CN115557919A - 一种美白抗氧化的抗坏血酸四异棕榈酸酯及其制备方法 - Google Patents
一种美白抗氧化的抗坏血酸四异棕榈酸酯及其制备方法 Download PDFInfo
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- OEWBEINAQKIQLZ-CMRBMDBWSA-N [(2s)-2-[(2r)-3,4-bis(2-hexyldecanoyloxy)-5-oxo-2h-furan-2-yl]-2-(2-hexyldecanoyloxy)ethyl] 2-hexyldecanoate Chemical compound CCCCCCCCC(CCCCCC)C(=O)OC[C@H](OC(=O)C(CCCCCC)CCCCCCCC)[C@H]1OC(=O)C(OC(=O)C(CCCCCC)CCCCCCCC)=C1OC(=O)C(CCCCCC)CCCCCCCC OEWBEINAQKIQLZ-CMRBMDBWSA-N 0.000 title claims abstract description 31
- 230000002087 whitening effect Effects 0.000 title claims abstract description 24
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- MHEDPJJXDOOCQO-UHFFFAOYSA-N 2-hexyldecanoyl chloride Chemical compound CCCCCCCCC(C(Cl)=O)CCCCCC MHEDPJJXDOOCQO-UHFFFAOYSA-N 0.000 claims abstract description 15
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- 229950004531 hexyldecanoic acid Drugs 0.000 claims abstract description 8
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 claims abstract description 7
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- OCZVHBZNPVABKX-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 OCZVHBZNPVABKX-UHFFFAOYSA-N 0.000 description 1
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
本发明公开了一种美白抗氧化的抗坏血酸四异棕榈酸酯及其制备方法，包括以下步骤：步骤一、2‑己基癸酸溶液中加入氯化试剂，加热至回流温度，搅拌，冷却后浓缩获得2‑己基癸酰氯；步骤二、向L‑抗坏血酸中加入溶剂和缚酸剂，冰浴下滴加2‑己基癸酰氯，然后在0‑50℃下搅拌数小时，再经萃取、水洗、干燥、浓缩、纯化获得抗坏血酸四异棕榈酸酯。该美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法制备的抗坏血酸四异棕榈酸酯，不仅保留了抗坏血酸即维生素C的抗氧化及防止血管硬化、治疗败血症的药理作用，而且具有脂溶性，增加了产品的适用范围，是一种高效、多功能的添加剂；在医药方面被用作医药的抗氧剂、稳定剂、增效剂。
Description
技术领域
本发明涉及美容护肤产品技术领域，尤其是一种美白抗氧化的抗坏血酸四异棕榈酸酯及其制备方法。
背景技术
抗坏血酸四异棕榈酸酯做为重要的抗坏血酸衍生物，是一种脂溶性抗氧化剂，它不仅保留了抗坏血酸即维生素C的抗氧化及防止血管硬化、治疗败血症的药理作用，而且具有脂溶性，增加了产品的适用范围，是一种高效、多功能的添加剂。在医药方面被用作医药的抗氧剂、稳定剂、增效剂；在保健食品方面主要用作人体抗氧化剂和营养强化剂；在化妆品领域主要用于化妆品的添加剂。其中，通过该方法中得到的抗坏血酸四异棕榈酸酯在高温下很稳定，在油中有很好的溶解性，同时具有优异的透皮吸收能力，在皮肤中分解成游离维生素C来实现生理机能。由于维生素C具有美白、抗老化等多种生理活性作用，并作为有效成分被应用于化妆品的各个领域中。
现有的酯化工艺技术产量低，存在质量不达标准、外观带淡黄色等技术问题，产品实用性和经济效益低下，生产收率不稳定，浪费了不必要的成本。
发明内容
本发明的目的旨在提供一种美白抗氧化的抗坏血酸四异棕榈酸酯及其制备方法，变革酯化工艺使其具有实质性特点，克服现有技术产量低、质量不达标准、外观带淡黄色等技术问题，使其更具产品实用性和好的经济效益，生产收率稳定，成本得到有效节约，以解决上述背景技术中提出的问题。
为解决上述问题，本发明提出了一种美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法，包括以下步骤：
步骤一、2-己基癸酸溶液中加入氯化试剂，加热至回流温度，搅拌，冷却后浓缩获得2-己基癸酰氯；
步骤二、向L-抗坏血酸中加入溶剂和缚酸剂，冰浴下滴加2-己基癸酰氯，然后在0-50℃下搅拌数小时，再经萃取、水洗、干燥、浓缩、纯化获得抗坏血酸四异棕榈酸酯。
进一步的，所述步骤一的具体方法如下：
(1)向四口烧瓶中加入153.8g2-己基癸酸，然后加入1.0L二氯甲烷，滴加107.1g氯化亚砜；
(2)加完后加热至回流温度，搅拌1h；
(3)将反应液浓缩得2-己基癸酰氯粗品，经蒸馏纯化得152.0g无色透明液体，收率92.1％。
进一步的，所述2-己基癸酸、氯化亚砜两者物质的量依此为600.0mmol、900.0mmol。
进一步的，所述步骤二的具体方法如下：
(1)向1.0L四口烧瓶中加入21.1gL-抗坏血酸，再在氮气保护下加入 300mlN-甲基吡咯烷酮和56.9g吡啶，冰浴下开始滴加148.2g2-己基癸酰氯， 0-5℃下搅拌3h；
(2)将反应液中加入甲基叔丁基醚和5％的盐酸洗3次，经水洗，饱和碳酸氢钠洗，饱和氯化钠洗后，用无水硫酸钠干燥，过滤浓缩得到抗坏血酸四异棕榈酸酯粗品；
(3)粗品经硅胶柱分离和活性炭脱色得无色透明的抗坏血酸四异棕榈酸酯112.5g，收率83.1％。
进一步的，所述L-抗坏血酸的、吡啶、2-己基癸酰氯三者物质的量依此为119.8mmol、718.8mmol、539.1mmol。
进一步的，所述步骤(3)中硅胶柱分离使用的溶剂比例为石油醚∶乙酸乙酯是25∶1。
本发明的有益效果为：
1、本发明方法制备的抗坏血酸四异棕榈酸酯，不仅保留了抗坏血酸即维生素C的抗氧化及防止血管硬化、治疗败血症的药理作用，而且具有脂溶性，增加了产品的适用范围，是一种高效、多功能的添加剂；在医药方面被用作医药的抗氧剂、稳定剂、增效剂；在保健食品方面主要用作人体抗氧化剂和营养强化剂；在化妆品领域主要用于化妆品的添加剂；
2、本发明变革酯化工艺使具有实质性特点，克服现有技术产量低、质量不达标准、外观带淡黄色等技术问题，使其更具产品实用性和好的经济效益，生产收率稳定，能达到80％以上，成本得到有效节约。
具体实施例
下面对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例一
本发明提供了美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法及其应用，
步骤一：制备2-己基癸酰氯
(1)向四口烧瓶中加入153.8g2-己基癸酸，然后加入1.0L二氯甲烷，滴加107.1g氯化亚砜；
(2)加完后加热至回流温度，搅拌1h；
(3)将反应液浓缩得2-己基癸酰氯粗品，经蒸馏纯化得152.0g无色透明液体，收率92.1％。
步骤二：制备血酸四异棕榈酸酯
(1)向1.0L四口烧瓶中加入21.1gL-抗坏血酸，再在氮气保护下加入 300mlN-甲基吡咯烷酮和56.9g吡啶，冰浴下开始滴加148.2g2-己基癸酰氯，0-5℃下搅拌3h；
(2)将反应液中加入甲基叔丁基醚和5％的盐酸洗3次，经水洗，饱和碳酸氢钠洗，饱和氯化钠洗后，用无水硫酸钠干燥，过滤浓缩得到抗坏血酸四异棕榈酸酯粗品；
(3)粗品经硅胶柱分离和活性炭脱色得无色透明的抗坏血酸四异棕榈酸酯112.5g，收率83.1％。
实施例二
抗氧化活性检测
1)DPPH活性测定
2)DPPH乙醇溶液的配制：准确称取3.94mg DPPH，加入无水乙醇溶解并定容至100mL容量瓶中，配制成0.1mM的DPPH溶液，低温(0-4℃)避光保存。量取不同体积的抗坏血酸四异棕榈酸酯加入到3mL DPPH溶液中，混合均匀，之后加水补足至4mL，517nm下测其吸光度，计算其清除率，计算公式如下：
其中A对照为不加样品溶液，只加入1.0mL纯化水的吸光度；A样品为不同体积样品溶液的吸光度。
实验结果如表1所示，实验结果表明抗坏血酸四异棕榈酸酯对DPPH自由基具有较强的清除能力。
表1抗坏血酸四异棕榈酸酯对DPPH自由基的清除率
实施例二
ABTS实验
所需溶液配制:实施例一中获得的抗坏血酸四异棕榈酸酯稀释3倍后，进行体外抗氧化实验。
1、4mM ABTS溶液：准确称取0.0384g ABTS置于10mL棕色容量瓶中，纯化水定容；
2、6mM过硫酸钾溶液：准确称取0.0066g过硫酸钾置于10mL容量瓶中，纯化水定容；ABTS工作液：7.4mM ABTS溶液与2.6mM过硫酸钾溶液以体积比 1:1混合，室温条件下避光静置12h备用，使用前用80％乙醇溶液稀释至吸光度为0.7±0.02。
样品对ABTS氧自由基的清除实验，准确量取不同体积的抗坏血酸四异棕榈酸酯样品液，加入到3.4mL的ABTS工作液中，之后加水定容至4.0mL,混合均匀，室温静置30min，之后在734nm下进行分光光度检测，通过吸光度变化计算其清除率，计算公式如下
其中A对照为不加样品溶液，只加入1.0mL纯化水的吸光度；A样品为不同体积样品溶液的吸光度。
实验结果如表2所示，结果表明抗坏血酸四异棕榈酸酯对ABTS自由基具有很好的清除率。
表2抗坏血酸四异棕榈酸酯对ABTS自由基的清除率实验
实施例三
美白功效检测
1)酪氨酸酶实验
准确称取酪氨酸酶粉末(1380u/mg，Sigma)0.00362g，用pH6.8 PBS 磷酸缓冲溶液定容至50mL，根据需求配制不同浓度梯度样品待测液，按照表 4添加样品检测液，之后放置37℃水浴锅中恒温10min；然后在A、C管中依次加入酪氨酸酶，每次加酶间隔30s，加酶后应立即涡旋15s混匀，反应15min。反应管恢复到室温后，紫外分光光度仪在475nm处测吸光值。
实验结果如表3所示，表明海茴香细胞提取物具有抑制酪氨酸酶的效果，因此具有美白的功效。
表3酪氨酸检测添加试剂表
| 单位(μL) | A | B | C | D |
| L-酪氨酸 | 800 | 800 | 800 | 800 |
| 样品 | 0 | 0 | 800 | 800 |
| PBS | 1500 | 2000 | 700 | 1200 |
| 酪氨酸酶 | 500 | 0 | 500 | 0 |
| 总体积 | 2800 | 2800 | 2800 | 2800 |
样品对酪氨酸酶的活性抑制率(％)：
式中：A—空白样板有酶体系吸光值；
B—空白样板无酶体系吸光值；
C—样品组有酶体系吸光值；
D—样品组无酶体系吸光值
海茴香植物细胞培养物提物液人体抗氧化和美白功效：将海茴香植物细胞培养物提物液以5％添加量添加至空白膏霜基质中，同时空白基质做对照，样品和空白基质配方如下表4，然后将制备好的霜给10名35-45的志愿者女性使用，使用42天后进行使用效果评价反馈。
结果如表4所示。
表4空白基质霜和试验用抗坏血酸四异棕榈酸酯霜的配方
表5女性志愿者使用后效果反馈
结论：除了在体外实验中抗坏血酸四异棕榈酸酯表现出良好的美白、抗氧化效果，同时人体实验，更加确定了抗坏血酸四异棕榈酸酯的美白、提亮和抗氧化的功效。
本发明进一步公开了具有美白抗氧化功效的抗坏血酸四异棕榈酸酯制备方法制备的抗坏血酸四异棕榈酸酯在用于具有美白、抗氧化功效的化妆品中的应用。实验结果显示抗坏血酸四异棕榈酸酯具有美白、抗氧化的功效。
尽管已经示出和描述了本发明的实施例，对于本领域的普通技术人员而言，可以理解在不脱离本发明的原理和精神的情况下可以对这些实施例进行多种变化、修改、替换和变型，本发明的范围由所附权利要求及其等同物限定。
Claims (6)
1.一种美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法，其特征在于，包括以下步骤：
步骤一、2-己基癸酸溶液中加入氯化试剂，加热至回流温度，搅拌，冷却后浓缩获得2-己基癸酰氯；
步骤二、向L-抗坏血酸中加入溶剂和缚酸剂，冰浴下滴加2-己基癸酰氯，然后在0-50℃下搅拌数小时，再经萃取、水洗、干燥、浓缩、纯化获得抗坏血酸四异棕榈酸酯。
2.根据权利要求1所述的一种美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法，其特征在于，所述步骤一的具体方法如下：
(1)向四口烧瓶中加入153.8g2-己基癸酸，然后加入1.0L二氯甲烷，滴加107.1g氯化亚砜；
(2)加完后加热至回流温度，搅拌1h；
(3)将反应液浓缩得2-己基癸酰氯粗品，经蒸馏纯化得152.0g无色透明液体，收率92.1％。
3.根据权利要求2所述的一种美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法，其特征在于：所述2-己基癸酸、氯化亚砜两者物质的量依此为600.0mmol、900.0mmol。
4.根据权利要求1所述的一种美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法，其特征在于，所述步骤二的具体方法如下：
(1)向1.0L四口烧瓶中加入21.1gL-抗坏血酸，再在氮气保护下加入300mlN-甲基吡咯烷酮和56.9g吡啶，冰浴下开始滴加148.2g2-己基癸酰氯，0-5℃下搅拌3h；
(2)将反应液中加入甲基叔丁基醚和5％的盐酸洗3次，经水洗，饱和碳酸氢钠洗，饱和氯化钠洗后，用无水硫酸钠干燥，过滤浓缩得到抗坏血酸四异棕榈酸酯粗品；
(3)粗品经硅胶柱分离和活性炭脱色得无色透明的抗坏血酸四异棕榈酸酯112.5g，收率83.1％。
5.根据权利要求4所述的一种美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法，其特征在于：所述L-抗坏血酸的、吡啶、2-己基癸酰氯三者物质的量依此为119.8mmol、718.8mmol、539.1mmol。
6.根据权利要求4所述的一种美白抗氧化的抗坏血酸四异棕榈酸酯的制备方法，其特征在于：所述步骤(3)中硅胶柱分离使用的溶剂比例为石油醚∶乙酸乙酯是25∶1。
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| CN117362250A (zh) * | 2023-10-08 | 2024-01-09 | 科乐美(广州)生物科技有限公司 | 一种利用氮掺杂活性炭催化剂催化合成抗坏血酸四异棕榈酸酯的方法 |
| CN118515635A (zh) * | 2024-07-23 | 2024-08-20 | 广州旭帆生物科技有限公司 | 一种抗坏血酸四异棕榈酸酯及其制备方法和在制备高渗透、抗氧化化妆品中的应用 |
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| CN111184682A (zh) * | 2020-04-02 | 2020-05-22 | 安赛搏(重庆)生物技术有限公司 | 一种具有美白抗氧化功效的海茴香细胞提取物的制备方法 |
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| CN111184682A (zh) * | 2020-04-02 | 2020-05-22 | 安赛搏(重庆)生物技术有限公司 | 一种具有美白抗氧化功效的海茴香细胞提取物的制备方法 |
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| CN116554133A (zh) * | 2023-04-03 | 2023-08-08 | 珠海市柏瑞医药科技有限公司 | 一种抗坏血酸四异棕榈酸酯的合成方法 |
| CN117362250A (zh) * | 2023-10-08 | 2024-01-09 | 科乐美(广州)生物科技有限公司 | 一种利用氮掺杂活性炭催化剂催化合成抗坏血酸四异棕榈酸酯的方法 |
| CN117362250B (zh) * | 2023-10-08 | 2024-05-10 | 科乐美(广州)生物科技有限公司 | 一种利用氮掺杂活性炭催化剂催化合成抗坏血酸四异棕榈酸酯的方法 |
| CN118515635A (zh) * | 2024-07-23 | 2024-08-20 | 广州旭帆生物科技有限公司 | 一种抗坏血酸四异棕榈酸酯及其制备方法和在制备高渗透、抗氧化化妆品中的应用 |
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Application publication date: 20230103 |