Foods
·
2024
·Vol. 13
·期 2
·261
·
IF 4.7
Shanshan Liu,Mingyue Shen,Jianhua Xie,Bohan Liu,Chang Li
2-Monochloropropane-1, 3-diol (2-MCPD) esters and 3-monochloropropane-1,2-diol (3-MCPD) esters, a class of substances potentially harmful to human health, are usually formed during the refining of vegetable oils under high temperature. The effects of endogenous antioxidants in vegetable oils on the formation of 2- and 3-MCPD esters is still unknown. In this study, the effects of endogenous antioxidants (α-tocopherol, stigmasterol and squalene) on the formation of 2- and 3-MCPD esters in model thermal processing of camellia oil were investigated. The possible formation mechanism of 2- and 3-MCPD esters was also studied through the monitoring of acyloxonium ions, the intermediate ions of 2- and 3-MCPD esters formation, and free radicals by employing infrared spectra and electron paramagnetic resonance (EPR), respectively. The results indicated that the addition of α-tocopherol had either promoting or inhibiting effects on the formation of 2- and 3-MCPD esters, depending on the amount added. Stigmasterol inhibited the formation of 3-MCPD ester and 2-MCPD ester at low concentrations, while promoting their formation at high concentrations. Squalene exhibited a promotional effect on the formation of 3-MCPD ester and 2-MCPD ester, with an increased promotion effect as the amount of squalene added increased. The EPR results suggested that CCl3•, Lipid alkoxyl, N3• and SO3• formed during the processing of camellia oil, which may further mediate the formation of chlorpropanol esters. This study also inferred that squalene promotes the participation of the free radical in chlorpropanol ester formation.Keywords:MCPD esters;endogenous antioxidants;camellia oil;mechanism
研究领域:
食品科学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD AND CHEMICAL TOXICOLOGY
·
2014
·
IF 2.61
Chang Li,Shao-Ping Nie,Yong-qiang Zhou,Ming-Yong Xie
3-monochoropropane-1, 2-diol (3-MCPD) esters from edible oils are considered to be a possible risk factor for adverse effects in human. In the present study, the exposure assessment of 3-MCPD esters to Chinese population was performed. A total of 143 edible oil and fat samples collected from Chinese markets were determined for the concentrations of 3-MCPD esters. The concentration data together with the data of fats consumed were analyzed by the point evaluation and probabilistic assessment for the exposure assessment. The point evaluation showed that the mean daily intake (DI) of 3-MCPD esters were lower than the value of provisional maximum tolerable daily intake (PMTDI) of 3-MCPD (2 µg/kg BW/d). The mean DI values in different age groups obtained from probabilistic assessment were similar to the results of the point evaluation. However, in high percentiles (95th, 97.5th, 99th), the DI values in all age groups were undesirably higher than the value of PMTDI. Overall, the children and adolescents exposed more to 3-MCPD esters than the adults. Uncertainty was also analyzed for the exposure assessment. Decreasing the level of 3-MCPD esters in edible oils and consuming less oil were top priority to minimize the risk of 3-MCPD esters.
研究领域:
食品安全
·
毒理学
·
营养学
✓ 已验证
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2015
·
IF 2.912
Chang Li,Hanbing Jia,Mingyue Shen,Yuting Wang,Shaoping Nie,Yi Chen,Yongqiang Zhou,Yuanxing Wang,Mingyong Xie
The capacities of six antioxidants to inhibit the formation of 3-monochloropropane-1,2 diol (3-MCPD) esters were examined in this study. Inhibitory capacities of the antioxidants were investigated both in chemical models containing the precursors (tripalmitoyl glycerol, 1,2-dipalmitoyl-sn-glycerol, monopalmitoyl glycerol, and sodium chloride) of 3-MCPD esters and in oil models (rapeseed oil and sodium chloride). Six antioxidants, butylated hydroxytoluene (BHT), butylated hydroxy anisole (BHA), tert-butyl hydroquinone (TBHQ), propyl gallate (PG), l-ascorbyl palmitate (AP), and α-tocopherol (VE), were found to exhibit inhibiting capacities on 3-MCPD ester formation both in chemical models and in oil models. TBHQ provided the highest inhibitory capacity both in chemical models and in oil models; 44% of 3-MCPD ester formation was inhibited in the presence of TBHQ (66 mg/kg of oil) after heating of rapeseed oil at 230 °C for 30 min, followed by PG and AP. BHT, BHA, and VE appeared to have weaker inhibitory abilities in both models. VE exhibited the lowest inhibition rate; 22% of 3-MCPD esters were inhibited in the presence of VE (172 mg/kg of oil) after heating of rapeseed oil at 230 °C for 30 min. In addition, the inhibition rates of PG and VE decreased dramatically with an increase in temperature or heating time. The results suggested that some antioxidants, such as TBHQ, PG, and AP, could be the potential inhibitors of 3-MCPD esters in practice.
研究领域:
食品科学
·
化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2016
·
IF 2.857
Yue Zhao,Yaqiong Zhang,Zhongfei Zhang,Jie Liu,Yi-Lin Wang,Boyan Gao,Yuge Niu,Xiangjun Sun,Liangli Yu
Formation of 3-monochloropropanediol (3-MCPD) esters from monostearoyl glycerol (MSG) was investigated under high temperature and low moisture conditions. Different organic and inorganic chlorides, including lindane, KCl, CaCl2, NaCl, MgCl2, AlCl3, CuCl2, MnCl2, SnCl2, ZnCl2, and FeCl3, were evaluated for their potential to react with MSG to form 3-MCPD and glycidyl esters at 120 and 240 °C using a UPLC-Q-TOF MS analysis. The results indicated that different chlorine compounds differed in their capacity to react with MSG and formed different products including 3-MCPD mono- and diesters, distearoylglycerol, and glycidyl esters. According to electron spin resonance (ESR) and Fourier transform infrared (FT-IR) spectroscopies, free radical mediated formation mechanisms involving either five-membered or six-membered cyclic acyloxonium free radicals (CAFR) from monoacylglycerol (MAG) were proposed. Tandem quadrupole-time-of-flight (Q-TOF) MS and MS/MS analyses confirmed the free radical mechanisms. In addition, the results from the present study showed that 3-MCPD monoester could be degraded upon thermal treatment and suggested a possible catalytic role of Fe3+ under the experimental conditions.
研究领域:
食品科学
·
分析化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Food Analytical Methods
·
2015
·Vol. 9
·期 4
·845-855
·
IF 1.956
Li Chang,Jia Hanbing,Wang Yuting,Shen Mingyue,Nie Shaoping,Xie Mingyong
A gas chromatography mass spectrometry (GC-MS) method was developed and validated for the determination of the sum of 3-monochloropropane-1,2-diol (3-MCPD) esters in edible oils. Meanwhile, the measurement uncertainty was estimated. Testing sample preparation was optimized, and the optimal condition was attained. Good linearity was observed with the GC-MS method for the concentration range of 0.05–5.0 mg/kg ( R
2 = 0.9994). It was proved to be an accurate and precise method for the determination of 3-MCPD esters according to the validation results. The recovery range was 89.0–104.6 %, and the limits of detection (LOD) and the limits of quantification (LOQ) were 25 and 50 μg/kg, respectively. Satisfactory reproducibility was achieved with lower than 15 %. Repeatability was determined and expressed as relative standard deviation (RSD), with the value range of 3.9–12.0 %.The contents of 3-MCPD esters were determined in 12 kinds of oils using this method. Measurement uncertainties were calculated by applying bottom-up approach. The main dominant sources were identified and quantified, which were standard solutions preparation, recovery, and calibration curve. It reminds that the predominant uncertainty sources should be paid much more attention during preparing the testing samples in the future.
研究领域:
食品科学
·
分析化学
✓ 已验证
产品关联
DOI
高影响因子
FOOD CONTROL
·
2025
·
IF 6.3
Yaoyao Zhang,Zhaohan Feng,Shangde Sun
The 3-monochloropropane-1, 2-diol esters (3-MCPDEs) and glycidyl esters (GEs), which are recognized as contaminants often produced during the deodorization process of refined edible oils, have garnered widespread attention and research interest in recent years due to their potential health risks to humans. Although there have been studies on the formation mechanisms of 3-MCPDEs and GEs, further clarification is still needed in the intrinsic synergistic effects of precursors. Herein, the synergistic effects of acylglycerols, including monoacylglycerols (MAGs), diacylglycerols (DAGs), and triacylglycerols (TAGs) on the formation of 3-MCPDEs and GEs were innovatively investigated through simulated deodorization experiments in model soybean oil systems. Additionally, the effects of simulated deodorization conditions, including temperatures, heating duration, chloride contents, and acylglycerol compositions on the production of 3-MCPDEs and GEs, were also investigated. The results indicated that under the simulated deodorization process and in the presence of chloride ions, the formation of 3-MCPDEs and GEs was facilitated by the synergistic interaction among MAGs, DAGs and TAGs. It is noteworthy that MAGs were more susceptible to forming 3-MCPDEs in the presence of chloride ions, whereas GEs predominantly resulted from the cyclization reaction of DAGs. Concurrently, when the MAGs content was less than 1%, or the presence of DAGs was less than 4% in the model system, the formation of both 3-MCPDEs and GEs was found to be below the EU regulatory limits, thus offering a solid theoretical basis for the control of 3-MCPDEs and GEs in refined oils.
研究领域:
食品科学
·
毒理学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2015
·
IF 2.912
Zhongfei Zhang,Boyan Gao,Xiaowei Zhang,Yuanrong Jiang,Xuebing Xu,Liangli (Lucy) Yu
This study investigated whether and how triacylglycerol (TAG) may serve as a precursor for 3-monochloro-1,2-propanediol (3-MCPD) fatty acid ester formation using tristearoylglycerol (TSG). TSG was reacted with inorganic chloride compounds including NaCl, KCl, FeCl2, CuCl2, ZnCl2, FeCl3 and dry HCl, or organic chlorine compound lindane at different temperatures. Only FeCl2 and FeCl3 were able to form 3-MCPD esters from TSG. Further electron spin resonance (ESR) determination of TSG, Fe2(SO4)3 and 5,5-dimethylpyrroline-N-oxide (DMPO) reactions revealed potential of Fe ion in promoting free radical generations under the experimental conditions. To further confirm the effect of Fe ion, chelating agent (EDTA-2Na) was added to the model reactions. The results showed for the first time that EDTA-2Na was able to reduce the generation of 3-MCPD esters. In addition, FT-IR examination indicated a possible involvement of a carbonyl group during the reaction. Taking all the observations together, the possible mechanisms, involving the formation of either a cyclic acyloxonium or a glycidol ester radical intermediate, were proposed for generating 3-MCPD fatty acid di- and mono- esters from TAG under a high temperature and low moisture condition, as well as the coformation of glycidol esters. The results from this study may be useful for reducing the level of 3-MCPD esters and related toxicants in the refined edible oils and food products.
研究领域:
食品科学
·
毒理学
·
化学
✓ 已验证
DOI
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
·
2025
·
IF 6.6
Haina Yuan,Zixiang Zhu,Gongshuai Song,Gongnian Xiao
This study investigated the formation and mitigation of 3-monochloro-1,2-propanediol (3-MCPD) ester in vegetable oils under storage, thermal processing, and chloride supplementation. Prolonged storage (>6 months) markedly accelerated formation (80.8–190 μg/kg·month -1 ), a rate substantially higher than in the initial 6 months (15.2–71.9 μg/kg·month -1 ), underscoring a previously underestimated risk in long-term stored oils even if levels remain below EU limits. Thermal treatment revealed a matrix-dependent dynamic equilibrium, with soybean oil peaking at 220°C (1250 μg/kg) and rapeseed oil at 180°C (997 μg/kg). Among chloride salts, CaCl 2 induced the highest 3-MCPD ester level (2189 μg/kg), revealing the critical, previously detailed role of metal cation properties (coordination capacity, charge density) beyond the mere presence of Cl - . Antioxidants provided dose-dependent mitigation (up to 49% suppression), though their efficacy was limited by thermal stability. Most significantly, mesoporous silica nanoparticles (MSNs) demonstrated exceptional efficacy, achieving a 98% adsorption removal rate of 3-MCPD esters from oil, with a high fitted maximum capacity (Q max = 412.5 μg/g). The combined strategy of antioxidant application followed by MSN treatment offers a novel, practical, and industrially viable solution for significantly reducing 3-MCPD ester exposure in oils and lipid-rich foods.
研究领域:
食品化学
·
食品安全
·
脂质科学
·
毒理学
·
食品加工
·
纳米材料应用
·
分子污染物
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）