Enzymatic synthesis of geranyl acetate inn‐hexane withCandida antarctica lipases

Abstract

Geranyl acetate is an important flavor and fragrance compound. Two immobilizedCandida antarctica lipases, SP382 and SP435, were investigated for their use in the synthesis of geranyl acetate by direct esterification. Yields between 95 and 99% molar conversion were obtained with 2 and 15% (w/w reactants) of SP435 and SP382 lipases, respectively. Optimum yields were obtained at 0.1M acetic acid and 0.12M geraniol after 16‐h incubation. No inhibitory effect was observed at increasing concentrations of geraniol. Addition of 60% (w/w reactants) water led to 50 and 60% reduction in the esterification activity of SP382 and SP435 lipases, respectively. The best yields were obtained at added water contents between 0–5% (w/w reactants). Solvents with a logP value of 0.85 or more gave reaction yields of more than 80% molar conversion. Higher logP values did not necessarily lead to higher conversion yields. The immobilized lipase SP382 was still active after reusing ten times in the direct esterification reaction.

Synthesis of geranyl acetate by lipase entrap‐immobilized in cellulose acetate‐TiO2 gel fiber

“…On the other hand, acetic acid inhibited the activities for all the lipases, as shown in Figure 4. The inhibitory effect of acetic acid has been reported previously (6)(7)(8)(9)(10), and it may be attributed to a lowering of pH in the vicinity of the enzyme. In addition, most lipases have little affinity for this two-carbon acid.…”

“…Terpene ester synthesis by lipase-catalyzed esterification has received much attention over the last two decades (6)(7)(8)(9)(10). Among the terpene esters synthesized by this method, the acetates of geraniol and citronellol are important flavor and fragrance compounds used in the food and cosmetic industries.…”

High performance enzymatic synthesis of oleyl oleate using immobilised lipase from Candida antartica

“…This observation may reflect the ability of the excess oleyl alcohol to distort the essential water layer from enzyme. At the same time, the excess of oleyl alcohol will hinder the interaction frequency between substrate and lipases (Kanasawud et al 1992;Claon and Akoh, 1994). This is may be due to the presence of high substrates concentration, the viscosity of the reaction mixture surrounding the enzyme molecule may be increased due to the increase in the alcohol leading to ineffective mixing of reactants and subsequent reduction in reaction rate (Erbeldinger et al 1998).This is contrary to what was reported by Chen et al 1995.…”

Lipase‐catalyzed production of biodiesel

“…There have been a considerable number of studies that report transesterification and interesterification reactions by using lipases with and without organic solvents (1)(2)(3)(4)(5)(6). Recently, research has centered on the use of lipases to transesterify higher-molecular weight fatty acids to alkyl esters.…”