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
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毒理学
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DOI
高影响因子
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
·
2020
·Vol. 97
·期 6
·603-614
·
IF 1.659
Jia Luo,Zeping Wang,Shangzhi Deng,Fan Zhang,Guirong Bao,Junni Mao,Wenjing Yang
Direct glycerolysis of novel edible Sacha Inchi ( Plukenetia volubilis L.) seed oil (PvLO) into diacylglycerols (DAG) and monoacylglycerols (MAG) was studied over solid Na 2 SiO 3 with or without microwave assistance. The glycerolysis yield was calculated by qualitative and semiquantitative analyses of 1 H NMR, 13 C NMR, and FT-IR spectra. The yields of ~33% 1, 3-DAG, ~16% 1, 2-DAG, ~40% 1-MAG, and ~2.3% 2-MAG were achieved after 16 hours at 120 °C in three consecutive cycles using acetone, with an interesterification rate of 92%. The modified oil showed enhanced gelation ability at low temperatures. The yield of 1, 2-DAG can be increased by adding acetone as solvent. The fatty acid compositions and unsaturated structure of lipids were less destroyed after alkaline glycerolysis. However, more α-linolenic and linoleic acids were transferred to the sn -2 position of glyceryl skeleton. The oxidative stability of the modified oil was still controllable. In summary, this work provides a feasible method to convert polyunsaturated plant oils into oils rich in DAG and MAG with less destructive impact on the olefinic structure of oil. Also, it provides a useful example of how to quickly evaluate the influence of chemical modification on the chemical structure of plant oils by using various spectral technologies.
研究领域:
食品科学
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化学工程
·
植物油脂加工
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DOI
高影响因子
Journal of Oleo Science
·
2022
·
IF 1.628
Lihong He,Jiawei Zheng,Siting Feng,Li Xu,Nanjing Zhong
In this study, lipase A from Candida antarctica (CALA) was immobilized onto the macroporous resin NKA-9. Immobilization conditions (pH, time and CALA concentration) were studied, enzymatic activity and immobilization efficiency (IE) up to 968.89 U/g and 53.19% were respectively obtained under optimal conditions (immobilization pH 5.0, time 5 h and CALA concentration at 30 mg/mL). Then, the NKA-9 supported CALA (CALA@NKA-9) samples were used to catalyze glycerolysis in solvent-free system. With 0.25 g of the present CALA@NKA-9 (soybean oil 3.52 g and glycerol 0.184 g) and after 12 h reaction at 50 °C, diacylglycerols (DAG) content up to 64.37% and triacylglycerols (TAG) conversion at 83.33% were obtained. The relationship between temperature and TAG conversion was LnV 0 = 13.9310-6.4212/T for CALA@NKA-9. Meanwhile, the activation energy (Ea) of CALA@NKA-9 was calculated to be 53.39 kJ/mol. In addition, reusability in the glycerolysis reaction was also evaluated, and 57.82% of the initial glycerolysis activity was retained after 9 consecutive applications. Furthermore, the CALA@NKA-9 was also used to catalyze the esterification (esterification of fatty acids with glycerol), however, the present CALA@NKA-9 cannot initiate the esterification. Therefore, the present CALA@NKA-9 is shown to be potential for DAG production through glycerolysis reaction.
研究领域:
生物技术
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酶工程
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化学工程
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生物化学
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DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2017
·
IF 4.529
Yuanyuan Fu,Renyong Zhao,Lu Zhang,Yanlan Bi,Hong Zhang,Cuihong Chen
The effect of the structure and composition of acylglycerol emulsifiers on the functionality of a palm-based shortening and quality of layer cake was investigated. The emulsifiers evaluated were distilled monoacylglycerol (DMG) and four acylglycerols (40% monoacylglycerol content) of octanoic acid (8:0), palmitic acid (16:0), stearic acid (18:0), and linoleic acid (18:2), designated as GMOct40, GMP40, GMS40, and GML40, respectively. The addition of GMP40 and GMS40 led to shortening with a higher solid fat content, finer crystals, and higher proportion of β’ form. These changes enhanced shortening’s function in aiding air incorporation and retention in cake batter, which improved the cake’s volume and crumb structure. However, the high monoacylglycerol content in DMG did not improve the properties of shortening and cake as compared to GMP40. In contrast, GML40 and GMOct40 had adverse effects on the functionality of shortening, which generated cakes with inferior crumb structure.
研究领域:
食品科学
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化学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
·
2023
·Vol. 100
·期 9
·733-741
·
IF 2
Zhenyu Wu,Jinjin Cai,Zhonghui Liu,Xiaojiang Liang,Shangzhi Yu,Yong Nie
In many regions, even if waste vegetable oil is used as raw material, the profits of biodiesel (fatty acid methyl ester, FAME) enterprises still remain restricted, and they are facing environmental problems caused by the by-product glycerol. Hence, value-added utilization of FAME and glycerol is a promising alternative to improve the competitiveness of biodiesel enterprises in the economy and environmental protection. In this paper, FAME and glycerol were utilized to prepare epoxidized acyl glycerides by transesterification and epoxidation. In the transesterification, acyl glycerides were prepared by reacting FAME and glycerol catalyzed by K 2 CO 3 . The contents of monoacyl glyceride, diacyl glyceride, and triacyl glyceride in the acyl glycerides were about 50%, 40%, and 10%, and the optimal conditions were a temperature of 200°C and the molar ratio of FAME to glycerol of 1:1. In the epoxidation, selectivity of epoxides was significantly affected by monoacyl glyceride content, and a treatment method was developed to control the monoacyl glyceride content <5%. In addition, the plasticity of epoxidized acyl glycerides to partially substitute dioctyl phthalate in polyvinyl chloride was studied, the overall mechanical properties, thermal stability, and extraction resistance were improved. In this work, FAME and glycerol were utilized to prepare epoxidized acyl glycerides with higher value-added, which provide a potential solution for improving the market competitiveness of biodiesel enterprises.
研究领域:
化学工程
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环境科学
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材料科学
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DOI
高影响因子
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY
·
2016
·Vol. 92
·期 7
·1801-1808
·
IF 2.738
Qinli Liu,Ting Yan,Zhao Jiang,Tao Fang
BACKGROUND The biodiesel by-product, crude glycerol including lower alcohols, could be used as the feedstock for producing monoacyglycerols (MAGs), which are commonly used as non-ionic surfactants and emulsifiers. In this work, lower alcohols (methanol, ethanol and isopropanol) in sub- and supercritical states were used as the solvents for MAG production. RESULTS Isopropanol is the best solvent for obtaining high monooleate (MOG) yield compared with methanol and ethanol. Moreover, the sub- and super-critical isopropanol shows better performance than the normal NaOH catalyzed or non-solvent process. The reaction loading of a batch reactor has a complicated effect on the yield. The maximum MOG yield can always be obtained at 60% loading. The square root modified quadratic model was utilized to analyze the relationship and to optimize reaction temperature (220–260 °C), reaction time (30–150 min), and isopropanol (0–4 mL). In the optimum condition (260 °C, 150 min, 4 mL of isopropanol), a high MOG yield of 67.8% can be obtained, well in agreement with the predicted value. CONCLUSION Isopropanol at sub- and super-critical state greatly improved the mass transfer between the immiscible reactants (triglyceride and glycerol). Compared with some methods with chemical catalyst, the method without any catalyst obtained higher MOG yield. © 2016 Society of Chemical Industry
研究领域:
生物化学
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可再生能源
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DOI
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2022
·
IF 7.425
Yali Li,Yi Zhang,Yibin Zhou,Yufei Zhang,Mingming Zheng
A novel and effective approach based on the two-step ethanolysis-esterification strategy was proposed for the controllable and simultaneous preparation of 1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL), 1,3-dioleoyl-2-palmitoyl-glycerol (OPO) and 1,3-dilinoleoyl-2-palmitoyl-glycerol (LPL) with adjustable proportions. Enzymatic ethanolysis of fractionated palm stearin was carried out to yield 2-monopalmitoylglycerol (79.4 ± 0.6 %) with over 91.0 % purity at the optimal conditions. The immobilized Candida sp. lipase (CSL) on octyl-functionalized ordered mesoporous silica (OMS-C 8 ) was applied to re-esterify 2-monopalmitoylglycerol with oleic acid and linoleic acid for the simultaneous production of OPL, OPO, and LPL. The total content in the final products was 81.5 %, with 91.3 % of palmitic acid (PA) content at the sn -2 position. Besides, OPL/OPO/LPL was conveniently prepared with suitable proportions for worldwide infants by adjusting the ratio of acyl donors. This paper provides a novel and effective two-step ethanolysis-esterification strategy for the development of human milk fat substitutes (HMFS).
研究领域:
食品科学
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化学工程
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生物技术
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产品关联
DOI
PubMed
高影响因子
Food Science and Technology
·
2023
·
IF 2.602
LI Ying,LEE Xiangjun,GUO Jianfeng,FENG Jingjing,XU Chenshuai,BAI Yujie,GUO Shiwei,WANG Fang
Palmitoleic acid (C16:1n7, POA), a 16-carbon ω-7 monounsaturated functional fatty acid, has been demonstrated a variety of beneficial properties to human health and a wide range of applications in nutrition, medical and chemical industries. Lipozyme® RM IM (Rhizomucor Miehei lipase), a Sn-1,3 specific lipase, was used to catalyze the hydrolysis of seabuckthorn fruit oil and produce monoglycates rich in palmitoleic acid. The fruit oil of seabuckthorn was used as the research object, the dosage of enzyme taking 10% wt.% oil, the influence of water/oil ratio, pH value and reaction temperature to hydrolysis rate were investigated, and then the response surface methodology was applied for optimizing the process conditions. Further, the relationship between the hydrolysis rate and the content of monoacylglycerol was studied under the optimal hydrolysis conditions. The result indicated that the optimal combined condition is as follows: the reaction temperature is 55°C, the pH is 7, the water-oil quality ratio is 1:1. The hydrolysis rate achieved 79.59% within 12 h in the condition above. Under the optimal conditions, the hydrolysis rate was positively correlated with the content of monoester, and the correlation coefficient was 0.999 within the first 10 h of the reaction. The hydrolysis rate was 66.76% at 10 h, and the content of monoglyceride reached the highest of 61.11%. Hereafter, the hydrolysis of monoglyceride began if the reaction continued. The content of palmitoleic acid increased from 27.11% to 40.84%, and that of linoleic acid increased from 4.51% to 33.34%, so the total amount of the two functional fatty acids reached 74.18%. Enzymatic hydrolysis can be an effective way to improve the function of seabuckthorn fruit oil.
研究领域:
食品科学
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生物化学
·
营养学
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产品关联
DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2020
·
IF 5.162
Xin Wang,Lihong He,Jianrong Huang,Nanjing Zhong
In this study, SBA-15 was modified by halogen & haloalkanes and later used to immobilize lipases. The hydrolysis activity and the glycerolysis performance of the immobilized lipases was carefully studied. Highest activity of the immobilized Candida antarctica lipase B (CALB), Lipase from Aspergillus oryzae (AOL), Lecitase® Ultra (LU) and lipase from Rhizomucor miehei (RML) was respectively at 5577, 12000, 2822 and 11,577 U/g; in addition, the highest activity was obtained from the lowest or moderate lipase loading, at 25.73, 90.72, 89.52 and 30.56 mg/g respectively. The mechanism of lipase immobilization was studied and it was through interfacial activation. The halogen & haloalkanes modification of SBA-15 afforded considerable glycerolysis activity for diacylglycerols (DAG) preparation. CALB@SBA-15-CH 2 CH 2 (CF 2 ) 5 CF 3 and CALB@SBA-15-CH 2 CH 2 (CF 2 ) 7 CF 3 were suitable for DAG production, they both exhibited good reusability in glycerolysis reaction, with 117.36% and 93.06% of their initial glycerolysis activity retained respectively after ten cycles of reuse. The relationships between temperature with triacylglycerols (TAG) conversion were ln V 0 = 3.13–3.07/T and ln V 0 = 7.90–4.64/T respectively for CALB@SBA-15-CH 2 CH 2 (CF 2 ) 5 CF 3 and CALB@SBA-15-CH 2 CH 2 (CF 2 ) 7 CF 3 ; in addition, their activation energy ( Ea ) was respectively at 25.50 and 38.54 kJ/mol.
研究领域:
生物化学
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酶工程
·
材料科学
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产品关联
DOI
PubMed
高影响因子
BIOPROCESS AND BIOSYSTEMS ENGINEERING
·
2015
·Vol. 38
·期 11
·2053-2061
·
IF 1.997
Zeng Chao-Xi,Qi Sui-Jian,Xin Rui-Pu,Yang Bo,Wang Yong-Hua
In this study, enzymatic selective esterification of oleic acid with glycerol based on deep eutectic solvent acting as substrate and solvent was studied. As choline chloride (ChCl) or betaine can effectively change the chemical reaction characteristics of glycerol when they are mixed with a certain molar ratio of glycerol, several factors crucial to the lipase catalytic esterification of glycerol with oleic acid was investigated. Results showed that, betaine had more moderate effects than ChCl on the lipase, and water content had an important influence of the esterification and the enzyme selectivity. Significant changes of the glyceride compositions and enzyme selectivity were found in ChCl adding system compared with pure glycerol system; optimum accumulation of DAG especially 1,3-DAG because of the eutectic effect of ChCl was found in this system. Furthermore, in a model 1,3-DAG esterification synthesis system catalyzed by Novozym 435, high content (42.9 mol%) of the 1,3-DAG could be obtained in ChCl adding system within 1 h.
研究领域:
生物化学
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食品科学
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产品关联
DOI
PubMed
高影响因子
Journal of Oleo Science
·
2020
·
IF 1.304
Maomao Kou,Siting Feng,Nanjing Zhong
In this study, Lecitase® Ultra (LU) was immobilized onto the parent and the amino-functionalized SBA-15. The immobilization conditions were studied and the activity of the parent SBA-15 supported LU (SBA-15-LU) was found to be at 2177.78 ± 101.84 U/g. After 3-aminopropyl and n-(2-aminoethyl)-3-aminopropyl groups functionalization, enzymatic activity was increased to 3555.56 ± 200.21 and 3444.44 ± 346.41 U/g respectively. The immobilized LU samples were then used to catalyze glycerolysis. The possibility for diacylglycerols (DAG) and monoacylglycerols (MAG) production was evaluated and it was found only suitable for DAG production. In addition, the glycerolysis activity of the immobilized LU was impaired by the tert-pentanol and solvent-free was found suitable. Similar DAG content over 50 wt% could be obtained from glycerolysis by the three immobilized LU samples. The reusability in glycerolysis was evaluated, and 9.79 % of the initial glycerolysis activity was remained from the SBA-15-LU after 5 cycles of reuse. Encouragingly, after 3-aminopropyl and n-(2-aminoethyl)-3-aminopropyl groups functionalization, 62.93 and 83.91% of their initial activity was respectively remained after 5 cycles of reuse.
研究领域:
生物化学
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酶工程
·
食品科学
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2022
·
IF 5.895
Zheng Zhou,Yu-Lian Li,Feng Zhao,Ran Xin,Xu-Hui Huang,Yu-Ying Zhang,Dayong Zhou,Lei Qin
Lipid structures affect lipid oxidation, causing differences in types and contents of volatiles and nonvolatiles in various foods. In this study, the oxidation differences of monoacylglycerol (MAG), triacylglycerol (TAG), phosphatidylethanolamine (PE), and phosphatidylcholine (PC) with oleoyl residues and oleic acid (FA) during thermal treatment were investigated. Volatiles and nonvolatiles were monitored by gas chromatography–mass spectrometry and ultrahigh-performance liquid chromatography-Q-Exactive HF-X Orbitrap Mass Spectrometer, respectively. The results showed that the structures of MAG and TAG could delay the chain initiation reaction. The polar heads of PC and PE remarkably influenced the oxidation rate and the formation of the oxidation products probably due to the hydrogen bonds formed with free radicals. Among the volatile oxidation products, aldehydes, acids, and furans with eight or nine carbon atoms accounted for the majority in FA, MAG, TAG, and PC samples, but PE samples mainly generated ketones with nine or 10 carbon atoms. The formation of nonvolatile products in TAG samples possessed significant stage-specific changes. Fatty acid esters of hydroxy fatty acids were only produced in the free fatty acid oxidation model. The activity of chemical bonds participating in the truncation reaction decreased to both sides from the double bond position.
研究领域:
食品化学
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脂质科学
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分析化学
·
物理化学
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）