Development of new non-toxic antioxidants with diverse hydrophobic properties is important due to growing concerns about the toxicity of artificial oil-soluble antioxidants, the comparatively low effectiveness of natural options, and the complex role hydrophobicity plays in antioxidant effectiveness. Using caffeic acid, a naturally occurring phenolic acid with potent antioxidant activity, a range of glyceryl caffeate esters (decanoate and palmitate) were prepared using lipase-catalysed esterification reactions. Glyceryl-1-caffeate (GC) was prepared from ethyl caffeate and glycerol (acting as both the solvent and the substrate), catalysed by immobilised Candida Antarctica lipase B (Novozym-435) at 80 °C under vacuum. Esterification of GC with decanoic acid using immobilised Thermomyces lanuginosus lipase (TLIM) or Novozym-435 was found to be selective towards mono-acylated or di-acylated products, respectively. The reaction was performed in an unconventional solvent, propylene carbonate (PC), which has many of the attributes of a green solvent. Product conversions in PC were comparable to the best performing conventional solvents. In contrast to conventional volatile solvents, the low volatility of PC allowed the reaction to be performed under vacuum, without the need for molecular sieves for removal of water produced during the reaction. Diisopropyl ether was effective at extracting the more lipophilic products from PC. Both the lipase (Novozym-435) and PC were reused four times with only a small loss in conversion efficiency. Glyceryl caffeate esters performed much better than α-tocopherol at protecting bulk tuna oil from oxidation (analysed using Rancimat). A comparison of glyceryl caffeate esters (decanoate/palmitate and mono-/di-acylated) showed that their antioxidant effectiveness in bulk tuna oil was not affected by chain-length, but compounds containing only one fatty ester were slightly more effective than those containing two fatty esters.

由于人们越来越关注人工油溶性抗氧化剂的毒性、天然选择的有效性相对较低以及疏水性在抗氧化有效性中的复杂作用，因此开发具有多种疏水特性的新型无毒抗氧化剂非常重要。使用咖啡酸（一种具有强抗氧化活性的天然酚酸），通过脂肪酶催化的酯化反应制备了一系列咖啡酸甘油酯（癸酸酯和棕榈酸酯）。Glyceryl-1-caffeate (GC) 由咖啡酸乙酯和甘油（作为溶剂和底物）制备，由固定化的南极念珠菌脂肪酶 B（Novozym-435）在 80°C 下真空催化。使用固定化嗜热丝孢菌用癸酸对 GC 进行酯化发现脂肪酶 (TLIM) 或 Novozym-435 分别对单酰化或双酰化产物具有选择性。该反应在非常规溶剂碳酸亚丙酯 (PC) 中进行，该溶剂具有绿色溶剂的许多属性。PC 中的产品转化率可与性能最佳的传统溶剂相媲美。与传统的挥发性溶剂相比，PC 的低挥发性允许反应在真空下进行，不需要分子筛来去除反应过程中产生的水。二异丙醚可有效地从 PC 中提取更亲脂的产品。脂肪酶 (Novozym-435) 和 PC 都重复使用了四次，转化效率只有很小的损失。在保护散装金枪鱼油免于氧化（使用 Rancimat 分析）方面，甘油咖啡酸酯比 α-生育酚表现得更好。咖啡酸甘油酯（癸酸酯/棕榈酸酯和单酰/二酰化）的比较表明，它们在散装金枪鱼油中的抗氧化效果不受链长的影响，但仅含有一种脂肪酸酯的化合物比含有两种脂肪酸的化合物更有效脂肪酯。