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Abstract
An efficient procedure for transesterification of methyl caffeate was developed to produce caffeic acid phenethyl ester analogues with Candida antarctica lipase B using an ionic liquid, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, as a solvent. The system provided 48.8 mM 2-cyclohexylethyl caffeate and 46.9 mM 3-cyclohexylpropyl caffeate with conversion yields of 97.6% and 93.8%, respectively. Reusability of the system was investigated, and the yield of 4-phenylbutyl caffeate was increased from 30.4 to 45.7 mM when the transesterification was carried out under reduced pressure to remove a by-product, methanol. Additionally, we showed that both 2-cyclohexylethyl caffeate and 3-cyclohexylpropyl caffeate exhibit strong antiproliferative activities, which are comparable to that of 5-fluorouracil by MTT assay.
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