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Eugenol
Molecular Catalysis · 2024 · IF 3.9

Selective hydrodeoxygenation of lignin-derived eugenol to propylcyclohexane over triazine polymer derived Co/NC-T catalyst

Zhiqin Li,Zongxuan Li,Meng Wu,Zegang Qiu,Yanan Zhu,Riguang Zhang

It is highly significant to develop effective catalysts made from non-precious metals for the hydrodeoxygenation (HDO) process of eugenol to propylcyclohexane. A triazine polymer (PAF-53) was employed as a template to synthesize a highly potential Co/NC-T (nitrogen-doped carbon modified by template) catalyst through one-pot pyrolysis method, aiming to facilitate the HDO reaction of eugenol. The results of the characterization indicated that Co nanoparticles (NPs) were incorporated within the structure of nitrogen-doped carbon. Adding the suitable quantity of PAF-53 could improve the distribution of Co NPs, increase the specific area and average pore diameter, and facilitate the generation of numerous carbon nanotubes that are sparse and porous. Furthermore, the incorporation of PAF-53 improved the interaction between Co and nitrogen-doped carbon, and endowed Co/NC-T with high mobile electrons. As revealed by density functional theory (DFT) calculations, the adsorption of eugenol molecules was obviously enhanced, and the parallel adsorption configuration was remarkably favorable. The conversion of eugenol over Co/NC-T-1:4 reached 100% and the selectivity of propylcyclohexane reached 98.4%, at 300 °C, 3 MPa H 2 and a liquid hourly space velocity of 12 h −1 . Moreover, the Co/NC-T-1:4 catalyst exhibited remarkable durability and scalability during the HDO process of eugenol.

CAS / MDL: 108-78-1
研究领域: 催化化学 · 材料科学 · 可再生能源
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Journal of Environmental Chemical Engineering · 2026 ·Vol. 14 ·期 5 ·124490 · IF 7.5

Eugenol-confined ZIF-8 modulates PLA nanofiber architecture for synergistic low-resistance and antibacterial PM filtration

Kaixin Qian,Xiao Ma,Mei Hong,Fuping Qian

Conventional air filtration media struggle to simultaneously address secondary biological pollution, the efficiency-permeability trade-off, and the environmental burden associated with disposable polymer filters. Direct blending of agglomerated or dense fillers can destabilize the electrospinning jet, disrupting the fiber network and increasing airflow resistance. In this study, biodegradable PLA nanofibers were combined with eugenol-loaded ZIF-8 nanoparticles to construct an antibacterial air filtration membrane. Prepared through an aqueous route, ZIF-8 served a dual function by regulating the architecture of the fibrous network and acting as a microporous reservoir for the natural antibacterial molecule eugenol. Comparison of pristine PLA, PLA/ZIF-8, and PLA/EUG@ZIF-8 membranes clarified each component's contribution. Pristine PLA provided a biodegradable fibrous matrix but showed inadequate filtration and negligible antibacterial activity. The incorporation of ZIF-8 optimized membrane morphology, enhanced particle capture, and imparted moderate bacterial inhibition. Notably, confinement of eugenol within ZIF-8 pores further enhanced antibacterial activity without disrupting the optimized membrane structure or air permeability. The PLA/EUG@ZIF-8 membrane delivered PM0.3, PM1.0, and PM2.5 filtration efficiencies of 99.62%, 99.99%, and 99.99%, respectively, with a low pressure drop of 69 Pa and a maximum quality factor of 0.1335 Pa⁻¹ . The composite also achieved near-complete inhibition of Escherichia coli (99.74%) and Staphylococcus aureus (99.48%). Numerical simulations showed a filtration trend consistent with the experimental results, indicating that the improved performance was mainly associatedwith the optimized fiber-pore structure rather than simple membrane densification. Thus, MOF-mediated natural antibacterials effectively fabricate biodegradable filters with excellent PM capture, low resistance, and strong antibacterial activity, promoting eco-friendly membranes.

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ACS Applied Polymer Materials · 2025 · IF 4.7

Degradable Eugenol-Derived Poly(thioether carbonate)/Bamboo Powder Thermoset Composite Prepared via Thiol–Ene Click Polymerization

Han Zhou,Qin Chen,Yang You,Yunqi Li,Yaozhu Tian,Haibo Xie

The design and synthesis of polymerizable monomers by using biobased chemicals have received great attention recently due to the nonrenewability and environmental problems of the traditional petroleum-based polymer industry. In this work, an eugenol-derived α,ω-diene aromatic carbonate monomer, namely, bis(4-allyl-2-methoxyphenyl) carbonate (BAMC), was synthesized by taking the inherent structural advantages of eugenol. In virtue of the structure of BAMC, a series of robust poly(thioether carbonate) thermosets were facilely prepared through atom-economical thiol–ene click polymerization. The curing behavior of BAMC with various thiols was investigated by 1H NMR, FTIR, and DSC, and the optimized curing conditions were determined and also applied to the preparation of the poly(thioether carbonate)/bamboo powder thermoset composite. The thermal and mechanical properties of the obtained poly(thioether carbonate) thermoset and poly(thioether carbonate)/bamboo powder thermoset composite were investigated by DSC, TGA, DMA, tensile strength tests, and dielectric tests to reveal the relationship between the structure and properties. The incorporation of bamboo powder enhanced the composite’s glass transition temperature (Tg) from 27.5 to 47.5 °C and tensile stress from 12.1 to 55.7 MPa, albeit with a drastic strain reduction from 153 to 5.3%. Additionally, varying thiol monomers enabled tunable flexibility and thermomechanical properties (Tg: 7.6–30.2 °C; stress: 5.5–21.1 MPa; strain: 153–344.9%), demonstrating versatile material design. This work provides significant insights for the design and synthesis of sustainable polymer thermoset composites by taking the structural features of biobased chemicals.

研究领域: 高分子化学 · 材料科学
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JOURNAL OF MOLECULAR LIQUIDS · 2024 · IF 5.3

Deciphering the binding mechanisms of eugenol and 2-methylpyrazine with human serum albumin using technical approach

Ying Yang,Jixiang Hu,Hui Wang,Lei Qiao,Yan Wang,Wenhua Tong,Liming Zhao

Eugenol (EGL) and 2-methylpyrazine (2-MTP) are common food additives that are used as flavors in a variety of foods. To study the effect of food additives on human serum albumin (HSA), it is necessary to deeply study the interaction of EGL and 2-MTP with HSA. Fluorescence, UV–vis absorption, circular dichroism (CD) and computational techniques showed EGL and 2-MTP bind statically to HSA, inducing conformational changes of HSA. We calculated the quenching constants (k sv ), binding constants (k q ), binding distances (r) and thermodynamic constants (ΔH 0 , ΔS 0 , ΔG 0 ) at four different temperatures. Based on thermodynamic analysis and molecular dynamics (MD) simulations, the main forces of 2-MTP-HSA and EGL-HSA systems are hydrophobic interaction and π-π accumulation, respectively. In addition, the interaction alters the physiological activity of HSA, esterase activity and free radical scavenging ability. This study provides valuable insights into the molecular interactions of food additive compounds EGL and 2-MTP with HSA, the findings provide theoretical reference for the development of new food additives and drugs in the future.

研究领域: 生物化学 · 食品科学 · 药物开发
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ACS Sustainable Chemistry & Engineering · 2020 · IF 7.632

Synthesis of Eugenol-Based Polyols via Thiol–Ene Click Reaction and High-Performance Thermosetting Polyurethane Therefrom

Yujing Hu,Yazhou Tian,Jue Cheng,Junying Zhang

The thiol–ene click reaction to prepare biobased polyols is a strategy to promote the green and environmental protection of polyurethane. The excessive usage of thiol and low conversion of carbon–carbon double bonds (C═C) would severely limit the properties of polyurethane (PU). In this work, a set of eugenol-based polyols were prepared via the thiol–ene click reaction. Interestingly, the conversion of the C═C was nearly 100% at the eugenol and various thiol compounds (—SH) in a stoichiometric ratio without excess of —SH. Then, the prepared polyols were reacted with diphenylmethane-diisocyanate (MDI), followed by a series of structure-adjustable thermosetting polyurethane networks with colorless transparency, high glass transition temperature (Tg), and good mechanical properties being obtained. In particular, the tensile strength was up to 54.88 MPa, and Tg can be adjusted from 36.45 to 77.21 °C. Moreover, it is revealed that the compounds with an allyl structure are conducive to the efficient click reaction, and its application in PU can be greatly extended.

研究领域: 材料科学 · 绿色化学
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Materials Today Communications · 2025 · IF 4.5

Bio-based eugenol flame retardant for simultaneously enhancing fire safety and mechanical performance of epoxy resin

Fei Wu,Fengqing Chen,Zhenghong Guo,Hangtian Hu,Lina Liu

With the swift advancement of green sustainability, efficient bio-based flame retardant is imperative to be created for epoxy resin (EP) especially in construction materials. This article designed a bio-based flame retardant (EUSP) which contains epoxy groups through the synthesis between epoxidation of eugenol and Phenyl trichlorosilane. The obtained flame retardant was applied for conventional E51 EP. The resultant EP composites achieved the V-0 rating in accordance with UL-94 standards and demonstrated a high limiting oxygen index (LOI) value of 30.2 % when 30 wt% EUSP was introduced. Compared to pristine E51 EP, the peak heat release rate (PHRR) and the peak smoke release rate (PSPR) were reduced by 38 % and 35.2 %, respectively. The flame-retardant effect of EUSP is achieved through the condensed phase flame retardant of silicon element. The silicon oxygen bond in EUSP reacts at the initial stage of combustion to form silicon dioxide. After the formation of silicon dioxide, a layer of silicon dioxide is formed outside under the promotion of combustible gas, which can reduce the internal exchange of external heat and epoxy resin and prevent the release of combustible gas inside the sample. Under the protection of the silicon dioxide layer, a compact and complete carbon layer is formed inside, which can further absorb the external heat, stabilize the internal temperature of the epoxy resin and protect the matrix. In comparison to the pristine E51 EP, the incorporation of 30 wt% EUSP resulted in an increase in both tensile strength and flexural strength, with values rising from 55.16 MPa and 90.69 MPa to 85.05 MPa and 146.83 MPa, respectively, representing a rise of 54.1 % and 67.3 %. This study provides a simple pathway for the preparation of bio-based flame retardants aimed at enhancing both the flame retardancy and mechanical properties of epoxy resin (EP).

研究领域: 高分子材料 · 阻燃技术 · 绿色化学 · 建筑材料 · 复合材料科学
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FOOD CHEMISTRY · 2025 · IF 9.8

Antibacterial and preservation properties of eugenol/diatomite modified superamphiphobic polyurethane films with secondary slow-release microstructures

Jiaqing Wu,Ran Zhang,Liangjun Liu,Qiuying Li,Jianrong Li,Tong Sun

In view of the disadvantages of food exudate juice during storage, a bionic superamphiphobic (SA) film was prepared. Different hydrophobic and oleophobic films were prepared by tape casting method with waterborne polyurethane (WPU) as film-forming matrix, diatomite (DME) as roughness construction factor, 1H,1H,2H,2H-perfluorooctane trichlorosilane (PFOTS) as low surface energy modifier, and eugenol (EG) as active antibacterial agent. The results show that the SA-EG-DME/WPU film has excellent superamphiphobic properties (WCA > 150°, OCA>120°). The film has secondary slow-release microstructures, and the embedding rate of eugenol is 82.03 %, which can play antibacterial role in a long time. After the composite film treatment, Shewanella putrefaciens collapses and shrinks, the cell membrane permeability increases, and the osmotic pressure is unbalanced. The WPU film exhibits excellent preservation properties for Salmon fillets due to the isolation juice property combined with the slow-release property of the preservative. The superamphiphobic film prepared in this study has potential application value in the field of food preservation.

CAS / MDL: 97-53-0 78-10-4
研究领域: 食品科学 · 材料科学 · 微生物学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2026 · IF 7.1

Eugenol-loaded Pickering emulsions with antifungal activity for extending the postharvest shelf life of sweet cherries

Zhanjun Chen,Jialin Yang,Haoyuan Luo,Henan Sun,Huiqiang Yu,Hao Yu,Sarengaowa,Ke Feng,Wenzhong Hu

Stable Pickering emulsions prepared by loading eugenol into chitosan-based particles • Strong antifungal activity exerted against Aspergillus niger and Penicillium citrinum • Quality deterioration of cherries delayed through Pickering emulsion coating Cherries, as non-climacteric fruits, are prone to browning, softening, and decay due to their thin skin and high respiration rate. Eugenol possesses broad-spectrum antimicrobial and antioxidant activities, but its application is limited by high volatility and poor water solubility. In this study, a chitosan-stabilized Pickering emulsion was developed to encapsulate eugenol and improve its stability and utilization. The antifungal activity of the emulsion against Aspergillus niger and Penicillium citrinum was evaluated, along with its effects on storage quality of fresh sweet cherries. The prepared emulsion exhibited an average particle size of 11.03 ± 0.67 μm and a zeta potential of 30.40 ± 0.56 mV, and remained stable under acidic conditions and below 60 °C. EUPE showed good antifungal activity against A. niger and P. citrinum , with inhibition zone diameters of 20.63 ± 0.06 mm and 20.12 ± 0.96 mm, respectively. When the EUPE concentration exceeded 8 mg/mL, the spore inhibition rates against both fungi were higher than 95%. The EUPE/CMC coating maintained better firmness and gloss, while showing lower total soluble solids and malondialdehyde contents during storage. The cherries maintained gloss and showed no mould growth. This work provides a promising strategy for natural postharvest preservation of cherries.

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Polymer Chemistry · 2024 · IF 4.1

A fully degradable epoxy resin based on a nontoxic triphenol derived from diphenolic acid and eugenol

Nianzhao Gao,Yang Lu,Jicheng Li,Feiyang Zhao,Minghui Ru,Shujun Zhao,Shuangfei Xiang,Feiya Fu,Hongyan Diao,Xiangdong Liu

The high toxicity of bisphenol A (BPA) is a major concern in the epoxy industry, but the challenge remains in developing bio-based alternatives to BPA that ensure human safety while providing superior mechanical properties and degradability in epoxy resins. In this study, a bio-based triphenol called DPA–EG ester (DEE) is synthesized from diphenolic acid (DPA) and eugenol (EG). Safety assessments for both cytotoxicity and endocrine toxicity demonstrate significantly lower toxic levels than BPA. Compared to the diglycidyl ether of bisphenol A (DGEBA), its epoxide derivative, DEE–EP, exhibits advantages in terms of higher Tg, enhanced toughness, and remarkable degradability in acidic conditions. After being cured with 4,4′-diaminodiphenyl sulfone (DDS), the DEE–EP resin achieved a higher Tg of 181 °C compared to DGEBA, which resulted in a Tg of 168 °C. Additionally, when DEE–EP is cured with succinic anhydride (SA), the resulting resin can be completely degraded under acidic conditions, suggesting great potential for efficient recycling of carbon fiber (CF) fabrics from composites. The unique molecular structure of DEE–EP is responsible for its advantages, as the hydroxyl group forms degradable ester bonds and the three phenyl glycidyl ether structures increase cross-linking density and rigidity in the network. This work presents a promising alternative to BPA, offering low toxicity, high toughness, and excellent degradability, thereby contributing to the development of sustainable bio-based epoxy resins with superior performance.

研究领域: 材料科学 · 环境科学 · 生物化学
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Food and Bioprocess Technology · 2020 ·Vol. 13 ·期 6 ·1024-1034 · IF 3.356

Orthogonal Optimization and Physicochemical Characterization of Water-Soluble Gelatin-Chitosan Nanoparticles with Encapsulated Alcohol-Soluble Eugenol

Wang Qian,Zhang Li,Ding Wu,Zhang Dequan,Reed Kevin,Zhang Boce

This study aimed to develop self-assembled gelatin-chitosan (Gel-CS) nanocapsules as a water-soluble delivery system for alcohol-soluble compounds. Eugenol (Eug) selected as the model molecule for its high solubility in alcohol and insolubility in water. The study also examined different reaction conditions and reagent loading ratios to optimize eugenol-embedded gelatin-chitosan nanocapsules (Eug-Gel-CS NPs) formation. The optimal loading ratio of Gel, CS, and Eug was 3:1:2, which yielded an average particle size of 229.09 nm and an encapsulation efficiency of 50.69%. The morphological characteristics of Eug-Gel-CS NPs were further demonstrated by transmission electron microscopy. The prepared Eug-Gel-CS NPs also exhibited potential controlled-release properties in aqueous phase with the in vitro release percentage of 69.47 ± 1.24% over 36 h. This nanocapsule system may provide a platform to expand the potential applications of Eug in food and nutrition.

CAS / MDL: 9012-76-4
研究领域: 食品科学 · 生物材料 · 药物递送
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Horticultural Plant Journal · 2020 · IF 1.524

Cold Stress-induced Glucosyltransferase CsUGT78A15 is Involved in the Formation of Eugenol Glucoside in Camellia sinensis

Mingyue Zhao,Binbin Cai,Jieyang Jin,Na Zhang,Tingting Jing,Jingming Wang,Yuting Pan,Zixiang Zhou,Yifan Zhao,Yingying Feng,Feng Yu,Mengting Zhang,Yating Li,Zhonghua Liu,Chuankui Song

Eugenol is a natural phenolic compound known for its health-promoting properties and its ability to add a floral scent to tea plants. Plant eugenol glycosides have been identified and shown to make important contributions to fruit floral quality. However, the details of their biosynthesis and metabolism in tea plants are still unknown. Here, eugenol glucoside was unambiguously identified as a native metabolite in the tea plant, and its biosynthesis was shown to be induced by low temperature treatment. Through the analysis of UGTs induced by low temperature, the glycosyltransferase CsUGT78A15 was identified in tea, and its encoded protein was shown to catalyze the glucosylation of eugenol. V max / K m ratios showed that eugenol was the most suitable substrate for CsUGT78A15. Sugar donor preference analysis showed that CsUGT78A15 had a higher selectivity for glucose, followed by galactose and glucuronic acid. The expression of CsUGT78A15 was correlated with the accumulation of eugenol glucoside in different tissues and genotypes of tea. Down-regulation of CsUGT78A15 led to a decreased eugenol glucoside content under cold stress, indicating that CsUGT78A15 plays an important role in the biosynthesis of eugenol glucoside under cold stress. The identification of eugenol glucoside in the tea plant and the discovery of a cold stress-induced eugenol glucosyltransferase in tea provide the foundation for the improvement of tea flavor under cold stress and the biotechnological production of eugenol glucoside.

研究领域: 植物生理学 · 分子生物学 · 生物化学
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TOXICOLOGY · 2021 · IF 4.221

Aspirin eugenol ester ameliorates paraquat-induced oxidative damage through ROS/p38-MAPK-mediated mitochondrial apoptosis pathway

Zhen-Dong Zhang,Ya-Jun Yang,Xi-Wang Liu,Zhe Qin,Shi-Hong Li,Jian-Yong Li

Paraquat (PQ) is an effective and commercially important herbicide that is widely used worldwide. However, PQ is highly toxic and can cause various complications and acute organ damage. Aspirin eugenol ester (AEE) is a potential new compound with anti-inflammatory and antioxidant stress pharmacological activity. The present study was to reveal the therapeutic effects and the protective effect of AEE against PQ-induced acute lung injury (ALI) with the help of PQ-induced oxidative damage in A549 cells and PQ-induced lung injury in rats. AEE might have no significant therapeutic effect on PQ-induced lung injury in rats. However, AEE had a significant protective effect on PQ-induced lung injury in rats. AEE pretreatment significantly reduced the stimulatory effect of PQ on malondialdehyde (MDA), the inhibitory effect of PQ on catalase (CAT) activity, superoxide dismutase (SOD) activity, glutathione peroxidase (GPx) activity, the ratio of GSH/GSSH, the activity of caspase-3 and the overexpression of p38 mitogen-activated protein kinase (MAPK) phosphorylation in vivo . In vitro , A549 cells were treated with 250 μM PQ for 24 h. Incubation of A549 cells with PQ led to apoptosis, and increased the level of superoxide anions, reactive oxygen species (ROS), malondialdehyde and the activity of caspase-3 and up-regulation of phosphorylated p38-MAPK, reduced mitochondrial membrane potential (ΔΨm) and the activity of SOD. However, after 24 h on AEE pretreatment of A549 cells, the above-mentioned adverse reactions caused by PQ were significantly alleviated. In addition, AEE pretreatment reduced p38-MAPK phosphorylation in PQ-treated A549 cells. SB203580, the specific p38-MAPK inhibitor, and p38-MAPK shRNA attenuated the activation of the p38-MAPK signaling pathway. N-acetylcysteine (NAC) reduced the level of phosphorylated p38-MAPK and the production of intracellular ROS and inhibited apoptosis. The results showed that AEE may inhibit PQ-induced cell damage through ROS/p38-MAPK-mediated mitochondrial apoptosis pathway.

CAS / MDL: 1910-42-5
研究领域: 药理学 · 毒理学 · 细胞生物学 · 分子生物学
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