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LWT-FOOD SCIENCE AND TECHNOLOGY · 2021 · IF 4.952

Effects of oxidation and hydrolysis of frying oil on MCPD esters formation in Chinese fried dough sticks

Yuan Yuan,Congcong Cui,Hui Liu,Xuenan Li,Yue Cao,Yan Zhang,Haiyang Yan

In this study, we investigated the influence of various factors on the formation of 2-monochloro-1,3-propanediol and 3-monochloro-1,2-propanediol (MCPD) esters in Chinese fried dough sticks. The results showed types of oil significantly affected the content of MCPD esters in fried dough sticks, with palm oil responsible for the highest. As well, temperature and time affected the content of MCPD esters ( P  < 0.05). Treatment at 200 °C for 4 min resulted in 1.87 mg/kg 3-MCPD esters and 0.68 mg/kg 2-MCPD esters, respectively. The dough containing 1 g/100 g NaCl was fried at 180 °C for 4 min, resulting in elevated levels of MCPD esters. MCPD esters in fried dough sticks constantly varied during the 8-h cycle in 3 consecutive days and the 12-h frying cycle. Pearson correlation test showed 3-MCPD esters had a positive correlation with 2-MCPD esters ( R  = 0.920), which allowed 3-MCPD esters to be a representative index of MCPD esters. A good correlation between the acid value (AV), p -anisidine value ( p -AnV), color (ΔΕ) of frying oil and MCPD esters in fried dough sticks was also found. The changes of MCPD esters of fried dough sticks were assumed to be caused by oxidation and hydrolysis of oil during frying.

研究领域: 食品安全 · 食品化学
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Foods · 2024 ·Vol. 13 ·期 2 ·261 · IF 4.7

Effects of Endogenous Antioxidants in Camellia Oil on the Formation of 2-Monochloropropane-1, 3-diol Esters and 3-Monochloropropane-1,2-diol Esters during Thermal Processing

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
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FOOD AND CHEMICAL TOXICOLOGY · 2014 · IF 2.61

Exposure assessment of 3-monochloropropane-1, 2-diol esters from edible oils and fats in China

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
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FOOD SCIENCE AND TECHNOLOGY RESEARCH · 2021 · IF 0.668

Phytosterols inhibit the formation of 3-monochloropropane-1,2-diol esters in model reactions and the possible mechanism

Zhe Zheng,Mingwu Qiao,Zhongwei Zhang,Chang Li

The effects of three phytosterols (β-sitosterol, stigmasterol, and campesterol) on the formation of 3-monochloropropane-1,2-diol (3-MCPD) esters and the possible mechanism were investigated in this study. Model reaction with 1,2-dipalmitoyl-sn-glycerol (DPG) and sodium chloride as the reacting precursors was adopted to investigate effects of three phytosterols on the formation of 3-MCPD esters. The results showed that three phytosterols exhibited inhibiting activity on the formation of 3-MCPD esters in the model reactions. ESR signal detection indicated that the phytosterols suppressed the formation of free radical in the model reactions. In addtion, 3-chloro-Δ5-cholestenes were detected in the reaction models by using UPLC-APCI-MS. It suggested that phytosterols reacted with chloride and transformed to 3-chloro-Δ5-cholestenes. Therefore, the possible mechanism of phytosterols inhibiting the formation of 3-MCPD esters could be proposed that phytosterols suppressed formation of free radical intermediates in model reactions and competed with DPG for chloride ion to reduce the formation of 3-MCPD esters.

研究领域: 食品科学 · 化学
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Foods · 2022 ·Vol. 11 ·期 24 ·4073 · IF 5.561

The Formation of 3-Monochloropropanediol Esters and Glycidyl Esters during Heat-Induced Processing Using an Olive-Based Edible Oil

Yingrui Ji,Dongming Lan,Weifei Wang,Kok Ming Goh,Chin Ping Tan,Yonghua Wang

With the prevalence of edible diacylglycerol (DAG) oil, which is beneficial to human, the generation of 3-monochloropropanediol esters (3-MCPDE) and glycidyl esters (GE) as well as the stability of physical properties during heat-induced processing still need to be explored. In this study, the experiment used olive-based edible oil with different contents of DAG (40, 60, and 80%) to make crackers and fry chicken. They were heated at 160 and 180 °C to determine the changes in 3-MCPDE and GE, the crackers’ hardness and gumminess, and the physical properties of the oil. During baking and frying, 3-MCPDE decreased, while the content of GE slightly increased with the prolonged heating duration. Finally, 3-MCPDE and GE were lower than 1.25 mg/kg and 1.00 mg/kg, respectively. The AV increased proportionally as duration increased and POV was below 0.30 g/100 g. In general, the changes in 3-MCPDE and GE were related to the heating temperature and duration, and not significantly (p> 0.05) related to the content of DAG.Keywords:3-MCPD ester;glycidyl ester;diacylglycerol;crackers;frying oil

研究领域: 食品科学 · 化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2015 · IF 2.912

Antioxidants Inhibit Formation of 3-Monochloropropane-1,2-diol Esters in Model Reactions

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
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2021 · IF 4.952

The effects of chloride and the antioxidant capacity of fried foods on 3-chloro-1,2-propanediol esters and glycidyl esters during long-term deep-frying

Zhaoxian Huang,Dan Xie,Zhenyu Cao,Zengwang Guo,Liang Chen,Lianzhou Jiang,Xiaonan Sui,Zhongjiang Wang

The effects of sodium chloride (NaCl) and tert-butylhydroquinone (TBHQ) on 3-monochloropropane-1,2-diol (3-MCPD) ester and glycidyl esters (GEs) contents were investigated during long-term deep-frying (177 °C, 4 days). The properties of fried food probably affect the formation of 3-MCPD esters and GEs in frying oil. Less NaCl promoted lower 3-MCPD ester and GEs contents, contents of 3-MCPD ester and GEs in the extracted oils from Youtiao (0 mg/kg TBHQ) reduced from 1.272 to 0.360 mg/kg and 0.559 to 0.346 mg/kg, respectively, while the amount of NaCl in Youtiao reduced from 1.5 to 0.0 g/100 g. TBHQ possibly decreased the 3-MCPD ester and GEs contents by suppressing the formation of radical intermediates. The 3-MCPD ester and GEs contents in the extracted oils from Youtiao (1.5 g/100 g NaCl) decreased from 1.221 to 0.893 mg/kg and 0.534 to 0.312 mg/kg, respectively, while the amount of TBHQ in Youtiao increased from 0 to 300 mg/kg. The formation of 3-MCPD esters might be accompanied by decomposition, GEs were rarely generated but decomposed during long-term frying. 3-MCPD esters and GEs entered fried food through frying oil, and the 3-MCPD ester and GEs contents in the extracted oil from Youtiao were closely related to those in the frying oils.

研究领域: 食品科学 · 化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2016 · IF 2.857

Formation of 3-MCPD Fatty Acid Esters from Monostearoyl Glycerol and the Thermal Stability of 3-MCPD Monoesters

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
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MOLECULES · 2023 ·Vol. 28 ·期 8 ·3616 · IF 4.6

Optimization of Physical Refining Process of Camellia Oil for Reduction of 3-Monochloropropane-1,2-Diol (3-MCPD) Ester Formation Using Response Surface Methodology on a Laboratory Scale

Liqun Zhang,Pinggu Wu,Xiaoling Xiang,Dajin Yang,Liyuan Wang,Zhengyan Hu

Refined and deodorized camellia oil has been reported to contain a high amount of 3-monochloropropane-1,2-diol esters (3-MCPDE) due to the high-temperature deodorization step. To reduce 3-MCPDE in camellia oil, the physical refining process of camellia oil was simulated on a laboratory scale. Response surface methodology (RSM) was designed to modify and optimize the refining process with five processing parameters (water degumming dosage, degumming temperature, activated clay dosage, deodorization temperature and deodorization time). The optimized new refining approach achieved a 76.9% reduction in 3-MCPDE contents, in which the degumming moisture was 2.97%, the degumming temperature was 50.5 °C, the activated clay dosage was 2.69%, the deodorizing temperature was 230 °C, and the deodorizing time was 90 min. A significance test and analysis of variance results demonstrated that the deodorization temperature and deodorization time contributed significantly to the reduction of 3-MCPD ester. The joint interaction effects of activated clay dosage and deodorization temperature were significant for 3-MCPD ester formation.Keywords:3-MCPD esters;response surface analysis;optimized refining process parameters;reduction of 3-MCPD

研究领域: 食品科学 · 化学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Food Additives and Contaminants Part A-Chemistry Analysis Control Exposure & Risk Assessment · 2023 · IF 2.9

Risk assessment of 3-monochloropropane-1,2-diol esters through dietary exposure from edible oils for the Zhejiang population in China by Monte Carlo simulation

Liqun Zhang,Pinggu Wu,Xiaoling Xiang,Huali He,Sha Yu

The purpose of this study was to assess the risk of 3-monochoropropane-1,2-diol (3-MCPD) esters from edible oils for the Zhejiang population in China. Exposure assessment of 3-MCPD esters was evaluated by Monte Carlo simulation based on the concentrations of 3-MCPD esters in edible oils combined with survey data on the eating habits of Chinese residents classified by age group and gender. The simulation results indicated that the mean daily intakes (CDI) of 3-MCPD esters for children 7–10 years old were 2.154 µg (kg BW d)−1 for boys and 2.049 µg (kg BW d)−1 for girls, which are lower than the provisional maximum tolerable daily intake (PMTDI) of 4 µg (kg BW d)−1 for 3-MCPD and 3-MCPD esters individually or in combination, set by the Joint FAO/WHO Expert Committee on Food Additives. The range of mean dietary intakes of 3-MCPD esters in different subpopulation groups ranged 1.242–1.672 µg (kg BW d)−1, which was lower than the PMTDI. However, the CDI values of 3-MCPD esters in high percentile exposure subgroups (95th, 99th) of males (7–49 years old) and females (7–10 and 50–75 years old) were all above 4µg (kg bw d)−1. Outside of the senior group (50–75 years old), males had more exposure to 3-MCPD than females. The average hazard indexes (HI) of 3-MCPD esters to male and female children were 1.257 and 1.024, respectively, indicating there was a risk, but no immediate measures are required to address this risk. The average HI of 3-MCPD esters to adolescent, adult, and seniors were all below 1, indicating risk for those age groups were at an acceptable level.

CAS / MDL: 1634-04-4 98-80-6
研究领域: 食品安全 · 毒理学 · 公共卫生
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JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY · 2023 ·Vol. 100 ·期 8 ·615-621 · IF 2

Enzymatic hydrolysis and detection of 3-monochloropropane-1,2-diol esters

Ting Xu,Qingru Zeng,Xin Liu,Shensheng Xiao,Xiaoming Jiang,Yuepeng Lu,Zhiyong Gong,Yonggui Gao,Min Fang

There are more and more studies on the detection method of 3-chloro-1,2-propanediol fatty acid esters (3-MCPD esters) at present, by comparing these methods for the determination of 3-MCPD esters. Indirect methods, which determine total amount of 3-MCPD after hydrolysis of the esters, have an advantage over direct methods. The existing indirect methods, however, may yield unreliable results or require long hours of alkaline methanolysis. In contrast, the indirect enzymatic hydrolysis method has mild conditions and more accurate results. In this study, we developed a reliable and rapid indirect method for determination of 3-MCPD esters. 3-MCPD esters were enzymolysis to 3-MCPD by indirect enzymatic hydrolysis method, and the conditions of enzymatic hydrolysis were optimized, the content of 3-MCPD after enzymatic hydrolysis was detected by gas chromatography–mass spectrometry (GC–MS) and the yield was calculated. Finally, the optimum conditions for enzymatic hydrolysis of 3-MCPD esters were determined. According to the optimal enzymatic hydrolysis condition, the contents of 3-MCPD esters in four food oils were determined. The method is simple and sensitive and can meet the requirement of 3-MCPD esters detection in general oils.

CAS / MDL: 9001-62-1
研究领域: 食品科学 · 分析化学
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Food Analytical Methods · 2015 ·Vol. 9 ·期 4 ·845-855 · IF 1.956

Determination of 3-Monochloropropane-1,2-Diol Esters in Edible Oil―Method Validation and Estimation of Measurement Uncertainty

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
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