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Eugenol
Microorganisms · 2021 ·Vol. 9 ·期 5 ·969 · IF 4.128

Limonin Enhances the Antifungal Activity of Eugenol Nanoemulsion against Penicillium Italicum In Vitro and In Vivo Tests

Yi Li,Runan Zhao,Yan Li,Zhiqin Zhou

Penicillium italicum, the cause of citrus blue mold, is a pathogenic fungus that seriously affects the postharvest quality of citrus fruit and causes serious economic loss. In this study, a eugenol nanoemulsion containing limonin, an antimicrobial component from citrus seeds, was prepared using a high-pressure microfluidizer and the antifungal activity of the nanoemulsions againstP. italicumwas evaluated based on the conidial germination rate, mycelial growth, and scanning electron microscopy analysis. The results showed that the minimum inhibitory concentration and the inhibition rate of limonin-loaded eugenol nanoemulsion was 160 μg/mL and 59.21%, respectively, which was more potent than that of the limonin-free eugenol emulsion. After treatment with the nanoemulsions, the integrity of theP. italicumcell membrane was disrupted, the cell morphology was abnormal, and the leakage of nucleic acid and protein was observed. In addition, the challenge test on citrus fruits revealed that the limonin-loaded eugenol emulsion inhibited citrus infection for longer periods, with an infection rate of 29.2% after 5 days. The current research shows that nanoemulsions containing limonin and eugenol have effective antifungal activity againstP. italicum, and may be used as a substitute for inhibiting blue mold in citrus fruits.Keywords:eugenol nanoemulsion;citrus blue mold;limonin;Penicillium Italicum;antifungal activity

CAS / MDL: 97-53-0
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Journal of Inorganic and Organometallic Polymers and Materials · 2021 ·Vol. 31 ·期 8 ·3290-3300 · IF 3.543

Enhancement in Adhesive and Thermal Properties of Bio‐based Epoxy Resin by Using Eugenol Grafted Cellulose Nanocrystals

Aziz Tariq,Zheng Jieyuan,Jamil Muhammad Imran,Fan Hong,Ullah Roh,Iqbal Mudassir,Ali Amjad,Khan Farman Ullah,Ullah Asmat

Bio-based epoxy resins are being used due to their green chemistry. They have better properties than petroleum-based epoxy resins. Recently, environment friendly nanomaterials have been used for different industrial applications. Cellulose nanocrystals (CNCs) are among the best naturally occurring materials. Therefore, the surface of cellulose nanocrystals are modified by eugenol-based silane coupling agent (EBSCA). Chemical composition and surface morphologies of CNCs were analyzed and characterized by FTIR, AFM, SEM, TEM and 1 H-NMR. The SEM and AFM results confirmed eugenol-based silane coupling agent was successfully grafted on cellulose nanocrystals. Modified CNCs demonstrated an excellent tensile strength (2190 MPa) and modulus (16.00 MPa), as well as storage modulus (1622 MPa) exhibited by 1wt% modified cellulose nanocrystals composites. Additionally, modified CNCs displayed hydrophobic behavior (CA = 102 ± 2°). The corresponding modified CNCs have significant applications in combination of high stiffness and strength to the epoxy resins. This study lays a foundation towards full bio-based, environment friendly polymers fabrication and consumptions most desirable in adhesive and mechanical industrial fields.

CAS / MDL: 64-17-5 67-56-1
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Scientific Reports · 2020 ·Vol. 10 ·期 1 ·1-12 · IF 3.998

Synthesis of mesoporous silica post-loaded by methyl eugenol as an environment-friendly slow-release bio pesticide

Chen Huayao,Chen Lishen,Shen Zhichuan,Zhou Hongjun,Hao Li,Xu Hua,Zhou Xinhua

Salicylaldimine, furfuralimine and benzaldehyde imine were adopted to modify mesoporous silica (MCM) respectively denoted as Sal-MCM, Fur-MCM and Ben-MCM before loading methyl eugenol (Me) for pesticide delivery. Me was adsorbed by Schiff base mesoporous silica without destructing regular hexagonal pore structure verified by the characterization results. DSC result implied that Me in amorphous state which was distributed in the pores of the mesoporous silica. The loading content of Me-Sal-MCM, Me-Fur-MCM and Me-Ben-MCM 67.89%, 73.34% and 73.84% which was higher than Me-MCM without modification (67.35%).Because the electrostatic interaction and π-π interaction between Schiff base and Me strengthened the adsorption capacity of the carrier. And the electrostatic interaction played a more important role in interaction between Me and Schiff base modified mesoporous silica. As a result, Schiff base modified sustained release system also has significantly longer sustained release time with a sequence of Me-Sal-MCM > Me-Ben-MCM > Me-Fur-MCM in release speed in negative correlation with the electric potential sequence. The behaviors of their sustained release performance can be fitted by First order kinetic model before Schiff base modification. After modification, their sustained release behaviors were consistent with Korsmeyer-Peppas equation with non-Fickian diffusion mechanism indicating that main impact on the release process after modification was no longer mainly controlled by the difference of the concentration. Finally, the highest lure rate of the modified MCM (Me-Fur-MCM) equals to the 73% of the pure Me due to its highest BET surface area and strongest interaction with Me among the three Schiff base modified samples. Therefore, the environment-friendly slow-release bio pesticide with long service life was prepared to reduce the damage on the environment caused by pesticide.

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JOURNAL OF SOLID STATE CHEMISTRY · 2019 · IF 2.291

Effect of organic template removal approaches on physiochemical characterization of Ni/Al-SBA-15 and eugenol hydrodeoxygenation

Xiangping Li,Han Yin,Jianguang Zhang,Juping Liu,Guanyi Chen

Template removing approaches can significantly impact the physiochemical properties of mesoporous molecular sieve materials. In order to better understand the relationship between template removing approaches and the properties of Ni/Al-SBA-15, four kinds of template removing approaches were introduced to remove the organic template from Al-SBA-15, respectively. The structural characteristics of these materials were analyzed by transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray fluorescence (XRF), powder X-ray diffraction (XRD), N 2 -sorption, Fourier transform infrared spectra (FT-IR), infrared spectra of pyridine adsorption (Py-FTIR), magic angle spinning-nuclear magnetic resonance (MAS-NMR), X-ray photoelectron spectroscopy (XPS) and gas chromatography-mass spectrometry (GC-MS). Ni/Al-SBA-15 of which the organic template was removed by two-step calcination method had the maximum specific surface area (619 ​m 2 /g). In contrast, Ni/Al-SBA-15 of which the organic template was removed using solvent extraction approaches had the lowest specific surface area (555 ​m 2 /g). The mesopore diameter of Ni/Al-SBA-15, using electric heating digestion method to remove the template, was significantly increased and the wall thickness was significantly decreased to 11.62 ​nm in comparison with the other samples. The selectivity of products during the process of eugenol hydrodeoxygenation was investigated. High hydrocarbons were obtained during catalytic hydrodeoxygenation over Ni/Al-SBA-15 of which the organic template was removed by using solvent extraction approaches. Compared with direct calcination process, two-step calcination was more effective in removing template and the corresponding catalyst was much more suitable for the hydrodeoxygenation process.

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Food Chemistry-X · 2023 · IF 6.1

Effects of eugenol on the structure and gelling properties of myofibrillar proteins under hydroxyl radical-induced oxidative stress

Deyin Pan,Jinming Ma,Jingjing Diao,Jiaqi Li,Hongsheng Chen

The effects of eugenol (EG; 0, 5, 20, and 50 mg/g protein) on the structure and gel properties of pork myofibrillar protein (MPs) under a hydroxyl radical-generating system were explored in this study. The results revealed that the addition of a high concentration of EG (50 mg/g protein) markedly reduced the carbonyl content and enhanced the fluorescence intensity, surface hydrophobicity, and protected the secondary structure of MPs, compared to oxidized MPs. In addition, the high concentration group noticeably increased the storage modulus ( G ′), gel strength, and water-holding capacity (WHC), and significantly hindered the oxidation-induced transformation of immobilized water of the MPs gel to free water and basically favored the formation of a finer and more homogeneous three-dimensional network structure, This work verified that the adding of EG could effectively improve the gel quality of oxidized MPs and more successfully delay oxidation-induced damage to muscle protein structure.

研究领域: 食品科学 · 蛋白质化学 · 氧化应激
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REACTIVE & FUNCTIONAL POLYMERS · 2026 · IF 5.4

Bio-based tetrafunctional thiol EUGSFH: Eco-friendly design and versatile features from eugenol to superior epoxy curing agent

Xiangyan Ji,Zhiyong Li,Xiaoge Li,Lamei Lu,Jingjing Meng

The biobased eugenol is mainly utilized as a source for epoxy monomers, but it is not readily available for hardeners. As to the related biobased epoxy resins, the multifunctional outlines are still largely undocumented. Herein, a novel bio-based tetrafunctional thiol curing agent, 3,3′-(6,6′-bis(3-mercaptopropoxy)-5,5′-dimethoxy-[1,1′-biphenyl] -3,3′-diyl)bis(propane-1-thiol)) (EUGSFH) was fabricated via oxidation coupling/allylation/thiol-ene click chemistry/hydrolysis. Moreover, oil-based 2,2-bis(((3-mercaptopropanoyl)oxy)methyl)propane-1,3-diyl bis(3-mercaptopropan-tate) (PETMP) was employed for comparison. It was disclosed that EUGSFH-cured networks had an activation energy as low as 64 kJ mol −1 , which was about 9 kJ mol −1 lower than that of PETMP. Among them, the biobased (E)-2,2′-(((5-(4-(oxiran-2-ylmethoxy)styryl)-1,3-phenylene)bis(oxy))bis(methylene))bis(oxirane) (OSPBBB) /EUGSFH allowed the networks with T g as high as 115 °C due to its high crosslinking density (~5.24 mol dm −3 ). Meanwhile, its initial decomposition temperature reached 352.8 °C, exceeding the PETMP counterpart as well. Except for the outstanding mechanical properties, the EUGSFH showed an excellent UV/blue light shielding feature in the 200–500 nm range. The relatively low dielectric loss ε”  < 0.04 indicated its suitability for high-frequency electronic packaging. Moreover, the ready alkaline hydrolysis of PETMP-cured matrices achieved 100% degradation via 1) (CO)-O cleavage of ester bonds via hydrolysis, 2) C S breakdown via Retro-Michael reaction, and 3) C O cleavage of the ether bonds, making the sustainable recycling of reinforcing materials. On the contrary, the EUGSFH-fabricated networks are chemically stable for long-life, durable applications. In light of green high-end function, EUGSFH may therefore significantly provide an upgrading avenue, especially for their sustainable applications in weather-resistant, optical, dielectric, and high-temperature scenarios.

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CHEMICAL ENGINEERING JOURNAL · 2026 · IF 12.5

β-Cyclodextrin–encapsulated eugenol essential oil in chitosan/polyvinyl alcohol coaxial electrospun films: Structural, release, and antibacterial properties

Yunfei Yu,Shengnan Wang,Chunlei Liu

β-Cyclodextrin–encapsulated eugenol essential oil (β-CD@EEO) was incorporated into chitosan/polyvinyl alcohol (CS/PVA) coaxial electrospun films to develop biodegradable active packaging materials. The structural, physicochemical, release, antioxidant, and antibacterial properties of the films were evaluated. Structural characterization confirmed successful encapsulation of EEO within β-CD and uniform distribution in the fibrous matrix, resulting in continuous films with predominantly amorphous structures. Incorporation of β-CD@EEO increased fiber diameter and surface hydrophobicity, while modifying internal morphology. Mechanical strength and water vapor permeability varied with EEO loading, whereas flexibility and thermal stability were improved compared with the control film. Release studies demonstrated sustained and temperature-dependent diffusion of EEO, with lower release rates at 4 °C. Antioxidant activity increased significantly with EEO concentration. The films also exhibited strong antibacterial activity against Escherichia coli and Staphylococcus aureus , confirming that the bioactivity of EEO was preserved after encapsulation and electrospinning. In practical application tests, the films effectively delayed microbial spoilage of bread, with the 2.5% EEO formulation showing optimal performance. Overall, β-CD@EEO-loaded CS/PVA electrospun films combine controlled release, antioxidant and antibacterial functions, and biodegradability, demonstrating strong potential as sustainable active packaging materials for food preservation.

CAS / MDL: 9002-89-5
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2026 · IF 8.7

Development and characterization of bioactive Dictyophora rubrovalvata polysaccharide/hydroxypropyl starch composite films loaded with eugenol for strawberry preservation

Yu-Jing Wang,Qian Zhu,Jie Guo,Jun-Ying Zhao,Qian-Yan Xu,Hui-Yu Ye,Ren-Yi Gui,Hong-Zhou Chen,Huan Xu

A composite film of DRP and HPS was developed. • DRP and HPS enhanced composite film properties through synergistic interaction. • The synergistic effect was due to the formation of hydrogen bonds between DRP and HPS. • Preservation abilities of strawberries were significantly strengthened with eugenol-loaded composite film. In this study, Dictyophora rubrovalvata polysaccharide (DRP) was introduced into starch (CS) and hydroxypropyl starch (HPS) matrices to develop a composite film with enhanced physicochemical properties and investigate its potential for use in fruit preservation. Films based on CS, CS-DRP, HPS and HPS-DRP were prepared via solution casting method. The structural characteristics of the films were investigated using rheology, spectroscopy, and textural analyses, alongside systematic evaluation of their physical properties. Results showed that among all groups, the HPS-DRP film exhibited the best polymer compatibility, with its film-forming solution demonstrating an elastic-dominated rheological system and a smooth, uniform microstructure. Meanwhile, the hydrogen-bond interactions between DRP and HPS conferred superior mechanical properties, barrier performance and thermal stability to the film, achieving a tensile strength of 4.55 MPa, an elongation at break of 86.81%, a water vapor permeability of 5.63 × 10 −10  g·m −1 ·s −1 ·Pa −1 , and a residual rate of 21.87% after thermal degradation. Following the incorporation of eugenol, the HPS-DRP composite film exhibited good antimicrobial activity and effectively extended the shelf life when applied to strawberry preservation. These results demonstrate that HPS-DRP composite film holds broad application prospects as an active packaging material in fruit preservation. Download: Download high-res image (119KB) Download: Download full-size image

CAS / MDL: 56-81-5
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AQUACULTURE · 2024 · IF 3.9

Anesthetic effects of eugenol on adult ridgetail white prawn (Exopalaemon carinicauda) and its protective effects under simulated transportation

Chengsong Zhang,Fuhua Li

Anesthesia is a common practice used to improve animal welfare and reduce the negative impacts of stress factors in aquaculture settings. However, few studies have been conducted to investigate the application of anesthetics in ridgetail white prawn ( Exopalaemon carinicauda ). In the present study, the anesthetic efficacy and protective effects of eugenol in adults of this species were evaluated. When the prawns ( n  = 5) were immersed in different concentrations of eugenol in the range of 0–240 μL/L for 30 min, the results showed that 180 and 240 μL/L could lead to quick sedative and anesthesia effects with 100% mortality after 30 min exposure, while 30 μL/L failed to induce any sedative and anesthesia effects. Further tests showed that adult individuals were quickly anesthetized by eugenol at a concentration of 60–90 μL/L with a 30 min immersion, while half of the prawns were sedated in 30 μL/L eugenol after 4 h exposure, then recovered at 2 h without any mortality. Furthermore, we checked the water quality parameters after the adult prawns were immersed in four eugenol concentrations (0, 10, 20, 30 μL/L) for 8 h of simulated transportation followed by a 96 h recovery, we found that 30 μL/L eugenol treatment could significantly decrease the ammonia nitrogen concentration , and increased the survival rate at 96 h post recovery. The oxidative responses of the prawns during the 8 h transportation at 30 μL/L eugenol followed by 96 h recovery period were analyzed. The results showed that eugenol administration significantly decreased the malonaldehyde (MDA) concentration and the activities of most antioxidant-related enzymes immediately. The present data indicated that eugenol was an efficient anesthetic, which could be used for long-distance transportation of this species. It exhibited excellent protective effects to improve the animal's welfare by improving water quality and alleviating oxidative stress .

CAS / MDL: 97-53-0
研究领域: 水产养殖学 · 动物福利 · 环境科学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Development, characterization, and biological activity of composite films: Eugenol-zein nanoparticles in pea starch/soy protein isolate films

Hao Cheng,David Julian McClements,Hao Xu,Zipei Zhang,Ruojie Zhang,Jianwei Zhao,Hui Zhou,Wu Wang,Zhengyu Jin,Long Chen

With an increasing emphasis on environmental protection and sustainability, natural polymers like proteins and polysaccharides are being utilized more frequently in the development of biodegradable food packaging. However, the limited properties of these biopolymers have restricted their widespread applicability within the food industry. To address this issue, eugenol-loaded zein nanoparticles (ZE NPs) were incorporated into pea starch/soy protein-based films, and their effect on the physicochemical properties of these films were investigated. The ZE NPs exhibited high compatibility with the pea starch-soy protein isolate (PES/SPI) matrix, enhancing the structural properties of the films by forming hydrogen bonds between the nanoparticles and the biopolymer network. Incorporating the nanoparticles enhanced the mechanical properties, thermal stability, ultraviolet shielding, surface hydrophobicity, and moisture barrier performance of the films. Furthermore, the films containing ZE NPs exhibited significant antioxidant and antibacterial activity, suggesting their potential application as preservatives in active food packaging materials. In conclusion, the incorporation of ZE NPs significantly enhanced the performance of PES/SPI-based films, which should expand their application as food packaging materials.

CAS / MDL: 97-53-0
研究领域: 食品科学 · 材料科学
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ACS Sustainable Chemistry & Engineering · 2025 · IF 7.3

Capsanthin/Bismuththiol/Epoxidized Soybean Oil/Eugenol: A Green Synthesis of Biobased Antifungal Coatings for Wood under LED Irradiation

Jun Li,Qian Ao,Xinyu Wu,Hongping Yuan,Yu Zhang,Xiaoyu Li,Hailan Lian

2,5-Dimercapto-1,3,4-thiadiazole (DMTD) was used as a cross-linking agent and photoinitiator in conjunction with capsanthin and iodonium salt to construct a photoinitiating system suitable for UV-LED irradiation. In a fully green synthesis method, this photoinitiating system enables the thiol-epoxy polymerization and thiol-ene polymerization of biobased monomers, such as epoxidized soybean oil and eugenol, with final conversion rates exceeding 70%. The structure of the prepared coating becomes denser with increasing DMTD content, leading to improved hydrophobicity, wear resistance, thermal stability, and hardness. At the optimal DMTD content of 20 wt %, the coating EP20 exhibited an adhesion level of 0, an Aspergillus niger (A. niger) infection value of 1, and a water contact angle of 109.7°. The addition of eugenol further enhanced the coating’s antifungal properties, reducing the A. niger infection value to 0. This approach provides significant guidance for achieving sustainable development through “sustainable (biobased prepolymers) + eco-friendly (bioinitiating systems) + green (environmentally friendly curing processes)”.

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MICROCHEMICAL JOURNAL · 2025 · IF 5.1

Facile synthesis of thiocyano-functionalized dendritic mesoporous silica spheres for efficient extraction of eugenol anesthetics from aquatic products

Jianbin Ju,Yuji Ruan,Huifeng Deng,Xiaowen Huang,Guihua Ruan,Yipeng Huang

In this work, thiocyano-functionalized monodisperse dendritic mesoporous silica microspheres (DMS-SCN) were successfully synthesized and utilized as efficient solid-phase extraction adsorbents for the enrichment of eugenol anesthetics in aquatic products. The thiocyano functionalization significantly improves the adsorption capacity of the adsorbent for the four eugenol anesthetics from 723–1092 μg g −1 to 2180–3885 μg g −1 in virtue of the reinforced permanent dipole interactions, π-π stacking interactions, and electrostatic interactions. By coupling DMS-SCN based solid phase extraction with HPLC (SPE-HPLC) method, an analytical method for determination of eugenol anesthetics in tilapia, carp and shrimp was successfully developed. This method achieves low detection limits ranging from 0.32 ng mL −1 to 0.82 ng mL −1 and exhibits a wide linear range from 1 ng mL −1 to 200ng mL −1 . The recoveries for the four eugenol anesthetics range from 85.16 % to 109.1 %, with relative standard deviations between 1.18 % and 8.37 %. The method demonstrates minimal matrix effects and high accuracy. The DMS-SCN based SPE-HPLC method is anticipated to be a valuable tool for the analysis of eugenol anesthetics in complex sample matrices.

研究领域: 分析化学 · 食品科学 · 环境科学
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