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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
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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
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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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FOOD CHEMISTRY · 2018 · IF 4.946

The molecularly imprinted polymer supported by anodic alumina oxide nanotubes membrane for efficient recognition of chloropropanols in vegetable oils

Xiuzhen Qiu,Xian-Yan Xu,Yong Liang,Huishi Guo

A new route to synthesize a covalent interaction-based molecularly imprinted polymer (MIP) material for 3-chloro-1,2-propanediol (3-MCPD) inside the nanopores of anodic alumina oxide (AAO) is presented. A series of adsorption experiments showed MIP had good extraction capacity and selectivity for 3-MCPD. In order to evaluate the usability of the MIP nanotubes membrane, a method combining AAO@MIP membrane extraction with gas chromatography – mass spectrometry (GC–MS) detection was developed for determination of chloropropanols. The limits of detection for the proposed method were 0.072 and 0.13 µg·L −1 , respectively, for 3-MCPD and 1,3-DCP. The average recoveries of 3-MCPD and 1,3-DCP spiked oil samples at three concentrations (0.01, 0.05 and 0.1 mg·kg −1 ) were in the range of 75.6–101.0% with a RSD of 3.3–8.4%, indicating the method would be suitable for determination of chloropropanols in vegetable oils.

研究领域: 食品科学 · 分析化学
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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 CHEMISTRY · 2020 · IF 6.306

Simple and rapid detection of free 3-monochloropropane-1,2-diol based on cysteine modified silver nanoparticles

Aka Alla Martin,Essy Kouadio Fodjo,Gouli Bi Irié Marc,Trokourey Albert,Cong Kong

A rapid colorimetric method using cysteine-modified silver nanoparticles (Cys-AgNPs) is applied for the detection of 3-monochloropropane-1,2-diol (3-MCPD). Indeed, in the presence of 3-MCPD, the color of Cys-AgNPs solution changes from yellow to pink within five minutes at 100 °C and pH 9.3. This change is mainly attributed to the ability of amino group of cysteine to react with 3-MCPD to form N-(2,3-dihydroxypropyl)-amino acid grafted on AgNPs (3-MCPD-Cys-AgNPs) in alkaline medium. This color change makes 3-MCPD to be clearly detectable by unassisted visual means even at 0.1 μg⋅mL −1 . Besides, using UV–Vis spectroscopic technique, a linear range from 0.1 μg⋅mL −1 to 1.25 μg⋅mL −1 for 3-MCPD detection is obtained, with a calculated detection limit of 0.084 μg⋅mL −1 . These results suggest that this sensing technique is sensitive to 3-MCPD and may have a substantial application in the rapid detection of food contaminants particularly, where quality and safety of food products are paramount concern.

研究领域: 食品科学 · 分析化学
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TALANTA · 2024 · IF 5.6

Simple and rapid determination of 3-monochloropropane-1,2-diol in food contact papers based on polydopamine-polyethyleneimine copolymerization

Min Fang,Zhaojie Wang,Qing Fu,Qing Yang,Lin Xu,Yuepeng Lu,Yong Yang,Xiaoming Jiang,Yongning Wu,Zhiyong Gong,Xin Liu

The aim of this work was to develop a fluorescence method based on the polydopamine-polyethyleneimine (PDA-PEI) copolymerization, which was subsequently applied for the determination of 3-monochloropropane-1,2-diol (3-MCPD) in food contact papers (FCMs). PEI could provide an alkaline environment and then react with dopamine (DA) to produce copolymers by Michael addition and Schiff-base reactions. This copolymer has a strong fluorescence emission at 527 nm. We found that amino groups of DA and PEI could also react with 3-MCPD in an alkaline medium, which improved the morphology and fluorescence intensity of PDA-PEI copolymers. The fluorescence intensity of the polymers was linear but inversely proportional to the concentration of 3-MCPD in the range of 10.0–500.0 μg kg −1 and the detection limit was 2 μg kg −1 . The standard addition method was used in FCMs to demonstrate the practical applicability and the spiked recoveries ranged from 99.8 to 110.3 %. Finally, the levels of 3-MCPD in different FCMs (n = 70) were determined by the proposed method. The detection frequencies ranged from 25 % to 100 % and both the highest detection frequency and levels were observed in kitchen papers. More than half of the samples did not comply with the limits recommended by the German Federal Institute for Risk Assessment, suggesting that 3-MCPD released from FCMs is a major route of human exposure.

研究领域: 食品安全 · 分析化学 · 材料科学
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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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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2013 · IF 2.906

Toxic Mechanisms of 3-Monochloropropane-1,2-Diol on Progesterone Production in R2C Rat Leydig Cells

Jianxia Sun,Shun Bai,Weibin Bai,Feiyan Zou,Lei Zhang,Zhijian Su,Qihao Zhang,Shiyi Ou,Yadong Huang

3-Monochloropropane-1,2-diol (3-MCPD) is a well-known food processing contaminant that has been shown to impede the male reproductive function. However, its mechanism of action remains to be elucidated. In this study, the effects of 3-MCPD on progesterone production were investigated using R2C Leydig cells. 3-MCPD caused concentration-dependent inhibition of cell viability at the IC25, IC50, and IC75 levels of 1.027, 1.802, and 3.160 mM, respectively. Single cell gel/comet assay and atomic force microscopy assay showed that 3-MCPD significantly induced early apoptosis. In addition, 3-MCPD significantly reduced progesterone production by reducing the expression of cytochrome P450 side-chain cleavage enzyme, steroidogenic acute regulatory protein, and 3β-hydroxysteroid dehydrogenase in R2C cells. The change in steroidogenic acute regulatory protein expression was highly consistent with progesterone production. Furthermore, the mitochondrial membrane potential and cAMP significantly decreased.

研究领域: 毒理学 · 生殖生物学 · 细胞生物学
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Foods · 2025 ·Vol. 14 ·期 10 ·1670 · IF 5.1

Quantitative Analysis of 3-Monochloropropane-1,2-diol in Fried Oil Using Convolutional Neural Networks Optimizing with a Stepwise Hybrid Preprocessing Strategy Based on Fourier Transform Infrared Spectroscopy

Xi Wang,Siyi Wang,Shibing Zhang,Jiping Yin,Qi Zhao

As one kind of ‘probable human carcinogen’ (Group 2B) compound classified by the International Agency for Research on Cancer, 3-MCPD is mainly formed during the thermal processing of food. Tedious pretreatment techniques are needed for the existing analytical methods to quantify 3-MCPD. Hence, a nondestructive sensing technique that offers low noise interference and high quantitative precision must be developed to address this problem. Following this, Fourier transform infrared spectroscopy association with an convolutional neural network (CNN) model was employed in this investigation for the nondestructive quantitative measurement of 3-MCPD in oil samples. Before building the CNN model, NL-SGS-D2was utilized to enhance the feature extraction capability of model by eliminating the background noise. Under the optimal hyperparameter settings, calibration model achieved a determination coefficient (R2C) of 0.9982 and root mean square error (RMSEC) of 0.0181 during validation, along with a 16% performance enhancement enabled by the stepwise hybrid preprocessing strategy. The LODs (0.36 μg/g) and LOQs (1.10 μg/g) of the proposed method met the requirements for 3-MCPD detection in oil samples by the Commission Regulation issued of EU. The method proposed by CNN model with hybrid preprocessing was superior to the traditional model, and contributed to the quality monitoring of edible oil processing industry.

研究领域: 食品科学 · 分析化学 · 人工智能
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