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JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH · 2021 · IF 1.571

Synthesis of sulfonate derivatives of carvacrol and thymol as anti-oomycetes agents

Gen-Qiang Chen,Di Sun,Jin-Ming Yang,Song Zhang,Yue-E Tian,Zhi-Ping Che,Sheng-Ming Liu,Jia Jiang,Xiao-Min Lin

Two series of sulfonate derivatives of carvacrol and thymol were synthesized and screened in vitro for their anti-oomycete activity against Phytophthora capsici, respectively. Among all of 32 derivatives, five compounds 3a, 4a, 4k, 3n, and 4n exhibited more potent anti-oomycete activity against P. capsici with EC50 values of 66.66, 62.94, 68.65, 61.24, and 52.91 mg/L, respectively. This suggested that introduction of different substitutions at the hydroxyl position of 1/2 could have remarkable effect on anti-oomycete activity. Overall, when R1 = isopropyl and R2 = methyl, the anti-oomycete activities of the compounds were higher than that of the corresponding compounds of R1 = methyl and R2 = isopropyl.

研究领域: 植物化学 · 农药科学 · 微生物学
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NATURAL PRODUCT RESEARCH · 2019 · IF 1.999

Synthesis and antifungal activity of carvacrol and thymol esters with heteroaromatic carboxylic acids

Kaibo Wang,Shanshan Jiang,Yunhai Yang,Liming Fan,Fawu Su,Min Ye

Aiming to obtain the more effective pathogen inhibitive ingredients and explore the influence of introducing different heterocyclic units to carvacrol and thymol esters, twenty ester derivatives with different heterocyclic units were synthesized. And the in vitro antifungal activity of title compounds against five plant pathogenic fungi was evaluated by mycelium growth rate method. The results showed that some carvacrol and thymol esters showed good to excellent antifungal activity, and compound 9d (4-bromo-5-isopropyl-2-methylphenyl picolinate) exhibited a broad antifungal spectrum. Preliminary study indicated that the introduction of furan, thiophene and pyridine unit could enhance the antifungal activity of carvacrol and thymol esters against Botrytis cinerea and a bromine atom on the para position of benzene moiety could enhance their antifungal activity.

研究领域: 植物化学 · 植物保护学 · 药理学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2019 · IF 3.714

Antibacterial activity and mechanism of thymol against Alicyclobacillus acidoterrestris vegetative cells and spores

Rui Cai,Mingquan Zhang,Lu Cui,Yahong Yuan,Yifei Yang,Zhouli Wang,Tianli Yue

Alicyclobacillus acidoterrestris has received much attention due to its unique thermo-acidophilic property and implication in the spoilage of pasteurized juices. The aim of this study was to investigate the antibacterial characteristics and mechanisms of thymol against A. acidoterrestris vegetative cells and spores. Minimum inhibition concentration (MIC) and minimum bactericidal concentration (MBC) of thymol against vegetative cells were both 0.25 mg/mL. MIC of thymol against spores was 0.5 mg/mL, and the MBC was greater than 1.0 mg/mL. Thymol could effectively inhibit A. acidoterrestris growth, spore germination and guaiacol production. When treated by thymol, the leakage of nucleic acids and proteins from A. acidoterrestris cells and spores increased significantly. SDS-PAGE investigation of bacterial proteins showed that the loss of soluble proteins was obvious as well. Scanning electron microscopy observation exhibited that A. acidoterrestris cells or spores treated with thymol had a severe morphological damage. These results demonstrated that thymol exerted its good antibacterial activities by destroying the integrity of the cell and spore. This study provides a new method for the inactivation of A. acidoterrestris in fruit juice.

研究领域: 食品科学 · 微生物学
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ACS Applied Polymer Materials · 2026 · IF 5.2

Multifunctional Bioinspired Janus Membranes Integrating Thymol/ZnO Synergy for Diabetic Wound-Microenvironment Regulation

Fan Li,Yu Wu,Jinke Guo,Zhuoming Chen,Binjie Xin,Zhengxin He

Chronic diabetic wounds are characterized by persistent infection, oxidative stress, and moisture imbalance. However, effectively managing these concurrent pathological factors within the complex wound microenvironment remains a significant clinical challenge. Herein, we report the development of a multifunctional Janus nanofibrous membrane via sequential electrospinning of a thymol (THY)-incorporated hydrophilic polyacrylonitrile (PAN)/polyvinylpyrrolidone (PVP) layer and a zinc oxide (ZnO)-incorporated hydrophobic polylactic acid (PLA) layer, integrating structural bioinspiration with organic–inorganic synergy for comprehensive microenvironment management. By mimicking the desert beetle’s elytra, the membrane exhibits asymmetric wettability (the hydrophilic side shows a water contact angle (WCA) dropping to 0° within 0.37 s), enabling autonomous and unidirectional exudate transport (hydrostatic pressure difference: 52 mm) to prevent exudate accumulation. Importantly, the system capitalizes on a “permeabilization–penetration” synergy between THY and ZnO: THY disrupts bacterial membranes, facilitating the infiltration of Zn2+ to eradicate pathogens. The system achieves nearly 100% antibacterial efficiency against Escherichia coli and Staphylococcus aureus while exhibiting significant antioxidant activity, as evidenced by an 86% 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging rate. In vivo evaluations in a diabetic mouse model confirmed that the Janus membrane significantly accelerates wound closure through enhanced re-epithelialization and organized collagen deposition, achieving 78.04% wound closure on day 4 and near-complete closure by day 14, thereby outperforming all control groups. In summary, this “all-in-one” Janus platform enables precise microenvironment regulation through the integrated control of interfacial moisture and multipathway therapeutic relief.

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FOOD CHEMISTRY · 2024 · IF 8.5

Formation, stability, and antimicrobial efficacy of eutectic nanoemulsions containing thymol and glycerin monolaurate

Yaojin Ge,Hang Liu,Shengfeng Peng,Lei Zhou,David Julian McClements,Wei Liu,Jun Luo

In this study, based on the discovery of thymol/glycerol monolaurate (GML) eutectic solvent, we studied the effect of GML as a multi-functional component (ripening inhibitor and antibacterial agent) on the formation, stability and antibacterial activity of eutectic nanoemulsions, and investigated the preservation of nanoemulsion in fresh pork. These results indicated that the formation of eutectic solvent was due to the hydrogen bonding between thymol and GML in the molten state. And eutectic nanoemulsions prepared with medium GML concentrations (20%, 40%, and 60%) of eutectic solvents as oil phases had small droplet diameters (<150 nm), exhibited sustained-release characteristics, and had excellent physicochemical stability. Moreover, the addition of GML enhanced the antibacterial activity of thymol nanoemulsion against S. aureus . as seen by their ability to inhibit affect formation more effectively. Treatment of fresh pork with optimized eutectic nanoemulsions (40% thymol/60% GML) extended its shelf life during refrigeration, which was mainly attributed to the ability of the encapsulated essential oil to inhibit microbial growth and lipid oxidation. These results provide a novel strategy to control Ostwald ripening and maintain the high antibacterial activity of thymol in nanoemulsion-based delivery systems.

研究领域: 食品科学 · 纳米技术 · 微生物学 · 药学
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Environmental Technology & Innovation · 2021 · IF 5.263

Catalytic ozonation of thymol with a novel CoCe-MMO catalyst: Kinetics and mechanism

Siqi Fan,Jinshan Song,Yi Xia,Qizhou Dai

In this study, a novel ozonation catalyst CoCe mixed metal oxide (CoCe-MMO) was prepared for the degradation of organic wastewater containing thymol . The results showed that the addition of CoCe-MMO could effectively enhance the effect of thymol degradation, and the thymol could be completely removed after 40 min of reaction. The reaction kinetics was calculated. It accords with the quasi-first order reaction kinetics, and the reaction rate constant is about 0.1357 min −1 . The enhancement mechanism was discussed and the CoCe-MMO could react with ozone to produce strong oxidizing free radicals-hydroxyl radicals (•OH). The catalyst was characterized by XRD, SEM , and XPS . The results showed that the catalyst continued the lamellar laminated structure of its precursor, and present a higher crystallinity and smaller crystal grain size (about 58-70 nm), which would promote the production of •OH. The •OH and O 3 O3 could attack the ortho-position of thymol for peacekeeping, making it gradually converted into small molecule acids, and finally completely degraded into CO 2 and H 2 H2 O. The stability and reusability of the catalyst were also studied and the CoCe-MMO catalyst could maintain high activity after three cycles. And the metal ion leaching rates of Co and Ce are 0.39 mg/L and 0.03 mg/L respectively, which is lower than the emission standard. This paper showed that the catalyst has good application prospect and could provide technical support for pharmaceutical wastewater pollution control with catalytic ozonation.

研究领域: 环境科学 · 催化化学
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2025 · IF 5.6

Preparation of thymol-loaded Pickering emulsion gel film and its application in wound healing

Yan Hu,Jiasi Zhao,Hudie Fu,Shengpeng Zhu,Yuqing Wang,Fengning Lu,Lirong Huang,Shanwei Long,Xiaojun Li,Li Kang,Xinzhou Yang

At present, the treatment of diabetic wounds is challenging and time-consuming. In this study, a delivery system combining thymol-loaded Pickering emulsion and gel film has been investigated to accelerate wound healing. The nanoparticles (SPI-CMC) composed of soy protein isolate (SPI) and carboxymethyl cellulose (CMC) were used to stabilize Pickering emulsion and loaded into polyvinyl alcohol (PVA)-porous starch (PS)-hyaluronic acid (HA) gel membrane (PPH) matrix. The PPH matrix was loaded with thymol (PPH+T), which effectively solves the problem of solubility and compatibility of thymol. Moreover, the PPH+T matrix based on Pickering emulsion and gel membrane achieving the antibacterial, anti-inflammatory, angiogenesis and tissue collagen formation effect. The composite gel membrane exhibited a long-term sustained release of thymol for up to 48   h, and had good antibacterial activity against Escherichia coli ( E.coli ) and Staphylococcus aureus ( S.aureus ). The antibacterial diameters of the two were 19.73   ± 1.375 mm and 21.94   ± 0.486 mm, respectively. It was verified in animal experiments that the healing of normal wounds and diabetic wounds was accelerated, and the final healing rates were 97% and 94%, respectively. Therefore, the composite gel membrane prepared in this study has great potential in wound antibacterial and healing, and provides a basis for effective treatment of chronic wounds.

CAS / MDL: 9002-89-5 9004-32-4
研究领域: 生物医学工程 · 药剂学 · 伤口护理 · 药物递送系统 · 纳米技术
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PEST MANAGEMENT SCIENCE · 2024 · IF 3.8

Discovery of novel piperidine-containing thymol derivatives as potent antifungal agents for crop protection

Xiaoqun Yang,Shichun Jiang,Meng Zhang,Tingting Li,Zhichao Jin,Xingxing Wu,Yonggui Robin Chi

BACKGROUND Plant fungal diseases pose a significant threat to crop production. The extensive use of chemical pesticides has led to growing environmental safety risks and pesticide resistance of various plant pathogens. Therefore, it is an urgent task to explore novel eco-friendly fungicidal agents with high efficacy to combat fungal infection. RESULTS In this study, we rationally designed a series of novel thymol derivatives by incorporation of the sulfonamide moiety and evaluated their biological activities against plant pathogenic fungi. The bioassay results underscored the remarkable in vitro antifungal activity of compounds 5m and 5t against Phytophthora capsici ( P. capsici ), with EC 50 values of 8.420 and 8.414 μ g/mL, respectively. Their efficacies were superior to that of widely used commercial fungicides azoxystrobin (AZO, 20.649 μ g/mL) and cabendazim (CAB, 251.625 μ g/mL). Furthermore, compound 5v exhibited excellent in vitro antifungal activity against Sclerotinia sclerotiorum ( S. sclerotiorum ), with an EC 50 value of 12.829 μ g/mL, significantly outperforming AZO (63.629 μ g/mL). In vivo bioassays demonstrated the impactful activity of compound 5v against S. sclerotiorum , achieving over 98% curative and protective efficacies at the concentration of 200 μ g/mL. Further mechanistic investigations unveiled that compound 5v induced mycelial shrinkage and collapse in S. sclerotiorum , resulting in organelle damage and the accumulation of antioxidant enzyme activity. CONCLUSION The significant antifungal efficacy of the prepared thymol derivatives shall encourage further exploration of compound 5v as a promising candidate to develop novel fungicides for crop protection. © 2024 Society of Chemical Industry.

研究领域: 农业科学 · 植物病理学 · 化学生物学
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JOURNAL OF APPLIED POLYMER SCIENCE · 2021 ·Vol. 138 ·期 33 ·50911 · IF 3.125

Green cinnamaldehyde and thymol modified zinc oxide with double synergistic antibacterial effects in polypropylene

Yanqin Shi,Jiaqi Shen,Dieshuang Yang,Junnan Du,Songyan Lu,Meng Ma,Huiwen He,Si Chen,Xu Wang

The green cinnamaldehyde (CA) and thymol (THY) separately or successively modified O-ZnO (O-ZnO-CA, O-ZnO-THY, and O-ZnO-CA-THY) were prepared after (3-aminopropyl) triethoxysilane (KH550) was grafted to the surface of ZnO (O-ZnO) and characterized by FTIR, TGA, and SEM. Polypropylene composites (PP/O-ZnO-CA, PP/O-ZnO-THY, and PP/O-ZnO-CA-THY) were prepared by melting the modified O-ZnO and PP. The antibacterial tests showed that the antibacterial rate of PP/O-ZnO-CA and PP/O-ZnO-THY against S. aureus and E. coli was obviously enhanced. It indicated an excellent synergetic antibacterial effect of O-ZnO and the little CA or THY grafted on the surface of O-ZnO. The antibacterial effect of O-ZnO-CA and O-ZnO-THY was related to the hydrophobic and hydrophilic groups contained in CA and THY. Importantly, CA and THY in O-ZnO-CA-THY exhibited another excellent synergetic antibacterial effect against both S. aureus and E. coli . The antibacterial rate of three PP composites containing 4 phr O-ZnO-CA-THY against S. aureus and E. coli reached 95% and 90%, respectively. The mechanism was regarded as that CA and THY grafted onto the same O-ZnO improved the contact probability between antibacterial agents and bacteria. Moreover, O-ZnO-CA, O-ZnO-THY, and O-ZnO-CA-THY had excellent migration resistance in the PP matrix.

研究领域: 材料科学 · 微生物学
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FOOD CHEMISTRY · 2021 · IF 7.514

Long-term quality retention and decay inhibition of chestnut using thymol loaded chitosan nanoparticle

Xiaohong Guo,Lijun Chu,Tingting Gu,Sonia Purohit,Liping Kou,Boce Zhang

Thymol (TMO) was loaded into chitosan nanoparticles (CSNPs) to inhibit chestnuts decay during storage. Three chestnut treatments were evaluated, including the CK (uncoated control), CSNPs (coated with chitosan nanoparticles), and TMO-CSNPs (coated with thymol-loaded chitosan nanoparticles). Quality assessments of chestnuts were conducted periodically for up to 180 days, which included starch content, amylase activity, water content, respiration rate, weight loss rate, microbiological indicators, decay rate, and quality evaluation. Results indicated that TMO-CSNPs had significantly less nutrient loss in soluble sugar (10.61%) and starch content (27.72%) compared with CK, which was attributed to low metabolic activities as evident in low amylase activity and respiration rate. Moreover, TMO-CSNPs significantly inhibited the growth of mold and yeast (4.17 log CFU g −1 on day 180) and kept the lowest decay rate (5.33%). This study demonstrates the potential of food nanomaterial as an alternative strategy to promote food security and supply chain resilience.

CAS / MDL: 9012-76-4 7758-29-4
研究领域: 食品科学 · 微生物学 · 植物保护
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FOOD CONTROL · 2021 · IF 5.548

Characterization of sodium alginate-based films incorporated with thymol for fresh-cut apple packaging

Jingxin Chen,Ankang Wu,Mingliang Yang,Yonghong Ge,Penta Pristijono,Jianrong Li,Baocheng Xu,Hongbo Mi

The non-antibacterial and relatively poor mechanical properties of sodium alginate film limit its application for fresh-cut fruit packaging. The phenolic compound thymol has prominent antioxidant and antibacterial activities. The physical and functional properties of thymol/sodium alginate composite films and their ability to preserve fresh-cut apples were investigated. Thymol/sodium alginate composite films were observed to have high tensile strength, elongation at break and UV–vis light blocking capability, but low water vapor permeability, water solubility, and swelling ratio compared with standard sodium alginate film without thymol. The composite films also showed notable scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radicals. In addition, the composite films exhibited remarkable inhibition of the growth of Staphylococcus aureus and Escherichia coli . Furthermore, thymol/sodium alginate films could effectively reduce weight loss, retain nutrition and surface color of fresh-cut apple slices. Therefore, sodium alginate films with thymol have strong potential as a cling wrap material used in the packaging of fresh-cut fruits.

CAS / MDL: 9005-65-6
研究领域: 食品科学 · 材料科学
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Foods · 2022 ·Vol. 11 ·期 23 ·3818 · IF 5.561

Controlled Release of Thymol by Cyclodextrin Metal-Organic Frameworks for Preservation of Cherry Tomatoes

Zhicheng Li,Yanan Sun,Xiaodan Pan,Tong Gao,Ting He,Chun Chen,Bin Zhang,Xiong Fu,Qiang Huang

Thymol is a phenol monoterpene with potential antifungal, antioxidant and antibacterial activities. Due to the low water solubility and high volatility of thymol, encapsulation serves as an effective tool during application. In the present study, cyclodextrin (CD)-based metal-organic-frameworks (MOFs) were synthesized using α-CD, β-CD, and γ-CD as organic building blocks, and further complexed with thymol to produce three CD-MOF-THY inclusion complexes (ICs). The encapsulation content, release kinetics and fruit preservation effect of ICs were analyzed. Results showed that thymol was well embedded in γ-CD-MOFs, with the highest encapsulation content of 286.7 ± 8.4 mg/g. Release kinetics revealed that CD-MOFs exhibited a controlled release effect toward thymol for 35 days. The release kinetics of three ICs fit the Rigter–Peppas model well, with γ-CD-MOF-THY showing the lowest release rate constant of 2.85 at 50 °C, RH 75%. Moreover, γ-CD-MOF-THY exhibited a remarkable preservation performance on cherry tomatoes with the lowest decay index (18.75%) and weight loss (5.17%) after 15 days of storage, suggesting this material as a potential fresh-keeping material for fruit and vegetable preservation.Keywords:CD-MOF;thymol;encapsulation;controlled release;cherry tomatoes

CAS / MDL: 17465-86-0 89-83-8
研究领域: 食品科学 · 材料科学 · 农业科学
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