Zieniuk Bartłomiej, Groborz Katarzyna, Wołoszynowska Małgorzata, Ratusz Katarzyna, Białecka-Florjańczyk Ewa, Fabiszewska Agata
Department of Chemistry, Institute of Food Sciences, Warsaw University of Life Sciences-SGGW, 159c Nowoursynowska St., 02-776 Warsaw, Poland.
Analytical Department, Łukasiewicz Research Network-Institute of Industrial Organic Chemistry, 6 Annopol St., 03-236 Warsaw, Poland.
Biomolecules. 2021 Feb 19;11(2):314. doi: 10.3390/biom11020314.
The aim of the study was to compare the effect of the substituent and its position in the aromatic ring on the antioxidant activity of hexanoic acid esters obtained in reactions catalyzed by immobilized lipase B from . 4-Hydroxybenzyl hexanoate, 2-hydroxybenzyl hexanoate, 4-methoxybenzyl hexanoate, and vanillyl hexanoate were obtained with conversion yields of 50 to 80%. The antioxidant activity of synthesized esters, their alcohol precursors and BHT (Butylated HydroxyToluene) was compared with DPPH (2,2-diphenyl-1-picrylhydrazyl), CUPRAC (cupric ion reducing antioxidant capacity), and CBA (crocin bleaching assay) methods. Furthermore, it was investigated whether the presence of vanillyl hexanoate in a concentration of 0.01 and 0.1% affected the oxidative stability of sunflower and rapeseed oils in the Rancimat test. It was observed that the antioxidant activity of hexanoic acid esters depends on the presence and position of the hydroxyl group in the aromatic ring. The highest activities were found for vanillyl alcohol, vanillyl hexanoate, and BHT. The addition of the ester and BHT significantly extended the induction times of the tested oils, and these compounds exhibited similar activity. Vanillyl hexanoate increased the induction time from 4.49 to 5.28 h and from 2.73 to 3.12 h in the case of rapeseed and sunflower oils, respectively.
该研究的目的是比较取代基及其在芳环中的位置对由[具体来源]固定化脂肪酶B催化反应中获得的己酸酯抗氧化活性的影响。4-羟基苄基己酸酯、2-羟基苄基己酸酯、4-甲氧基苄基己酸酯和香草基己酸酯的转化率为50%至80%。采用DPPH（2,2-二苯基-1-苦基肼）、CUPRAC（铜离子还原抗氧化能力）和CBA（藏红花素漂白试验）方法比较了合成酯、其醇前体和BHT（丁基化羟基甲苯）的抗氧化活性。此外，还研究了浓度为0.01%和0.1%的香草基己酸酯的存在是否会影响Rancimat试验中向日葵油和菜籽油的氧化稳定性。观察到己酸酯的抗氧化活性取决于芳环中羟基的存在和位置。香草醇、香草基己酸酯和BHT的活性最高。酯和BHT的添加显著延长了受试油的诱导时间，并且这些化合物表现出相似的活性。在菜籽油和向日葵油中，香草基己酸酯分别将诱导时间从4.49小时增加到5.28小时和从2.73小时增加到3.12小时。
