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Updated: Feb 11, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Lipase-catalysed esters synthesis of cafestol and kahweol
Fábio Junior Moreira Novaes1, Ivaldo Itabaiana Junior2, Felipe Korbus Sutili3
1Universidade Federal do Rio de Janeiro, Instituto de Química, Laboratório de Análise de Aromas, Avenida Athos da Silveira Ramos, 149, Bloco A, Sala 626, Rio de Janeiro, RJ 21941-895, Brazil; Universidade Federal do Rio de Janeiro, Instituto de Química, LADETEC, Avenida Horacio Macedo, 1281, Rio de Janeiro, RJ 21941-598, Brazil.
Abstract:
Cafestol and kahweol (C&K), two coffee diterpene alcohols with structural similarity which exhibit anticarcinogenic effects, were isolated from green coffee Arabica beans, followed by their lipase-catalysed esterification and purification by preparative high-performance liquid chromatography (HPLC). The isolation and enzymatic synthesis parameters of C&K esters were studied, with the latter optimised by a Central Composite Design; both procedures were monitored by gas chromatography. Scale up and improved isolation conditions resulted in 1.29 g of C&K, with 98% purity from 300 g of green Arabica beans. The highest C&K ester yields were observed using an alcohol:fatty acid molar ratio of 1:5, 73.3 mg mL-1 of CAL-B enzyme, 70 °C and 240 rpm for 3 days in toluene, leading to 85-88% conversion among a variety of tested C&K esters, including n-C14:0-C20:0, C18:1, C18:2 and C18:3.
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