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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
研究领域: 材料科学 · 绿色化学
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FOOD AND CHEMICAL TOXICOLOGY · 2013 · IF 3.01

Genotoxic evaluation of aspirin eugenol ester using the Ames test and the mouse bone marrow micronucleus assay

Jianyong Li,Xiaojun Kong,Xiwang Li,Yajun Yang,Jiyu Zhang

Aspirin eugenol ester (AEE) is a promising drug candidate for treatment of inflammation, pain and fever and prevention of cardiovascular diseases with less side effects and it is important to characterize its genotoxicity. In this study, the genotoxicity of AEE was assessed with two standard genotoxicity assays of the Salmonella typhimurium mutagenicity assay (Ames test) and the mouse bone marrow micronucleus assay. In the Ames test , Salmonella strains TA97, TA98, TA100, TA102 and TA1535 were treated with or without the metabolic activation with a S9 fraction from Acroclor-induced rat liver. The doses of AEE were 5   mg/plate, 2.5   mg/plate, 1.25   mg/plate, 0.625   mg/plate and 0.3125   mg/plate, respectively. In the above tested strains, mutagenicity with or without the S-9 mixture was not detected. In the mammalian erythrocyte micronucleus assay, fifty mice were divided into five groups evenly and the AEE dose at 5000   mg/kg, 2500   mg/kg and 1250   mg/kg and the cyclophosphamide dose at 40   mg/kg as a positive control, the 0.5% of CMC-Na as negative control were administered. The results showed that AEE did not induce any significant increase in micronucleated erythrocytes after 24   h ( p   <   0.01). Our results suggested that AEE was non-genotoxic in vivo or in vitro .

研究领域: 药理学 · 毒理学 · 遗传学
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JOURNAL OF POLYMERS AND THE ENVIRONMENT · 2021 ·Vol. 30 ·期 5 ·2099-2108 · IF 3.667

Combining Renewable Eleostearic Acid and Eugenol to Fabricate Sustainable Plasticizer and Its Effect of Plasticizing on PVC

Ma Yufeng,Song Fei,Yu Juan,Wang Nannan,Jia Puyou,Zhou Yonghong

The recent studies on sustainable plasticizer mainly focus on raw material source, synthesis method and plasticization, but the effect of chemical functional groups (epoxy group and ester group) of sustainable plasticizer on compatibility and thermal stability of plasticized polyvinyl chlorid (PVC) materials has been ignored. In this study, two kinds of sustainable plasticizers (eleostearic acid eugenol ester (EAEE) and epoxidized EAEE) were synthesized to plasticize PVC films using eleostearic acid and eugenol. Compared to EAEE, PVC plasticized with epoxidized EAEE showed more flexible and thermal stability. Due to forming more hydrogen bonds between PVC chains and epoxidized EAEE than that of PVC chains, the efficient plasticizing on PVC with epoxidized EAEE was more than EAEE. Because of the flexible alkane chains and polar group (ester groups and epoxy groups) in the structure of epoxidized EAEE, the intermolecular interaction force with PVC was stronger than EAEE, and there was homogeneous and smooth surface of plasticized PVC films. Graphical Abstract

研究领域: 材料科学 · 化学工程
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

Methyl Eugenol Binds Recombinant Gamma-Aminobutyric Acid Receptor-Associated Protein from the Western Flower Thrips Frankliniella occidentalis

Li Wang,Maoxi Huang,Zilin Wu,Min Huang,Yunlong Yan,Baoan Song,Xiangyang Li,Qing X. Li

The western flower thrips (Frankliniella occidentalis) is a major pest insect in agriculture. However, few insecticides are effective for their control. The recombinant gamma-aminobutyric acid receptor-associated protein (rGABARAP) was examined as a potential target of the monoterpenoids responsible for their insecticidal activities. The insecticidal activity of anethole, linalool, and methyl eugenol (ME) was evaluated in the laboratory. The half-maximum lethal concentration (LC50) of ME against second-instar nymphs of F. occidentalis was 5.5 mg/L using membrane and leaf immersion methods, while that of spinosyn A was 1.0 mg/L. The dissociation constants of ME binding to rGABARAP were 1.30 and 4.22 μmol/L, respectively, according to microscale thermophoresis (MST) and isothermal titration calorimetry (ITC) measurements. A molecular docking study showed interactions between ME and Tyr174 via π–π stacking. The MST and ITC experiments showed loss of specific binding between ME and the rGABARAPY174A mutant. Therefore, Tyr174 is a key amino acid residue of rGABARAP involving ME binding. The results revealed GABARAP as a potential target for the development of monoterpenoid insecticides.

研究领域: 昆虫学 · 害虫管理 · 生物化学 · 分子生物学
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APPLIED SURFACE SCIENCE · 2023 · IF 6.7

Durable antibacterial cotton fiber surface fabricated by the thiol-ene click reaction between eugenol and L-cysteine

Wenjia Huang,Yong Li,Maoshuang Chen,Jinlin Chen,Jun Liu,Shuangfei Xiang,Feiya Fu,Xiangdong Liu,Ni Li

Cotton fabric plays an important role in the textile industry, but suffers from bacterial proliferation. The incorporation of naturally occurred phenols onto cotton fiber surfaces has the potential to yield powerful antibacterial effects, yet a simple and feasible method for their covalent grafting is currently lacking. In this study, we present a cleaning technique for preparing antibacterial cotton fabrics by using eugenol (Eug) and L-Cysteine (Cys) as finishing agents. The reactive carboxyl group of Cys is utilized to link Cys molecules onto cotton fibers via an esterification, followed by linking Eug molecules to the Cys moieties through thiol-ene click reaction. Simulated reactions validate the chemical mechanism of the thiol-ene click reaction between Eug and Cys, confirming its feasibility for various applications. Experimental results demonstrate that the modified fabrics achieve high bacteriostatic reduction rates (BR) against both Escherichia coli and Staphylococcus aureus . It is inferred that the Eug moieties incorporated onto the cotton fibers furnish phenolic groups, which interact with saccharides and proteins to exert bactericidal effects. The resulting fabrics also display exceptional antibacterial durability, maintaining over 95 % antibacterial activity after enduring durability tests. Meanwhile, the original properties of the fabrics (strength, flexibility, etc.) are minimally affected by the modification process.

研究领域: 纺织科学 · 材料化学 · 生物医学工程
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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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