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    靳旭康, 段奇, 李秀婷, 韩朝阳, 王小永. 脂肪酸低共熔溶剂对姜黄素的溶解作用[J]. 华东理工大学学报(自然科学版). DOI: 10.14135/j.cnki.1006-3080.20230228001
    引用本文: 靳旭康, 段奇, 李秀婷, 韩朝阳, 王小永. 脂肪酸低共熔溶剂对姜黄素的溶解作用[J]. 华东理工大学学报(自然科学版). DOI: 10.14135/j.cnki.1006-3080.20230228001
    JIN Xukang, DUAN Qi, LI Xiuting, HAN Zhaoyang, WANG Xiaoyong. Dissolution of Curcumin by Deep Eutectic Solvent of Fatty Acids[J]. Journal of East China University of Science and Technology. DOI: 10.14135/j.cnki.1006-3080.20230228001
    Citation: JIN Xukang, DUAN Qi, LI Xiuting, HAN Zhaoyang, WANG Xiaoyong. Dissolution of Curcumin by Deep Eutectic Solvent of Fatty Acids[J]. Journal of East China University of Science and Technology. DOI: 10.14135/j.cnki.1006-3080.20230228001

    脂肪酸低共熔溶剂对姜黄素的溶解作用

    Dissolution of Curcumin by Deep Eutectic Solvent of Fatty Acids

    • 摘要: 制备了辛酸(C8)分别与癸酸(C10)、月桂酸(C12)及肉豆蔻酸(C14)形成的C8-C10、C8-C12、C8-C14 3种脂肪酸低共熔溶剂(DES)。3种脂肪酸DES对姜黄素的溶解度分别为1.11、1.24、1.44 mmol/L,比姜黄素在水中的溶解度分别提高了约29、32、38倍。通过Gaussian模拟计算,得到姜黄素与C8、C10、C12及C14形成的分子缔合物的吉布斯自由能分别为−48.49、−64.27、−91.26、−120.59 kJ/mol。姜黄素与烷基链最长的C14形成“三明治”型分子缔合物,具有最强的氢键和疏水缔合作用,使姜黄素在C8-C14脂肪酸DES中表现出最高的溶解度、紫外吸收和荧光发射强度。姜黄素在C8-C10、C8-C12、C8-C14 3种脂肪酸DES中均具有显著提高的稳定性和1,1-二苯基-2-三硝基苯肼(DPPH)自由基清除能力。

       

      Abstract: Three deep eutectic solvents (DESs) were prepared by mixing caprylic acid (C8) with decanoic acid (C10), lauric acid (C12) and myristic acid (C14) at a molar ratio of n(C8):n(C10) = 2:1, n(C8):n(C12) = 5:1 and n(C8):n(C14) = 6:1, respectively. The melting points of the DES mixtures were lower than those of the individual fatty acid components and other prepared DES mixtures with different molar ratios. Using the absorbance-concentration standard curve, the solubility of curcumin in the C8-C10, C8-C12 and C8-C14 DES was determined to be 1.11, 1.24 and 1.44 mmol/L, respectively, which were 29, 32 and 38 times higher than those of curcumin in water. Gaussian simulation was used to calculate the Gibbs free energies of the molecular complexes formed by curcumin and the C8, C10, C12 and C14 fatty acid, and the values were determined to be −48.49, −64.27, −91.26、 −120.59 kJ/mol, respectively. According to the electrostatic density diagram drawn by Multiwfn and VMD, the association manner between curcumin and the fatty acids was obtained. Curcumin and C14 with the longest alkyl chain formed a "sandwich" typed complex, in which curcumin and C14 had strong hydrogen bonding and hydrophobic interactions. making curcumin show the highest solubility ability, the strongest UV-Vis absorption and fluorescence emission intensities in the C8-C14 DES. The stability and DPPH free radical scavenging ability of curcumin dissolved in DESs were found to be much better than in water.

       

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