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JOURNAL OF MOLECULAR LIQUIDS · 2023 · IF 6

Insight of interaction in kojic acid/urea derivatives deep eutectic solvent from physicochemical characterization and computation simulation

Yu Cao,Shangtao Chen,Dongshun Deng

In recent years, the excellent performance of deep eutectic solvents (DES) has garnered increasing attention in the pursuit of sustainable solvents. This study employs natural and biodegradable kojic acid (KA) as a hydrogen bond donor (HBD) and environmentally friendly urea derivatives as hydrogen bond acceptor (HBA) to construct a series of novel type V KA/urea derivatives DESs. The as-obtained DESs were systematically characterized by density, viscosity, refractive index, speed of sound, thermal gravimetric analysis, FT-IR and NMR spectrums . The behavior of components in the DESs were deduced on the basis of thermal expansion coefficient ( α P ), apparent molar volume ( V 2∅ ), free volume ( F m ), and spectroscopic analysis. The interactions in the DESs were further cross-checked by Quantum chemical calculation and molecular dynamics simulation. The consistent sequence of interaction strength in the DESs was TMU-KA > DMI-KA > DMPU-KA. For KA molecule, the hydroxyl H on ring displayed lower activity than that on the side-chain due to the dual impact of conjugation and volume repulsion effect. The obtained information can provide help for understanding structure-property relationship and exploring potential utilization for present KA/Urea DESs.

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Food Analytical Methods · 2013 ·Vol. 7 ·期 1 ·109-115 · IF 1.969

Sensitive and Efficient Electrochemical Determination of Kojic Acid in Foodstuffs Based on Graphene-Pt Nanocomposite-Modified Electrode

Wang Li,Qi Wei,Su Rongxin,He Zhimin

A differential pulse voltammetric (DPV) method for the determination of kojic acid was developed. Glassy carbon (GC) electrode was modified with composite nanomaterials of graphene (GR) sheets and platinum (Pt) nanoparticles. Electrochemical behavior of kojic acid on the electrode was studied, which indicated that the nanocomposite-modified electrode could efficiently promote electrocatalytic oxidation of kojic acid based on synergistic effect of excellent electrical conductivity and high catalytic activity of GR and Pt. A rapid, sensitive, and simple electrochemical method was then developed for determination of kojic acid using the constructed electrode. Under the optimized conditions, the oxidation peak current exhibited a wide linear range from 0.2 to 1,000 μM towards the concentration of kojic acid with a sensitivity of 139.3 μA mM −1 , and the limit of detection was as low as 0.2 μM. The modified electrode was also used for quantitative analysis of kojic acid in food samples, and the recoveries were between 97.5 and 101.3 %, indicating feasibility of the electrochemical method for kojic acid analysis in routine detection. In view of optimization and validation results as well as applicability to real samples, this method could be considered as a good alternative for routine analysis of kojic acid in foodstuffs.

CAS / MDL: 18497-13-7 16940-66-2
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JOURNAL OF FOOD SCIENCE · 2023 ·Vol. 88 ·期 3 ·977-987 · IF 3.9

Effects of kojic acid on changes in the microstructure and myofibrillar protein of duck meat during superchilled storage

Wenfu Hou,Yile Lin,Yujie Zhang,Tingting Liu,Juan Du,Yang Yi,Hongxun Wang

This study investigated the effect of 0.8% (m/v) kojic acid treatment on changes in the microstructure and myofibrillar protein of duck meat covered with oxygen-permeable polyvinylchloride (PVC) film (9 ± 0.5 µM) during superchilled storage (−1.65 ± 0.5°C). The superchilled samples exhibited wider gaps between muscle fibers at 5 weeks storage compared with kojic acid–treated groups. Based on the variation of water status, the water-holding capacity decreased significantly ( p < 0.05), and bound water and immobilized water were gradually converted into free water during superchilled storage. For kojic acid–treated samples, however, no major changes were observed with respect to muscle structure, water status, and protein degradation at 6 weeks. The 0.8% (m/v) kojic acid treatment increased the water-holding capacity, reduced carbonyl content and protein degradation, and decreased the α-helix contents loss of myofibrillar proteins. Kojic acid treatment effectively protected myofibrillar protein structure from being destroyed during superchilled storage, suggesting that this method was a good way to reduce protein oxidation and prolonged its shelf life.

CAS / MDL: 501-30-4
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MICROCHIMICA ACTA · 2019 ·Vol. 186 ·期 8 ·1-8 · IF 5.479

Kojic acid capped gold nanoclusters with aggregation-induced emission for fluorometric screening of the activity of alkaline phosphatase

Li Yuanyuan,Du Qianqian,Zhang Xiaodan,Cao Haiyan,Huang Yuming

The authors describe the preparation of gold nanoclusters (AuNCs) capped with kojic acid. The capped AuNCs exhibit bright green fluorescence (peaking at 500 nm upon excitation at 375 nm), a nanosecond lifetime (0.37 ns), and a quantum yield (QY) of 22% in aqueous solution. This is higher than most of the previously reported AuNCs. The QY increases to 58% due to aggregation-induced emission in ethanol solution, and the lifetime is prolonged to 1.3 ns. The fluorescence of the KA-AuNCs is quenched by Eu(III) ion but is recovered by addition of phosphate due to its stronger affinity for Eu(III). Under the catalytic action of alkaline phosphatase (ALP), ascorbic acid phosphate (AAP) is transformed to free phosphate. On this basis, a fluorogenic assay for ALP was established. Response is linear in the 0.2 to 20 U·L −1 activity range, and the detection limit is 0.04 U·L −1 (at S/ N  = 3). The assay was successfully applied to the determination of the activity of ALP in spiked human serum and also to screen for its inhibitors. Highly luminescent and stable gold nanoclusters (AuNCs) with aggregation-induced emission property were synthesized through non-thiolate ligand kojic acid (KA) and demonstrated as an efficient probe for screening for alkaline phosphatase (ALP) activity and its inhibitors.

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Current Research in Food Science · 2025 · IF 7

Multifunctional kojic acid-tetrahydroisoquinoline hybrids: Synthesis, tyrosinase inhibition, and applications in the anti-browning of fresh-cut mushrooms

Min Lv,Longkang Cao,Yulu Ding,Shan Gao,Yinxin Wu,Rong Li,Wenjian Tang,Lili Zhu

Novel kojic acid-tetrahydroisoquinoline hybrids ( 4a–4p ) were designed and synthesized to address the need for safe tyrosinase inhibitors in food preservation. Compound 4c emerged as the most potent inhibitor, exhibiting 40-fold greater activity (IC 50  = 1.27 μM) than kojic acid. Kinetic studies identified 4c as a mixed-type inhibitor ( K i  = 1.48 μM, K is  = 15.35 μM), with molecular docking revealing strong binding to tyrosinase's active site via copper chelation and hydrophobic interactions. Safety evaluations in zebrafish embryos and mammalian cell lines confirmed minimal cytotoxicity. Furthermore, 4c showed broad-spectrum antimicrobial activity against E. coli , S. aureus and B. cinerea . In practical applications, 4c effectively suppressed enzymatic browning in fresh-cut mushrooms. These results underscore 4c as a promising candidate for multifunctional food preservatives, combining anti-browning efficacy, microbial inhibition, and biocompatibility. This study provides a strategic framework for developing hybrid inhibitors to enhance food quality and safety.

CAS / MDL: 501-30-4
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FOOD CHEMISTRY · 2023 · IF 8.8

Novel kojic acid-1,2,4-triazine hybrids as anti-tyrosinase agents: Synthesis, biological evaluation, mode of action, and anti-browning studies

Min He,Meiyan Fan,Wei Yang,Zhiyun Peng,Guangcheng Wang

A class of new kojic acid hybrids ( 7a-7o ) bearing a 1,2,4-triazine moiety were prepared, and their inhibitory activities and mechanism on tyrosinase were investigated. All derivatives showed good to excellent anti-tyrosinase activity with IC 50 values ranging from 0.34 ± 0.06 μM to 8.44 ± 0.73 μM. In kinetic study, compound 7m was a mixed-type inhibitor with K i and K is of 0.73 and 1.27 μM, respectively. The interaction mechanism toward tyrosinase of compound 7m was further elaborated in combination with molecular docking and various spectral techniques. The results showed that compound 7m could change the secondary structure of tyrosinase to reduce its catalytic activity. Anti-browning assays demonstrated that 7m inhibited the browning of bananas effectively during storage. What’s more, 7m was found to have low cytotoxicity in vitro . In conclusion, compound 7m has the potential to be applied as an anti-browning agent.

CAS / MDL: 501-30-4
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JOURNAL OF MOLECULAR LIQUIDS · 2020 · IF 5.065

Equilibrium solubility of kojic acid in four binary solvents: Determination, model evaluation, Hansen solubility parameter, thermodynamic properties and quantum chemical calculations

Renren Sun,Haixia He,Yameng Wan,Lei Yuan,Liyuan Li,Jiao Sha,Gaoliang Jiang,Yu Li,Tao Li,Baozeng Ren

Using the laser monitoring method, the solubility of kojic acid (KA) in the four binary solvents {[( N , N -dimethylformamide) DMF, ( N , N -dimethylacetamide) DMAC, (dimethyl sulfoxide) DMSO and ( N -methylpyrrolidone) NMP] + ethyl acetate} was measured at various temperatures. The results revealed that the experimental solubility values of KA have positive correlations with mass fraction of co-solvents and temperature in investigated four binary solvents. The solubility order of KA with mass fraction of co-solvents being w 1  = 0.2000, 0.4000 and 0.6000 is: DMSO + ethyl acetate  > NMP + ethyl acetate > DMAC+ ethyl acetate > DMF + ethyl acetate, respectively. However, in DMAC ( w 1  = 0.8005) + ethyl acetate, the solubility values of KA overtook that in NMP ( w 1  = 0.8004) + ethyl acetate at the higher temperature. The miscibility behaviors of KA with tested four binary solvents was revealed by the Hansen Solubility Parameters (HSPs). According to the calculated interaction energy, KA can be more easily dissolved in the solvent which has larger interaction energy with KA. Additionally, the measurement solubility data was mathematically correlated by the NRTL, Three-Suffix Margules, UNIQUAC models and Apelblat equation. The thermodynamic parameters (Δ dis G o , Δ dis H o , Δ dis S o , ζ H , ζ TS ) of KA dissolution processes in investigated four binary solvents were evaluated utilizing the van't Hoff equation. The positive Δ dis H o and Δ dis S o , indicate that the dissolution processes of KA are endothermic and entropy-driven in all chosen binary solvents. And the main contributor of Δ dis G o is positive enthalpy.

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Food Analytical Methods · 2013 ·Vol. 7 ·期 7 ·1458-1464 · IF 1.969

Study on the Electrochemical Properties of Kojic Acid at a Poly(glutamic Acid)-Modified Glassy Carbon Electrode and Its Analytical Application

Ma Xinying,Chao Mingyong

A poly(glutamic acid)-modified glassy carbon electrode (PGA/GCE) for the electrochemical determination of kojic acid was developed. The polymerization mechanism of glutamic acid at the glassy carbon electrode, the electrocatalytic mechanism of the poly(glutamic acid) film toward kojic acid, and the electrochemical behavior of kojic acid at the PGA/GCE were investigated. The studies revealed that the oxidation of kojic acid at the PGA/GCE is greatly facilitated, which is attributed to the weakening of the bond energy between oxygen and hydrogen due to the formation of hydrogen bond between hydroxyl group in kojic acid and the nitrogen atom in poly(glutamic acid). The oxidation of kojic acid at the PGA/GCE is a one proton–one electron process. The catalytic effect was further used to determine kojic acid by cyclic voltammetry. The oxidation peak current shows a linear relationship with the concentrations of kojic acid in the range of 8.00 × 10 −6 to 6.60 × 10 −4  mol L −1 with the detection limit of 8.00 × 10 −7  mol L −1 . The modified electrode shows excellent sensitivity, selectivity, and stability and has been applied to detect kojic acid in a variety of food products with satisfactory results.

CAS / MDL: 501-30-4
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ANALYST · 2022 ·Vol. 147 ·期 23 ·5579-5585 · IF 5.227

Facile and sensitive photoelectrochemical detection of kojic acid in food products: a general strategy for immobilization-free analysis of enzyme inhibitors

Nan Zhang,Peiwen Hu,Chunyuan Zhu,Shuangming Guo,Hong Yang

As one of the representative secondary metabolites in fermentation processes and common additives in modern industry, kojic acid (KA) has been mired in controversy in recent years due to its potential toxicity and carcinogenicity. Hence, it is of high importance to develop novel analysis strategies for KA to surveil its rational utilization and ensure public health. Based on enzyme modulated sensitization of TiO2 NPs and the inhibition effect of KA towards tyrosinase (Tyr), we report a facile and sensitive photoelectrochemical (PEC) sensor for KA in food samples. On an operational level, this protocol excluded the tedious immobilization process of traditional PEC enzyme sensors, allowing the crucial catalysis and sensitization process to take place in a small centrifuge tube, making the experimental process concise and fast. Under optimized conditions, a linear detection range of 10−7 M to 10−3 M was achieved, with a detection limit of 3.2 × 10−8 M. Furthermore, the feasibility of the strategy in food samples was validated in vinegar and wheat flour. This protocol would hold great promise for real application in diverse food products, and offer a general prototype for future immobilization-free and quick analysis of other enzyme inhibitors.

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LWT-FOOD SCIENCE AND TECHNOLOGY · 2020 · IF 4.006

Synergistic effect of kojic acid and tea polyphenols on bacterial inhibition and quality maintenance of refrigerated sea bass (Lateolabrax japonicus) fillets

Ruifei Wang,Xinyi Hu,Addo Keren Agyekumwaa,Xiaofeng Li,Xinglong Xiao,Yigang Yu

Fresh fish are highly perishable because their high content of protein and unsaturated fatty acids are easily oxidized and/or degraded under the influence of bacteria and the external environment. In this study, four natural preservatives (phenyllactic acid, kojic acid , tea polyphenols and thymol) were initially screened for antimicrobial activity against spoilage bacteria commonly found in fish by in vitro antibacterial tests. The results suggested that kojic acid (KA) and tea polyphenols (TP) exhibited a strong synergistic antibacterial effect against spoilage bacteria. Hence, the effects of KA and/or TP on the preservation of refrigerated sea bass ( Lateolabrax japonicus ) fillets after soaking treatments were determined. Changes in physicochemical parameters, indexes of fish freshness and microbial enumeration were examined. KA, TP and KA-TP treatments were effective in inhibiting bacterial growth and delaying lipid oxidation in fish flesh, resulting in lower TVB-N and TBARS than the control. Meanwhile, the freshness and physical qualities (color and texture) of fish fillets were also stabilized by the three treatments. Moreover, the KA-TP treatment showed the best effect on refrigerated fish preservation among the three treatments and extended the shelf-life by 5–6 days, suggesting that KA-TP have the potential to become a compound preservative for aquatic products.

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INDUSTRIAL CROPS AND PRODUCTS · 2025 · IF 6.2

A new selective separation strategy of eucalyptus hemicelluloses with the synergistic effect of hydroxyl and ketone groups in kojic acid pretreatment

Yun Ma,Yi Xie,Hui Liu,Yadan Luo,Baojie Liu,Chengrong Qin,Chen Liang,Caoxing Huang,Shuangquan Yao

In this study, eucalyptus hemicellulose was separated using kojic acid (KA), which contains hydroxyl and ketone groups. The maximum selectivity and hemicellulose separation yield were obtained (KA concentration of 10 %, 160 °C, and 50 min). The xylose separation increased from 79.36 ± 2.93 % to 84.36 ± 2.95 % after the KA pretreatment. The lignin separation decreased by 9.56 ± 0.06 % and 4.81 ± 0.26 % compared with acetic acid (AA) and salicylic acid (SA) pretreatment. It had the lowest condensed and highest noncondensed phenolic hydroxyl contents. The depolymerization and condensation of lignin were inhibited by the ketone group in KA. A synergistic effect of the hydroxyl acid and ketone groups on the efficient and selective separation of hemicellulose was discovered. This study provides a new approach for pretreating hemicellulose using novel multifunctional organic acids.

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Food Analytical Methods · 2021 ·Vol. 14 ·期 10 ·2076-2087 · IF 3.366

Molecular Simulation-Aided Preparation of Molecularly Imprinted Polymeric Solid-Phase Microextraction Coatings for Kojic Acid Detection in Wheat Starch and Flour Samples

Wang Dan,Yang Yi,Xu Zhigang,Liu Yujian,Liu Zhimin,Lin Tao,Chen Xinglian,Liu Hongcheng

An effective method based on molecularly imprinted polymer solid-phase microextraction (MIP-SPME) to assess the risk of kojic acid (KA) in food was proposed in this work. KA is widely used in the food industry but may have potential hazards, such as carcinogenicity. Herein, theoretical simulation and UV–vis spectrum were applied to investigate the synthesis procedure of MIP. The molecular simulation was in marked contrast with the traditional complicated preparation optimization of MIP-SPME coating. The prepared MIP-SPME fiber coating was a mesoporous material with high porosity, the leading cause of better mass transfer of target analytes in complex media. Furthermore, a novel theoretical simulation method of annealing operation was used to obtain the hydrogen bond interaction force for every possible or even dominate action site in the template-monomer system. In addition, compared to the existing approaches of KA determination, this method exhibited ultralow limits of quantification (0.20 and 0.72 μg L −1 ); it was successfully used for the selective trace detection of KA in wheat flour and starch. The proposed MIP-SPME approach, as a strategy for the risk assessment of KA, is proven to have great stability, high sensitivity and reproducibility.

CAS / MDL: 675-10-5
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