School of Chemical Engineering, Sichuan University, Chengdu 610065, China.
School of Chemical Engineering, Sichuan University, Chengdu 610065, China.
Food Chem. 2018 Sep 15;260:183-192. doi: 10.1016/j.foodchem.2018.04.008. Epub 2018 Apr 5.
Tertiary butylhydroquinone (TBHQ) is a water-insoluble antioxidant. In this study, three cyclodextrin inclusion complexes were prepared to improve the water solubility of TBHQ and expand its range of application. Analysis of phase solubility indicated that TBHQ can form 1:1 inclusion complex with hydroxypropyl-beta-cyclodextrin (HP-β-CD) and dimethyl-beta-cyclodextrin (DM-β-CD) and 1:2 inclusion complex with beta-cyclodextrin (β-CD). The possible inclusion configuration between TBHQ and CDs was determined through FT-IR, PXRD, DSC, NMR, and SEM analyses. Results were validated by theoretical study of AutoDock molecular docking. The scavenging effects of the inclusion complexes were not effective on DPPH radical but higher on hydroxyl, superoxide and ABTS+ radicals than that of TBHQ monomer. Moreover, the water solubility of TBHQ increased after complexation with HP-β-CD and DM-β-CD. The stability of TBHQ is related to the type of storage materials used, and the stability can be improved by complexation with CDs.
叔丁基对苯二酚（TBHQ）是一种不溶于水的抗氧化剂。本研究制备了三种环糊精包合物，以提高 TBHQ 的水溶性并扩大其应用范围。相溶解度分析表明，TBHQ 可与羟丙基-β-环糊精（HP-β-CD）和二甲基-β-环糊精（DM-β-CD）形成 1:1 的包合物，与β-环糊精（β-CD）形成 1:2 的包合物。通过 FT-IR、PXRD、DSC、NMR 和 SEM 分析确定了 TBHQ 和 CDs 之间可能的包合构型。结果通过 AutoDock 分子对接的理论研究进行了验证。包合物对 DPPH 自由基的清除效果不如 TBHQ 单体有效，但对羟基自由基、超氧自由基和 ABTS+自由基的清除效果高于 TBHQ 单体。此外，TBHQ 与 HP-β-CD 和 DM-β-CD 络合后，其水溶性增加。TBHQ 的稳定性与所使用的储存材料的类型有关，通过与 CDs 络合可以提高稳定性。
