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丁基羟基茴香醚(BHA)有2-叔丁基-4-羟基茴香醚(2-BHA)和3-叔丁基-4-羟基茴香醚(3-BHA)两种同分异构体。为了研究BHA同分异构体的抗氧化特性，本文建立了结合重结晶与柱层析的方法，对市售BHA抗氧化剂商品进行分离纯化，并采用气相色谱对纯化产物进行分析。结果表明：在以正庚烷为溶剂，结晶温度25℃，料液比为1∶7 g/mL的条件下对市售BHA商品进行重结晶，所得母液再以乙酸乙酯-正己烷为洗脱剂，利用硅胶层析柱进行分离，3-BHA的纯度从原料的93.58%提升至99.46%，回收率为83.21%;2-BHA的纯度从原料的6.42%提升到99.75%，回收率为76.67%。通过DPPH自由基与ABTS+自由基清除试验考察了BHA同分异构单体及其不同比例混合物的抗氧化活性，结果表明：2-BHA、3-BHA的抗氧化活性具有自由基特异性，对DPPH自由基的清除率IC50分别为22.46、17.56μg/mL，对ABTS+自由基的清除率IC50分别为45.13、62.45μg/mL；当2-BHA和3-BHA按质量比7∶3混合时，混合体对DPPH自由基清除率优于单体。本研究为后续深入开展BHA异构体的精准应用提供了理论依据。
Abstract：Butylated hydroxyanisole(BHA) commercially exists as a mixture of two isomers :2-tert-butyl-4-hydroxyanisole(2-BHA) and 3-tert-butyl-4-hydroxyanisole(3-BHA). In order to systematically investigate their individual antioxidant properties,an integrated method combining recrystallization and silica gel column chromatography for the separation and purifcation of isomers from commercial BHA products was developed. The purifcation process was monitored and quantifed using gas chromatography. Under optimized conditions—utilizing n-heptane as the solvent,a crystallization temperature of 25 ℃,and a solid-to-liquid ratio of 1∶7 g/mL—the commercial BHA was effectively recrystallized. The resulting mother liquor was subsequently separated via silica gel column chromatography using an ethyl acetate and n-hexane eluent system. Following purifcation,the purity of 3-BHA increased from 93.58% in the raw material to 99.46%(with an 83.21% recovery rate),while the purity of 2-BHA improved from 6.42% to 99.75%(with a 76.67% recovery rate). The antioxidant activities of the purifed individual isomers and their binary mixtures at varying mass ratios were evaluated using DPPH and ABTS + radical scavenging assays. The results revealed that the antioxidant effcacy of 2-BHA and 3-BHA was radical-dependent. The IC50 values for DPPH radical scavenging were 22.46 μg/mL for 2-BHA and 17.56 μg/mL for 3-BHA,whereas those for ABTS + radical scavenging were 45.13 μg/mL and 62.45 μg/mL,respectively. Notably,a mixture of 2-BHA and 3-BHA at a mass ratio of 7∶3 exhibited a synergistic enhancement in DPPH radical scavenging activity compared to either pure isomer. This optimized separation method establishes a theoretical framework for the targeted application and in-depth investigation of individual BHA isomers.
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基本信息:
DOI：10.19804/j.issn1006-2513.2026.9.004
中图分类号:TS202.3
引用信息:
[1]柳青池,赵王杰,戴素仪,等.丁基羟基茴香醚同分异构体的分离纯化及其抗氧化活性[J].中国食品添加剂,2026,37(09):28-35.DOI:10.19804/j.issn1006-2513.2026.9.004.
基金信息:
国家自然科学基金(21776050)
2026-01-21
2026
2026-03-16
2026-03-24
2026
1
2026-09-02
2026-09-02
2026-09-02