyst to produce the ester of Formula 1.