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TOXICOLOGY LETTERS · 2011 · IF 3.581

The estrogenic potential of salicylate esters and their possible risks in foods and cosmetics

Zhaobin Zhang,Chengxia Jia,Ying Hu,Libei Sun,Jian Jiao,Liang Zhao,Desheng Zhu,Jun Li,Yonglu Tian,Huicheng Bai,Ruobao Li,Jianying Hu

Salicylate esters (SEs), a class of chemicals extensively used as flavor and fragrance additives in foods, beverages and a wide variety of consumer products, are suspected to have estrogenic activity based on chemical analysis of in silica molecular docking. We evaluated the estrogenic potentials of phenyl salicylate (PhS), benzyl salicylate (BzS), phenethyl salicylate (PES), ethyl salicylate (ES) and methyl salicylate (MS) using an in vitro human estrogen receptor α (hERα)-coactivator recruiting assay and in vivo immature rodent uterotrophic bioassays. We found that PhS, BzS and PES showed obvious in vitro hERα agonistic activities; BzS in particular exhibited a higher estrogenic activity compared to bisphenol A (BPA). The uterine weights were significantly increased in mice treated with 11.1, 33.3, 100 and 300   mg/kg/day BzS and 33.3   mg/kg/day PES and rats treated with 3.7, 11.1, 33.3 and 100   mg/kg/day BzS for 3 days ( P   <   0.05). Finally, we transformed the daily intakes and the dermal exposures of SEs in the real world into estradiol equivalent concentrations (EEQs). We found that the EEQ of BzS daily intake in consumers in the U.S. and the EEQs of dermal BzS and PES exposure among high-volume users worldwide were higher than the maximum secure daily estradiol intake recommended by the U.S. Food and Drug Administration (FDA). In particular, the EEQ for dermal BzS exposure was up to 162   ng EEQ/kg, which is 3.3 times higher than the maximal acceptable daily E 2 intake recommended by the Joint FAO/WHO Expert Committee on Food Additives (JECFA).

研究领域: 毒理学 · 环境科学 · 食品科学 · 药理学
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PEST MANAGEMENT SCIENCE · 2019 ·Vol. 76 ·期 2 ·589-596 · IF 3.255

Efficacy of binary combinations between methyl salicylate and carvacrol against thrips Anaphothrips obscurus: laboratory and field trials

Xiao-Peng Lu,Jia-Huan Liu,Hua Weng,Zhi-Qing Ma,Xing Zhang

BACKGROUND Thrips Anaphothrips obscurus are one of the cosmopolitan major pests feeding on cereals and other grasses. In order to develop alternatives of chemical insecticides for thrips control, based on fumigant activity screening and evaluation of 22 essential oil (EO) compounds against the thrips, the binary interactions of methyl salicylate and carvacrol (MS-C) with high fumigant toxicity were studied systematically by bioassay and field trials. RESULTS The bioassay results showed that six in 22 EO compounds had high fumigant toxicity against both the second-instar nymphs and adults of A. obscurus , including methyl salicylate, carvacrol, thymol, trans -cinnamaldehyde, diallyl trisulfide, and L-perillaldehyde. Furthermore, the combination of methyl salicylate mixed with carvacrol at a volume ratio of 5:5 exhibited the most significant synergism against A. obscurus , with a poison ratio value of 1.32 and a co-toxicity coefficient of 151.15. The optimal formulation of microemulsion (ME) was composed of 5% methyl salicylate, 5% carvacrol, 46% adjuvant and 44% deionized water. The result of dynamic light scattering and stability showed that MS-C 10% ME was a transparent, single-phase and homogeneous liquid system. Field trials indicated that the ME displayed a significant control efficacy of about 89.17% on thrips in peppers, and 82.59% in broad bean on the seventh day post application with a dosage of 600.0 g A.I hm –2 , respectively. CONCLUSION The binary combination of MS-C possesses strikingly synergistic action against thrips A. obscurus , and the MS-C 10% ME has the potential to be developed as a botanical pesticide product for thrips control. © 2019 Society of Chemical Industry

研究领域: 植物保护 · 昆虫学
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RSC Advances · 2016 ·Vol. 6 ·期 94 ·91659-91668 · IF 3.289

Fabrication of highly selective molecularly imprinted membranes for the selective adsorption of methyl salicylate from salicylic acid

Yanli Mao,Minjia Meng,Li Yan,Fengquan Sun,Yongsheng Yan,Shijuan Liu

Herein, highly selective molecularly imprinted membranes (MIM) for methyl salicylate (MS) are synthesized with 4-vinylpyridine (4-VP), acrylamide (AM) or methacrylic acid (MAA) as the functional monomer based on the Al2O3 microporous ceramic membrane. Fast kinetic equilibrium for the rebinding of MS was found on all the imprinted membranes. Compared with AM-MIM and MAA-MIM, 4-VP-MIM presents a stronger adsorption capacity and higher permeation selectivity for MS due to the formation of ionic bonds between MS and 4-VP. SEM analysis shows that the surface morphology of the membranes is strongly influenced by the concentration of vinyltrimethoxysilane. Compared with 4-VP-MIM (1, 2 or 4), 4-VP-MIM3 possesses higher kinetic equilibrium adsorption, binding capacity and better selectivity for MS. It was found that the pseudo-second-order kinetic model is suited to describe the kinetic of 4-VP-MIM3, as determined by multiple regression analysis. The adsorption isotherm analysis exhibits that 4-VP-MIM3 has the maximum adsorption capacity for MS. Moreover, the selectivity experiment shows that the selectivity coefficients of 4-VP-MIM3 for MS relative to salicylic acid (SA) and phenol are 2.4185 and 2.2277, respectively, which are close to the predicted selectivity coefficient values.

研究领域: 材料科学 · 化学工程
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RSC Advances · 2013 ·Vol. 4 ·期 1 ·1-7 · IF 2.562

SO3H-functionalized Brønsted acidic ionic liquids as efficient catalysts for the synthesis of isoamyl salicylate

Duan-Jian Tao,Jing Wu,Zhen-Zhen Wang,Zhang-Hui Lu,Zhen Yang,Xiang-Shu Chen

Six Brønsted acidic ionic liquids (BAILs) composed of [HSO4] were prepared, characterized, and used as catalysts of low dosage in the synthesis of isoamyl salicylate. The effects of various parameters such as the kind of BAILs, temperature, catalyst loading, and molar ratio of the reactants on the conversion of salicylic acid were also examined in detail. The results suggested that the catalytic performances of BAILs were of close relevance to their Hammett acidities. The SO3H-functionalized BAILs 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate ([BSmim][HSO4]) and N-(4-sulfonic acid) butyl triethylammonium hydrogen sulfate ([BSEt3N][HSO4]) of strong acidities exhibited excellently catalytic activities and selectivities in the esterification of salicylic acid with isoamyl alcohol. The fully optimized geometries of [BSmim][HSO4] and [BSEt3N][HSO4] further manifest that their strong acidities are derived from the strong interactions between the anion with the sulfonic acid group. In addition, it was found that [BSmim][HSO4] could be also recovered easily and used repetitively at least six times without obvious decline in activity and quantity.

CAS / MDL: 1633-83-6 616-47-7
研究领域: 化学 · 催化材料科学
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TRIBOLOGY INTERNATIONAL · 2022 · IF 5.62

Salicylate ester derivatives as lubricant: Snergism of multiple interactions to improve tribological performances

Qianqian Yan,Haojie Ma,Rui Dong,Yunyun Yan,Ping Wen,Mingjin Fan

In this work, multiple interactions are considered to designedly synthesize salicylate derivatives as lubricants (S-C6, S-C8 and S-C10), and explore their effects on lubrication performances on steel-steel mating surfaces, compared to commercial isooctyl sebacate lubricant (1088). The optimal reduction by 13.3% in coefficient of friction and 70.2% in wear volume is achieved. The hypothetical lubrication mechanism reveals that cooperation of multiple interactions including coordination, cation···π, π···π stacking and van der Waal probably exists to drive salicylate molecules into forming a robust and thickened lubrication film with multi-layered structures shearing easily, which ensures the excellent lubrication. In contrary, either weak coordination or/and van der Waal’s interactions exists for 1088. This finding will push forward the recognition of lubrication explorations into the molecular level.

研究领域: 材料科学 · 化学工程
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POLYMER COMPOSITES · 2023 · IF 5.2

Preparation, characterization, and in vitro biological evaluation of salicylic acid-modified polyphenylene sulfide/quartz fiber/hydroxyapatite composite with high mechanical property for bone replacement

Shijie Cai,Dawei Yan,Xiaolu Chen,Hulin Yang,Chaobi Chen,Xiaodan Li,Yonggang Yan,Haohao Ren

The surface inertness of pure polyphenylene sulfide (PPS) limits its application in orthopedic implant materials. On that basis, modified PPS containing hydroxyl and carboxyl groups, that is, SAPPS was synthesized by nucleophilic substitution of dihalide monomers and sodium sulfide under high pressure. And consequently, a kind of ternary composite consisting of polyphenylene sulfide salicylate/quartz fiber/hydroxyapatite (SAPPS/QF/HA) was developed. The structure, composition, cross section morphology, degradation behavior, mechanical property, and biological property of all the composites were characterized by Fourier transform infrared spectroscopy, x-ray diffraction, differential scanning calorimetry, thermogravimetric analyzer, scanning electron microscope, energy dispersive spectrometer, and in vitro cytocompatibility tests. The composites exhibited good thermal property, which achieved a high melting point (277.8°C) and decomposition temperature (493.9–502.7°C at 5% weight loss). When the mass fraction of 20 wt% QF and 20 wt% HA was added in the pure SAPPS, the bending yield strength and bending modulus of the composite (SAPPS/20QF/20HA) were 177.4 MPa and 8.03 GPa, respectively, which increased by 61.6% and 158.2% compared with that of the pure SAPPS. Observing the considerable proliferation and adhesion of mouse bone marrow mesenchymal stem cells (mBMSCs) in the experiment, we demonstrated that the SAPPS and its composites were non-toxic, and the SAPPS/QF/20HA composites had the most prominent effect in promoting the proliferation and adhesion of mBMSCs. Highlights Salicylic acid-modified polyphenylene sulfide was studied as a biomaterial. The composite material has mechanics matching with human cortical bone. Cell experiments showed that all materials were nontoxic.

研究领域: 生物材料学 · 骨科材料科学
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CHINESE JOURNAL OF ANALYTICAL CHEMISTRY · 2015 · IF 0.754

Preparation and Evaluation of New Cellulose Acetylsalicylate Chiral Stationary Phase

Yang LI,Jin-Ke ZHU,Hua FENG,Lian-Jie LI,Deng-Gao JIANG

Cellulose acetylsalicylate chiral stationary phase (ACSP) was synthesized by using cellulose and o -acetylsalicylryl chloride, and its enantioseparation ability was evaluated by high performance liquid chromatography (HPLC). Commercial Chiralcel OJ column was evaluated for comparison. The effects of mobile phase composition and double ester carbonyls of derivative on enantioseparation were investigated. The structure of the obtained derivative was characterized by infrared (IR) spectroscopy and thermogravimetric analysis. Hexane-isopropanol (90:10–80:20, V/V , 0.1% DEA or TFA) was selected by comparison of four mobile phases, namely hexane-isopropanol, hexane-ethanol, hexane-methanol-isopropanol and hexane-methanol-dichloroethane. Seven racemates of catecholamines and amides were used to evaluate its chiral recognition ability in normal phase elution mode, and the regularity and characteristics of the novel chiral stationary phase were explored. The chromatographic results showed that cellulose ACSP exhibited high enantioseparation ability for catecholamines and some racemates with amide group due to the hydrogen-bond, dipole interaction of carbonyls of acetylsalicylate and the π-π interaction with benzene ring, and the optimum amount of diethylamine or trifluoroacetic acid was 0.1%.

CAS / MDL: 919-30-2
研究领域: 化学 · 分析化学 · 药学
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JOURNAL OF SOL-GEL SCIENCE AND TECHNOLOGY · 2020 ·Vol. 97 ·期 2 ·466-478 · IF 2.008

Synthesis of phenylalanine and leucine dipeptide functionalized silica-based nanoporous material as a safe UV filter for sunscreen

Ma Haohua,Wang Jianqiang,Zhang Wenpei,Guo Cheng

To allay concerns that sunscreen ingredients are harmful to skin health, we have developed phenylalanine (Phe) and leucine (Leu) dipeptide functionalized silica-based nanoporous material (Phe-Leu-OMe-Meso) as a safe ultraviolet filter for skin protection from UVA/UVB sun irradiation. The selected peptide-based functional molecules are composed of natural amino acids, which have obvious advantages compared with other biological molecules and organic molecules, such as low toxicity and high stability. Octyl salicylate (OS) is adopted as the drug molecule to observe the adsorption behavior of the nanoporous materials. The results confirm that Phe groups effectively improve the OS loaded capacity of Phe-Leu-OMe-Meso by aromatic π – π stacking interaction, and the experimental data obey the pseudo-second-order kinetic model and the Langmuir, Freundlich, Temkin isotherm model. Moreover, in vitro evaluation of the spectrophotometric sun protection factor indicates that Leu groups make Phe-Leu-OMe-Meso possess an excellent sunscreen efficacy close to that of mesoporous TiO 2 and exhibit a synergistic effect with OS on sun protection. In summary, the dipeptide functionalization of silica-based nanoporous material has an excellent prospect in the application of sunscreen.

研究领域: 材料科学 · 生物学 · 皮肤病学
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Frontiers of Materials Science · 2022 ·Vol. 16 ·期 4 ·1-9 · IF 2.612

Ultrasensitive methyl salicylate gas sensing determined by Pd-doped SnO2

Zhu Chaoqi,Li Xiang,Wang Xiaoxia,Su Huiyu,Ma Chaofan,Guo Xiang,Xie Changsheng,Zeng Dawen

Efficient chemical warfare agents (CWAs) detection is required to protect people from the CWAs in war and terrorism. In this work, a Pd-doped SnO 2 nanoparticles-based gas sensor was developed to detect a nerve agent simulant named methyl salicylate. The sensing measurements of methyl salicylate under different Pd doping amounts found that the 0.5 at.% Pd-doped SnO 2 exhibited a significant improvement in the detection of methyl salicylate at the ppb (1 ppb = 10 −9 ) level, and the response value to 160 ppb methyl salicylate is 0.72 at 250 °C. Compared with the pure SnO 2 , the response value is increased by 4.5 times, which could be attributed to the influence of the noble metal Pd on the oxygen state and its catalytic effect. In addition, the 0.5 at.% Pd-doped SnO 2 sensor still has an obvious response to 16 ppb methyl salicylate with a response value of 0.13, indicating the lower detection limit of the sensor.

研究领域: 材料科学 · 化学传感器 · 纳米技术 · 环境监测
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Desalination and Water Treatment · 2025 · IF 1

Boron extraction from original alkaline brine using synergistic extraction system

Licheng Zhang,Yongming Zhang,Feiyu Kong,Xiaowu Peng,Lijuan Li

This paper presents a novel system and method for the extraction and separation of boron from alkaline solutions. The extraction system consists of a 1:1 molar ratio of 2-octanol and salicylate ester, which effectively extracts boron from the solution. The extraction efficiency of boron increases with the pH of the solution, reaching up to 75% in a single extraction stage when pH > 9. The study also investigates the effects of extraction ratio, extraction time, and extraction temperature on the extraction performance. Under optimized conditions, using natural salt lake brine from Tibet as the raw material, a three-stage countercurrent extraction process can achieve a boron extraction rate of 95%. After subsequent stripping and concentration, boric acid can be directly produced with a purity exceeding 99%. Moreover, the extraction system demonstrates good stability during the extraction-stripping cycle. FT-IR and Raman spectrum were employed to investigate the main functional group of the extraction process, and DFT was used to study the coordination mechanism. This work provides an effective pathway for the comprehensive utilization of boron in alkaline solutions.

CAS / MDL: 10043-35-3 1330-43-4
研究领域: 化学工程 · 湿法冶金 · 分离科学 · 环境化学 · 材料科学
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FOOD CHEMISTRY · 2024 · IF 8.5

The combination of metabolome and transcriptome clarifies the inhibition of the Alternaria toxin accumulation by methyl ferulate

Shuai Ge,Ying Xie,Ke Ding,Saiqing Xu,Haishan Xu,Xia Chang,Huan Li,Rongrong Wang,Zisheng Luo,Yang Shan,Shenghua Ding

As one of the most typical pathogens in fruit postharvest diseases, Alternaria alternata ( A. alternata ) can produce Alternaria toxins (ATs) aggravating fruit decay and harming human health. In this study, ATs (tenuazonic acid, alternariol monomethyl ether, and alternariol) production was inhibited effectively by 200 and 8000 mg/L MF (methyl ferulate) in vitro and in vivo. 1-Octen-3-ol and 3-octanol were the potential iconic volatile organic compounds of ATs (R 2  > 0.99). MF induced oxidative stress, resulting in physiological and metabolic disorders, membrane lipid oxidation and cell damage. It decreased precursors and energy supply by disturbing amino acid metabolism, ABC transporters, citrate cycle, pentose and glucuronate interconversions to regulate ATs synthesis. MF down-regulated the genes related to ATs synthesis ( PksJ , AaTAS1 , and OmtI ), transport ( AaMFS1 and MFS ), and pathogenicity to affect ATs production and virulence. This study provided a theoretical basis for the control of ATs production.

CAS / MDL: 641-38-3 67-56-1
研究领域: 植物病理学 · 分子生物学 · 代谢组学 · 转录组学
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