JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2023
·
IF 6.1
Linghui Kong,Xinyi Fan,Limin Guo,Qingqing Jiang,Jianbo Xiao,Daming Fan,Mingfu Wang,Yueliang Zhao
In this study, we investigated the inhibitory effects of three soybean isoflavones and two soybean phytosterols on the formation of 3-chloropropane-1,2-diol fatty acid esters (3-MCPDE) and aldehydes in heated soybean oil model. 0.4 mM of genistin, genistein, daidzein, stigmasterol, and β-sitosterol significantly reduced 3-MCPDE formation by 25.7, 51.4, 21.4, 61.6, and 55.7%, and total aldehydes formation by 42.03, 43.94, 28.36, 54.74, and 39.23%, respectively. Further study showed that stigmasterol reduced the content of glycidyl esters (GEs) and glycidol, two key intermediates of 3-MCPDE, and prevented fatty acids degradation in the oils. Moreover, the effects of continuous frying time on the content of stigmasterol and the migration of stigmasterol were evaluated in the fried dough sticks model system. The content of stigmasterol in soybean oil was found to be significantly decreased with prolonged heating time. The concentrations of stigmasterol in fried dough sticks and the migration rates of stigmasterol from soybean oil to fried dough sticks decreased with repeated frying sessions. In addition, stigmasterol undergoes oxidative changes during heat treatment, and the oxidation products including 5,6α-epoxystigmasterol, 5,6β-epoxystigmasterol, 7α-hydroxystigmasterol, 7β-hydroxystigmasterol, stigmasterlol-3β,5α,6β-triol, and 7-ketostigmasterol were identified in the frying oils but not in the fried dough sticks. Overall, stigmasterol could be added to soybean oil to reduce 3-MCPDE and aldehydes formation, and reacting with GEs/glycidol and protection of lipid acids from oxidation may be the mechanism of action of stigmasterol.
研究领域:
食品科学
·
植物化学
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产品关联
DOI
PubMed
高影响因子
Catalysis Science & Technology
·
2019
·Vol. 9
·期 12
·3270-3278
·
IF 5.726
Dan Liu,Chengwei Qiu,Minbo Li,Yanyu Xie,Lu Chen,Huaxiang Lin,Jinlin Long,Zizhong Zhang,Xuxu Wang
Kornblum oxidation (benzyl bromide to benzaldehyde) can be realized efficiently by NaOH-modified graphitic carbon nitride (g-C3N4). Different from the oxidation reaction carried out at high temperature using DMSO as an oxidant, our reaction is eco-friendly because it is carried out at room temperature under LED light irradiation using molecular oxygen as an oxidant, which avoids the problems of toxicity, pollution and purification. Alkali treatment leads to the surface deprotonation of g-C3N4 to form NaOH-modified g-C3N4 (Na/g-C3N4). The modifications of the electronic structure and surface chemical environment of g-C3N4 facilitate light absorption and formation of ˙O2− and therefore make the conversion of benzyl bromide reach up to 99%. This work demonstrates a green and sustainable route for benzaldehyde production and the superiority of g-C3N4 for organic syntheses.
研究领域:
有机化学
·
环境科学
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DOI
高影响因子
Food Chemistry-X
·
2025
·
IF 8.2
Mantong Zhao,Zhongyuan Liu,Mengyin Zha,Ying Sun,Haohao Shi,Xueying Zhang,Chuan Li,Guanghua Xia
The effect of aldehydes from lipid oxidation on the generation of heterocyclic amine 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) during pan-frying of golden pompano fillets was investigated. It was observed the aldehydes that contribute to thiobarbituric acid reactive substances (TBARS) value significantly promoted PhIP generation ( p < 0.05). The defat treatment of fresh fish tissue significantly reduced the PhIP formation in pan-fried products ( p < 0.05). During pan-frying, massive aldehydes were generated in a time-dependent manner with acrolein, propanal, hexanal, 4-hydroxy-nonenal (HNE), and 2,4-decadienal (DDE) as the abundant species. In the established chemical model, these aldehydes congruously promoted PhIP formation with the increased concentration, especially acrolein, HNE and DDE. Therefore, aldehydes could significantly enhance the PhIP generation under processing. However, except for propanal and hexanal, the promoting effect was slightly decreased with high levels of aldehydes addition due to the strong electrophilic properties and participation of reaction with the amino group of phenylacetaldehyde, creatinine, even PhIP.
研究领域:
食品科学
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毒理学
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产品关联
DOI
PubMed
高影响因子
Applied Sciences-Basel
·
2019
·Vol. 9
·期 9
·1792
·
IF 2.217
Anqiu Liu,Xiaochen Wang,Daming Gao,Le Wang,Junjie Cheng,An Wang,Zehui Zhang
Chemoselective hydrogenation of aldehydes with heterogeneous catalysts under mild conditions is of great importance but remains a major challenge. Herein, an efficient strategy was developed for low temperature chemoselective hydrogenation of aldehydes with broad substrate scope over a magnetic material supported palladium catalyst (γ-Fe2O3@HAP-Pd). Aldehydes bearing various reducible functional groups readily underwent hydrogenation to give the corresponding primary alcohols with moderate to excellent yield at room temperature in aqueous solutions. The Hammett equation revealed that the hydrogenation of aromatic aldehydes proceeded via an anionic intermediate. Additionally, when the temperature increased to 70 °C, toluene was obtained by the deoxygenation of benzaldehyde in excellent yield. Furthermore, the γ-Fe2O3@HAP-Pd could be recycled up to six times without loss of activity and metal leaching.Keywords:selective hydrogenation;aldehydes;Pd catalysts;mild conditions
研究领域:
催化化学
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材料科学
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DOI
高影响因子
SYNTHESIS-STUTTGART
·
2015
·Vol. 48
·期 02
·231-237
·
IF 2.689
Yongbo Zhou,Zhongwen Li,Xiao Yang,Xiulin Chen,Mei Li,Tieqiao Chen,Shuang-Feng Yin
A simple and environmentally benign method was developed for the synthesis of chalcones in high to excellent yields by a phosphorous acid promoted alkyne–aldehyde hydration–condensation in an oil/water two-phase system. The method is the first efficient protocol for the preparation of chalcones that is mediated by a simple Brønsted acid in a two-phase system.
研究领域:
有机化学
·
绿色化学
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DOI
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
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2020
·
IF 4.006
Meizhen Xie,Xiyu Dong,Yan Yu,Leqi Cui
Lipid oxidation is a major food safety issue for edible oils . The objective of this study was to develop a simple method for detecting lipid oxidation through the color change of a composite film. Schiff's reagent which can form color compound with lipid oxidation products—aldehydes was incorporated into polyvinyl alcohol (PVA) to form the composite film. The effects of PVA molecular weight (Mw), Schiff's reagent/PVA ratio and glycerol content on the response of the composite film to aldehyde were investigated. Sunflower seed oil with various extent of oxidation was used to evaluate the effectiveness of the composite film for lipid oxidation detection. The results showed that the composite film formed with lower PVA Mw turned from colorless to purple upon aldehyde exposure. Higher Schiff's reagent/PVA ratio and glycerol content led to shorter response time and larger color change after aldehyde exposure. The color change of the composite film was linearly (R 2 = 0.96) related to aldehyde concentration. The oxidation status of four sunflower seed oil samples out of five were correctly identified by the composite film. Although the accuracy of this method was 80% in this study, it still shows great potential for lipid oxidation detection application.
研究领域:
食品科学
·
化学
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产品关联
DOI
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Mantong Zhao,Ying Sun,Yikai Huang,Wei Yang,Haohao Shi,Jiamei Wang,Zhongyuan Liu,Xueying Zhang,Chuan Li,Guanghua Xia,Haohao Wu,Xuanri Shen,Dayong Zhou
The effects of phenolic acid grafted-chitosan hydrocolloids (CS-g-GA/FA) on aldehyde contents from lipid oxidation in golden pompano fillets during pan-frying was investigated with an established high-performance liquid chromatography-mass spectrum method. Results indicated that pan-frying induced profound lipid oxidation and aldehydes generation with propanal, hexanal, nonanal, trans , trans -2,4-decadienal, and 4-hydroxy-2-nonenal as the abundant species. CS-g-FA and CS-g-GA effectively decreased their contents by 23.74–27.42 %, 61.69–67.42 %, 41.83–53.91 %, 29.91–48.79 %, and 61.57–65.39 % after 3 min. Most aldehyde contents decreased with the extension of pan-frying time due to the volatilization and reaction. In terms of substrate depletion, CS-g-phenolic acids effectively inhibited unsaturated fatty acids oxidation due to their decent antioxidant activity than CS. The significant lower retention rates of aldehydes in the CS-g-phenolic acids groups compared with control in chemical mode confirmed the carbonyl ammonia condensation. These results suggested that CS-g-phenolic acids serve as novel coating to reduce hazardous compounds during aquatic products thermal processing.
研究领域:
食品科学
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海洋生物学
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产品关联
DOI
PubMed
高影响因子
Molecular Catalysis
·
2024
·
IF 3.9
Hui Cao,Yu Liu,Yanqiu Li,Yingxiong Wang,Yan Qiao
The α-hydroxyketones and 1,2-diols are versatile building blocks for the preparation of many natural and synthetic bioactive compounds. In this study, N-heterocyclic carbon (NHC) promoted coupling of several aldehydes with formaldehyde enabled the synthesis of 1,2-diols in moderate to high yields. The highly selective conversion of several aldehydes and formaldehyde into 1,2-diols and α-hydroxyketones was achieved in a one-pot two-step process via [BHMIm][OAc] as a key intermediate. In the first step, formaldehyde was quantitatively converted to [BHMIm][OAc] through the carbene addition. In the second step, 1,2-diol was produced through the intermediate-promoted aldol reaction. The results showed that benzaldehyde was capable to react with [BHMIm][OAc] efficiently, with a 54.1% yield of 1,2-diol after the 3-hour reaction at 85 °C. Among the tested benzaldehyde derivatives, the 4-nitrobenzaldehyde showed the highest yield of 1,2-diol (73.3%) under the optimized reaction conditions. Incorporation of an electron rich group on benzaldehyde promoted carbene regeneration. With 4-methoxybenzaldehyde as the substrate, the yield of α-hydroxyketone reached a maximum of 30.6%. Additionally, dihydroxyacetone derivatives were detected in the system. In situ NMR technique confirmed that it was generated from the further reaction of the carbene/1,2-diol complex with another aldehyde. Based on the results of NMR spectroscopy and mass spectrometry, a possible reaction pathway was also proposed.
研究领域:
有机化学
·
合成化学
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产品关联
DOI
高影响因子
JOURNAL OF FOOD COMPOSITION AND ANALYSIS
·
2022
·
IF 4.52
Qiuyu Lin,Jiannan Sun,Yuanchao Wang,Meiying Ye,Heyong Cheng
Due to endogenous existence and hazardous properties, the quantification of fatty and aromatic aldehydes in food matrices is indispensable to food safety. Current analytical methodologies for aldehydes in food suffer from several drawbacks (typically complicated pretreatment, long analysis time and low analytical throughput, low sensitivity, etc.). In this work, a highly sensitive, high-throughput and sample pretreatment-free method for aldehyde analysis was developed to address the above problems, where in situ extraction and derivatization of aldehydes with hydrazines to hydrazones were integrated into reactive paper spray ionization mass spectrometry (reactive PSI-MS) considering weakly ionizable properties of aldehydes. Four aldehydes, formaldehyde, acetaldehyde, propionaldehyde and benzaldehyde were reacted with dansyl hydrazine in 1.5 % v/v HAc acidified methanol on the qualitative fast-speed filter paper for 5 min, and then a voltage (+4 kV) was applied to initiate paper spray for mass spectrometry detection with internal calibration by dansyl amide. Once the completion of MS analysis , the glass plate was moved to introduce the second triangular tip towards the MS inlet (5 mm apart) for next trial, achieving high-throughput reactive PSI-MS analysis (60 h −1 ). The four aldehydes showed good linearity in the concentration range from 2 to 150 μM with low detection limits of 0.03–0.15 μM. The method was applied to direct quantification of four aldehydes in 15 kinds of foods such as vegetables, fruits and meat products. The proposed method has the advantages of simple operation, high efficiency and high sensitivity, making it attractive to routine analysis of aldehydes in food, environmental and biological samples.
研究领域:
分析化学
·
食品安全
·
质谱分析
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DOI
高影响因子
JOURNAL OF CATALYSIS
·
2020
·
IF 7.888
Yunchao Feng,Sishi Long,Guihua Yan,Binglin Chen,Jonathan Sperry,Wanjie Xu,Yong Sun,Xing Tang,Xianhai Zeng,Lu Lin
Manganese catalyzed transfer hydrogenation (CTH) of aldehydes is an attractive method for the synthesis of alcohols. Here, we report a novel and efficient MnO@C-N catalyst for the CTH of biomass-derived 5-hydroxymethylfurfural and other aldehydes to alcohols in high yields. Catalytic experimental studies showed that the MnO and nitrogen-doping are responsible for the high selectivity and high conversion, respectively. Isotopic labelling experiments demonstrated that the CTH of aldehydes to alcohols over MnO@C-N is via a route by direct hydrogen transfer . Kinetic studies revealed that the N-doping can improve the reaction rate and reduce the activation energy of the aldehydes conversion. DFT calculations also indicated that both pyridine N and pyrrolic N doping can reduce the energy barrier for acetone desorption by the interaction between N and hydroxyl-H of alcohol. Furthermore, MnO@C-N showed good recyclability for at least five reaction cycles. We anticipate that these results can drive progress in the manganese catalyzed transfer hydrogenation reaction.
研究领域:
化学
·
催化科学
·
材料科学
✓ 已验证
DOI
高影响因子
Nature Communications
·
2022
·Vol. 13
·期 1
·1-12
·
IF 17.694
Cui Zhihao,Dong Xing’an,Cho Sung Gu,Tegomoh Modeste N.,Dai Weidong,Dong Fan,Co Anne C.
Deoxygenation of aldehydes and their tautomers to alkenes and alkanes has implications in refining biomass-derived fuels for use as transportation fuel. Electrochemical deoxygenation in ambient, aqueous solution is also a potential green synthesis strategy for terminal olefins. In this manuscript, direct electrochemical conversion of vinyl alcohol and acetaldehyde on polycrystalline Cu to ethanol, ethylene and ethane; and propenol and propionaldehyde to propanol, propene and propane is reported. Sensitive detection was achieved using a rotating disk electrode coupled with gas chromatography-mass spectrometry. In-situ attenuated total reflection surface-enhanced infrared absorption spectroscopy, and in-situ Raman spectroscopy confirmed the adsorption of the vinyl alcohol. Calculations using canonical and grand-canonical density functional theory and experimental findings suggest that the rate-determining step for ethylene and ethane formation is an electron transfer step to the adsorbed vinyl alcohol. Finally, we extend our conclusions to the enol reaction from higher-order soluble aldehyde and ketone. The products observed from the reduction reaction also sheds insights into plausible reaction pathways of CO 2 to C 2 and C 3 products.
研究领域:
化学工程
·
电化学
·
能源科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
·
2019
·
IF 3.714
Jun Cao,Xin Jiang,Qianyuan Chen,Hao Zhang,Huihui Sun,Wei-Min Zhang,Chuan Li
Olive and camellia oils were monitored and compared during heating at 120 °C, 150 °C and 180 °C for 24 h to determine the possible thermal oxidation mechanism of oleic acid triglyceride. The results demonstrated that octanal, nonanal, decanal, 2-decenal and 2-undecenal were the characteristic carbonyls for oleic acid-rich oils. The oxidation rule of oil was easily determined at 120 °C, at which point changes in the acid value, peroxide value , anisidine value and carbonyl compounds corresponded to changes in fatty acids and tocopherols . However, the oxidation rule of oil was different at higher temperatures. According to the evolution of five characteristic aldehydes, four types of oxidation pathways of oleic acid triglyceride were obtained: Decanal and 2-undecenal came from the homolysis of 8- hydroperoxide. Nonanal was from the homolysis of 10- hydroperoxide and 9- hydroperoxide. Octanal was from the homolysis of 11- hydroperoxide. 2-Decenal was from the homolysis of 9- hydroperoxide. Homolysis B-scission of 10-hydroperoxide (nonanal), 11-hydroperoxide (octanal) and 8- hydroperoxide (decanal) was predominant at 120 °C, but was weakened as the temperature increased to 180 °C. Hence, the temperature had a significant effect on the formation and decomposition of hydroperoxide positional isomers.
研究领域:
食品科学
·
生物化学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）