Enzymatic Synthesis of Thymol Octanoate, a Promising Hybrid Molecule

Abstract

Interest in the synthesis and application of thymol esters has increased in recent years due to the numerous applications associated with its biological activities. The enzymatic synthesis of thymol octanoate by esterification of thymol and octanoic acid was explored using soluble lipases and immobilized lipase biocatalysts in solvent-free systems. Candida antarctica lipase B in its soluble form was the most active biocatalyst for this reaction. Different thymol and lipase feeding strategies were evaluated to maximize thymol octanoate production. The results suggest that there could be lipase inhibition by the ester product of the reaction. In this way, the optimal reaction condition was given using a thymol/acid molar ratio of 1:4 mol/mol. Under these conditions the conversion of thymol was close to 94% and the lipase maintained more than 90% of its initial activity after the reaction, showing the potential of the enzyme to be used in successive reaction cycles.

3-Acetyl-11-keto-β-boswellic Acid-Based Hybrids Alleviate Acetaminophen-Induced Hepatotoxicity in HepG2 by the Regulation of Inflammatory and Oxidative Stress Pathways: An Integrated Approach

“…This is in agreement with previous studies indicating that hydrazones have lower stability in an acidic medium rather than basic or neutral conditions, while esters tend to act as prodrugs in relatively basic pH, leading to a continuous release of the active substrate. Nevertheless, esters have substantial resistance to acid hydrolysis. , Still, the obtained data infer that the gastric or intestinal environment might not affect the absorption of both compounds since they showed reasonable stability in both acidic and slightly basic environments.…”

“…Nevertheless, esters have substantial resistance to acid hydrolysis. 75,76 Still, the obtained data infer that the gastric or intestinal environment might not affect the absorption of both compounds since they showed reasonable stability in both acidic and slightly basic environments.…”

Theophylline-based hybrids as acetylcholinesterase inhibitors endowed with anti-inflammatory activity: synthesis, bioevaluation,in silicoand preliminary kinetic studies

“…Importantly, both compounds exhibited substantive resistance to acid hydrolysis. 65,66 Based on the data we gathered, it can be inferred that both compounds are not greatly affected by gastric or intestinal fluids. This suggests that they have the ability to be absorbed into the body without undergoing substantial breakdown.…”