柚皮素三乙胺盐一水合物的制备、晶体结构及溶解度

doi:10.11944/j.issn.1000-0518.2017.04.160248

摘要/Abstract

摘要：

柚皮素是一种天然黄酮类化合物,几乎不溶于水。利用晶体工程学原理可以有效改善天然产物的溶解性。本文合成了柚皮素和三乙胺的有机盐一水合物[C₁₅H₁₁O₅]^-·[C₆H₁₆N]⁺·H₂O,测定了其晶体结构。解析结果表明,有机盐水合物属于单斜晶系,P2₁/n空间群。柚皮素7取代位的羟基上的质子转移到了三乙胺的N原子上,并形成了N⁺—H••••O^-氢键。羟基阴离子与4'取代位上的羟基形成了O—H••••O^-氢键,产生了一维的氢键链状结构。水分子通过两种氢键作用将一维的氢键链连接成二维的氢键网络。形成三乙胺盐一水合物后,柚皮素在水中的溶解度增加了20倍。

关键词: 柚皮素, 有机盐, 晶体结构, 溶解度

Abstract:

Naringenin is a kind of flavonoid compound. It is practically insoluble in water. The solubility of natural compounds could be effectively improved by principles of crystal engineering. In this paper, an organic salt monohydrate of naringenin with trimethylamine, [C₁₅H₁₁O₅]^-·[C₆H₁₆N]⁺·H₂O, was prepared and its crystal structure was successfully determined. The results show that the organic salt hydrate crystallized in monoclinic crystal system and P2₁/n space group. The proton in 7-substituted hydroxyl of naringenin is transferred to the N atom of trimethylamine forming N⁺—H••••O^- hydrogen bond. The resulting hydroxyl anion is involved in O—H••••O^- hydrogen bonding with 4'-substituted hydroxyl, which gives rise to a one-dimensional hydrogen-bonded chain-like structure. Water molecule further connects the 1D chain into a 2D hydrogen-bonded network through two kinds of hydrogen-bonding interactions. After forming triethylamine salt hydrate, the solubility of naringenin in water is increased by 20 times.

Key words: naringenin, organic salt, crystal structure, solubility

林芳霞, 邱冰清, 娄本勇. 柚皮素三乙胺盐一水合物的制备、晶体结构及溶解度[J]. 应用化学, 2017, 34(4): 481-485.

LIN Fangxia, QIU Bingqing, LOU Benyong. Preparation, Crystal Structure and Solubility of Triethylamine Salt Monohydrate of Naringenin[J]. Chinese Journal of Applied Chemistry, 2017, 34(4): 481-485.

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