Eco-Friendly Solvents for Bioactives: Solubilization of Hydroxycinnamic Acids in Glycerol-Derived Ethers

IF 7.1 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

ACS Sustainable Chemistry & Engineering Pub Date : 2025-06-05 DOI:10.1021/acssuschemeng.5c0026910.1021/acssuschemeng.5c00269

Sara Gracia-Barberán, María Lanau, Alejandro Leal-Duaso, Pilar López Ram de Viu, Ana M. Mainar, José A. Mayoral and Elísabet Pires*,

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引用次数: 0

Abstract

Hydroxycinnamic acids, such as coumaric, ferulic, and caffeic acids, stand out for their pharmacological and cosmetic applications due to their bioactive properties. However, their low solubility in water and conventional solvents can be considered a drawback for their effective utilization. This study investigates the solubility of these acids in renewable glycerol-derived ethers, which exhibit good ecotoxicological profiles and tunable physicochemical properties. Experimental solubility data revealed that monoethers and diethers with shorter alkyl chains significantly enhance the solubility of the studied hydroxycinnamic acids. The findings were further corroborated by COSMO-RS modeling, highlighting the importance of both hydrogen-bond donor capacity and polarity-polarizability in solubility enhancement. Hydrotropic effects of glycerol ethers in water were also experimentally demonstrated, indicating their potential in pharmaceutical and industrial formulations. These results underscore the efficacy of glycerol-derived solvents as sustainable alternatives for solubilizing hydroxycinnamic acids, paving the way for greener and more efficient applications.

Glycerol ether solvents exhibit outstanding properties and hydrotropic ability for the solubilization of hydroxycinnamic acids: ferulic, coumaric, and caffeic acids.

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生物活性的环保溶剂：羟基肉桂酸在甘油衍生醚中的增溶作用

羟基肉桂酸，如香豆酸、阿魏酸和咖啡酸，因其生物活性特性而在药理学和化妆品应用中脱颖而出。然而，它们在水和常规溶剂中的溶解度低，这是它们有效利用的一个缺点。本研究研究了这些酸在可再生甘油衍生醚中的溶解度，这些醚具有良好的生态毒理学特征和可调的物理化学性质。实验溶解度数据表明，具有较短烷基链的单醚和二醚显著提高羟基肉桂酸的溶解度。COSMO-RS模型进一步证实了这一发现，强调了氢键供体容量和极性极化能力在提高溶解度方面的重要性。甘油醚在水中的亲水效应也被实验证明，表明它们在制药和工业配方中的潜力。这些结果强调了甘油衍生溶剂作为羟基肉桂酸可持续增溶替代品的有效性，为更环保、更高效的应用铺平了道路。甘油醚溶剂对羟基肉桂酸（阿魏酸、香豆酸和咖啡酸）的增溶表现出优异的性质和亲水能力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Sustainable Chemistry & Engineering CHEMISTRY, MULTIDISCIPLINARY-ENGINEERING, CHEMICAL

CiteScore

13.80

自引率

4.80%

发文量

1470

审稿时长

1.7 months

期刊介绍： ACS Sustainable Chemistry & Engineering is a prestigious weekly peer-reviewed scientific journal published by the American Chemical Society. Dedicated to advancing the principles of green chemistry and green engineering, it covers a wide array of research topics including green chemistry, green engineering, biomass, alternative energy, and life cycle assessment. The journal welcomes submissions in various formats, including Letters, Articles, Features, and Perspectives (Reviews), that address the challenges of sustainability in the chemical enterprise and contribute to the advancement of sustainable practices. Join us in shaping the future of sustainable chemistry and engineering.