Use of essential oils as media for the enantioselective esterification of the monoterpene perillyl alcohol catalyzed by lipase

• Published in: European Journal of Lipid Science and Technology
• Main Authors: Skouridou, Vasso, Stamatis, Haralambos, Kolisis, Fragiskos N.
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2003
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/ejlt.200390026; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejlt.200390026; https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejlt.200390026

Abstract The synthesis of perillyl alcohol esters by direct esterification catalyzed by immobilized lipase from Candida antarctica (Novozyme 435) was studied. For this purpose, fatty acids with a chain length from 3‐16 were used. The reactions were carried out in mixtures of α‐pinene and myrcene as well as in pure organic solvents. It was found that the esterification rates increased from 3.7‐6.9 mM/min when using decreasing concentrations of myrcene in α‐pinene (100‐0%). Higher rates and conversions were obtained with decanoic acid as the acyl donor (6.9 mM/min, 81.5%), while lower conversions were obtained with fatty acids of shorter (propionic acid, 5.6%) or longer (hexadecanoic acid, 62.5%) carbon chain. In addition, it was found that the effect of the water activity depended on the chain length of the acyl donor and the composition of the solvent mixture. Also, esterification rates increased from 1.8‐6.9 mM/min with increasing hydrophobicity of the solvent (logP from 0.9‐4.8) of the organic solvent used. Finally, it was found that Candida antarctica lipase presented a preference in the esterification of (S)‐(—)‐ and (R)‐(+)‐perillyl alcohol in favor of the (R)‐(+) enantiomer. The enantioselectivity was found increased with increasing logP, whereas the water activity of the reaction mixture did not affect the enantioselectivity significantly.