脂肪酸低共熔溶剂对姜黄素的溶解作用

O645.16; 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).C8-C10、C8-C12、C8-C14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、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...

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Published in华东理工大学学报（自然科学版） Vol. 50; no. 2; pp. 214 - 220
Main Authors 靳旭康, 段奇, 李秀婷, 韩朝阳, 王小永
Format Journal Article
LanguageChinese
Published 华东理工大学化学与分子工程学院,上海 200237 01.05.2024
Subjects
溶解
氢键
疏水作用
hydrophobic interaction
低共熔溶剂(DES)
low eutectic solvent(DES)
dissolve
姜黄素
curcumin
hydrogen bond
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Abstract O645.16; 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).C8-C10、C8-C12、C8-C14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、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和最强的紫外吸收及荧光发射强度.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.
AbstractList O645.16; 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).C8-C10、C8-C12、C8-C14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、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和最强的紫外吸收及荧光发射强度.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_FL 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 mmol/L 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.
Author 靳旭康
韩朝阳
王小永
李秀婷
段奇
AuthorAffiliation 华东理工大学化学与分子工程学院,上海 200237
AuthorAffiliation_xml – name: 华东理工大学化学与分子工程学院,上海 200237
Author_FL LI Xiuting
DUAN Qi
HAN Zhaoyang
JIN Xukang
WANG Xiaoyong
Author_FL_xml – sequence: 1
  fullname: JIN Xukang
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  fullname: DUAN Qi
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  fullname: LI Xiuting
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  fullname: HAN Zhaoyang
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  fullname: WANG Xiaoyong
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  fullname: 靳旭康
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  fullname: 段奇
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  fullname: 韩朝阳
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  fullname: 王小永
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DocumentTitle_FL Dissolution of Curcumin by Deep Eutectic Solvent of Fatty Acids
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Keywords 溶解
氢键
疏水作用
hydrophobic interaction
低共熔溶剂(DES)
low eutectic solvent(DES)
dissolve
姜黄素
curcumin
hydrogen bond
Language Chinese
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PublicationTitle 华东理工大学学报（自然科学版）
PublicationTitle_FL Journal of East China University of Science and Technology(Natural Science Edition)
PublicationYear 2024
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Snippet O645.16; 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).C8-C10、C8-C12、C8-C14对姜黄素的溶解度分别为1.11、1.24、1.44...
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StartPage 214
Title 脂肪酸低共熔溶剂对姜黄素的溶解作用
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Volume 50
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