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LWT-FOOD SCIENCE AND TECHNOLOGY · 2019 · IF 3.714

Sensory-directed flavor analysis of off-flavor compounds in infant formula with deeply hydrolyzed milk protein and their possible sources

Ping Yang,Chen Liu,Huanlu Song,Lijin Wang,Xueqing Wang,Jiacai Hua

Off-flavor compounds in IF-DHMP were identified using sensory-directed analysis. In total, 56 types of aroma-active compounds were identified in the off-flavor (OF) samples, positive control (PC) samples, and accelerated oxidation (AO) samples. The Aroma Extraction Dilution Analysis (AEDA) results showed that methional, generated via Maillard reaction , was the most important component with the highest dilution factor in OF. The results of aroma recombination, omission and spiking experiment revealed that compounds such as pentanal, methional, ( E )-2-nonenal, 3-methylbutanal, ( E )-2-heptenal, nonanal, ( E,E )-2,4-heptadienal, 1-penten-3-one, 1-octen-3-one, and ( E,E )-2,4-nonadienal were the major sources of off-flavor in OF. We observed that the off-flavor in OF samples originated due to proteolysis, Maillard reaction, or lipid oxidation during processing rather than due to lipid oxidation during storage.

研究领域: 食品科学 · 化学感官科学 · 分析化学 · 婴幼儿营养
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MOLECULES · 2022 ·Vol. 27 ·期 2 ·352 · IF 4.927

Evolution Analysis of Free Fatty Acids and Aroma-Active Compounds during Tallow Oxidation

Shiqing Song,Feiting Zheng,Xiaoyan Tian,Tao Feng,Lingyun Yao,Min Sun,Lei Shi

To explore the role of fatty acids as flavor precursors in the flavor of oxidized tallow, the volatile flavor compounds and free fatty acid (FFAs) in the four oxidization stages of tallow were analyzed via gas chromatography (GC)–mass spectrometry (MS), the aroma characteristics of them were analyzed by GC–olfactory (GC-O) method combined with sensory analysis and partial least-squares regression (PLSR) analysis. 12 common FFAs and 35 key aroma-active compounds were obtained. Combined with the results of odor activity value (OAV) and FD factor, benzaldehyde was found to be an important component in unoxidized tallow. (E,E)-2,4-Heptadienal, (E,E)-2,4-decadienal, (E)-2-nonenal, octanal, hexanoic acid, hexanal and (E)-2-heptenal were the key compounds involved in the tallow flavor oxidation. The changes in FFAs and volatile flavor compounds during oxidation and the metabolic evolution of key aroma-active compounds are systematically summarized in this study. The paper also provides considerable guidance in oxidation control and meat flavor product development.Keywords:oxidized tallow;aroma-active compounds;solvent-assisted flavor evaporation;gas chromatography-olfactometry;partial least-squares regression

研究领域: 食品科学 · 分析化学 · 农业化学
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Frontiers in Chemistry · 2020 · IF 3.693

Poly(ethylene glycol)s With a Single Cinnamaldehyde Acetal Unit for Fabricating Acid-Degradable Hydrogel

Zhao Xinyue,Shan Pengfei,Liu Haiwei,Li Daai,Cai Peihan,Li Zhongyu,Li Zhihui

A synthetic route to prepare a poly(ethylene glycol) with a single cinnamaldehyde acetal unit in the polymer chain, was successfully established using a newly synthesized cinnamaldehyde acetal diethylene glycol (CADEG) as initiator. This HO-PEG(ca)-OH is non-toxic and would be degraded into a cinnamaldehyde and two PEG diols in acid environment. A whole polyethylene glycol based hydrogel was easily fabricated by thiol-ene “click” reaction in alkalescence aqueous solution using acrylate-PEG(ca)-acrylate and 4-arm PEG-SH as raw materials at room temperature. The gel time was dependent on the pH of the solution and its alkalinity can promote gel. The hydrogel can be degradable in acidic conditions and the stronger the acidity, the faster the degradation. This HO-PEG(ca)-OH also can be used in synthesis of cinnamaldehyde containing PEG derivatives, block copolymers or other acid degradable materials.

研究领域: 材料科学 · 生物医学工程
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ANALYTICA CHIMICA ACTA · 2024 · IF 5.7

Highly sensitive and selective electrochemical biosensor using odorant-binding protein to detect aldehydes

Cong Peng,Yutong Sui,Chaohua Fang,Hongxu Sun,Wenxin Liu,Xinying Li,Chen Qu,Wenhui Li,Jiemin Liu,Chuandong Wu

Recently, various biosensors based on odorant-binding proteins (OBPs) were developed for the detection of odorants and pheromones. However, important data gaps exist regarding the sensitive and selective detection of aldehydes with various carbon numbers . In this work, an OBP2a-based electrochemical impedance spectroscopy (EIS) biosensor was developed by immobilizing OBP2a on a gold interdigital electrode, and was characterized by EIS and atomic force microscopy . EIS responses showed the OBP2a-based biosensor was highly sensitive to citronellal , lily aldehyde, octanal , and decanal (detection limit of 10 −11  mol/L), and was selective towards aldehydes compared with interfering odorants such as small-molecule alcohols and fatty acids (selectivity coefficients lower than 0.15). Moreover, the OBP2a-based biosensor exhibited high repeatability (relative standard deviation: 1.6%–9.1 %, n = 3 for each odorant), stability (NIC declined by 3.6 % on 6th day), and recovery (91.2%–96.6 % on three real samples). More specifically, the sensitivity of the biosensor to aldehydes was positively correlated to the molecular weight and the heterocyclic molecule structure of the odorants. These results proved the availability and the potential usage of the OBP2a-based EIS biosensor for the rapid and sensitive detection of aldehydes in aspects such as medical diagnostics, food and favor analysis, and environmental monitoring.

CAS / MDL: 288-32-4
研究领域: 生物传感器 · 电化学 · 分析化学 · 环境监测 · 医疗诊断 · 食品分析
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2023 · IF 4.2

Continuous Synthesis of Methacrolein over Sulfonic Acid Resin Catalysts: Unraveling the Effect of Acid Strength and Solvent Permittivity

Tianhao Zhang,Yuhang Bian,Luming Wang,Hui Zhao,Gang Wang,Chunshan Li

Herein, a novel continuous fixed-bed process for methacrolein (MAL) production via aldol condensation of formaldehyde with propionaldehyde over a sulfonic acid resin was developed, which exhibited high efficiency and remarkable catalytic stability. The influence of Brønsted acid strength and solvent permittivity on aldol reaction was revealed, and the optimal sulfonic acid resin (NKC-9) with suitable acid strength (H0 = 0.46) was identified. Meanwhile, the occupancy of water molecules on acid sites, which would lead to side reactions and catalyst deactivation, could be effectively inhibited through the construction of a liquid–solid catalytic system in non-polar media. The propionaldehyde conversion and MAL yield could reach up to 97.3 and 90.1% after optimization using the response surface method, respectively. Kinetic studies revealed that the surface reaction was the rate-limiting step with an activation energy of 57.1 kJ/mol. No deactivation behavior was observed for this kind of catalyst after 300 h on stream.

研究领域: 化学工程 · 催化 · 有机化学
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EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY · 2019 ·Vol. 121 ·期 7 ·1900040 · IF 1.852

Malondialdehyde, 4-Hydroxy-2-Hexenal, and 4-Hydroxy-2-Nonenal in Vegetable Oils: Formation Kinetics and Application as Oxidation Indicators

Lukai Ma,Guoqin Liu,Xinqi Liu

The formation of three toxic reactive aldehydes, malondialdehyde (MDA), 4-hydroxy-hexenal (HHE), and 4-hydroxy-2-nonenal (HNE), is investigated in five commonly consumed vegetable oils using a method based on the Schaal oven test. HHE is only detected in linseed oil (LO) and rapeseed oil (RO), while MDA and HNE are found to be present in all tested oils. The formation potential of MDA, HHE, and HNE in the tested oils is closely related to the initial polyunsaturated fatty acid (PUFA) content in the oil. Correlation analyses reveal low correlation coefficients for MDA, determining its unsuitability to evaluate the oxidation of oils with low PUFA content, such as palm oil and camellia oil; in contrast, HHE and HNE show sufficient correlations with other oxidation indices in all tested oils. Furthermore, regression analysis indicates that HHE content can predict the oxidation of ω-3 type oil, while HNE content can estimate oxidative deterioration of ω-6 type oils. Particularly, HNE content can also evaluate the oxidation of ω-9 type oils such as PO and CLO with relatively low PUFA level for the high correlations (>0.991, P < 0.01) toward the total oxidation value (TOTOX). Practical Applications : Edible oil consumption continues to increase worldwide. Therefore, it is very important to understand the conditions under which potentially health-damaging compounds are formed in these oils and to develop methods to inhibit their formation or eliminate them from the oils. This study investigates the formation of three toxically reactive aldehydes, namely MDA, HHE, and HNE, through lipid oxidation, specifically PUFA peroxidation. The application of these aldehydes as oxidation indicators for different vegetable oils is also explored. This work could prove beneficial for the quality control of vegetable oils in the edible oil industry. The formation of three toxic aldehydes, MDA, HHE, and HNE in different types of vegetable oils is investigated. Considerable amounts of MDA, HHE, and HNE is found in all the tested oils. The results show the formation of these three aldehydes is competitive. Besides, MDA content is not appropriate to evaluate the oxidation of oils with low PUFA content, such as PO and CLO; while HHE and HNE can characteristically depict the oxidation of ω-3 and ω-6 type oil.

CAS / MDL: 75-09-2
研究领域: 食品科学 · 营养学
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ENERGY & FUELS · 2020 · IF 3.421

Synthesis of Jet Fuel Range Cycloalkanes with Cyclopentanone and Furfural

Qiang Liu,Xinghua Zhang,Qi Zhang,Qiying Liu,Chenguang Wang,Longlong Ma

In this work, high-density jet fuel range cycloalkanes were synthesized in high yields (∼80%) by solvent-free aldol condensation of cyclopentanone and furfural followed by hydrodeoxygenation (HDO). Sodium-promoted magnesium–aluminum mixed oxides (Na–MgAlO) exhibited a high catalytic activity in the aldol condensation of cyclopentanone and furfural under a solvent-free condition. Furfural conversion of 99.4% with almost 100% selectivity for 2-(2-furylmethylidene) cyclopentanone and 2,5-bis(2-furylmethylidene) cyclopentanone were obtained over the 5.7%Na–MgAlO catalyst under mild conditions (80 °C, 2 h). The Na–MgAlO catalysts were characterized by multiple technologies, such as N2 physisorption, powder X-ray diffraction, Fourier transform infrared spectra, and CO2 temperature-programmed desorption, and so on. It was found that the high catalytic activity for aldol condensation of cyclopentanone and furfural was clearly related to the amount and strength of basicity of Na–MgAlO catalysts. Finally, the condensation products were converted to jet fuel range cycloalkanes by HDO over Pd/C and HZSM-5 catalysts. The density, heating value, and freezing point of the HDO liquid products were 0.83 g/cm3, 43.1 MJ/Kg, and −27.7 °C, respectively. The results suggest that these cycloalkanes are promising as blending components for jet fuel.

研究领域: 能源化学 · 催化化学
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JOURNAL OF CHEMICAL RESEARCH · 2018 · IF 0.668

A Practical Oxidative Conversion of Aldehydes into N-Chloroaldimines

Can Jin,Feng Wang,Bin Sun,Xiaohui Zhuang

A novel method for the preparation of N-chloroaldimines from commonly available aromatic aldehydes has been developed. The reaction proceeded effectively by two steps: aldehydes were initially transformed into imines and then chloro-substitution with NaClO2 gave the N-chloroaldimines. This simple protocol allows for the preparation of a variety of aromatic N-chloroaldimines in moderate to excellent yields without the isolation of the imine intermediate. We also found that 3-nitrobenzaldehyde and 4-cyanobenzaldehyde were converted into the related benzonitrile directly under the standard conditions.

CAS / MDL: 112926-00-8
研究领域: 有机化学 · 合成化学
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Molecular Catalysis · 2018 · IF 0

Mechanistic insights on catalytic conversion fructose to furfural on beta zeolite via selective carbon-carbon bond cleavage

Yueqing Wang,Xiaohai Yang,Hongyan Zheng,Xianqing Li,Yulei Zhu,Yongwang Li

The mechanism for the formation of furfural by dehydration of d -fructose via selective carbon-carbon (C C) bond cleavage was investigated over beta zeolite (Hβ). Several different pore size zeolites were employed to determine the shape selectivity of fructose isomers. Zeolitic pore sizes that smaller than the kinetic diameter of cyclic fructose also produced yield furfural (∼22.5%), while the high yield (66.0%) of hydroxymethylfurfural (HMF) can be achieved over large pore zeolite (USY zeolite), which could accommodate the cyclic fructose. These results indicated that the furfural formation likely began with acyclic fructose. In situ 13 C NMR and GC MS studies, using labeled 13 C-1-fructose as substrate, suggested that the conversion of fructose to furfural involved with splitting of the C5-C6 bond. Furthermore, the C1 compound from the cleavage of C C bond was identified as formaldehyde, inferring that the selective scission of C C bond was ascribe to the retro-aldol reaction. Interestingly, in situ NMR studies implied that the acyclic fructose mainly derived from pyranose forms. In addition, compared with glucose, fructose directly converted to furfural at the higher yield and reaction rate.

研究领域: 催化化学 · 有机化学
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APPLIED CATALYSIS A-GENERAL · 2022 · IF 5.723

Efficient conversion of furfural to furfural amine over 4Ru1Co/AC catalyst

Le Gou,Longfei Xie,Yuanyuan Wang,Liyi Dai

The production of amine intermediates from biomass is capturing increasing attention. Herein, an efficient conversion of furfural to furfural amine over RuCo/AC catalyst under hydrothermal conditions has been investigated. The effects of different carriers, bimetals, and reaction conditions were systematically investigated in green solvents (water). Fully conversion of furfural and high furfural amine yield (92.13%) at 80 ℃ for 1 h over 4Ru1Co/AC. The excellent catalytic performance of 4Ru1Co/AC was attributed to its high acidity and good hydrogenation ability, as well as the synergistic effect between Ru-Co alloy formations and the activated carbon. Importantly, the highly selective preparation of furfural to furfural amine is a promising way to high-value utilization of cellulosic biomass in green solvents.

研究领域: 化学工程 · 催化反应 · 绿色化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2017 · IF 3.154

Simultaneous Analysis of Malondialdehyde, 4-Hydroxy-2-hexenal, and 4-Hydroxy-2-nonenal in Vegetable Oil by Reversed-Phase High-Performance Liquid Chromatography

Lukai Ma,Guoqin Liu

A group of toxic aldehydes such as, malondialdehyde (MDA), 4-hydroxy-2-hexenal (HHE), and 4-hydroxy-2-nonenal (HNE) have been found in various vegetable oils and oil-based foods. Then simultaneous determination of them holds a great need in both the oil chemistry field and food field. In the present study, a simple and efficient analytical method was successfully developed for the simultaneous separation and detection of MDA, HHE, and HNE in vegetable oils by reversed-phase-high-performance liquid chromatography (RP-HPLC) coupled with photodiode array detector (PAD) at dual-channel detection mode. The effect of various experimental factors on the extraction performance, such as coextraction solvent system, butylated hydroxytoluene addition, and trichloroacetic acid addition were systematically investigated. Results showed that the linear ranges were 0.02–10.00 μg/mL for MDA, 0.02–4.00 μg/mL for HHE, and 0.03–4.00 μg/mL for HNE with the satisfactory correlation coefficient of >0.999 for all detected aldehydes. The limit of detection (LOD) and limit of quantification (LOQ) of MDA, HHE, and HNE were ∼0.021and 0.020 μg/mL, ∼0.009 and 0.020 μg/mL, and ∼0.014 and 0.030 μg/mL, respectively. Their recoveries were 99.64–102.18%, 102.34–104.61%, and 98.87–103.04% for rapeseed oil and 96.38–98.05%, 96.19–101.34%, and 96.86–99.04% for French fries, separately. Under the selected conditions, the developed methods was successfully applied to the simultaneous determination of MDA, HHE, and HNE in different tested vegetable oils. The results indicated that this method could be employed for the quality assessment of vegetable oils.

研究领域: 食品科学 · 分析化学
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INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY · 2019 ·Vol. 55 ·期 4 ·1833-1842 · IF 2.281

Formation of malondialdehyde, 4-hydroxy-hexenal and 4-hydroxy-nonenal during deep-frying of potato sticks and chicken breast meat in vegetable oils

Lukai Ma,Guoqin Liu,Weiwei Cheng,Xinqi Liu,Huifan Liu,Qin Wang,Guoxing Mao,Xintong Cai,Charles Brennan,Margaret A. Brennan

Summary The present work investigated the formation of three toxic aldehydes, malondialdehyde (MDA), 4-hydroxy-hexenal (HHE) and 4-hydroxy-nonenal (HNE), during deep-frying of different foods in corn oil (CO), rapeseed oil (RO) and linseed oil (LO). Besides, their contents in French fries (FF) and fried chicken breast meat (FCBM) were also explored. Results showed that the MDA/HHE/HNE levels in frying groups were all lower than those in control, indicating the incorporation into the fried foods. Apart from the different levels, MDA/HHE/HNE in FF and FCBM possessed similar variation tendencies, revealing the matrix-mediated distribution. The combined exposure assessment based on the threshold of toxicological concern (TTC) levels was conducted, and risks of exceeding the limitation values (1.5 μg kg bw −1 day −1 ) for HNE in CO and HHE in LO were exhibited. The consumption of both FF and FCBM should be regulated, considering the levels of MDA, HHE and HNE these fried foods may contain.

CAS / MDL: 75-09-2
研究领域: 食品科学 · 毒理学 · 营养学
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