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Journal articles on the topic 'Ester glycidyle'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

Le Thanh, Tam, Duy Nguyen Thanh, Kiet Ly Tuan, Tan Phu Minh, Hung Nguyen Quoc, and Hai Chu Van. "Simultaneous determination of fatty acid esters 2-chloro-1, 3-propandiol(2-mcpd), 3-chloro-1,2- propandiol(3-mcpd) and glycidol in vegetable oils by gas chromatography mass spectrometry GC-MS/MS." Heavy metals and arsenic concentrations in water, agricultural soil, and rice in Ngan Son district, Bac Kan province, Vietnam 2, no. 3 (September 27, 2019): 67–73. http://dx.doi.org/10.47866/2615-9252/vjfc.78.

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The food contaminants including 3-chloro-1,2-propanediol (3-MCPD) and 3-MCPD fatty acid esters have been a matter of great concern in the past few years due to their toxicity and their occurrence in numerous foods. Recently, significant amounts of the isomeric compounds 2-chloro-1,3-propanediol (2-MCPD) fatty acid esters have been detected in refined oil samples. Gas Chromatography (GC) coupled with mass spectroscopy (MS) was used for the quantification of fatty acid esters of 2-Chloro-1,3-propandiol (2-MCPD), 3-Chloro-1,2- propandiol (3-MCPD) and glycidol in oil. Internal standards including 3-MCPD-ester-d5 (rac 1,2-bis-palmitoyl-3-chloropropanediol-d5), 2-MCPD-ester-d5 (1,3-Distearoyl-2- chloropropanediol-d5) and Glycidyl sterate-d5 were added to samples. Spiked samples were, then, incubated in NaBr/H2SO4 and H2SO4/MeOH solutions. They were, eventually, extracted with ethyl acetate and n-hexane solvents in order to convert Glycidyl esters to free MCPD and glycidol in samples before using phenylboronic acid derivative. The limit of quantitation was of 0.1 ppm (mg/kg). The recoveries at the concentration of 0.1 mg/kg ranged from 80 to 120% and the repeatability and reproducibility were less than 10%.

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2

Shimamura, Yuko, Ryo Inagaki, Hiroshi Honda, and Shuichi Masuda. "Does External Exposure of Glycidol-Related Chemicals Influence the Forming of the Hemoglobin Adduct, N-(2,3-dihydroxypropyl)valine, as a Biomarker of Internal Exposure to Glycidol?" Toxics 8, no. 4 (December 13, 2020): 119. http://dx.doi.org/10.3390/toxics8040119.

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Glycidyl fatty acid esters (GE) are constituents of edible oils and fats, and are converted into glycidol, a genotoxic substance, in vivo. N-(2,3-dihydroxypropyl)valine (diHOPrVal), a hemoglobin adduct of glycidol, is used as a biomarker of glycidol and GE exposure. However, high background levels of diHOPrVal are not explained by daily dietary exposure to glycidol and GE. In the present study, several glycidol-related chemicals (glycidol, (±)-3-chloro-1,2-propanediol, glycidyl oleate, epichlorohydrin, propylene oxide, 1-bromopropane, allyl alcohol, fructose, and glyceraldehyde) that might be precursors of diHOPrVal, were administered to mice, and diHOPrVal formation from each substance was examined with LC-MS/MS. DiHOPrVal was detected in animals treated with glycidol and glycidyl oleate but not in mice treated with other chemicals (3-MCPD, epichlorohydrin, propylene oxide, 1-bromopropane, allyl alcohol, fructose, and glyceraldehyde). The amount of diHOPrVal per administered dose produced from other chemicals was negligible compared to the amounts associated with dietary glycidol and GE. The present study provides important knowledge for exploring other sources for internal exposure to glycidol.

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3

Goh, Kok Ming, Yu Hua Wong, Faridah Abas, Oi Ming Lai, Masni Mat Yusoff, Tai Boon Tan, Yonghua Wang, Imeddedine Arbi Nehdi, and Chin Ping Tan. "Changes in 3-, 2-Monochloropropandiol and Glycidyl Esters during a Conventional Baking System with Addition of Antioxidants." Foods 9, no. 6 (June 4, 2020): 739. http://dx.doi.org/10.3390/foods9060739.

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Shortening derived from palm oil is widely used in baking applications. However, palm oil and the related products are reported to contain high levels of monochloropropandiol (MCPD) ester and glycidyl ester (GE). MCPD and glycidol are known as process contaminants, which are carcinogenic and genotoxic compounds, respectively. The objective was to evaluate the effects of antioxidant addition in palm olein and stearin to the content of MCPD esters and GE in baked cake. Butylated hydroxyanisole (BHA), rosemary extract and tocopherol were used to fortify the samples at 200 mg/kg and in combinations (400, 600 and 800 mg/kg rosemary or tocopherol combined with 200 mg/kg BHA). The MCPD esters and GE content, radical formation and the quality of the fats portion were analyzed. The results showed that palm olein fortified with rosemary extract yielded less 2-MCPD ester. The GE content was lower when soft stearin was fortified with rosemary. ESR spectrometry measurements showed that the antioxidants were effective to reduce radical formation. The synergistic effects of combining antioxidants controlled the contaminants formation. In conclusion, oxidation stability was comparable either in the single or combined antioxidants. Tocopherol in combination with BHA was more effective in controlling the MCPD esters and GE formation.

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4

Azmi, N. N. A. N., Y. H. Leong, T. C. Tan, and M. Y. Ang. "Monochloropropanediols (MCPD) esters and glycidyl esters (GE) in infant formulas and challenges of palm oil industry in Malaysia: a review." Food Research 5, no. 1 (February 13, 2021): 488–96. http://dx.doi.org/10.26656/fr.2017.5(1).503.

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Infant formula is an exclusive diet that offers the requisite nutrients for infants up to 6 months prior to the introduction of solids in their diet. Vegetable oils in infant formulas that serve as a source of fat could be contamination of monochloropropanediols (MCPD) and glycidol. The toxicity of MCPD and glycidol was highlighted in several studies implied health risk for exposed children, especially with their low body weight. This paper reviewed the occurrence of MCPD and glycidyl esters in infant formulas marketed in various countries, including risk assessment and associated estimated dietary exposure. From the selected studies published between 2015 to 2019, the presence of the contaminants was detected, but their concentrations decreased over the years indicating a low potential health risk to infants. These have been linked to the success of the vegetable oil producers' implementation of mitigation strategies. The paper also discusses the infant formula market in Malaysia, as well as the association of the use of palm oil in infant and follow-up formula in the Malaysian market. As one of the largest producers and exporters of palm oil and palm oil by-products, Malaysia is taking serious steps and the mitigation strategies it is exercising to reduce the level of MCPD and glycidol to comply with the regulation proposed by the European Commission. However, more studies are needed to gain a clearer view of the association between the use of palm oil in infant formulas and the occurrence of MCPD esters and glycidols, as well as their risk assessment.

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5

Nguyễn Thành, Duy, Tâm Lê Thanh, Kiệt Lý Tuấn, Tấn Phú Minh, Hùng Nguyễn Quốc, and Hải Chu Vân. "Xác định đồng thời nhóm Acid béo 2-Chloro-1,3-Propandiol (2-MCPD), 3-Chloro-1,2-propandiol (3-MCPD) và glycidol trong dầu thực vật bằng sắc ký khí ghép khối phổ GC-MS/MS." Heavy metals and arsenic concentrations in water, agricultural soil, and rice in Ngan Son district, Bac Kan province, Vietnam 2, no. 3 (September 27, 2019): 67–73. http://dx.doi.org/10.47866/2615-9252/vjfc.715.

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Trong những năm gần đây, một số chất gây ô nhiễm thực phẩm như 3-chloro-1,2-propanediol (3-MCPD) và ester acid béo 3-MCPD đã được tìm thấy trong nhiều loại thực phẩm. Trong đó, một lượng đáng kể các hợp chất acid béo 2-chloro-1,3-propanediol (2-MCPD) đã được phát hiện trong các loại dầu tinh chế. Kỹ thuật sắc ký khí ghép khối phổ được sử dụng để định lượng các acid béo dạng ester bao gồm 2-Chloro-1,3-propandiol (2-MCPD), 3-Chloro-1,2-propandiol (3-MCPD) và glycidol trong dầu. Mẫu được chuẩn bị bằng cách sử dụng các nội chuẩn bao gồm 3-MCPD-ester-d5 (rac 1,2-bis-palmitoyl- 3-chloropropanediol-d5), 2-MCPD-ester-d5 (1,3-Distearoyl-2-chloropropanediol-d5) và Glycidyl sterate-d5, tiến hành 2 bước ủ mẫu bằng dung dịch NaBr/H2SO4 và H2SO4/MeOH, trích ly với dung môi ethyl acetate, n-hexan để chuyển đổi Glycidyl ester thành MCPD và glycidol dạng tự do trong mẫu trước khi sử dụng dẫn xuất phenylboronic acid. Giới hạn định lượng là 0,1 mg/kg tương ứng, hiệu suất thu hồi ở nồng độ 0,1 mg/kg khoảng 80 - 120% với độ lặp lại và độ tái lập thấp hơn 10%.

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6

Bognár, Erzsébet, Gabriella Hellner, Andrea Radnóti, László Somogyi, and Zsolt Kemény. "Formation of Glycidyl Esters During The Deodorization of Vegetable Oils." Hungarian Journal of Industry and Chemistry 46, no. 2 (December 1, 2018): 67–71. http://dx.doi.org/10.1515/hjic-2018-0021.

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Abstract Glycidyl esters are foodborne contaminants formed during the production of fats and oils, especially during the deodorization of palm oil. The hydrolyzed free form of glycidol has been categorized as probably carcinogenic to humans by the World Health Organization’s International Agency for Research on Cancer. The aim of this research was to study the formation of glycidyl esters during the lab-scale deodorization of the three most widely produced seed oils in the world (sunflower, rapeseed and soybean). The effects of two independent factors – temperature and residence time – were analyzed by a 32 full factorial experimental design and evaluated by response surface methodology. In accordance with findings in the literature, the greatest amount of glycidyl esters was formed in the soybean oil matrix. For all three oils, the effects of both residence time and temperature were significant, while the latter was more so. To reduce the formation of glycidyl esters, milder deodorization is required, which is limited because of the purposes sought by the thermal operation and removal of volatile minor components and contaminants.

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7

Dubois, Mathieu, Anna-Maria Empl, Greg Jaudzems, Quentin Basle, and Erik Konings. "Determination of 2- and 3-MCPD as well as 2- and 3-MCPD Esters and Glycidyl Esters (GE) in Infant and Adult/Pediatric Nutritional Formula by Gas Chromatography Coupled to Mass Spectrometry Method, First Action 2018.03." Journal of AOAC INTERNATIONAL 102, no. 3 (May 1, 2019): 903–14. http://dx.doi.org/10.5740/jaoacint.18-0266.

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Abstract Background: Monochloropropanediol (MCPD) and its fatty acid esters as well as glycidyl fatty acid esters are substances generated during oil refining or food processing. The free form released during digestion, 3-MCPD and glycidol, have shown adverse effects in animal studies. Objective: So far, the available analytical methods have not been validated in a collaborative study for infant and adult nutritional formulas. This manuscript describes a single-laboratory validation method in view of a future multilaboratory validation trial. Methods: The method described is for the direct determination of 2- and 3-MCPD and indirect determination of 2- and 3-MCPD esters and glycidyl esters in infant and adult/pediatric nutritional formulas by GC coupled to MS. Results: The analytical range was found to be 4–2000 μg/kg powder formula and 0.7–333 μg/kg liquid formula for fatty acid esters of MCPD and glycidol, and 2.5–750 μg/kg samples for free MCPD. The recovery rates were within 91–124% for all samples. Repeatability precision was <20% at levels close to the LOQ. Conclusions: The results met the Standard Method Performance Requirements® (SMPR) set by the AOAC Stakeholder Panel on Infant Formula and Adult Nutritionals. Highlights: The AOAC Expert Review Panel approved the present method as AOAC Official First Action 2018.03.

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8

Yıldırım, A., and A. Yorulmaz. "The effect of rosemary extract on 3-MCPD and glycidyl esters during frying." Grasas y Aceites 69, no. 4 (October 5, 2018): 273. http://dx.doi.org/10.3989/gya.0347181.

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The aim of the present work was to evaluate the effect of rosemary extract (Rosmarinus Officinalis L.) on the 3-MCPD and glycidyl ester contents during deep-fat frying. Firstly, the potato samples were soaked in different concentrations of NaCl and they were fried in sunflower oils containing different concentrations of rosemary extract. Subsequently, repeated frying was carried out with sunflower oil enriched with rosemary extract. The frying oil and the oil extracted from potato samples were analyzed in terms of the contents of 3-MCPD and glycidyl esters according to DGF C VI 18 (10) method. The results demonstrated that the content of 3-MCPD and glycidyl esters in frying oil was not significantly affected by different NaCl and rosemary extract concentrations during short term frying; however, the amount of 3-MCPD esters was found to be lower for the potato crisps enriched with rosemary extract during repeated frying cycles.

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9

Kuhlmann, Jan. "2-Monochloropropanediol (2-MCPD), 3-Monochloropropanediol (3-MCPD), and Glycidol in Infant and Adult/Pediatric Nutritional Formula: Single-Laboratory Validation, First Action 2018.12." Journal of AOAC INTERNATIONAL 102, no. 4 (July 1, 2019): 1205–20. http://dx.doi.org/10.5740/jaoacint.19-0026.

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Abstract Background: Fatty acid esters of glycidol, 2-Monochloropropanediol (MCPD), and 3-MCPD are heat-induced foodborne processing contaminants with possible adverse health effects. These compounds occur frequently in refined edible oils. Consequently, glycidyl esters and 2- and 3-MCPD esters might also be present in foods that contain refined edible oils. Objective: This manuscript describes the single-laboratory validation of an analytical method for the quantitative determination of glycidol, 2-MCPD, and 3-MCPD present as fatty acid esters or as free 2- or 3-MCPD in infant and adult/pediatric nutritional formula. Methods: Technically, the presented method is based on the combination of a Heat-Ultrasound Pressure-supported Solvent Extraction and a GC–MS determination of glycidol, 2-MCPD, and 3-MCPD. From a chemical perspective, the method includes an alkaline catalyzed transesterification, conversion of the unstable glycidol into monobromopropanediol, and the parallel derivatization of all analytes with phenylboronic acid. Results: Validation results showed that method linearity for all analytes in powdered and liquid infant formula ranged from 0.9981 to 0.9999 (n = 18). Repeatability relative standard deviation values for concentration levels between 1.3 μg/kg and 331 μg/kg were in the range of 1 to 12%. Relative recoveries were found to be between 93 and 107%. The analytes were quantifiable down to 5–10 μg/kg in powdered samples and 1–2 μg/kg in liquid samples. Conclusions: The reported results met actual AOAC Standard Method Performance Requirements. Highlights: In terms of consumer protection, the presented method is a novel approach for the sensitive and accurate determination of glycidol, 2-MCPD, and 3-MCPD in infant formula and related foodstuffs.

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10

Shimizu, Masao, Petra Weitkamp, Klaus Vosmann, and Bertrand Matthäus. "Influence of chloride and glycidyl-ester on the generation of 3-MCPD- and glycidyl-esters." European Journal of Lipid Science and Technology 115, no. 7 (May 7, 2013): 735–39. http://dx.doi.org/10.1002/ejlt.201200310.

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11

Appel, Klaus E., Klaus Abraham, Edith Berger-Preiss, Tanja Hansen, Elisabeth Apel, Sven Schuchardt, Carla Vogt, Nadiya Bakhiya, Otto Creutzenberg, and Alfonso Lampen. "Relative oral bioavailability of glycidol from glycidyl fatty acid esters in rats." Archives of Toxicology 87, no. 9 (May 7, 2013): 1649–59. http://dx.doi.org/10.1007/s00204-013-1061-1.

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12

Ahmad Tarmizi, Azmil Haizam, Raznim Arni Abd Razak, Abdul Niefaizal Abdul Hammid, and Ainie Kuntom. "Effect of Anti-Clouding Agent on the Fate of 3-Monochloropropane-1,2-Diol Esters and Glycidyl Esters in Palm Olein during Repeated Frying." Molecules 24, no. 12 (June 25, 2019): 2332. http://dx.doi.org/10.3390/molecules24122332.

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Issues on 3-monochloropropane-diol-1,2-diol (MCPD) esters and glycidyl esters in refined oil have gained much attention when these heat-induced contaminants are associated with health implications. Oil that undergoes the frying process could influence the fates of 3-MCPD esters and glycidyl esters, especially with the addition of an anti-clouding agent. In this study, we investigated the effect of polyglycerol fatty acid esters (PGE) on the transients of 3-MCPD esters and glycidyl esters in palm olein (POo) during intermittent frying. Thermal resistance of POo fortified with PGE (0.1% to 0.4%) was assessed for 8 h of daily frying operations at 180 °C across five consecutive days. The addition of PGE decelerated the reduction of 3-MCPD esters and glycidyl esters with the progression of frying. The presence of these compounds coincided with the amount of oil taken up by the fried product. The inclusion of PGE in POo also induced higher augmentation of polar compound fractions, i.e., oxidised triacylglycerols (OxTAG) and polymerised triacylglycerols (PTAG), but gave comparable free fatty acid (FFA), p-anisidine value (AnV), total chloride and fatty acid composition (FAC) with control oil (POo). The results also showed that the presence of chloride in POo did not onset further formation of 3-MCPD esters and glycidyl esters throughout the frying period. As the behaviours of 3-MCPD esters and glycidyl esters were affected by PGE, only a sufficient amount should be added into POo to ensure oil clarity at a realistic period.

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13

Tanaka, Shinji, Takuya Nakashima, Toshie Maeda, Manussada Ratanasak, Jun-ya Hasegawa, Yoshihiro Kon, Masanori Tamura, and Kazuhiko Sato. "Quaternary Alkyl Ammonium Salt-Catalyzed Transformation of Glycidol to Glycidyl Esters by Transesterification of Methyl Esters." ACS Catalysis 8, no. 2 (January 11, 2018): 1097–103. http://dx.doi.org/10.1021/acscatal.7b03303.

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14

Wang, Ru, Mengru Tao, Yamin Zhu, Daming Fan, Mingfu Wang, and Yueliang Zhao. "Puerarin inhibited 3-chloropropane-1,2-diol fatty acid esters formation by reacting with glycidol and glycidyl esters." Food Chemistry 358 (October 2021): 129843. http://dx.doi.org/10.1016/j.foodchem.2021.129843.

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15

Wu, Ping-Yi, Hsuan Chen, Nan-Wei Su, Tai-Ying Chiou, and Wei-Ju Lee. "First Determination of Glycidyl Ester Species in Edible Oils by Reverse-Phase Ultra-Performance Liquid Chromatography Coupled with an Evaporative Light-Scattering Detector." Molecules 26, no. 9 (May 5, 2021): 2702. http://dx.doi.org/10.3390/molecules26092702.

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In this work, a new ultra-performance liquid chromatograph-evaporative light-scattering detector (UPLC-ELSD) method for quantitation of glycidyl esters (GE) contents in edible oils is presented. The method features complete separation of five GE species within 20 min by a C18 column and gradient elution with a mobile phase consisting of 85% and 2.5% methanol aqueous solutions. The coefficients of regression (R2) were all ≥0.9999 for the linear-quadratic regression curves of GE species in a concentration range of 5~80 μg/mL. The intraday and interday recoveries (%) of GE species in solvent were in a range of 81.3~107.3%, and the intraday and interday coefficients of variation (CVs, %) were all ≤8.6%. The average recovery (%) of GE species spiked in extra-virgin olive oil samples ranged from 88.3~107.8% and the intermediate precision (CV, %) of ≤14% indicated acceptable accuracy and precision. The method exhibited limit of quantification (LOQ) for each GE species (0.6 μg glycidol equivalents/g oil). The method was applied to determine GE concentrations of six commercial oil samples, and total glycidol equivalents were consistent with data obtained by GC-MS method. This UPLC-ELSD method could be adopted for precursory screening and research purposes to improve food safety when MS detectors are unavailable.

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16

Castell, Pere, Angels Serra, Virginia C�diz, and Marina Gali�. "Crosslinking of trimellitimide glycidyl ester derivatives." Journal of Applied Polymer Science 72, no. 4 (April 25, 1999): 537–42. http://dx.doi.org/10.1002/(sici)1097-4628(19990425)72:4<537::aid-app10>3.0.co;2-d.

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17

Bukowska, Agnieszka, Wiktor Bukowski, and Beata Mossety-Leszczak. "Synthesis of glycidyl esters." Journal of Chemical Technology & Biotechnology 74, no. 12 (December 1999): 1145–48. http://dx.doi.org/10.1002/(sici)1097-4660(199912)74:12<1145::aid-jctb162>3.0.co;2-a.

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18

Li, Qiaoguang, Xujuan Huang, He Liu, Shibin Shang, Zhanqian Song, and Jie Song. "Preparation and properties of room temperature vulcanized silicone rubber based on rosin-grafted polydimethylsiloxane." RSC Advances 8, no. 26 (2018): 14684–93. http://dx.doi.org/10.1039/c7ra13672b.

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19

Ikeda, Naohiro, Kenkichi Fujii, Miko Sarada, Hitoshi Saito, Masayoshi Kawabata, Kiyoko Naruse, Katsuyuki Yuki, et al. "Genotoxicity studies of glycidol fatty acid ester (glycidol linoleate) and glycidol." Food and Chemical Toxicology 50, no. 11 (November 2012): 3927–33. http://dx.doi.org/10.1016/j.fct.2012.08.022.

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20

Nizam, Ainul Farhani Ahmad, and Mohd Sabri Mahmud. "Food quality assurance of crude palm oil: a review on toxic ester feedstock." OCL 28 (2021): 23. http://dx.doi.org/10.1051/ocl/2021011.

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Palm oil, the commodity produced mainly in Indonesia and Malaysia, is widely used for deep-frying of fast food and food derivatives. European and American markets of palm oil are affected by the concern of the toxicity potential from monochloropropanediol esters (MCPDE) and glycidyl ester (GE) that are undesirably produced from monoacylglycerol (MAG), diacylglycerol (DAG) and chlorine in refineries. Improvement of oil palm plantation, fruit harvest and oil extraction process in palm oil mills is necessary before the refinery process so that hydrolysis reactions that produce MAG and DAG and chlorine contamination can be minimized in crude palm oil (CPO). This review focuses on the quality control currently employed in the mills especially in managing free fatty acid (FFA) formation as the indicator of the hydrolysis reactions along with other quality control parameters and the reduction of chlorine content.

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Girard, Lauren, Kithsiri Herath, Hernando Escobar, Renate Reimschuessel, Olgica Ceric, and Hiranthi Jayasuriya. "Development of UHPLC/Q-TOF Analysis Method to Screen Glycerin for Direct Detection of Process Contaminants 3-Monochloropropane-1,2-diol Esters (3-MCPDEs) and Glycidyl Esters (GEs)." Molecules 26, no. 9 (April 22, 2021): 2449. http://dx.doi.org/10.3390/molecules26092449.

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The U.S. Food and Drug Administration’s (FDA′s) Center for Veterinary Medicine (CVM) has been investigating reports of pets becoming ill after consuming jerky pet treats since 2007. Renal failure accounted for 30% of reported cases. Jerky pet treats contain glycerin, which can be made from vegetable oil or as a byproduct of biodiesel production. Glycidyl esters (GEs) and 3-monochloropropanediol esters (3-MCPDEs) are food contaminants that can form in glycerin during the refining process. 3-MCPDEs and GEs pose food safety concerns, as they can release free 3-MCPD and glycidol in vivo. Evidence from studies in animals shows that 3-MCPDEs are potential toxins with kidneys as their main target. As renal failure accounted for 30% of reported pet illnesses after the consumption of jerky pet treats containing glycerin, there is a need to develop a screening method to detect 3-MCPDEs and GEs in glycerin. We describe the development of an ultra-high-pressure liquid chromatography/quadrupole time-of-flight (UHPLC/Q-TOF) method for screening glycerin for MCPDEs and GEs. Glycerin was extracted and directly analyzed without a solid-phase extraction procedure. An exact mass database, developed in-house, of MCPDEs and GEs formed with common fatty acids was used in the screening.

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22

Goh, Kok Ming, Yu Hua Wong, Chin Ping Tan, and Kar Lin Nyam. "A summary of 2-, 3-MCPD esters and glycidyl ester occurrence during frying and baking processes." Current Research in Food Science 4 (2021): 460–69. http://dx.doi.org/10.1016/j.crfs.2021.07.002.

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23

Chen, Hong Yan, Hua Bo Huang, and Ji Hui Wang. "Effects of Carbon Nanotube Functionalization on the Mechanical Properties of Vinyl Ester Composites." Advanced Materials Research 233-235 (May 2011): 2315–18. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.2315.

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Chemically functionalized muliti-walled carbon nanotubes (MWCNTs)/vinyl ester resin (VE) nanocomposites were prepared. MWCNTs were first treated by H2SO4/HNO3 acid mixture, and then carboxylated MWCNTs were grafted of methacrylic acid glycidyl ester (GMA). Raman microscopy and Fourier transform infrared spectroscopy (FT-IR) analyses proved the effectivenss of acid-treatment and chemical functionalization. Furthermore, chemical functionalization did not greatly disrupt carbon nanotubes structure and Transmission electron microscopy (TEM) showed that there was a GMA thin layer on the MWCNTs surface, which contributes to the homogenous dispersion of MWCNTs in vinyl ester resin matrix and the CNTs-VE interfacial interaction. Thus the nanocomposites containing MWCNT-GMA possess larger storage modulus values as well as higher glass transition temperatures (Tg).

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24

Demydova, A., I. Levchuk, O. Аksonova, S. Molchenko, and I. Demidov. "Comparison of acid degumming methods and their influence on the formation of 3-MCPD-esters and glycidyl esters in sunflower oil deodorization." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 4 (July 2021): 50–57. http://dx.doi.org/10.32434/0321-4095-2021-137-4-50-57.

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Degumming is the first stage in processing of vegetable oils, and it is aimed at removing phospholipids. The article compares the results of degumming by phosphoric and citric acids, their effects on the extraction of calcium and magnesium ions from oils, these ions being the main components of nonhydratable phospholipids. We showed the appropriateness of combining citric and succinic acids (the final content of phospholipids in oil was 0.034%, whereas it was equal to 0.048% when citric acid was used) and citric and ascorbic acids (the final content of phospholipids in oil was 0.040%). We studied the effect of acid degumming on the formation of 3-MCPD-esters and glycidyl esters. The content of glycidyl esters after degumming with citric acid and phosphoric acid was 310 g kg–1 and 200 g kg–1, respectively. After degumming with citric acid and phosphoric acid, the content of 3-MCPD-esters in the deodorized oil was 680 g kg–1 and 470 g kg–1, respectively. On the contrary, aqueous degumming does not increase the content of these esters in the deodorized sunflower oil (the content is less than 100 g kg–1) and its implementation can be recommended as one of the ways to prevent the formation of these toxic substances during deodorization.

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25

Ward, J. P. "Synthesis of hydroxy thiol esters from glycidol esters." Chemistry and Physics of Lipids 47, no. 3 (July 1988): 217–24. http://dx.doi.org/10.1016/0009-3084(88)90014-x.

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26

Kocaman, S., A. Cerit, U. Soydal, M. E. Marti, and G. Ahmetli. "Evaluation of Fatty Acid Waste in the Synthesis of Oligo(Ether-Ester)s." International Journal of Polymer Science 2019 (April 2, 2019): 1–8. http://dx.doi.org/10.1155/2019/1519593.

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In this study, the waste of sunflower oil refinement was converted to a fatty acid glycidyl ester (FAGE). An unsaturated oligo(ether-ester) (OEE) was synthesized by ring-opening polymerization using propylene oxide (PO) and FAGE. Oligo(ether-ester) production was achieved with a high yield of 80% at 5 h and 0°C when the mole ratio of PO : FAGE was 1 : 1. Synthesized OEE was characterized by FTIR and several chemical analysis methods. According to the TGA results, T5, T10, and T50 values of OEE-styrene copolymers increased up to a 7 : 3 mole ratio then decreased. The weight losses of these copolymers changed in the range of 3-5%. The data of longitudinal and transversal wave velocities showed that copolymers with styrene had better elastic properties and impact resistances compared to those with pure polystyrene.

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27

Stadler, Richard H. "Monochloropropane-1,2-diol esters (MCPDEs) and glycidyl esters (GEs): an update." Current Opinion in Food Science 6 (December 2015): 12–18. http://dx.doi.org/10.1016/j.cofs.2015.11.008.

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28

Craft, Brian D., and Kornél Nagy. "Mitigation of MCPD-ester and glycidyl-ester levels during the production of refined palm oil." Lipid Technology 24, no. 7 (July 2012): 155–57. http://dx.doi.org/10.1002/lite.201200207.

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29

Serra, A., V. Cádiz, A. Mantecón, and P. A. Martinez. "New glycidyl ester compounds containing a preformed imide ring—I." Tetrahedron 41, no. 4 (January 1985): 763–68. http://dx.doi.org/10.1016/s0040-4020(01)96454-3.

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30

Han, Lipeng, Jiahui Li, Shujie Wang, Weiwei Cheng, Lukai Ma, Guoqin Liu, Dongxue Han, and Li Niu. "Sesame oil inhibits the formation of glycidyl ester during deodorization." International Journal of Food Properties 24, no. 1 (January 1, 2021): 505–16. http://dx.doi.org/10.1080/10942912.2021.1900236.

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31

Lok, C. M., A. P. J. Mank, and J. P. Ward. "Synthesis of glycidol esters and mono/di-acylglycerols from glycidol." Chemistry and Physics of Lipids 36, no. 4 (March 1985): 329–34. http://dx.doi.org/10.1016/0009-3084(85)90040-4.

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32

Bauer, M., and J. Bauer. "Networks from cyanic acid esters and glycidyl ethers." Makromolekulare Chemie. Macromolecular Symposia 30, no. 1 (October 1989): 1–11. http://dx.doi.org/10.1002/masy.19890300103.

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33

Katsuragi, Yoshihisa. "Recent glycidyl fatty acid esters in food safety." Journal of Lipid Nutrition 25, no. 1 (2016): 15–24. http://dx.doi.org/10.4010/jln.25.15.

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34

HAN, LIPENG, YE HE, SHUJIE WANG, WEIWEI CHENG, LUKAI MA, GUOQIN LIU, DONGXUE HAN, and LI NIU. "Effects of Methyl Cellulose and Soybean Protein Isolate Coating on Amount of Oil and Chemical Hazards in Chinese Fried Dough Cake." Journal of Food Protection 84, no. 8 (March 26, 2021): 1333–39. http://dx.doi.org/10.4315/jfp-21-062.

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ABSTRACT Fat-related diseases and chemical hazards produced during the frying process pose a major threat to human health. Coatings have been used as a practical method to reduce the amount of oil and chemical hazards associated with fried foods. Methyl cellulose (MC) and soy protein isolate were used as coating materials to pretreat Chinese fried dough cake (CFDC) before frying. The 1.5% MC concentration was the best choice for coating to simultaneously lower oil and chemical hazards in CFDC. The CFDC prepared using 1.5% MC had 11.3% oil, 73.70 μg/kg acrylamide, 0.15 mg KOH/100 kg acid, 8.54 mmol/kg peroxide, p-anisidine value of 6.36, 0.36 μg/g malondialdehyde, 0.13 μg/g 4-hydroxy-2-(E)-hexenal (HHE), 0.51 μg/g 4-hydroxy-2-(E)-nonenal (HNE), and 4,272 μg/kg glycidyl ester. In contrast, the uncoated CFDC had 19.2% oil, 117.55 μg/kg acrylamide, 0.25 mg KOH/100 kg acid, 14.40 mmol/kg peroxide, p-anisidine value of 9.76, 0.63 μg/g malondialdehyde, 0.23 μg/g HHE, 0.86 μg/g HNE, and 5,758 μg/kg glycidyl ester. MC and soy protein isolate enhanced the oil barrier of the coating film, which effectively reduced the heat transfer coefficients, oil transfer, oil oxidation, and chemical hazards in the CFDC. Our work on this edible coating contributes to methods for control of oil and chemical hazards in fried foods. HIGHLIGHTS

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35

Goh, Kok Ming, Yu Hua Wong, May Yen Ang, Samuel Chao Ming Yeo, Faridah Abas, Oi Ming Lai, and Chin Ping Tan. "Comparison assessment between SIM and MRM mode in the analysis of 3-MCPD ester, 2-MCPD ester and glycidyl ester." Food Research International 121 (July 2019): 553–60. http://dx.doi.org/10.1016/j.foodres.2018.12.013.

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36

Sadowska-Rociek, Anna. "Monochloropropanediol esters and glycidyl esters in dietary supplements based on fish oils." Food Additives & Contaminants: Part B 13, no. 4 (August 10, 2020): 305–12. http://dx.doi.org/10.1080/19393210.2020.1803419.

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37

Mognonov, D. M., O. Zh Аyurova, and O. V. Il'ina. "Synthesis of aminoanthraquinone-containing structured-painted epoxy resins." Plasticheskie massy, no. 5-6 (July 2, 2019): 24–26. http://dx.doi.org/10.35164/0554-2901-2019-5-6-24-26.

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The 1-aminoanthraquinone glycidyl ester (GEAA) obtained by reaction of N-alkylation of 1-aminoanthraquinone with epichlorohydrin was used in the synthesis of a structurally colored epoxy resin by co-polycondensation with with diphenylolpropane and epichlorohydrin. Structurally colored epoxy resin is a viscous liquid with a molecular weight of 400–1000, colored orange and soluble in organic solvents. The optimal amount of GEAA (from 0.1 to 0.5% wt.) is established, which provides high color intensity (molar extinction coeffi cient 0.16–1.38·104).

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38

GETMANCHUK, YU P., and I. N. ITSKOVSKAYA. "ChemInform Abstract: Synthesis and Polymerization of 9-Anthracenecarboxylic Acid Glycidyl Ester." ChemInform 22, no. 8 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199108170.

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39

Makarenko, Mariia A., Alexey D. Malinkin, and Vladimir V. Bessonov. "Gas chromatography/tandem mass spectrometry with long-term alkaline transesterification for the determination of esters of monochloropropanediols and glycidol with fatty acids in edible vegetable oils and fats." Hygiene and sanitation 100, no. 6 (June 28, 2021): 640–46. http://dx.doi.org/10.47470/0016-9900-2021-100-6-640-646.

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Introduction. The article discusses the method of determination of 2-, 3-monochloropropanediol (2-MCPDE, 3-MCPDE) and glycidyl (GE) fatty acids esters in edible vegetable oils and fats by slow alkaline transesterification and GC-MS/MS. Many toxicological data showed these substances to have the potential for human health risks if consumed; in addition, existing determination methods have various limitations. So, there is a need to expand the variety of 2-MCPDE, 3-MCPDE and GE determination methods. Materials and methods. 2- and 3-MCPD esters, and glycidyl esters in their corresponding free forms were measured by slow alkaline transesterification with GC-MS/MS. Results. Multiple reactions monitoring mode parameters were optimized. Compared to SIM operating mode, MRM mode improved the selectivity and increased the signal-to-noise ratio. The method was linear in the range of 0.3 mg/kg - 30.0 mg/kg for each analyte. Recovery, tested in this range, was found to be 87.5%-113.6 %. Conclusion. The method discussed here was based on the ISO 18363-2: 2018 standard. In contrast to the last one, we used tandem chromatography-mass spectrometry to detect analytes and a method of absolute calibration with internal standards to quantitate them. In addition, it is proposed to analyze a spiked sample during the sequence of unknown samples to improve the quality of results.

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Otera, Junzo, and Shinjiro Matsuzaki. "A Convenient Synthesis of Glycidyl Esters (2,3-Epoxypropyl Alkanoates)." Synthesis 1986, no. 12 (1986): 1019–20. http://dx.doi.org/10.1055/s-1986-31856.

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41

Li, Shou Hai, Xue Juan Yang, Kun Huang, Mei Li, and Jian Ling Xia. "Preparation and Characterization of Dimer Fatty Acids-Based Vinyl Ester Resin Monomer." Advanced Materials Research 721 (July 2013): 86–89. http://dx.doi.org/10.4028/www.scientific.net/amr.721.86.

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Novel dimer fatty acids-based vinyl ester resin monomer was prepared via simple ring-opening and esterification reaction with the aid of dimer fatty acids (DA) and glycidyl methacrylate (GMA) as raw material. The effects of different catalyst system, reacting time and reacting temperature on the yield, color, and viscosity of the final product were analyzed. The results of optimal experiments showed that BTEAC catalyst could make the final product with moderate viscosity and lighter color, the optimal BTEAC catalyst addition amount was 0.5wt.%, the optimal reacting temperature and reacting time was 115 °C and 2h, respectively. FTIR and 13C-NMR demonstrated that the target product had been successfully synthesized.

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42

Gao, Su Hua, Gang Xian Zhang, and Feng Xiu Zhang. "Surface Modification of Polyester Fibers by Encasing Sucrose Ester and Grafting Soybean Protein." Advanced Materials Research 331 (September 2011): 133–38. http://dx.doi.org/10.4028/www.scientific.net/amr.331.133.

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Polyester has many superior characteristics such as high strength, durability, and good wash-and-wear properties. But it is not comfortable to wear. Modifying polyester fiber with animal and plant protein was seldom reported, and the fastness of protein was not good enough because there are only few hydroxyl groups on the surface of polyester fibers. In this study, sugar ester(SE) which had both hydrophobic aliphatic chain and hydrophilic hydroxyl groups were encased into surface layer of polyester fiber at high temperature and pressure. The hydrophobic part of sugar ester could be inserted into the polyester fiber, and the reactive hydroxyl groups would stay on the surface of polyester fiber. Then soybean proteins could be grafted on the surface of polyester fiber with sugar ester glycidyl ether (SEGE) as crosslinking compound. Surface morphology and structure of the fabric were studied by SEM、FT-IR、XRD、DSC. The results showed that the surface of polyester fiber was covered by SE and soybean protein overlay film, the encased sugar ester and grafted soybean protein fiber had little change on structure, and the proper grafting temperature was 100°C, time 30min. Encasing and grafting technology is a promising method for modification of polyester fiber.

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43

Zhang, Jinglin, Wendi Zhang, Yuanzheng Zhang, Mingquan Huang, and Baoguo Sun. "Effects of Food Types, Frying Frequency, and Frying Temperature on 3-Monochloropropane-1,2-diol Esters and Glycidyl Esters Content in Palm Oil during Frying." Foods 10, no. 10 (September 24, 2021): 2266. http://dx.doi.org/10.3390/foods10102266.

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3-Monochloropropanediol esters (3-MCPDE) and glycidyl esters (GE) have high toxicity and have drawn global attention because of their widespread occurrence in refined oils and oil-based foods. In this study, the effects of food type (potato chips and chicken breasts), frying frequency, and frying temperature on the formation of 3-MCPDE and GE in palm oil (PO) were investigated. The results showed that 3-MCPDE was formed easier in chicken breasts than potato chips. The GE content decreased in PO after it was used for frying potato chips and chicken breasts with or without NaCl. Frying frequency was an influencing factor in the formation of 3-MCPDE and the decrease in GE in PO. Frying temperature was positively correlated with GE degradation, while it had a bidirectional effect on the formation of 3-MCPDE. The formation kinetic equations indicated that 3-MCPDE and GE followed zero-order reactions in PO. The estimated activation energy (Ea) of 1,2-bis-palmitoyl-3-chloropropanediol (Pa-Pa, 41.05 kJ/mol) was lower than those of the other three types of 3-MCPDE; this is the first theoretical explanation for why PO contains more 3-MCPD than other edible oils. Among GEs, glycidyl oleate (Li-GE) was degraded more readily than other GEs.

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44

Tran, Chinh-Hoang, Min-Woong Lee, Sang-Woo Park, Jae-Eon Jeong, Soo-Jeong Lee, Wenliang Song, PilHo Huh, and Il Kim. "Heterogeneous Double Metal Cyanide Catalyzed Synthesis of Poly(ε-caprolactone) Polyols for the Preparation of Thermoplastic Elastomers." Catalysts 11, no. 9 (August 26, 2021): 1033. http://dx.doi.org/10.3390/catal11091033.

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A series of polycaprolactones (PCLs) with molecular weights of 950–10,100 g mol−1 and Ð of 1.10–1.87 have been synthesized via one-pot, solvent-free ring-opening polymerization (ROP) of ε-caprolactone (CL) using a heterogeneous double metal cyanide (DMC) catalyst. Various initiators, such as polypropylene glycol, ethylene glycol, propylene glycol, glycerol, and sorbitol, are employed to tune the number of hydroxyl end groups and properties of the resultant PCLs. Kinetic studies indicate that the DMC-catalyzed ROP of CL proceeds via a similar mechanism with the coordination polymerization. Branched PCLs copolymers are also synthesized via the DMC-catalyzed copolymerization of CL with glycidol. The α,ω-hydroxyl functionalized PCLs were successfully used as telechelic polymers to produce thermoplastic poly(ester-ester) and poly(ester-urethane) elastomers with well-balanced stress and strain properties.

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45

Wong, Yu Hua, Kok Ming Goh, Kar Lin Nyam, Imededdine Arbi Nehdi, Hassen Mohamed Sbihi, and Chin Ping Tan. "Effects of natural and synthetic antioxidants on changes in 3-MCPD esters and glycidyl ester in palm olein during deep-fat frying." Food Control 96 (February 2019): 488–93. http://dx.doi.org/10.1016/j.foodcont.2018.10.006.

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46

Ohba, Tadahiro, Kanji Suyama, and Masamitwsu Shirai. "Photocrosslinking of Oligomers Bearing Glycidyl Sulfonate Ester Units and Their Redissolution Property." Journal of Photopolymer Science and Technology 19, no. 6 (2006): 709–12. http://dx.doi.org/10.2494/photopolymer.19.709.

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47

Miyamoto, Masatoshi, Yasumichi Saeki, Chan Woo Lee, Yoshiharu Kimura, Hidemasa Maeda, and Koji Tsutsui. "Novel Isomerization Polymerization of Glycidyl Acetate To Produce a Poly(ortho ester)." Macromolecules 30, no. 20 (October 1997): 6067–73. http://dx.doi.org/10.1021/ma9610018.

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48

Risangud, Nuttapol, Noppakhate Jiraborvornpongsa, Supasin Pasee, Pakkanun Kaewkong, Nootcharee Kunkit, Piyarat Sungkhaphan, and Wanida Janvikul. "Poly(ester‐ co ‐glycidyl methacrylate) for digital light processing in biomedical applications." Journal of Applied Polymer Science 138, no. 42 (July 16, 2021): 51391. http://dx.doi.org/10.1002/app.51391.

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49

Goh, Kok Ming, Yu Hua Wong, Faridah Abas, Oi Ming Lai, Ling Zhi Cheong, Yong Wang, Yonghua Wang, and Chin Ping Tan. "Effects of shortening and baking temperature on quality, MCPD ester and glycidyl ester content of conventional baked cake." LWT 116 (December 2019): 108553. http://dx.doi.org/10.1016/j.lwt.2019.108553.

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50

Aasa, Jenny, Efstathios Vryonidis, Lilianne Abramsson-Zetterberg, and Margareta Törnqvist. "Internal Doses of Glycidol in Children and Estimation of Associated Cancer Risk." Toxics 7, no. 1 (February 1, 2019): 7. http://dx.doi.org/10.3390/toxics7010007.

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The general population is exposed to the genotoxic carcinogen glycidol via food containing refined edible oils where glycidol is present in the form of fatty acid esters. In this study, internal (in vivo) doses of glycidol were determined in a cohort of 50 children and in a reference group of 12 adults (non-smokers and smokers). The lifetime in vivo doses and intakes of glycidol were calculated from the levels of the hemoglobin (Hb) adduct N-(2,3-dihydroxypropyl)valine in blood samples from the subjects, demonstrating a fivefold variation between the children. The estimated mean intake (1.4 μg/kg/day) was about two times higher, compared to the estimated intake for children by the European Food Safety Authority. The data from adults indicate that the non-smoking and smoking subjects are exposed to about the same or higher levels compared to the children, respectively. The estimated lifetime cancer risk (200/105) was calculated by a multiplicative risk model from the lifetime in vivo doses of glycidol in the children, and exceeds what is considered to be an acceptable cancer risk. The results emphasize the importance to further clarify exposure to glycidol and other possible precursors that could give a contribution to the observed adduct levels.

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