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乙酸乙酯-羟丙基-β-环糊精包合物的制备与表征。

Fabrication and characterization of ethyl acetate-hydroxypropyl-β-cyclodextrin inclusion complex.

机构信息

Shanghai Institute of Technology, Shanghai, PR China.

3035 Sable Ridge Dr, Ottaw, Ontario, Canada.

出版信息

J Food Sci. 2021 Aug;86(8):3589-3597. doi: 10.1111/1750-3841.15835. Epub 2021 Jul 15.

Abstract

Flavors play crucial role in food industry. Ethyl acetate, as probably one of the most used of all flavor chemicals by volume, is used widely in many industries. However, ethyl acetate is not too stable and can be slowly decomposed by moisture. Furthermore, ethyl acetate is a volatile liquid insoluble in water and it does not last long enough. In order to solve these problems, hydroxypropyl-β-cyclodextrin was used as wall material to encapsulate ethyl acetate in this work. The product was characterized by Fourier transform infrared (FTIR) spectroscopy and thermalgravimetric analysis (TGA). The results showed that the peaks at 1,744 and 1,056 cm in the FTIR spectrum of ethyl acetate disappeared in the FTIR spectrum of ethyl acetate-hydroxypropyl-β-cyclodextrin inclusion complex. After the encapsulation of ethyl acetate, the O-H and C-H stretching absorption of hydroxypropyl-β-cyclodextrin changed. The TGA results showed that from 77°C to 292°C ethyl acetate is released from the ethyl acetate-hydroxypropyl-β-cyclodextrin inclusion complex in temperatures far beyond ethyl acetate 77°C boiling point. This phenomenon confirmed that the lastingness and thermal stability of ethyl acetate can be improved by the formation of an inclusion complex. The loading capacity of ethyl acetate was 4.86 ± 0.08% and ethyl acetate:hydroxypropyl-β-cyclodextrin stoichiometry is close to 1:1. The interaction of ethyl acetate and hydroxypropyl-β-cyclodextrin was investigated using molecular mechanics calculation. The binding energy was calculated and the possible conformation of ethyl acetate-hydroxypropyl-β-cyclodextrin inclusion complex was optimized to the minimum energy. The binding energy minimum is at the 0.44 × 10  m point and its value is -103.9 kJ/mol. PRACTICAL APPLICATION: Encapsulation of ethyl acetate in hydroxypropyl-β-cyclodextrin is a possible way to protect ethyl acetate, improve its stability, water solubility, and may also enhance its lastingness.

摘要

风味在食品工业中起着至关重要的作用。乙酸乙酯作为所有风味化学物质中使用量最大的物质之一,被广泛应用于许多行业。然而,乙酸乙酯不太稳定,会被水分缓慢分解。此外,乙酸乙酯是一种挥发性液体,不溶于水,且持续时间不够长。为了解决这些问题,本工作采用羟丙基-β-环糊精作为壁材,对乙酸乙酯进行包合。采用傅里叶变换红外光谱(FTIR)和热重分析(TGA)对产物进行了表征。结果表明,在乙酸乙酯的 FTIR 光谱中,1744 和 1056 cm 处的峰在乙酸乙酯-羟丙基-β-环糊精包合物的 FTIR 光谱中消失。乙酸乙酯包合后,羟丙基-β-环糊精的 O-H 和 C-H 伸缩吸收发生变化。TGA 结果表明,从 77°C 到 292°C,在远高于乙酸乙酯 77°C 沸点的温度下,乙酸乙酯从乙酸乙酯-羟丙基-β-环糊精包合物中释放出来。这一现象证实,通过形成包合物可以提高乙酸乙酯的持效性和热稳定性。乙酸乙酯的载药量为 4.86±0.08%,乙酸乙酯:羟丙基-β-环糊精的化学计量比接近 1:1。采用分子力学计算研究了乙酸乙酯与羟丙基-β-环糊精的相互作用。计算了结合能,并对乙酸乙酯-羟丙基-β-环糊精包合物的可能构象进行了优化,使其达到最低能量。结合能最小值在 0.44×10 m 点,其值为-103.9 kJ/mol。实际应用:将乙酸乙酯包合在羟丙基-β-环糊精中是保护乙酸乙酯、提高其稳定性和水溶性的一种可能途径,也可能增强其持效性。

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