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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY · 2017 ·Vol. 53 ·期 3 ·459-461 · IF 0.603

New synthesis of 4-methoxyisophthalic acid

Liu X. J.,Yan Y. N.,Wang S. Q.,Li X.,Liu X. G.

A new synthetic route to 4-methoxyisophthalic acid, the key intermediate in the synthesis of Picotamide, is reported. The new protocol starts from commercially available and cheap 4-methylphenol and includes four steps: esterification, Fries rearrangement, methylation, and oxidation; the overall yield is 49%. Unlike the traditional Blanc chloromethylation/oxidation scheme, the proposed procedure avoids using volatile and corrosive hydrochloric acid.

研究领域: 有机化学 · 药物化学
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Horticultural Plant Journal · 2022 · IF 4.24

Effects of fresh-cut and storage on glucosinolates profile using broccoli as a case study

Xiaoxin Huang,Bing Cheng,Yaqin Wang,Guangmin Liu,Liping Hu,Xiaolu Yu,Hongju He

Glucosinolates (GLS) contribute to the unique flavour, nutrition, and plant defence of the Cruciferous vegetables. Understanding the GLS changes through postharvest processing is essential for defined preservation. In this study, four different fresh-cut types, whole flower (W), floret (F), quarterly cut floret (QF) and shredded floret (FS) of broccoli, were stored for 0, 1, 2 and 3 day (s) to explore GLS responses to postharvest treatments. As a result, seven GLS were identified, mainly including glucoraphanin (RAA), neoglucobrassicin (NEO), and glucobrassicin (GBC) and accounting for 52.69%, 20.12% and 14.99% of the total GLS (21.92 ± 0.48) μmol · g -1 DW, respectively. FS had the sharpest decrease in GLS after three days of storage (6.55 ± 0.37) μmol · g -1 DW, while QF had the least (10.16 ± 0.33) μmol · g -1 DW. All GLS components decreased over storage, except for 4-methoxyglucobrassicin (4 ME) in FS and QF, suggesting its key role in serious wound defence. The results suggested certain postharvest approaches influenced the flavour and nutrition of broccoli.

CAS / MDL: 7681-52-9 7558-79-4
研究领域: 食品科学 · 植物化学
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Scientific Reports · 2021 ·Vol. 11 ·期 1 ·1-10 · IF 4.38

Identification and field verification of an aggregation pheromone from the white-spotted flower chafer, Protaetia brevitarsis Lewis (Coleoptera: Scarabaeidae)

Zhang Xiaofang,Wang Liuyang,Liu Chunqin,Liu Yongqiang,Mei Xiangdong,Wang Zhongyue,Zhang Tao

The white-spotted flower chafer (WSFC), Protaetia brevit arsis Lewis, is native to East Asia. Although their larvae are considered a potential resource insect for degrading plant residues, producing protein fodder, and processing to traditional medicine, adult WSFCs inflict damage to dozens of fruit and economic crops. The control of the WSFC still relies heavily on pesticides and the inefficient manual extraction of adults. Here, we report the identification and evaluation of the aggregation pheromone of WSFCs. From the headspace volatiles emitted from WSFC adults, anisole, 4-methylanisole, 2-heptanone and 2-nonanone were identified as WSFC-specific components. However, only anisole and 4-methylanisole elicited positive dose–response relationship in electroantennography tests, and only 4-methylanisole significantly attracted WSFCs of both sexes in olfactometer bioassays and field experiments. These results concluded that 4-methylanisole is the aggregation pheromone of WSFCs. Furthermore, we developed polyethylene vials as long-term dispensers of 4-methylanisole to attract and kill WSFCs. The polyethylene vial lures could effectively attracted WSFCs for more than four weeks. Pheromone-based lures can be developed as an environmentally friendly protocol for monitoring and controlling WSFC adults.

研究领域: 昆虫学 · 农业害虫防治 · 化学生态学
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APPLIED CATALYSIS A-GENERAL · 2019 · IF 4.63

Kinetic model of resolution of 4-methoxymandelic acid enantiomers by lipase-catalyzed transesterification reaction

Xin Yuan,Panliang Zhang,Weifeng Xu,Kewen Tang

This paper reports the kinetics resolution of ( R , S )-4-methoxymandelic acid (4-MMA) by lipase AK-catalyzed transesterification reaction, using vinyl acetate (VA) as acyl donor in methyl tert-butyl ether (MTBE). Considering the Ping-Pong bi-bi mechanism with 4-methoxymandelic acid inhibition, the kinetic model was established. Kinetic parameters were obtained by fitting time-concentration curves for different initial 4-methoxymandelic acid concentrations. The average relative error below 3.0% indicated that the model predictions were in good agreement with the experimental data. Furthermore, the kinetic model was employed to predict the effects of enzyme loading, initial vinyl acetate concentration and reaction time on enantiomeric excess (ee s ) and conversion of substrate (c), and to optimize the conditions. The excellent results with high conversion of 4-MMA (50.2%) and large enantiomeric excess of substrate (98.6%) were achieved under the optimal conditions.

研究领域: 生物化学 · 有机化学
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ACS Omega · 2019 · IF 2.584

Porous Fe@C Composites Derived from Silkworm Excrement for Effective Separation of Anisole Compounds

Yuxiang Wu,Yan Huang,Hong Huang,Yaseen Muhammad,Zuqiang Huang,Joseph Winarta,Yanjuan Zhang,Shuangxi Nie,Zhongxing Zhao,Bin Mu

Silkworm excrement is a very useful biomass waste, composed of layer-structured fats and proteins, which are great precursors for carbon composite materials. In this work, new porous composites derived from silkworm excrement were prepared for selective separation of flavor 4-methylanisole from the binary 4-methylanisole/4-anisaldehyde mixture. In particular, the silkworm excrement, possessing a unique nanosheet structure, is converted into a graphite-like carbon by a simple calcination strategy followed by a metal-ion-doping procedure. This Fe@C composite exhibits a special nano-spongy morphology, anchoring Fe3C/Fe5C2 on the carbon nanosheets. Density functional theory simulations showed that 4-methylanisole presents a stronger π–π interaction and attraction forces with sp2 carbon nanosheets in Fe@C composites than 4-anisaldehyde. The selective adsorption experiments further confirmed that the Fe@C composites exhibited a 4-methylanisole capacity of 7.3 mmol/g at 298 K and the highest selectivity of 17 for an equimolar 4-methylanisole/4-anisaldehyde mixture among the examined adsorbents including MOFs and commercial activated carbon materials, which demonstrates the potential of this low-cost and eco-friendly porous carbon material as a promising sustainable adsorbent.

研究领域: 材料科学 · 环境科学
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FLAVOUR AND FRAGRANCE JOURNAL · 2025 · IF 2

The Anti-Inflammatory Activities of Sphagnum palustre L. Ethanol Extract to Control Inflammation in RAW264.7 Cells

Zhi Wu,Jiahui Zheng,Yang Xu,Dairong Wang,Qingbin Han,Ping Liu,Xiaorong Liu,Lanyue Zhang

Discomfort caused by inflammation leads to stress and anxiety in patients and seriously decreases the patients' quality of life. People prefer to use natural products instead of anti-inflammatory drugs because of their low toxicity and side effects. Studies have shown that Sphagnum palustre L. ( S. palustre ) can be used as medicinal plant, but few studies have focused on its anti-inflammatory effects. This study explored the mechanism of action of the ethanol extract of the peat moss plant S. palustre on lipopolysaccharide-induced inflammation in macrophage RAW264.7 cells. Components in S. palustre ethanol extracts (SPE) were identified by HPLC-MS, which mainly included 4-methoxybenzaldehyde, 4-methoxycinnamaldehyde and oleanolic acid. The effects of different concentrations (6.25–100 μg/mL) of SPE after 24 h administration were evaluated to establish a cellular inflammation model. Three biological replicates were performed based on each experiment, the MTT assay results showed that a low concentration of SPE promoted cell proliferation marked by Formazan. In a neutral red uptake assay, the SPE group was effectively inhibited the cell phagocytosis rate. With the increase of SPE concentration, intracellular ROS release decreased, which detected by DCFH-DA. Immunofluorescence assay result showed that SPE inhibited the release of reactive oxygen species from macrophages with fluorescent markers and DAPI. SPE inhibited the release of nitric oxide from macrophages as well. What's more, SPE significantly decreased the protein expression of interleukin (IL)-1, IL-6, and nuclear factor (NF)-κB according to enzyme-linked immunosorbent and immunocytochemical assays. SPE reduces inflammation in macrophage RAW264.7 cells and thus is a promising natural anti-inflammatory plant.

研究领域: 药理学 · 免疫学 · 细胞生物学 · 药用植物研究
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JOURNAL OF ENVIRONMENTAL SCIENCE AND HEALTH PART A-TOXIC/HAZARDOUS SUBSTANCES & ENVIRONMENTAL ENGINEERING · 2025 · IF 2.1

Analyzing the interactions between 2-ethylhexyl 4-methoxycinnamate and bovine serum albumin under coexistence and encapsulation of β-cyclodextrin

Xinming Li,Jiali Gu,Hongrui Liu,Yang Gao

2-ethylhexyl 4-methoxycinnamate (EHMC), a UV filter commonly used in sunscreen products, is also an emerging environmental pollutant that interferes with the structure and function of bovine serum albumin (BSA). A study was conducted on the interaction between EHMC and BSA when they coexist and are encapsulated within β-cyclodextrin (β-CD). Multiple spectra demonstrate, both qualitatively and quantitatively, that β-CD coexistence and encapsulation weaken the interaction between EHMC and BSA, resulting in a more difficult binding process between the two and inhibiting EHMC-induced conformational changes in BSA. Once encapsulated by β-CD, the inclusion complex (IC) was weakly bound to BSA (Kb=(7.63 ± 0.01)×104 M−1), and it had no significant impact on BSA’s structure. Despite this, β-CD did not significantly alter EHMC’s UV shielding ability.

CAS / MDL: 111689-03-3
研究领域: 生物化学 · 环境科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF LUMINESCENCE · 2016 · IF 2.693

Theory and experiment studies of the 1,4-bis(4-methoxylstyryl)benzene as a wavelength shifter of liquid scintillator

Zhanlong Zheng,Jiayi Zhu,Yutie Bi,Yewei Xu,Qianfeng Zhang,Xing Zhang,Junjiang Li,Lin Zhang

A novel wavelength shifter of the 1,4-bis(4-methoxylstyryl)benzene (bis-4-MOSB) was synthesized by employing the classical Horner-Wadsworth-Emmons reaction. Feasible analysis of the bis-4-MOSB as the wavelength shifter in a ternary liquid scintillator, in which p-xylene (PX) was as the solvent and 2,5-diphenyloxazole (PPO) was as the primary fluor, was carried out. The optimum prescription with 3.5   g/L PPO and 25   mg/L bis-4-MOSB was obtained with regard to the light yield. A series of characterization tests based on the optimal formulation were performed. Compared with the 1,4-bis(2-methylstyryl)benzene (bis-MSB), the maximum absorption peak at 356   nm and maximum emission peak at 421   nm in n-hexane with the red shift of 10   nm and 3   nm, respectively, were measured accordingly. The light yield characterized by using a relative measurement method achieved as high as 75.85% of the anthracene crystal. A brief density functional calculation was conducted to have an insight into the electronic structure characteristic of the bis-4-MOSB in the scintillation process.

研究领域: 化学 · 物理学
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2021 ·Vol. 413 ·期 23 ·5695-5702 · IF 4.157

Altering the substituents of salicylic acid to improve Berthelot reaction for ultrasensitive colorimetric detection of ammonium and atmospheric ammonia

Yu Haili,Zhang Guihua,Cai Yanhua,Dong Faqin

The Berthelot reaction is a classic method for detection of ammonium (NH 4 + ) and atmospheric ammonia (NH 3 ) by using salicylic acid (SA) as the chromogenic substrate. However, there lacks a method for improving the activity of the Berthelot reaction to enhance the analytical performance for detection of NH 4 + and NH 3 . Here, five SA analogues with electron-withdrawing groups (-F) and electron-donating groups (-CH 3 and -OCH 3 ) at different positions of the aromatic ring have been chosen as the alternative to SA for Berthelot reaction. Among these analogues, 4-methoxysalicylic acid (4-OCH 3 -SA) shows the best colorimetric response and color change at a NH 4 + concentration of 30 μM, and the sensitivity of 4-OCH 3 -SA-based colorimetric assay for NH 4 + increases 1.75-fold compared with that of SA-based colorimetric method. This enhancement effect is attributed to the strong electron-donating property of 4-OCH 3 group, activating the two-step electrophilic aromatic substitution reaction in the Berthelot reaction. Additionally, visual and sensitive detection of NH 3 is realized, along with a low limit of detection down to 0.037 ppm. Furthermore, we demonstrate that this assay is reliable and practical for detection of NH 4 + and NH 3 in real water and air samples with good accuracy.

研究领域: 分析化学 · 环境科学
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INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY · 2020 ·Vol. 56 ·期 1 ·178-184 · IF 2.773

2-Hydroxy-4-methoxybenzaldehyde inhibits the growth of Aspergillus flavus via damaging cell wall, cell membrane, manipulating respiration thus creating a promising antifungal effect on corn kernels

Qian Li,Xiaoman Zhu,Yanli Xie,Shilin Ren

Summary This study investigated the antifungal activity and the potential antifungal mechanisms of 2-hydroxy-4-methoxybenzaldehyde (HMB) against Aspergillus flavus ( A. flavus ). The minimum inhibitory concentration (MIC) of HMB in preventing spore germination was 70 μg mL −1 . HMB at MIC disrupted cell wall integrity by reducing the number of septa by 86.66% ( P < 0.05) in mycelia and increased cell membrane permeability by about 14-fold ( P < 0.05) evidenced by propidium iodide (PI) staining. Furthermore, HMB at MIC inhibited respiration by 33.33%. These results revealed that the antifungal activity of HMB against A. flavus could be attributed to the damaged cell wall integrity, cell membrane permeability and respiration metabolism. What’s more, A. flavus was completely restrained in corn kernels due to HMB. Therefore, HMB could be applied as an effective antifungal agent.

CAS / MDL: 673-22-3
研究领域: 微生物学 · 植物病理学 · 食品科学
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Materials · 2016 ·Vol. 9 ·期 9 ·779 · IF 2.728

Multichromic Polymers Containing Alternating Bi(3-Methoxythiophene) and Triphenylamine Based Units with Para-Protective Substituents

Yingfei Hou,Lingqian Kong,Xiuping Ju,Xiaoli Liu,Jinsheng Zhao,Qingshan Niu

Two novel triphenylamine-based thiophene derivative monomers, 4-cyano-4′,4″-di(4-methoxythiophen-2-yl)triphenylamine and 4-methoxy-4′,4″-di(4-methoxythiophen-2-yl)triphenylamine, were successfully synthesized. The corresponding polymers including poly (4-cyano-4′,4″-di(4-methoxythiophen-2-yl)triphenylamine) and poly (4-methoxy-4′,4″-di(4-methoxythiophen-2-yl)triphenylamine) were electrochemically synthesized and characterized by multiple test method. The electrochemical measurements and spectroelectrochemical analyses revealed that both of the two polymers had quasi-reversible redox behavior and multi-electrochromic properties. The two polymer films showed reversible electrochemical oxidation, excellent optical contrasts in NIR region (62% at 1070 nm for the first polymer, and 86% at 1255 nm for the second polymer), satisfactory coloration efficiencies and fast switching times. The research on the application of the as prepared polymer in the fabrication of electrochromic device was also conducted, employing PCMTPA or PMMTPA as the anodically coloring materials.Keywords:4-cyanotriphenylamine;4-methoxytriphenylamine;bithiophenes derivatives;electrochromism;spectroelectrochemistry;electrochromic devices

研究领域: 材料科学 · 电化学 · 高分子化学 · 光电技术
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Frontiers in Microbiology · 2024 · IF 4

2-Hydroxy-4-methoxybenzaldehyde, a more effective antifungal aroma than vanillin and its derivatives against Fusarium graminearum, destroys cell membranes, inhibits DON biosynthesis, and performs a promising antifungal effect on wheat grains

Li Qian,Wang Chong,Xiao Hongying

Fusarium graminearum (F. graminearum) is a severe pathogen threatening the safety of agriculture and food. This study aimed to explore the antifungal efficacies of several plant-derived natural compounds (vanillin and its derivatives) against the growth of F. graminearum and investigate the antifungal mechanism of 2-hydroxy-4-methoxybenzaldehyde (HMB), the strongest one. The minimum inhibitory concentration (MIC) of HMB in inhibiting mycelial growth was 200 μg/mL. HMB at MIC damaged cell membranes by increasing the permeability by about 6-fold (p < 0.05) as evidenced by propidium iodide (PI) staining. Meanwhile, the content of malondialdehyde (MDA) and glycerol was increased by 45.91 and 576.19% by HMB treatment at MIC, respectively, indicating that lipid oxidation and osmotic stress occurred in the cell membrane. Furthermore, HMB exerted a strong antitoxigenic role as the content of deoxynivalenol (DON) was remarkably reduced by 93.59% at MIC on 7th day. At last, the antifungal effect of HMB against F. graminearum was also confirmed on wheat grains. These results not only revealed the antifungal mechanism of HMB but also suggested that HMB could be applied as a promising antifungal agent in the preservation of agricultural products.

研究领域: 植物科学 · 食品安全 · 微生物学 · 农业化学
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