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第 36 卷第 6 期 精 细 化 工 Vol.36, No.6
201 9 年 6 月 FINE CHEMICALS June 2019

食品与饲料用化学品
原儿茶酸烷基酯在水包油乳液中的抗氧化行为

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李 进，武雪菲，米晓培，黄师荣 ，万 慧
（湘潭大学 生物与食品工程系，湖南 湘潭 411105）

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摘要：以原儿茶酸（PA）和系列正烷基醇为原料，采用直接酯化法合成了 4 种 PA 烷基酯。用 IR 和 HNMR 表
征了其结构，用 DPPH 法和 ABTS 法测定了其自由基清除能力，用 Schaal 烘箱实验考察了其在水包油乳液中的
抗氧化效率。结果表明，PA 酯化后增强了其对自由基的清除能力，并且随着烷基链长的增加清除能力增强。PA
酯化提高了其在水包油乳液中的抗氧化效率，并随烷基链长的增加，抗氧化效率先增大后下降，原儿茶酸辛酯
的抗氧化效率最佳。各种 PA 烷基酯在乳化剂吐温 20 的体积分数为 4%、油与水体积比 2∶8 的菜籽油乳液中的
抗氧化效率最佳。与添加 PA 的乳液相比，添加 PA 烷基酯的乳液的共轭二烯含量（CD）值达到 1 的时间以及
p-茴香胺含量（AV）值达到 6 的时间均显著增加。
关键词：原儿茶酸；酯化；乳液；抗氧化
中图分类号：TS202.3 文献标识码：A 文章编号：1003-5214 (2019) 06-1173-08

Antioxidant Behavior of Protocatechuic Acid Alkyl
Esters in Oil-in-water Emulsion

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LI Jin, WU Xue-fei, MI Xiao-pei, HUANG Shi-rong , WAN Hui
（Department of Biological and Food Engineering, Xiangtan University, Xiangtan 411105, Hunan, China）

Abstract: Four protocatechuic alkyl esters were synthesized by direct esterification reaction with
protocatechuic acid and a series of alkyl alcohols as raw materials, and their structures were identified by
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infrared and HNMR spectroscopy. DPPH assay and ABTS assay were used to determine their free radical
scavenging capacity. The Schaal oven test was used to determine their antioxidant efficiency in oil-in-water
emulsion. The results showed that the free radical scavenging capacity of protocatechuic acid alkyl esters
was higher than that of PA, and it increased with the increase of alkyl chain length. Esterification of
protocatechuic acid enhanced its antioxidant activity in the oil-in-water emulsion. As the alkyl chain length
increased, the antioxidant efficiency first increased and then decreased. Octyl protocatechuate showed the
best maximum antioxidant efficiency. The maximum of antioxidant efficiency of all protocatechuic alkyl
esters was obtained when the volume fraction of emulsifier was 4% in rapeseed oil emulsions with oil to
water volume fraction 2∶8. For the emulsions containing protocatechuic alkyl esters, the time of the
conjugated diene value to reach 1 and the time of p-anisidine value to reach 6 were obviously improved
compared with those of the emulsion using protocatechuic acid as emulsifier.
Key words: protocatechuic acid; esterification; emulsion; antioxidant
Foundation items: Natural Science Foundation of Hunan Province (2016JJ2120); Hunan 2011
Collaborative Innovation Center of Chemical Engineering & Technology with Environmental Benignity
and Effective Resource Utilization

收稿日期：2018-07-13; 定用日期：2019-01-21; DOI: 10.13550/j.jxhg.20180519
基金项目：湖南省自然科学基金资助项目（2016JJ2120）；“环境友好与资源高效利用化工新技术”湖南省高校 2011 协同创新中心资
助项目
作者简介：李 进（1992—），男，硕士生，E-mail：476996440@qq.com。联系人：黄师荣（1974—），男，副教授，电话：13257326380，
E-mail：hwangee@163.com。