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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2024 · IF 3.8

Experimental and Molecular Insights into Efficient Deterpenation of Essential Oil Intensified by Extraction with Deep Eutectic Solvent

Lexuan Zhao,Hongye Cheng,Zhiwen Qi

Deep eutectic solvents (DESs) have been widely utilized to intensify separations by adjusting their structures and properties, particularly in extractive deterpenation of essential oils as green alternatives to conventional organic solvents. In this work, experimental and molecular insights into efficient deterpenation intensified by a DES containing tetrabutylammonium bromide (TBAB) and levulinic acid (LEA) were investigated with citral extraction from lemon essential oil as a case study. DES formation and preferred liquid operating window were determined through solid–liquid equilibrium; an excellent extraction performance was observed at varying citral concentrations via liquid–liquid equilibria. Extraction process was simulated with a well-correlated nonrandom two-liquid model, and a 7-fold concentration of terpenoids was achieved under optimal conditions. Fourier transform infrared spectra and molecular dynamics simulations elucidated the DES formation and extraction mechanisms. Hydrogen-bonding interactions primarily mediated by −COOH group of LEA and Br– anion of TBAB resulted in lower freezing points of DES, thereby enhancing extraction performance. The results provide valuable insights into the practical applications of DESs in separating structurally similar natural products.

CAS / MDL: 1643-19-2 629-50-5
研究领域: 化学工程 · 天然产物分离
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JOURNAL OF MOLECULAR LIQUIDS · 2022 · IF 6.633

Selection of deep eutectic solvents for extractive deterpenation of lemon essential oil

Zexian Qin,Hongye Cheng,Zhen Song,Lijun Ji,Lifang Chen,Zhiwen Qi

Lemon essential oil is a complex mixture with citral as the primary terpenoid and limonene as the main terpene. Isolation of terpene and terpenoid, known as deterpenation, is crucial for improving the essential oil quality. In this work, liquid–liquid extraction with deep eutectic solvents (DESs) is utilized for lemon essential oil deterpenation. The performance of 77 DESs formed by seven hydrogen bond acceptors (HBA) with eleven hydrogen bond donors (HBD) is evaluated using COSMO-RS model and verified experimentally. The influences of HBA and HBD structures are investigated and explained by σ-profile. Among 77 DESs, the DES composed of tetrabutylammonium bromide and levulinic acid, namely TBAB:LEA(1:2), is finally selected due to its better performance than the conventional solvent hydrous ethanol. The excellent performance of TBAB:LEA(1:2) in deterpenation of natural lemon essential oil suggests it is a promising solvent in the downstream processing of natural essential oil.

研究领域: 化学工程 · 分析化学 · 食品科学
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FOOD CONTROL · 2018 · IF 3.667

Development of finger citron (Citrus medica L. var. sarcodactylis) essential oil loaded nanoemulsion and its antimicrobial activity

Ze-hua Li,Ming Cai,Yuan-shuai Liu,Pei-long Sun

In this work, various surfactants and cosurfactants were selected to develop nanoemulsions of finger citron essential oil (FCEO). Five suitable mixtures of surfactants were obtained: Cremophor EL/1, 2-propanediol (1:1, m/m), Cremophor EL/glycerol (1:1, m/m), Tween 80/ethanol (3:2, m/m), Tween 80/PEG-400 (3:2, m/m) and Tween 80/1, 2-propanediol (3:1, m/m). These five nanoemulsions showed a good stability with average droplet sizes kept below 20 nm for at least 28 days. All of them had low polydispersity index. Antimicrobial activities of these five nanoemulsions against bacteria ( E. coli , B. subtilis and S. aureus ) and molds ( A. niger and P. citrinum ) were tested, in which the nanoemulsion with Cremophor EL enhanced the antibacterial ability. However, the antifungal activities of these nanoemulsions were weaker than expected. These developed FCEO loaded nanoemulsions have good physical stability and antibacterial activity, suggesting their potential application in food and beverage fields.

研究领域: 食品科学 · 植物学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

Sequence-Selected C13-Dipeptide Self-Assembled Hydrogels for Encapsulation of Lemon Essential Oil with Antibacterial Activity

Tan Hu,Yang Xu,Gang Xu,Siyi Pan

Supramolecular self-assembling peptide hydrogels are attracting attention. The switching of even one amino acid may lead to differences in structure and functions of peptide hydrogels. Herein, we investigate the effect of substitution of a single amino acid residue on the gelation properties of C13-dipeptide hydrogels. We show that four C13-R1Y (C13-VY, C13-FY, C13-WY, and C13-YY) can form hydrogels with drastically tunable rigidity (the G′ values were 5.74, 0.16, 27.74, and 67.90 KPa, respectively). Moreover, C13-WY and C13-YY hydrogels with high stability and excellent mechanical properties formed β-sheet nanofiber cross-linked networks. Furthermore, we applied four hydrogels into encapsulation of lemon essential oil (LEO). The peptide hydrogels had a high encapsulation rate and slowly released the LEO. Importantly, the LEO-loaded hydrogels showed enhanced antibacterial activity than free LEO. Our results clearly demonstrate the significance of side-chain interactions in determining hydrogel properties and their potential application in encapsulation for nutrition agents and hydrophobic drugs.

CAS / MDL: 90-80-2
研究领域: 生物化学 · 材料科学 · 药学
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Food Packaging and Shelf Life · 2025 · IF 10.6

Antimicrobial packaging activity enhancement by lemon essential oil pickering emulsion stabilized with nanocellulose microgel particles

Feng Cai,Zhengyin Duan,Dehai Yu,Zhaoping Song,Peng Lu

The incorporation of lemon essential oil (LEO) into cellulose nanofibrils (CNF) shows great promise in the field of sustainable antimicrobial packaging, but is challenged by poor water dispersibility of LEO and the low retention within the film. In this study, nanocellulose microgel (MG) was designed as particle stabilizers for emulsifying LEO and highly stable high internal phase Pickering emulsions (HIPE) were successfully fabricated. MG particles were constructed through chemical bonding of polyethyleneimine onto 2,2,6,6-tetramethylpiperidinyl-1-oxide (TEMPO)-oxidized nanocellulose, characterized with excellent interfacial wetting properties (reduction of oil-water interfacial tension from 11.36 to 7.84 mN/m) and antimicrobial activity (the MIC for Listeria monocytogenes was 125 μL/mL). The HIPE was obtained by dispersing LEO into MG water dispersion (0.5 wt%). The HIPE with LEO fraction as high as 75 % maintained stability within pH 5 to pH 9 without phase separation after 6 days. Films cast from HIPE and CNF blends have excellent integrity and high LEO content (38.94 %). When HIPE was added at 9.6 wt%, LEO was effectively encapsulated by CNF and MG, embedded in the film with high retention, and exhibited significant antibacterial effects against Listeria monocytogenes , antibacterial rate up to 100 %. This work, based on MG, achieves high internal phase emulsification of LEO and enhanced retention within the film, providing a novel perspective and strategy for efficient encapsulation of essential oils and their economical application in antimicrobial packaging.

研究领域: 食品科学 · 材料科学 · 微生物学
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JOURNAL OF CHROMATOGRAPHY A · 2021 · IF 4.759

Amphiphilic triblock copolymer as the gas chromatographic stationary phase with high-resolution performance towards a wide range of isomers and the components of lemon essential oil

Ruijuan Duan,Meiling Qi

This work presents the investigation of using the amphiphilic triblock copolymer composed of poly(ethylene oxide)(PEO)-poly(propylene oxide) (PPO)-poly(ethylene oxide) (PEO) (denoted as EPE) as the stationary phase for gas chromatographic (GC) analyses . The EPE capillary column exhibited moderate polarity and column efficiency of 4348 plates/m determined by naphthalene at 120 °C ( k  = 11.52) . Different from the PEG and polysiloxane homopolymers, it showed high-resolution performance towards a wide range of aliphatic and aromatic isomers in terms of polarity and acid-base properties. Particularly, the EPE column displayed distinct advantages for separating the critical isomers of alkanes, anilines and phenols and the components of the lemon essential oil over the commercial PEG and polysiloxane columns. In addition, the EPE column exhibited excellent separation repeatability and reproducibility with the relative standard deviation (RSD) values in the range of 0.03% – 0.08% for run-to-run, 0.14% – 0.61% for day-to-day and 3.1% – 4.0% for column-to-column, respectively. Moreover, the EPE column was investigated in terms of thermal stability, the minimum allowable operating temperature (MiAOT) and sample loadability. Its application to GC-MS analysis of the essential oil demonstrated its feasibility for practical analyses. This work demonstrates the promising future of triblock copolymers as a new class of selective stationary phases for GC analyses, which is barely reported up to date. The findings of this work is of important value for fundamental researches and practical applications.

研究领域: 分析化学 · 材料科学
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FOOD CHEMISTRY · 2025 · IF 9.8

Preparation and characterization of Salecan β-glucan-based edible film loaded with lemon essential oil nanoemulsion: Effects on the preservation of chilled pork

Jiao Lin,Juan Dai,Qian Yang,Jiarui Li,Jing Xiao,Yuexin Zhang,YuKun Huang,Lijun Wang,Pengfei Chen,Buyi Xu,Juan Zhao,Xiao Yang,Xianggui Chen

Chilled meat is highly prone to microbial spoilage, and edible films with antimicrobial properties offer a feasible solution. In this study, oil-in-water (O/W) nanoemulsions loaded with lemon essential oil (LEO) were developed. Nanoemulsification improved the antioxidant and antimicrobial activities of LEO. The edible films, using Salecan β-glucan as the matrix and incorporating varying ratios of LEO nanoemulsion, demonstrated uniform oil distribution and desirable appearance. Kinetic modeling showed a slow release of LEO from the film by a diffusion-dominated coupled mechanism. The film with 5 % LEO nanoemulsion displayed superior mechanical strength, barrier properties, and prolonged essential oil release, significantly inhibiting spoilage bacteria. Preservation tests confirmed its efficacy in controlling pH, total viable count, TVB-N, and lipid oxidation, thereby prolonging the shelf-life of chilled pork and significantly delaying deterioration in quality indicators such as color and texture. This approach presents a promising method for developing innovative edible films for chilled meat preservation.

CAS / MDL: 1898-66-4 9005-65-6
研究领域: 食品科学 · 生物技术
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FOOD CHEMISTRY · 2022 · IF 9.231

Preparation and characterization of chitosan-based antimicrobial films containing encapsulated lemon essential oil by ionic gelation and cranberry juice

Kabirou Odjo,Qais Ali Al-Maqtari,Hang Yu,Yunfei Xie,Yahui Guo,Mi Li,Yuhang Du,Kunfeng Liu,Yulun Chen,Weirong Yao

Research about biodegradable antimicrobial films continues to receive a lot of attention due to the plastic pollution crisis and the need for environment-friendly and safe food products. In this study, we developed chitosan-based antimicrobial films using a combination of encapsulated lemon essential oil (LEO) by ionic gelation and cranberry juice and evaluated the performance of the films. Our results indicated that the incorporation of LEO microspheres and cranberry juice into the chitosan films improved the UV barrier and thermal properties as well as antioxidant activity of the films. The increase in antioxidants was consistent with the chemical components in LEO and cranberry juice as determined by GC–MS; some of which possess antioxidant properties. Furthermore, following antimicrobial activity test, considerable inhibition halo of 11 and 20 mm were observed respectively against fungi Candida albicans and Penicillium roqueforti , particularly in presence of the film containing both LEO microspheres and cranberry juice.

CAS / MDL: 9012-76-4
研究领域: 材料科学 · 食品科学 · 生物技术
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