Identification, separation and identification of transformed products of TBHQ in different oil storage processes

Abstract

Abstract: Tertiary butylhydroquinone (TBHQ) is widely used as an antioxidant in oil and oil-rich foods. TBHQ contains two active phenolic hydroxyl groups, which can be easily converted during oil storage. Using lard, soybean oil and palm oil as raw materials, the storage process was simulated to analyze the TBHQ transformation during the storage of oil samples. The results show that: With the extension of storage time, the sum of the remaining amount of TBHQ and the production of 2-tert-butyl 1, 4-Benzoquinone (TBBQ) in the oil samples would be less than the original addition of TBHQ. The same chromatographic peaks except TBHQ and TBBQ were found in the gas chromatograms of methanol extracts from different oil samples. The unknown chromatographic peaks were isolated and purified by Prep-LC, and the structures of the unknown compounds were identified and characterized by UPLC-QTOF-MS, NMR, UV and FTIR. Another conversion product of TBHQ in fats is 2-methylally hydroquinone (MAHQ).

Key words: tert-butylhydroquinone (TBHQ), tert-butylquinone (TBBQ), 2-methylallyl-hydroquinon (MAHQ), Separation and purification, Structural identification

CLC Number:

TS221

Jun Li. Identification, separation and identification of transformed products of TBHQ in different oil storage processes[J]. FOOD SCIENCE, 0, (): 0-0.

References

[1]毕艳兰.油脂化学[M].北京:中国轻工业出版社, 2023:97-133.
[2]曾裕, 尹浩, 苏沛, 等.对种食用油保质期内品质变化的影响[J].中国食物与营养, 2020, 26(04):38-41
[3]王庆波, 檀琮萍, 张雷, 等.食用油氧化酸败的影响因素及其防治[J].江苏调味副食品, 2014, 03(0):9-12
[4]Yu N, Ye Q, Nie X, et al.Distribution of 2-tert-butyl-1, 4-benzoquinone and its precursor, tert-butylhydroquinone, in typical edible oils and oleaginous foods marketed in Hangzhou City, China[J].Food Chemistry, 2021, 361(Nov.1):130039-130039
[5]潘东升, 俞进开, 李海光, 等.充氮保鲜对一级大豆油保质期品质影响的研究[J].保鲜与加工, 2022, 22(11):29-32
[6]Liu C, Li J, Bi Y, et al.Thermal Losses of Tertiary Butylhydroquinone (TBHQ) and Its Effect on the Qualities of Palm Oil[J].Journal of Oleo Science, 2016, 65(9):739-748
[7]Li J, Bi Y, Liu W, et al.Effect of Acid Value on TBHQ and BHT Losses in Heating Oils: Identification of the Esterification Products of TBHQ and Free Fatty Acids[J].Journal of the American Oil Chemists' Society, 2014, 91(10):1763-1771
[8]胡明明, 张权, 吴思纷, 等.基于主成分分析的西式快餐条件下煎炸油品质评价[J].食品工业科技, 2023, 44(11):287-296
[9]Ye Q, Meng X, Jiang L.Identification and assessment of residual levels of the main oxidation product of tert-butylhydroquinone in frying oils after heating and its cytotoxicity to RAW 264.7 cells[J].Food Chemistry, 2018, 264(May17):293-300
[10]陈华凤.油脂中抗氧化剂、及其转化产物的研究[J].质量技术监督研究, 2018, No.58(04):16-19
[11]范小龙, 朱正伟, 吴婉琴, 等.植物油中叔丁基对苯二酚转化产物的识别确证与测定[J].食品工业科技, 2022, 43(11):303-309
[12]Li J, Bi Y, Yang H, et al.Antioxidative Properties and Interconversion oftert-Butylhydroquinone andtert-Butylquinone in Soybean Oils[J].Journal of Agricultural and Food Chemistry, 2017, 65(48):10598-10603
[13]Li J, Bi Y, Liu W, et al.Simultaneous Analysis of Tertiary Butylhydroquinone and 2-tert-Butyl-1,4-benzoquinone in Edible Oils by Normal-Phase High-Performance Liquid Chromatography[J].Journal of Agricultural and Food Chemistry, 2015, 63(38):8584-8591
[14]Xu X, Bi Y, Wang H, et al.Transformation of TBHQ in Lard and Soybean Oils During Room Temperature Storage[J].European Journal of Lipid Science and Technology, 2019, 121(8):1800510-1800510
[15]温运启, 刘玉兰, 王璐阳, 等.不同食用植物油中维生素组分及含量研究[J].中国油脂, 2017, 42(03):35-39
[16]顾强, 王慧君, 雷春妮, 等.基于维生素组成的植物油掺棕榈油鉴别研究[J].食品安全质量检测学报, 2022, 13(16):5345-5350
[17]杨李胜, 刘志鹏, 柯华南.甲醇萃取法在食用油中酚类抗氧化剂检测中的应用研究[J].食品安全质量检测学报, 2019, 10(19):6483-6488
[18]Ignacio Cacho J, Campillo N, Vinas P, et al.Determination of synthetic phenolic antioxidants in edible oils using microvial insert large volume injection gas-chromatography[J].Food Chemistry, 2016, 200(JUN.1):249-254
[19]叶沁.油脂煎炸过程中TBBQ生成规律、危害控制及其细胞毒性研究[D]. 浙江工业大学, 2019.
[20]周珏, 李云虹.乙腈萃取-气相色谱法快速测定食用油中的3种抗氧化剂[J].食品安全导刊, 2022, 09(0):146-151
[21]彭毓敏, 朱峰, 周炎, 等.利用制备液相色谱系统分离中药槐花米中的芦丁[J].佛山科学技术学院学报自然科学版, 2020, 38(03):60-64
[22]倪冰冰, 刘宏, 于立洋, 等.基于––技术的五倍子单宁成分分析[J].林业科学研究, 2023, 36(01):11-21
[23]Shin H, Jang J, Lee M K, et al.Cell extraction method coupled with LC-QTOF MS/MS analysis for predicting neuroprotective compounds from Polygonum tinctorium[J].Journal of Pharmaceutical and Biomedical Analysis, 2022, 220(Aug.8):114988-114988
[24]施斌, 袁荔, 唐天宇, 等.特丁基对苯二酚的光谱及密度泛函研究[J].物理学报, 2021, 70(05):104-111
[25]Shi B, Yu J, Tang T, et al.Study on UV Spectrum and Antioxidant Properties of 3-tert-Butyl-4-hydroxyanisole Molecule[J].Russian Journal of Physical Chemistry A, 2021, 95(2):343-348