Page 108 - 《精细化工》2023年第2期

第 40 卷第 2 期 精 细 化 工 Vol.40, No.2
20 23 年 2 月 FINE CHEMICALS Feb. 2023

医药与日化原料
油酸和十二烷二酸的氨基酸酯合成及其抗菌性

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张鉴伟 1,2 ，卢 江
（1. 中山大学 化学学院，广东 广州 510000；2. 西陇科学股份有限公司，广东 汕头 515000）

摘要：以 L-丙氨酸乙酯盐酸盐、甘氨酸乙酯盐酸盐、L-蛋氨酸甲酯盐酸盐、L-亮氨酸乙酯盐酸盐和 L-酪氨酸甲
酯盐酸盐在 1-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐和 1-羟基苯并三唑（HOBt）的作用下分别与油酸进行
反应，生成了 5 种油酸的氨基酸衍生物；将 L-丙氨酸乙酯盐酸盐和甘氨酸乙酯盐酸盐分别与十二烷二酸进行反
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应，生成了两种十二烷二酸的氨基酸衍生物，7 种产物的收率均≥75%。利用 FTIR、TGA、 HNMR 和 LC-MS
对产物进行了表征，测试了产物的水油分散性，考察了产物对金黄色葡萄球菌和大肠杆菌的抑菌性。结果表明，
所合成的脂肪酰氨基酸酯均能在水油体系中分散，且具有较强的生物抗菌性，其中，0.01 mg 油酸酰亮氨酸乙酯
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能有效地抑制金黄色葡萄球菌（菌数由 2.0×10 CFU/mL 降至 1.4×10 CFU/mL），而相同质量油酸酰酪氨酸甲
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酯则能抑制大肠杆菌（菌数由 2.0×10 CFU/mL 降至 1.8×10 CFU/mL）。
关键词：脂肪酸；氨基酸；油酸酰氨基酸酯；十二烷二酸酰氨基酸酯；水油分散性；抗菌性；日化原料
中图分类号： TQ421 文献标识码：A 文章编号：1003-5214 (2023) 02-0330-07

Synthesis and antibacterial activities of amino acid esters from

oleic acid and dodecanedioic acid

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1,2
ZHANG Jianwei , LU Jiang
（1. School of Chemistry, Sun Yat-sen University, Guangzhou 510000, Guangdong, China; 2. Xilong Scientific Co., Ltd.,
Shantou 515000, Guangdong, China）

Abstract: Five types of oleic acid derivatives were produced by reaction of oleic acid with L-alanine ethyl
ester hydrochloride, glycine ethyl ester hydrochloride, L-methionine methyl ester hydrochloride, L-leucine
ethyl ester hydrochloride and L-tyrosine methyl ester hydrochloride, respectively, in presence of
1-ethyl-(3-dimethyllaminopropyl)carbodiie hydrochlide and 1-hydroxybenzotriazole. In addition, two types
of dodecanedioic acid derivatives were also synthesized via reactions of dodecanedioic acid with L-alanine
ethyl ester hydrochloride and glycine ethyl ester hydrochloride, respectively. It was found that the yields of
all seven products were higher than or equal 75%. The structures of the products obtained were then
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characterized by FTIR, TGA, HNMR and LC-MS, followed by evaluations on the dispersibilities and the
antibacterial activities against Staphylococcus aureus and Escherichia coli. The results showed that these
fatty acid acyl amino acid esters exhibited good dispersity in both aqueous and organic phases, and obvious
antimicrobial activities. Oleoyl leucine ethyl ester (0.01 mg) could effectively inhibit the growth of
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Staphylococcus aureus (the number of bacteria was decreased from 2.0×10 CFU/mL to 1.4×10 CFU/mL),
while oleoyl tyrosine methyl ester with the same mass showed significant growth inhibition effect on
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Escherichia coli (the number of bacteria was decreased from 2.0×10 CFU/mL to 1.8×10 CFU/mL).
Key words: fatty acid; amino acid; oleoyl amino acid ester; dodecyl diacid amino acid ester; water oil
dispersion; antibacterial activity; cosmetic materials

[1]
生物抗菌剂在人类历史的发展进程中起着至关 来，越来越多的研究聚焦于生物抗菌剂在食品 、
[2]
重要的作用，与人类的生产生活息息相关。近 10 年 化妆品 、涂料 [3-4] 和个人护理品行业 [5-6] 中的应用。

收稿日期：2022-04-20; 定用日期：2022-07-22; DOI: 10.13550/j.jxhg.20220375
作者简介：张鉴伟（1992—），男，博士，E-mail：332760217@qq.com。