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CN106588701A - 一种氨基酸衍生物、制备方法及其应用 - Google Patents

一种氨基酸衍生物、制备方法及其应用 Download PDF

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CN106588701A
CN106588701A CN201611096104.2A CN201611096104A CN106588701A CN 106588701 A CN106588701 A CN 106588701A CN 201611096104 A CN201611096104 A CN 201611096104A CN 106588701 A CN106588701 A CN 106588701A
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fatty
acid
amino acid
salt
acylamino
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史鲁秋
苏桂珍
孔惠
胡海霞
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Nanjing Huashi New Material Co Ltd
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Nanjing Huashi New Material Co Ltd
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Abstract

一种脂肪酰氨基酸酯和脂肪酰氨基酸所形成的盐，其对微生物具有抑制或者杀灭作用的盐的方法，该类衍生物同时具有高效、温和及广谱杀菌等性能，可广泛应用于食品、饮料、饲料、家居护理以及个人护理等产品中。本发明的脂肪酰氨基酸酯和脂肪酰氨基酸的盐为液体，方便添加与使用，对常见的微生物具有很好的抑制作用，可以替代传统的防腐剂，具有高安全性、低刺激性，降低过敏及毒性风险，并且具有易降解、环境友好等优点。

Description

一种氨基酸衍生物、制备方法及其应用
技术领域
本发明涉及一种氨基酸衍生物、制备方法，以及该衍生物作为微生物抑制剂，在食品、饲料、家居护理以及个人护理品中的应用。
背景技术
防腐剂用于食品、饲料、化妆品以及家具护理品中，主要作用是抑制微生物的生长和繁殖，以延长产品的保存时间，抑制产品腐败变质。随着化妆品、食品等行业的迅速发展，选择安全、高效的防腐体系，是目前政策法规、消费者以及研究工作者非常关注的问题。
许多传统防腐剂都被证实具有一定的负面作用，如DMDMH会释放甲醛，卡松系列含氯对某些肤质有刺激作用，布罗波尔可能会生成致癌物亚硝胺，IPBC可能导致摄入碘，三氯新对环境有负面影响。而尼泊金酯类，其苯环可能会在脂肪组织中累积或在特定的测试系统中显示某种模拟女性激素雌激素的能力。
法规对于防腐剂的使用规范也越来越严格，异塞唑晽酮类、甲醛释放体、羟苯酯类防腐剂的使用日趋受到限制。越来越严格的化妆品法规、消费者的安全意识的提高以及对防腐剂理解的误区、安全等因素，这一系列的变化促使传统防腐剂的使用总量明显下滑，亟待新的防腐剂开发与应用。
月桂酰精氨酸乙酯盐酸盐是一类安全性、效果非常好的防腐剂，被应用于存食品、化妆品的防腐；被粮农组织/世卫组织联合食品添加剂专家委员会(JECFA)批准使用；另外，月桂酰精氨酸乙酯盐酸盐还符合欧盟、澳大利亚、加拿大以及新西兰等国家和地区的相关法规。
月桂酰精氨酸乙酯盐酸盐是一种白色粉末，不利于添加到配方中，熔点在50-58℃，加入配方中时，需要预先将固体加热融化或使用溶剂溶解后，再添加到配方体系中，使得其添加非常麻烦，另外，即使选用溶剂溶解，其溶解度也非常有限，如其甘油中仅最大溶解仅20%左右。
本发明提供一种精氨酸乙酯衍生物，该类产品熔点低，常温为澄清透明的液体，可以非常方便地溶于甘油等常见溶剂，溶解度高达70%，可以非常方便的用于食品、药品以及化妆品。
发明内容
本发明的目的是提供一种脂肪酰氨基酸酯和脂肪酰氨基酸所形成的盐，该类衍生物为液体形式，对微生物具有更好的抑制或者杀灭效果，可方便与广泛应用于食品、饮料、医药、家居护理以及个人护理等产品中。
本发明所提供的脂肪酰氨基酸和脂肪酰氨基酸酯形成的盐，对常见的的微生物具有很好的抑制作用，可以替代传统的防腐剂。
本发明的化合物具有天然来源、高安全性、低刺激性，降低过敏及毒性风险，并且具有易降解、环境友好等优点。
本发明提供的技术方案：一种利用脂肪酰氨基酸酯和脂肪酰氨基酸成盐的方法，将脂肪酰氨基酸酯和脂肪酰氨基酸成盐后，抑菌效果显著增强。
本发明所述脂肪酰氨基酸酯和脂肪酰氨基酸所形成的盐，对微生物具有抑制或者杀灭作用的盐的方法，具体步骤为：
（1）溶解：将脂肪酰氨基酸酯溶于溶剂，加热到50-55℃溶解；
（2）成盐：脂肪酰氨基酸加到步骤（1）所得的脂肪酰氨基酸酯溶液中，混合搅拌至澄清透明；
（3）将步骤（2）中复配形成的盐减压蒸馏，除去溶剂。
步骤（1）中脂肪酰氨基酸酯具有(a) ~ (d)的化学结构，可以为通式(a) ~ (d)中的一种或几种的组合：
I. 精氨酸衍生物及其常见的盐，其结构通式如式(a)：
(a)
其中，R1是甲基、乙基、丙基或丁基；R2是碳原子数为6-22的脂肪酰基；
II. 鸟氨酸衍生物及其常见的盐，其结构通式如式(b)：
(b)
其中，R1是甲基、乙基、丙基或丁基；R2是碳原子数为6-22的脂肪酰基；
III. 赖氨酸衍生物及其常见的盐，其结构通式如式(c)：
(c)
其中，R1是甲基、乙基、丙基或丁基；R2是碳原子数为6-22的脂肪酰基；
IV. 组氨酸衍生物及其常见的盐，其结构通式如式(d)：
(d)
其中，R1是甲基、乙基、丙基或丁基；R2是碳原子数为6-22的脂肪酰基。
步骤（1）中的溶剂为水或者乙醇；
步骤（2）中的脂肪酰氨基酸，可以为一种或多种物质的组合，由碳原子数为5-21的脂肪酸和氨基酸缩合而成，其中氨基酸选自丙氨酸、精氨酸、天冬氨酸、半胱氨酸、谷氨酰胺、谷氨酸、组氨酸、异亮氨酸、甘氨酸、天冬酰胺、亮氨酸、赖氨酸、甲硫氨酸、苯丙氨酸、脯氨酸、丝氨酸、苏氨酸、色氨酸、酪氨酸、缬氨酸。
对本发明所述脂肪酰氨基酸酯和脂肪酰氨基酸所形成的盐的抑菌体系进行评估测试。
①防腐挑战测试：将脂肪酰氨基酸酯和脂肪酰氨基酸复配形成的盐体系加入到护肤品配方中，通过欧盟标准BP2002 XVIC 防腐效果测试方法分别对加入不同盐的配方溶液进行防腐挑战测试。
②最小抑菌浓度测试：针对脂肪酰氨基酸酯和脂肪酰氨基酸复配形成的盐体系及月桂酰精氨酸乙酯进行防腐效果测试。防腐效果测试菌种见表1：
③斑贴试验：针对脂肪酰氨基酸酯和脂肪酰氨基酸复配形成的盐体系及月桂酰精氨酸乙酯进行皮肤过敏性测试。
本发明所述的复配形成的盐体系与一般的化妆品原料具有很好的配伍性，与表面活性剂、油脂、溶剂、抗氧化剂等其他组分的复配性很好，与化妆品原料混匀乳化后，能使膏、霜、乳等基质细腻均匀，长期存放不分层、不渗水，剂型稳定。
以下通过实施例的具体实施方式再对本发明的上述内容作进一步的详细说明，但不仅限于以下的实施例。本发明包含上述技术思想下，根据本领域普通技术知识和惯用手段做出的各种替换或变更，均应包括在本发明的范围内。
具体实施方式
为了更好的理解发明的实质，下面通过实例来详细说明发明内容，但本发明内容并不局限于此。以下各实施例中所用的脂肪酰氨基酸、脂肪酰氨基酸酯均为自制。
实施例1
（1）称取月桂酰精氨酸乙酯76.9g（0.2mol），加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol月桂酰谷氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品月桂酰精氨酸乙酯月桂酰谷氨酸盐为黄色液体，凝固点14℃。
实施例2
（1）称取0.1mol椰油酰赖氨酸丙酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol月桂酰甘氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品椰油酰赖氨酸丙酯月桂酰甘氨酸盐为黄色液体，凝固点为18℃。
实施例3
（1）称取0.1mol月桂酰鸟氨酸乙酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol月桂酰肌氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品月桂酰鸟氨酸乙酯月桂酰肌氨酸盐为黄色透明液体，熔点13℃。
实施例4
（1）称取0.2mol月桂酰组氨酸乙酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol月桂酰天冬氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品月桂酰组氨酸乙酯月桂酰天冬氨酸盐为黄色液体，凝固点为10℃。
实施例5
（1）称取0.1mol椰油酰精氨酸丁酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol棕榈酰脯氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品椰油酰精氨酸丁酯棕榈酰脯氨酸盐为无色液体，凝固点为11℃。
实施例6
（1）称取0.1mol棕榈酰赖氨酸甲酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol辛基酰酪氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品棕榈酰赖氨酸甲酯辛基酰酪氨酸盐为淡黄色液体，凝固点为16℃。
实施例7
（1）称取0.1mol十八烷基酰组氨酸丁酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol癸基酰丙氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品十八烷基酰组氨酸丁酯癸基酰丙氨酸盐为无色透明液体，凝固点为15℃。
实施例8
（1）称取0.1mol己基酰鸟氨酸丙酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol月桂酰缬氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品己基酰鸟氨酸丙酯月桂酰缬氨酸盐为无色透明液体，凝固点为18℃。
实施例9
（1）称取0.1mol二十烷基酰精氨酸甲酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol椰油酰亮氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品二十烷基酰精氨酸甲酯椰油酰亮氨酸盐为黄色液体，凝固点为12℃。
实施例10
（1）称取0.1mol十六烷基酰组氨酸乙酯，加入30mL乙醇，60℃水浴加热溶解；
（2）将0.1mol二十二烷基酰丝氨酸加入（1）中，搅拌混合均匀，得到盐体系；
（3）将（2）中得到的体系减压蒸馏，除去乙醇；
（4）所得产品十六烷基酰组氨酸乙酯二十二烷基酰丝氨酸盐为黄色澄清透明液体，凝固点12℃。
实施例1-10所对应的脂肪酰氨基酸酯、脂肪酰氨基酸及所得的盐体系样品代号见表2：
实施例11
将上述抑菌盐体系进行产品配方实验，配方见表3至表6。
实施例12
针对实施例1-10的抑菌盐体系，做防腐挑战实验，进行筛选验证。经过7天的菌类培养和28天周期的抑菌考察，结果判定见表7至表10。细菌、霉菌、酵母菌抑制实验的测试结果单位均为CFU/ml。
抑菌实验表明，脂肪酰氨基酸酯与脂肪酰氨基酸复配形成的盐体系对细菌、霉菌、酵母菌的抑制作用比较显著。
实施例13
针对实施例1-10中的抑菌盐体系及月桂酰精氨酸乙酯（LAE）进行化妆品相关的微生物（大肠杆菌、金黄色葡萄球菌、绿脓杆菌、洋葱假单胞菌、白色念珠菌、黑曲霉、糠秕马拉色菌）的最小抑菌浓度（MIC）值测试（单位：ug/mL）：
与月桂酰精氨酸乙酯盐酸盐相比，各抑菌体系对不同微生物的MIC值都低，说明抑菌体系对微生物的抑制作用更加显著。
实施例14
针对实施例1-10所得盐体系样品进行斑贴试验，并与月桂酰精氨酸乙酯盐酸盐（LAE）做比较。斑贴试验结果见表12。
斑贴试验表明，相比于月桂酰精氨酸乙酯盐酸盐，脂肪酰氨基酸酯类和脂肪酰氨基酸的盐体系刺激性更小。

Claims (10)

1.本发明提供了一种脂肪酰氨基酸酯与脂肪酰氨基酸反应而得的氨基酸衍生物。
2.根据权利要求1中所述，利用脂肪酰氨基酸酯和脂肪酰氨基酸而得的氨基酸衍生物，其特征在于：
(1)具有较低的凝固点，比脂肪酰氨基酸酯与脂肪酰氨基酸的熔点均要低，可以非常方便地添加到配方中，无需加热；
(2)具有非常好的溶解度，易溶于多元醇，如甘油、乙二醇、丙二醇、丁二醇、戊二醇、己二醇等；
(3)体系相容性好，与配方体系的其它产品，如表面活性剂、乳化剂等有较高的兼容性，可以广泛使用。
3.根据权利要求1中所述利用脂肪酰氨基酸酯和脂肪酰氨基酸成盐的方法，其具体步骤为：
(1)溶解：将0.1mol脂肪酰氨基酸酯溶于溶剂，加热到50-55℃溶解；
(2)成盐：0.1mol脂肪酰氨基酸加到步骤（1）所得的脂肪酰氨基酸酯溶液中，混合搅拌至澄清透明；
(3)将步骤（2）中复配形成的盐减压蒸馏，除去溶剂。
4.根据权利要求1中所述，利用脂肪酰氨基酸酯和脂肪酰氨基酸复配形成对微生物具有抑制或者杀灭作用的盐，其特征在于脂肪酰氨基酸酯具有(a) ~ (d)的化学结构，可以为通式(a) ~ (d)中的一种或几种的组合：
I. 精氨酸衍生物及其常见的盐，其结构通式如式(a)：
(a)
其中，R1是甲基、乙基、丙基或丁基；R2是碳原子数为6-22的脂肪酰基；
II. 鸟氨酸衍生物及其常见的盐，其结构通式如式(b)：
(b)
其中，R1是甲基、乙基、丙基或丁基；R2是碳原子数为6-22的脂肪酰基；
III. 赖氨酸衍生物及其常见的盐，其结构通式如式(c)：
(c)
其中，R1是甲基、乙基、丙基或丁基；R2是碳原子数为6-22的脂肪酰基；
IV. 组氨酸衍生物及其常见的盐，其结构通式如式(d)：
(d)
其中，R1是甲基、乙基、丙基或丁基；R2是碳原子数为6-22的脂肪酰基。
5.根据权利要求1中所述，利用脂肪酰氨基酸酯和脂肪酰氨基酸反应形成对微生物具有抑制或者杀灭作用的盐，其特征在于脂肪酰氨基酸由碳原子数为5-21的脂肪酸和氨基酸缩合而成，可以为一种或多种脂肪酰氨基酸的组合，其中氨基酸选自丙氨酸、精氨酸、天冬氨酸、半胱氨酸、谷氨酰胺、谷氨酸、组氨酸、异亮氨酸、甘氨酸、天冬酰胺、亮氨酸、赖氨酸、甲硫氨酸、苯丙氨酸、脯氨酸、丝氨酸、苏氨酸、色氨酸、酪氨酸、缬氨酸。
6.根据权利要求2中所述脂肪酰氨基酸酯与脂肪酰氨基酸成盐的方法，其特征在于步骤（1）中所用溶剂为水或者乙醇。
7.权利要求1-6中所述的氨基酸衍生物作为抑制微生物的用途，应用于食品、饮料。
8.权利要求1-6中所述的氨基酸衍生物作为抑制微生物的用途，应用于饲料。
9.权利要求1-6中所述的氨基酸衍生物作为抑制微生物的用途，应用于家居护理用品。
10.权利要求1-6中所述的氨基酸衍生物作为抑制微生物的用途，应用于个人护理用品。
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CN108815151A (zh) * 2017-11-03 2018-11-16 华东师范大学 月桂酰精氨酸乙酯作为饲料添加剂的用途
CN108992437A (zh) * 2017-11-03 2018-12-14 华东师范大学 月桂酰精氨酸乙酯作为兽用抗菌剂的用途
CN108992437B (zh) * 2017-11-03 2021-10-12 华东师范大学 月桂酰精氨酸乙酯作为兽用抗菌剂的用途
CN109984953A (zh) * 2019-05-22 2019-07-09 宁波御坊堂生物科技有限公司 一种蛋白肽沐浴、洁肤凝胶及其制备方法
CN109984953B (zh) * 2019-05-22 2022-08-19 宁波御坊堂生物科技有限公司 一种蛋白肽沐浴、洁肤凝胶及其制备方法
CN111170883A (zh) * 2020-01-06 2020-05-19 岳阳科罗德联合化学工业有限公司 一种脂肪酰氨基酸多羟基酯类化合物及其制备方法

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