SCI和EI收录∣中国化工学会会刊

Chinese Journal of Chemical Engineering ›› 2022, Vol. 44 ›› Issue (4): 268-274.DOI: 10.1016/j.cjche.2021.04.005

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Characterization and structure analysis of the heterosolvate of erythromycin thiocyanate

Yuanjie Li1, Qiuxiang Yin1,2, Meijing Zhang1,2, Ying Bao1,2, Baohong Hou1,2, Jingkang Wang1,2, Jiting Huang3, Ling Zhou1   

  1. 1 School of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300350, China;
    2 Collaborative Innovation Center of Chemical Science and Chemical Engineering (Tianjin), Tianjin 300072, China;
    3 Luoxin Pharmaceutical (Shanghai) Co., Ltd., Shanghai 201203, China
  • Received:2021-01-18 Revised:2021-04-08 Online:2022-06-18 Published:2022-04-28
  • Contact: Jiting Huang,E-mail:jitinghuang@luoxin.cn;Ling Zhou,E-mail:zhouling@tju.edu.cn

Characterization and structure analysis of the heterosolvate of erythromycin thiocyanate

Yuanjie Li1, Qiuxiang Yin1,2, Meijing Zhang1,2, Ying Bao1,2, Baohong Hou1,2, Jingkang Wang1,2, Jiting Huang3, Ling Zhou1   

  1. 1 School of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300350, China;
    2 Collaborative Innovation Center of Chemical Science and Chemical Engineering (Tianjin), Tianjin 300072, China;
    3 Luoxin Pharmaceutical (Shanghai) Co., Ltd., Shanghai 201203, China
  • 通讯作者: Jiting Huang,E-mail:jitinghuang@luoxin.cn;Ling Zhou,E-mail:zhouling@tju.edu.cn

Abstract: Erythromycin thiocyanate is widely used for the production of other macrolide antibiotics. In this work, a novel heterosolvate of this pharmaceutical compound has been obtained and characterized for the first time, which was transformed from the dihydrate form in the acetone solvent through evaporation crystallization. Thermal behavior together with compositional analysis revealed that both water and acetone molecules participated in the formation of the crystal lattice which is rarely reported before. The general chemical name of the heterosolvate may be defined as erythromycin thiocyanate sesquihydrate hemiacetonate. Furthermore, studies on solid-state spectral analysis provided strong evidence of intermolecular hydrogen bonds in heterosolvate crystals. According to the crystal structure determined by single crystal X-ray diffraction, the formation mechanism of the heterosolvate is proposed in which strong multi-hydrogen bondings between water and solute molecules form the layer structure. While acetone molecules form single-hydrogen bonds with solutes and reside in channels between layers. This well explains why acetone solvent is easy to escape from the crystal structure during desolvation.

Key words: Erythromycin thiocyanate, Heterosolvate, Structure analysis, Crystallization, Thermodynamic properties, Transition

摘要: Erythromycin thiocyanate is widely used for the production of other macrolide antibiotics. In this work, a novel heterosolvate of this pharmaceutical compound has been obtained and characterized for the first time, which was transformed from the dihydrate form in the acetone solvent through evaporation crystallization. Thermal behavior together with compositional analysis revealed that both water and acetone molecules participated in the formation of the crystal lattice which is rarely reported before. The general chemical name of the heterosolvate may be defined as erythromycin thiocyanate sesquihydrate hemiacetonate. Furthermore, studies on solid-state spectral analysis provided strong evidence of intermolecular hydrogen bonds in heterosolvate crystals. According to the crystal structure determined by single crystal X-ray diffraction, the formation mechanism of the heterosolvate is proposed in which strong multi-hydrogen bondings between water and solute molecules form the layer structure. While acetone molecules form single-hydrogen bonds with solutes and reside in channels between layers. This well explains why acetone solvent is easy to escape from the crystal structure during desolvation.

关键词: Erythromycin thiocyanate, Heterosolvate, Structure analysis, Crystallization, Thermodynamic properties, Transition