Preparation, Crystal Structure and Solubility of Triethylamine Salt Monohydrate of Naringenin

doi:10.11944/j.issn.1000-0518.2017.04.160248

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (4): 481-485.DOI: 10.11944/j.issn.1000-0518.2017.04.160248

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Preparation, Crystal Structure and Solubility of Triethylamine Salt Monohydrate of Naringenin

LIN Fangxia,QIU Bingqing,LOU Benyong()

Department of Chemistry and Chemical Engineering,Minjiang University,Fuzhou 350108,China

Received:2016-06-14 Accepted:2016-08-24 Published:2017-03-31 Online:2017-03-31
Contact: LOU Benyong
Supported by:
Supported by National Undergraduate Innovative Training Program(No.201510395010), the Natural Science Foundation of Fujian Province(No.2015J01599)

Abstract

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

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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Preparation, Crystal Structure and Solubility of Triethylamine Salt Monohydrate of Naringenin

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