Effect of cationic Gemini surfactants ethonium and decamethoxin on the spectral properties, solubility and tautomerism of the curcumin

IF 1.6 4区工程技术 Q3 CHEMISTRY, APPLIED

Journal of Surfactants and Detergents Pub Date : 2024-04-11 DOI:10.1002/jsde.12756

Valentyna M. Barvinchenko, Olga O. Kazakova, Natalia O. Lipkovska

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Abstract

The properties of natural polyphenol curcumin in water solutions of cationic Gemini surfactants decamethoxin and ethonium, which have similar positively charged nitrogen hydrophilic head groups but different spacer sizes and lengths of hydrophobic tails have been investigated in a wide range of concentrations by using UV–Vis spectroscopy and quantum-chemical calculations. It was found that curcumin dissolves in the organized micellar media of these surfactants in the enol tautomeric form and its solubility increases 400 times compared to water. The binding constants of curcumin with decamethoxin and ethonium were determined by the solubility method. Significant differences in the influence of premicellar concentrations of cationic Gemini surfactants on the solubility and tautomeric transformations of curcumin were revealed. In contrast to decamethoxin, ethonium at a concentration below the CMC promotes a significant increase in the solubility of curcumin and a shift in the tautomeric equilibrium towards the formation of its keto form.

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阳离子双子座表面活性剂乙基和癸甲氧羰基对姜黄素光谱特性、溶解度和同分异构体的影响

通过紫外可见光谱和量子化学计算，研究了天然多酚姜黄素在阳离子 Gemini 表面活性剂癸甲氧基和乙基水溶液中的特性，这两种表面活性剂具有相似的带正电的氮亲水头基，但疏水尾的间隔尺寸和长度不同。研究发现，姜黄素以烯醇同分异构形式溶解在这些表面活性剂的有组织胶束介质中，其溶解度比水增加了 400 倍。通过溶解度法测定了姜黄素与癸甲氧羰基和乙基的结合常数。结果表明，阳离子 Gemini 表面活性剂的前胶束浓度对姜黄素的溶解度和同分异构体转化的影响存在显著差异。与癸甲氧基醚相比，浓度低于 CMC 的乙铵盐能显著提高姜黄素的溶解度，并使同分异构体平衡向形成其酮型转变。

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来源期刊

Journal of Surfactants and Detergents 工程技术-工程：化工

CiteScore

3.80

自引率

6.20%

发文量

审稿时长

4 months

期刊介绍： Journal of Surfactants and Detergents, a journal of the American Oil Chemists’ Society (AOCS) publishes scientific contributions in the surfactants and detergents area. This includes the basic and applied science of petrochemical and oleochemical surfactants, the development and performance of surfactants in all applications, as well as the development and manufacture of detergent ingredients and their formulation into finished products.