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Eugenol
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
✓ 已验证 产品关联 DOI PubMed 高影响因子
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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.

✓ 已验证 DOI 高影响因子
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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.

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Frontiers in Pharmacology · 2020 · IF 4.225

Aspirin Eugenol Ester Protects Vascular Endothelium From Oxidative Injury by the Apoptosis Signal Regulating Kinase-1 Pathway

Huang Mei-Zhou,Zhang Zhen-Dong,Yang Ya-Jun,Liu Xi-Wang,Qin Zhe,Li Jian-Yong

Aspirin eugenol ester (AEE) is a new potential pharmaceutical compound possessing anti-inflammatory, anti-cardiovascular disease, and antioxidative stress activity. The pharmacological activities of AEE are partly dependent on its regulation of cell apoptosis. However, it is still unclear how AEE inhibits cell apoptosis on the basis of its antioxidative stress effect. This study aimed to reveal the vascular antioxidative mechanism of AEE in response to H2O2-induced oxidative stress in HUVECs and paraquat-induced oxidative stress in rats. In the different intervention groups of HUVECs and rats, the expression of ASK1, ERK1/2, SAPK/JNK, and p38 and the phosphorylation levels of ERK1/2, SAPK/JNK, and p38 were measured. The effects of ASK1 and ERK1/2 on the anti-apoptotic activity of AEE in the oxidative stress model were probed using the corresponding inhibitors ASK1 and ERK1/2. The results showed that in the HUVECs, 200 μM H2O2 treatment significantly increased the phosphorylation of SAPK/JNK and the level of ASK1 but decreased the phosphorylation of ERK1/2, while in the HUVECs pretreated with AEE, the H2O2-induced changes were significantly ameliorated. The findings were observed in vitro and in vivo. Moreover, inhibition of ASK1 and ERK1/2 showed that ASK1 plays a vital role in the protective effect of AEE on H2O2-induced apoptosis. All findings suggested that AEE protects the vascular endothelium from oxidative injury by mediating the ASK1 pathway.

研究领域: 药理学 · 心血管疾病 · 细胞生物学 · 分子生物学
✓ 已验证 DOI PubMed 高影响因子
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PROGRESS IN ORGANIC COATINGS · 2025 · IF 7.3

Synergistic antibacterial and anti-adhesion effects of zinc-based eugenol-modified composite coatings for marine antifouling applications

Xinyue Liang,Xu Zhang,Fa-Qian Liu

Marine biofouling severely impedes the development of marine engineering, while existing coatings suffer from inadequate environmental compatibility and insufficient long-term efficacy. To address these limitations, this study reported the fabrication of eugenol-functionalized ZnO (ZnO@Eug) via a one-pot hydrothermal approach. Subsequently, ZnO@Eug was further modified with hexadecyl trimethyl ammonium bromide (CTAB) via electrostatic interactions to yield the ZnO@Eug@CTAB composite filler, which was then incorporated into a polydimethylsiloxane (PDMS) matrix to fabricate the ZnO@Eug@CTAB/PDMS (ZECP) composite coating. Benefiting from the synergistic effects of Zn 2+ , eugenol, and CTAB, the ZECP coating achieved 100 % antibacterial efficiency against E. coli after 24 h of co-cultivation with bacterial suspensions. Anti-algal and anti-marine organism experiments demonstrated that the ZECP coating effectively suppressed Chlorella colonization and prevented the attachment of conchs. Moreover, the ZECP coating displayed controlled Zn 2+ release behavior while maintaining a high water contact angle of 121° and low surface free energy of 20.2 mN·m −1 , thereby contributing to its long-term antifouling performance. Based on the dual functions of active antibacterial and anti-marine organism adhesion, the ZECP coating can be applied in the field of environmentally friendly marine antifouling coatings.

研究领域: 材料科学 · 海洋工程 · 表面化学 · 生物医学工程 · 环境友好材料 · 微生物学 · 高分子材料
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FOOD HYDROCOLLOIDS · 2020 · IF 7.053

Cutoff Ostwald ripening stability of eugenol-in-water emulsion by co-stabilization method and antibacterial activity evaluation

Runan Zhao,Rong Song,Gege Sun,Shilin Liu,Bin Li,Yanping Cao,Yan Li

Essential oil-loaded emulsion is known to be unstable against Ostwald ripening. Hence, aiming to cut off this phenomenon, we fabricated eugenol-in-water emulsion by using co-stabilization method including interfacial layer formed by cinnamaldehyde/chitosan (CA-chitosan) and surfactant of glycerol monocaprylate (GMC). Oiling-off occurred in the emulsion with GMC as the sole stabilizer. While only white precipitates appeared in the CA-chitosan-stabilized emulsions due to the higher density of eugenol . In the presence of co-stabilizers, the particle size of emulsions showed unimodal distribution and kept almost constant within three months. Although there were some white precipitates in the emulsion after long-time storage, oil droplets still kept intact under optical microscopy. This result indicated that co-stabilizers could help to suppress the process of Ostwald ripening. The addition of polyvinyl alcohol effectively enhanced the stability of emulsions against gravitational separation. Eugenol emulsions kept stable even when eugenol content was up to 5 and 10 wt%. Antibacterial assay and time-kill experiment indicated that encapsulated eugenol had better antibacterial activity and long-term antibacterial efficiency, as compared to free eugenol. The obtained knowledge provides a novel technique to prepare eugenol-in-water emulsions, which has good long-term stability and antibacterial activity.

研究领域: 食品科学 · 化学工程 · 生物学
✓ 已验证 DOI 高影响因子
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RENEWABLE ENERGY · 2020 · IF 6.274

Investigation on catalytic hydrodeoxygenation of eugenol blend with light fraction in bio-oil over Ni-based catalysts

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

In this work, HZSM-5, Al-SBA-15 and Al-SBA-15/HZSM-5 were adopted as supporting materials for the nickel-based catalysts used in hydrodeoxygenation process. Incipient wetness impregnation method was employed to load nickel species onto these materials. The physicochemical characterization was carried out using advanced instruments. The effect of composition of nickel-based catalysts on hydrodeoxygenation (HDO) reaction was studied. Support materials of nickel-based catalyst have a significantly impact on HDO activity. The highest selectivity (67.9%) of propyl-cyclohexane was obtained over nickel based Al-SBA-15/HZSM-5 catalyst, and nearly all the eugenol was completely hydrodeoxygenated after reaction. The impact of light fractions existed in bio-oil on phenols upgrading process was investigated. The conversion of eugenol mixed with light fractions reached nearly 100% for all the reactions. Eugenol mixed with light fractions as reactant could reduce ring break reaction during hydrodeoxygenation process. The selectivity of alkanes remained nearly unchanged after adding ethylene glycol into the reactant. However, the selectivity of propyl-cyclohexane was significantly decreased by mixing furfural or acetic acid with eugenol as reactant.

研究领域: 化学工程 · 能源科学
✓ 已验证 DOI 高影响因子
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Journal of Agriculture and Food Research · 2026 · IF 6.2

Eugenol-induced self-emulsification of gliadin-shellac hybrid composites for co-stabilization of vitamin K2 and D3

Jiaxin Lin,Tao Wang,Ren Wang,Wei Feng,Xiaohu Luo,Kai Huang,Jian He

Vitamin K 2 (VK 2 ) and vitamin D 3 (VD 3 ) can synergistically promote calcium absorption and reduce the prevalence of osteoporosis. Given their hydrophobicity and environmental sensitivity, stabilizing both these vitamins is pivotal for their application. In this study, we designed shellac-gliadin composites (SGCs) with favorable amphiphilicity, yielding a self-emulsifying delivery system (SEDS) upon mild mixing with eugenol. By increasing eugenol/SGCs mass ratio, SEDS was transformed from spherical to a network-like structure, forming tunable topological nanostructures with tailorable delivery performance and bioavailability. Based on the dual-step process, VK 2 was encapsulated during shellac-gliadin assembly, while VD 3 was co-encapsulated via self-emulsification. The generated dual-vitamin self-emulsifying system (DSEDS) improved the stability under UV-light and long-term storage for both vitamins with high encapsulation capacities of 48.05 and 9.36 mg/g for VK 2 and VD 3 , respectively. The dual-step strategy introduced a novel approach for loading various fat-soluble nutrients, with potential applications in food and nutrition industry.

CAS / MDL: 67-97-0
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PLANT JOURNAL · 2021 ·Vol. 109 ·期 6 ·1489-1506 · IF 6.486

Eugenol functions as a signal mediating cold and drought tolerance via UGT71A59-mediated glucosylation in tea plants

Mingyue Zhao,Jieyang Jin,Jingming Wang,Ting Gao,Yu Luo,Tingting Jing,Yutong Hu,Yuting Pan,Mengqian Lu,Wilfried Schwab,Chuankui Song

SUMMARY Cold and drought stress are the most critical stresses encountered by crops and occur simultaneously under field conditions. However, it is unclear whether volatiles contribute to both cold and drought tolerance, and if so, by what mechanisms they act. Here, we show that airborne eugenol can be taken up by the tea ( Camellia sinensis ) plant and metabolized into glycosides, thus enhancing cold and drought tolerance of tea plants. A uridine diphosphate (UDP)-glucosyltransferase, UGT71A59, was discovered, whose expression is strongly induced by multiple abiotic stresses. UGT71A59 specifically catalyzes glucosylation of eugenol glucoside in vitro and in vivo . Suppression of UGT71A59 expression in tea reduced the accumulation of eugenol glucoside, lowered reactive oxygen species (ROS) scavenging capacity, and ultimately impaired cold and drought stress tolerance. Exposure to airborne eugenol triggered a marked increase in UGT71A59 expression, eugenol glucoside accumulation, and cold tolerance by modulating ROS accumulation and CBF1 expression. It also promoted drought tolerance by altering abscisic acid homeostasis and stomatal closure. CBF1 and CBF3 play positive roles in eugenol-induced cold tolerance and CBF2 may be a negative regulator of eugenol-induced cold tolerance in tea plants. These results provide evidence that eugenol functions as a signal in cold and drought tolerance regulation and shed new light on the biological functions of volatiles in the response to multiple abiotic stresses in plants.

研究领域: 植物学 · 分子生物学 · 环境科学
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Food Bioscience · 2026 · IF 6.2

Integrated transcriptomics and lipidomics provide insights into the stage-specific antifungal mechanisms of eugenol against Fusarium graminearum

Xin Yang,Luzhou Cai,Yueling Luo,Lianqun Wu,Xinyue Wang,Yanping Wu,Kai Zhong,Hong Gao

Fusarium graminearum poses a major threat to global grain production due to its pathogenicity and mycotoxin contamination. This study explored the antifungal effects and characterized molecular alterations of eugenol, a plant-derived phenolic compound, against F. graminearum . An integrated multi-omics strategy combining transcriptomic and lipidomic analyses was employed to characterize stage-specific responses of conidia and mycelia to eugenol, complemented by phenotypic and biochemical assays. Eugenol exhibited pronounced dose-dependent antifungal activity, accompanied by compromised cellular integrity and disruption of lipid homeostasis. Notably, its mode of action displayed clear developmental specificity. In the conidial stage, eugenol may interfere with phosphatidylcholine transport and membrane lipid remodeling, potentially limiting the membrane supply required for polarized growth. In contrast, during the mycelial stage, eugenol exposure correlated with the induction of peroxisome-associated lipid catabolism and stress responses, likely resulting in metabolic imbalance and growth suppression. Collectively, these findings delineate a stage-specific landscape of F. graminearum responses to eugenol and propose a hypothetical model centered on lipid metabolic disruption, supporting the further development of eugenol-based antifungal strategies for controlling F. graminearum .

CAS / MDL: 97-53-0
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MOLECULES · 2026 ·Vol. 31 ·期 4 ·669 · IF 5.1

Intelligent Food Packaging Films Based on pH-Responsive Eugenol@ZIF-8/PVA-HACC with Enhanced Antimicrobial Activity

Jiarui Liu,Jiachang Feng,Zhefeng Xu,Jinsong Zhang,He Wang

Natural antibacterial food packaging materials endowed with environmental responsiveness are garnering substantial research interest in sustainable food preservation. This study reports the development of a pH-responsive antimicrobial composite film through encapsulation of eugenol—a natural phenolic compound—within zeolitic imidazolate framework-8 (ZIF-8). The engineered eugenol@ZIF-8 system demonstrated pH-dependent release characteristics, with cumulative release reaching 32.2% at pH 6 versus merely 0.61% at pH 7 over 4 h. Subsequent integration of this nanocarrier into a polyvinyl alcohol (PVA)/hydroxypropyltrimethyl ammonium chloride chitosan (HACC) matrix yielded a multifunctional composite film for active food packaging applications. The characterization of film revealed that while eugenol@ZIF-8 incorporation slightly compromised mechanical strength (tensile resistance decreased by 18.7%) and flexibility (elongation at break reduced to 54.3% of control), it significantly enhanced hydrophobicity (water contact angle increased to 92.5°) and thermal stability (decomposition temperature elevated by 34 °C). The composite film demonstrated synergistic antibacterial efficacy through the combined action of Zn2+ions, ZIF-8 nanostructures, and eugenol, achieving 88% inhibition againstE. coli.Practical validation through fresh noodle preservation trials confirmed the material’s effectiveness, with the optimized formulation (PVA-HACC-2% eugenol@ZIF-8, PHEZ2) extending shelf life by >5 days compared to conventional packaging. This work establishes a novel strategy for engineering intelligent ZIF-based packaging systems that respond to food spoilage microenvironments, offering significant potential for reducing food loss.

CAS / MDL: 97-53-0
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Insects · 2022 ·Vol. 13 ·期 11 ·1004 · IF 3.139

Monitoring the Methyl Eugenol Response and Non-Responsiveness Mechanisms in Oriental Fruit Fly Bactrocera dorsalis in China

Yinjun Fan,Changzhen Zhang,Yu Qin,Xinhui Yin,Xinyi Dong,Nicolas Desneux,Hongxu Zhou

Simple SummaryBactrocera dorsalisis a highly invasive polyphagous pest of fruit and vegetable, causing severe economic loss and trade restrictions by ovipositing inside hosts. Cryptic feeding habits of larval stages, strong flight ability of adults and prevalence of insecticide resistance reduce the efficiency of chemical control. Currently, the most cost-effective tool is olfaction-based trapping. Methyl eugenol (ME), a naturally occurring compound in some plants, alone or combination with insecticides has been widely used as a male attractant to monitor and controlB. dorsalispopulations for seven decades. Intense ME selection under laboratory conditions has resulted in the evolution of non- responsiveness inB. dorsalisand field management strategies based on ME has failed to eradicate recolonization ofB. dorsalisin some islands. However, the levels of ME responsiveness inB. dorsalisfield populations in China is unknown. In this study, we found that field populations had lower ME sensitivity compared to the susceptible strain. Furthermore, the results of olfactory organs, gene expressions and the bioassays showed that odorant binding protein (BdorOBP2, BdorOBP83b) and P450 may be involved in the lower sensitivity. The findings will guide the use of lures combined with insecticides and help to exploit molecular targets for the development of new attractants.AbstractBactrocera dorsalisis a notorious polyphagous pest in China, and its management strategies largely depend on methyl eugenol (ME), which has been widely used as an attractant to monitor and eradicateB. dorsalispopulations for seven decades. However, the non-responsiveness levels in fieldB. dorsalispopulations to ME is unknown. In this study, we monitored the response to ME in field populations from the four most heavily infested provinces in China, and the results showed that the populations had lower sensitivity to ME relative to GZS susceptible strain. The percent responsiveness of the lowest sensitivity population was 5.88-, 3.47-, and 1.47-fold lower relative to the susceptible strain at doses of 1, 10, and 100 µL of ME, respectively. Gene expression analysis and inhibitor assays further revealed that odorant binding protein (BdorOBP2, BdorOBP83b) and the P450 enzyme system may be associated with the lower response to ME. To our knowledge, this work is the first to report that the P450 enzyme system confers a lower responsiveness to lure insects. These findings provided valuable insights for exploiting ME non-responsiveness to protect sterile males from ME-based control strategies and the use of lures combined with insecticides.Keywords:methyl eugenol;non-responsiveness;odorant binding protein;P450;trapping

研究领域: 昆虫学 · 分子生物学 · 农业科学
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