Synthesis of Octyl Dihydrocaffeate and Its Transesterification with Tricaprylin Catalyzed by Candida antarctica Lipase

• Main Authors: Feddern, Vivian, Yang, Zhiyong, Xu, Xuebing, Badiale-Furlong, Eliana, Souza-Soares, Leonor
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2011
• Subjects: Antarc*; Antarctica
• Online Access: https://pure.au.dk/portal/da/publications/synthesis-of-octyl-dihydrocaffeate-and-its-transesterification-with-tricaprylin-catalyzed-by-candida-antarctica-lipase(b3675aae-eacb-4b42-bc03-17a40df86f4d).html; https://pure.au.dk/ws/files/39461690/ie200034y.pdf

This work aimed at producing a phenolic ester from dihydrocaffeic acid (DHCA), besides carrying out transesterification reactions of this ester with tricaprylin. The esterification reaction was performed in two ratios (1:1 and 1:3 DHCA:octanol), and the transesterification was done in four ratios (1:1, 1:2, 1:5, and 1:10) between the produced ester and tricaprylin. In the last, a Central Composite Rotatable Design was employed, varying the amount of enzyme (1.6-18.4%), reaction time (9.9-35.1 h), and temperature (43.2-76.8 °C) on reagent consumption percentage. Novozym 435 was the catalyst in all reactions. The highest ester yield (50%) occurred in 8 days. In transesterification reactions, higher consumption of the produced ester was achieved at ratios 1:5 and 1:10, obtaining, respectively, 29.6% and 21.1% of octyl dihydrocaffeate residual, in 24 h. At higher temperatures and time above 26 h, there was less octyl dihydrocaffeate residual (18.7%). Three different phenolic compounds were identified