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INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY · 2015 · IF 3.082

Effects of preservatives on Alicyclobacillus acidoterrestris growth and guaiacol production

Rui Cai,Yahong Yuan,Zhouli Wang,Chunfeng Guo,Bin Liu,Chunqing Pan,Laping Liu,Tianli Yue

Alicyclobacillus acidoterrestris can survive the pasteurization process, multiply in pasteurized juices and produce guaiacol which causes medicinal or antiseptic off-flavors. Chemical preservatives have the potential to suppress outgrowth of surviving populations during subsequent storage of fruit juices. In the present study, the individual effects of potassium sorbate , sodium benzoate , potassium metabisulfite , dehydroacetic acid , ethyl 4-hydroxybenzoate, cinnamic acid and ε-polylysine on A. acidoterrestris growth and guaiacol production were firstly evaluated in a laboratory medium. Of the seven preservatives investigated, only dehydroacetic acid, cinnamic acid and ε-polylysine were effective both in controlling growth and guaiacol formation by A. acidoterrestris . Then, these three antimicrobials were applied to apple juice. Through the addition of 270   mg/L dehydroacetic acid, 108   mg/L cinnamic acid or 100   mg/L ε-polylysine, the A. acidoterrestris counts were reduced by 3.43, 3.17 and 4.78   log   colony   forming   unit   (CFU)/mL, respectively, and no guaiacol was detected after 14   days of storage. Sensory evaluation revealed that the addition of these three preservatives did not affect the organoleptic properties of the apple juice. Results obtained in this paper could be very useful for a better control of A. acidoterrestris -related spoilage in the fruit juice/beverage industry.

研究领域: 食品科学 · 微生物学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2021 ·Vol. 102 ·期 1 ·250-258 · IF 3.639

Maillard reaction products and guaiacol as production process and raw material markers for the authentication of sesame oil

Rui Liu,Hengye Chen,Shuo Wang,Liuna Wei,Yongjie Yu,Wei Lan,Jian Yang,Lanping Guo,Haiyan Fu

BACKGROUND Sesame oil has an excellent flavor and is widely appreciated. It has a higher price than other vegetable oils because of the high price of its raw materials, and different processing techniques also result in products of different quality levels, which can command different prices. In the market, there is a persistent problem of adulteration of sesame oil, driven by economic interests. The screening of volatile markers used to distinguish the authenticity of sesame oil raw materials and production processes is therefore very important. RESULTS In this work, six markers related to the production processes and raw materials of sesame oil were screened by gas chromatography–tandem mass spectrometry (GC-MS/MS) combined with chemometric analysis. They were 3-methyl-2-butanone, 2-ethyl-5-methyl-pyrazine, guaiacol, 2,6-dimethyl-pyrazine, 5-methyl furfural, and ethyl-pyrazine. The concentration of these markers in sesame oil is between 10 and1000 times that found in other vegetable oils. However, only 3-methyl-2-butanone and 2-ethyl-5-methyl-pyrazine differed significantly as the result of the use of different production processes. Except for guaiacol, which was mainly derived from raw materials, the other five compounds mentioned above all result from the Maillard reaction during thermal processing. The six compounds mentioned above are sufficient to distinguish fraud involving sesame oil raw materials and production processes, and can identify accurately adulteration levels of 30% concentration. CONCLUSION In this study, the classification markers can identify the adulteration of sesame oil accurately. These six compounds are therefore important for the authenticity of sesame oil and provide a theoretical basis for the rapid and accurate identification of the authenticity of sesame oil. © 2021 Society of Chemical Industry.

研究领域: 食品科学 · 分析化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ACS Sustainable Chemistry & Engineering · 2024 · IF 7.1

Preparation of Poly(guaiacol methacrylate-methyl methacrylate) Dielectric Films through Biobased Origin Guaiacol

Leipeng Liu,Haochen Yun,Xiaofei Chen,Yuanduo Duan,Zhe Ji,Shenghua Lv,Yuehong Zhang

Film capacitors make extensive use of polymer dielectrics. However, most of the currently studied dielectric film substrate feedstocks are from fossil energy sources. Herein, a series of biobased dielectric copolymers poly(guaiacol methacrylate-methyl methacrylate) [P(GEMA-MMA)] originating from the biobased origin guaiacol have been reported. P(GEMA-MMA) was produced by copolymerizing GEMA and MMA. Anew type of dielectric film with excellent comprehensive performance was obtained. The guaiacol structure in the copolymer has higher HOMO levels that could take charge traps and capture free charge carriers in the polymer, thus endowing the polymer with excellent energy storage performance. P(GEMA-MMA)-1:7 possess a high breakdown strength Eb of 710.5 MV/m at room temperature, which was 32.5% higher than that of pure PMMA. The charge–discharge efficiency was 87.0% at 500 MV/m, which was much higher than that of pure PMMA (70% under 500 MV/m). Even at 100 °C, the energy storage efficiency of P(GEMA-MMA)-1:7 still can be maintained at a high level of 84.7%. This work offers a practical method for producing biobased dielectric films with outstanding all-round performance.

研究领域: 材料科学 · 能源存储 · 高分子化学
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CHINESE JOURNAL OF CATALYSIS · 2026 · IF 17.2

Electrocatalytic hydrodeoxygenation of guaiacol on Pt/TiO2: The modulation on guaiacol adsorption and H spillover

Yiwei Zhao,Zuhang Jin,Cheng Tao,Rui Du,Yongzheng Shi,Chao Zhang

The synthesis of KA oil (a cyclohexanone-cyclohexanol mixture) from guaiacol through mild electrocatalytic approach represents a sustainable strategy for biomass valorization. Herein, we report the electrocatalytic conversion of guaiacol to KA oil over the reduced Pt/TiO 2 catalysts. The TiO 2 -induced hydrogen spillover effect facilitates strategic modulation of H ads (H*) coverage on Pt surfaces, thereby effectively suppressing competitive aromatic ring hydrogenation and excessive hydrogen evolution reactions. Comparative studies of electrocatalysis and thermocatalysis have demonstrated that Pt active sites serve as the dominant catalytic centers. However, H spillover significantly influences reactivity and selectivity, particularly in the electrocatalytic pathways. The electrocatalytic system demonstrates preferential C–O bond cleavage with KA oil selectivity around 70%. This work provides valuable insights into the regulation of metal-support interactions in the design of electrocatalysts.

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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2016 · IF 1.207

Investigation on molar heat capacity, standard molar enthalpy of combustion for guaiacol and acetyl guaiacol ester

Changshuai Shen,Wenli Li,Cairong Zhou

The molar heat capacities ( C p ) of guaiacol (CAS 90-50-1) and acetyl guaiacol ester (AGE, CAS 613-70-7) were determinated from 290   K to 350   K by differential scanning calorimetry (DSC), and expressed as a function of temperature. Two kinds of group contribution models were used to estimate the molar heat capacities of both guaiacol and AGE, the average relative deviation is less than 10%. The standard molar enthalpies of combustion of guaiacol and AGE were −   3590.0   kJ·mol −   1 and −   4522.1   kJ·mol −   1 by a precise thermal isolation Oxygen Bomb Calorimeter. The standard molar enthalpies of formation of guaiacol and AGE in a liquid state at 298.15   K were calculated to be −   307.95   kJ·mol −   1 and −   448.72   kJ·mol −   1 , respectively, based on the standard molar enthalpies of combustion. The thermodynamic properties are useful for exploiting the new synthesis method, engineering design and industry production of AGE using guaiacol as a raw material.

CAS / MDL: 1460-57-7 90-05-1
研究领域: 物理化学 · 热力学
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INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY · 2015 · IF 3.082

Precursors and metabolic pathway for guaiacol production by Alicyclobacillus acidoterrestris

Rui Cai,Yahong Yuan,Zhouli Wang,Chunfeng Guo,Bin Liu,Laping Liu,Yutang Wang,Tianli Yue

Alicyclobacillus acidoterrestris has recently received much attention due to its implication in the spoilage of pasteurized fruit juices, which was manifested by the production of guaiacol. Vanillic acid and vanillin have been accepted as the biochemical precursors of guaiacol in fruit juices. The purpose of this study was to try to find other precursors and elucidate details about the conversion of vanillic acid and vanillin to guaiacol by A . acidoterrestris . Four potential substrates including ferulic acid, catechol, phenylalanine and tyrosine were analyzed, but they could not be metabolized to guaiacol by all the thirty A . acidoterrestris strains tested. Resting cell studies and enzyme assays demonstrated that vanillin was reduced to vanillyl alcohol by NADPH-dependent vanillin reductase and oxidized to vanillic acid by NAD(P) + -dependent vanillin dehydrogenases in A . acidoterrestris DSM 3923. Vanillic acid underwent a nonoxidative decarboxylation to guaiacol. The reversible vanillic acid decarboxylase involved was oxygen insensitive and pyridine nucleotide-independent.

研究领域: 微生物学 · 食品科学
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Journal of Ocean University of China · 2024 ·Vol. 23 ·期 5 ·1275-1286 · IF 1.4

Photochemical Production of Methyl Halides with Guaiacol as the Precursor

Yang Fan,Zhang Yan,Wu Guanyu,He Zhen,Yang Guipeng

Methyl halides are crucial trace greenhouse gases in the atmosphere, playing a significant role in global climate change and the atmospheric environment. This study investigated the photochemical production of methyl halides in an artificial seawater system using guaiacol as a precursor through laboratory simulation experiments. The influences of various environmental factors, including illumination time, radiation wavebands, illumination intensity, concentrations of guaiacol and halide ions (X − ), Fe 3+ , salinity, dissolved oxygen (DO), and pH value on the photochemical production of methyl halides were examined. We demonstrated that increased illumination intensity and duration promote the photochemical production of methyl halides, with a notable enhancement under UV-B radiation. Guaiacol and halide ions were identified as key precursors, and their high concentrations facilitated the formation of methyl halides. Additionally, different types of halide ions exhibited a competitive relationship in producing methyl halides. The study found that an increase in pH inhibited the photochemical formation of CH 3 I due to the reaction between OH − and ·CH 3 . Dissolved oxygen was found to inhibit the photochemical formation of CH 3 I while promoting the formation of CH 3 Cl. Conversely, an appropriate concentration of Fe 3+ enhanced the photochemical production of methyl halides. Field observations indicated a high photochemical production of methyl halides in the natural waters near Qingdao’s coastal area, likely due to the high concentration of dissolved organic matter (DOM), which supports photochemical reactions. Furthermore, the photochemical production of methyl halides in natural seawater was significantly higher than in dark conditions, underscoring the importance of illumination in promoting these photochemical processes in seawater.

CAS / MDL: 7758-02-3 7681-11-0
研究领域: 环境科学 · 海洋化学
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CATALYSIS LETTERS · 2019 ·Vol. 150 ·期 3 ·837-848 · IF 2.372

Selective Hydrodeoxygenation of Guaiacol to Cyclohexanol Catalyzed by Nanoporous Nickel

Lu Jiqing,Liu Xing,Yu Guanqun,Lv Jinkun,Rong Zeming,Wang Mei,Wang Yue

Abstract Cyclohexanol is an important feedstock in the chemical industry and the selective hydrodeoxygenation of lignin-derived guaiacol to cyclohexanol have gained increasing research attention in recent years. In this work, a series of nanoporous metal catalysts were employed for the hydrodeoxygenation of guaiacol and nanoporous Ni (NP-Ni) exhibited high catalytic performance for the preparation of cyclohexanol. With water as solvent, 100% conversion of guaiacol and over 90% selectivity to cyclohexanol were achieved at 180 °C and 2 MPa for 4 h. In order to further promote the stability of NP-Ni, induction melting, vacuum arc melting and mechanical alloying were separately employed for the preparation of NiAl precursor alloy. Mechanical alloying seemed to be an effective method for the alloying process and the as-prepared NP-Ni could keep almost stable after 10 times recycling. Furthermore, the reaction mechanism was investigated with NP-Ni for guaiacol hydrodeoxygenation. Scanning electron microscope (SEM), Brunauer–Emmett–Teller (BET) surface area analysis, X-ray photoelectron spectroscopy (XPS), high-resolution transmission electron micrographs (TEM), energy dispersive spectrometer (EDS) and X-ray diffraction (XRD) were employed for the characterization of NiAl alloy and the optimal preparation methods of NP-Ni were acquired according to the characterization results. Graphic Abstract

研究领域: 化学工程 · 材料科学 · 能源化学
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Nanomaterials · 2022 ·Vol. 12 ·期 19 ·3388 · IF 5.719

Cobalt–Graphene Catalyst for Selective Hydrodeoxygenation of Guaiacol to Cyclohexanol

Qichang Guo,Jingbo Mao,Shenmin Li,Jingmei Yin,Yang Lv,Jinxia Zhou

Herein, cobalt-reduced graphene oxide (rGO) catalyst was synthesized with a practical impregnation–calcination approach for the selective hydrodeoxygenation (HDO) of guaiacol to cyclohexanol. The synthesized Co/rGO was characterized by transmission electron microscopy (TEM), high-angle annular dark-field scanning TEM (HAADF-STEM), X-ray photoelectron spectroscopy (XPS), Raman spectroscopy, X-ray diffraction (XRD), and H2temperature-programmed reduction (H2-TPR) analysis. According to the comprehensive characterization results, the catalyst contains single Co atoms in the graphene matrix and Co oxide nanoparticles (CoOx) on the graphene surface. The isolated Co atoms embedded in the rGO matrix form stable metal carbides (CoCx), which constitute catalytically active sites for hydrogenation. The rGO material with proper amounts of N heteroatoms and lattice defects becomes a suitable graphene material for fabricating the catalyst. The Co/rGO catalyst without prereduction treatment leads to the complete conversion of guaiacol with 93.2% selectivity to cyclohexanol under mild conditions. The remarkable HDO capability of the Co/rGO catalyst is attributed to the unique metal–acid synergy between the CoCxsites and the acid sites of the CoOxnanoparticles. The CoCxsites provide H while the acid sites of CoOxnanoparticles bind the C-O group of reactants to the surface, allowing easier C-O scission. The reaction pathways were characterized based on the observed reaction–product distributions. The effects of the process parameters on catalyst preparation and the HDO reaction, as well as the reusability of the catalyst, were systematically investigated.Keywords:cobalt–graphene catalyst;Co single atoms;Co oxide nanoparticles;hydrodeoxygenation;guaiacol;cyclohexanol

研究领域: 催化 · 材料科学 · 化学工程
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ACS Sustainable Chemistry & Engineering · 2026 · IF 7.6

Aqueous-Phase Reforming of Guaiacol: Coproduction of Phenol and Green Hydrogen

Shaoteng Yuan,Hao Meng,Tianyao Shen,Wenxin Guo,Hongbo Bao,Lei Wang,Yusen Yang,Min Wei

Lignin, a methoxy-rich aromatic biopolymer, represents a promising renewable feedstock for the sustainable production of fuels and chemicals. However, achieving high catalytic activity and selectivity for the upgrading conversion of lignin derivatives without external hydrogen input remains a challenge. Herein, we report an inverse-encapsulated NiMgAl IE catalyst synthesized via hydrothermal etching, which enables the selective demethoxylation of guaiacol into phenol while simultaneously generating hydrogen through in situ aqueous-phase reforming of dissociated methoxy groups. Under mild reaction conditions (180 °C and 1 MPa), guaiacol conversion reaches 91.6%, with a phenol selectivity of 88.9% and a hydrogen production rate of 429.6 μmol g–1 h–1. An in-depth investigation based on kinetic isotope effect studies, in situ spectroscopies, and DFT calculations substantiates that the Ni0–Niv–AlOx interface serves as the intrinsic active site, in which the surface Ni0 sites facilitate water dissociation, the adjacent nickel vacancies promote guaiacol adsorption, and the AlOx coating layer assists in C–O bond activation. Techno-economic analysis confirms the pronounced economic feasibility and promising industrial scalability of phenol–hydrogen coproduction from guaiacol through aqueous-phase reforming (ROI, 20%; payback, 3.9 years). This study highlights a green, cost-effective, and scalable aqueous strategy for the coproduction of phenol and green hydrogen, providing mechanistic insights and design principles for advanced biomass valorization catalysts.

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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Water-assisted catalytic transfer hydrogenation of guaiacol to cyclohexanol over Ru/NiAl2O4

Yuying Zhao,Jiahui Zhan,Rui Hu,Gang Luo,Jiajun Fan,James H. Clark,Shicheng Zhang

Extensive use of grey hydrogen in traditional hydrodeoxygenation (HDO) severely reduces the sustainable development of lignin valorization processes. Conversely, the catalytic transfer hydrogenation (CTH) mediated by green hydrogen is an alternative strategy that promotes the sustainability of in-situ hydrogenation of lignin. In this work, a bifunctional catalyst (Ru/NiAl 2 O 4 ) was developed to assist the proposed green hydrogen-driven cosolvent system composed of isopropanol and water for the CTH of guaiacol. Results indicate that 95% conversion of guaiacol and 80% cyclohexanol selectivity can be achieved at 200 ℃ within 3 h with a high water/isopropanol ratio (6/4), significantly increasing the greenness   and sustainability. Furthermore, the recycling experiments verify the stability of the catalyst’s active sites. Analysis of the mechanism suggests that the high efficiency of such system can be attributed to the activation of metal and acid dual functional sites of Ru/NiAl 2 O 4 catalyst on aromatic rings and C-O bonds. The acceleration of the in-situ hydrogen supply is due to hydrogen exchange between water and isopropanol. The participation of water in the reaction is also demonstrated by the presence of deuterium in the product after the reaction in D 2 O. This work provided the insights into the development of a strategy for the production of cyclohexanol from lignin derivatives by an in-situ CTH system.

研究领域: 化学工程 · 可再生能源
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Frontiers of Chemical Science and Engineering · 2024 ·Vol. 18 ·期 5 ·1-10 · IF 4.3

Selective hydrodeoxygenation of guaiacol to cyclohexanol using activated hydrochar-supported Ru catalysts

Li Kaile,Yu Shijie,Li Qinghai,Zhang Yanguo,Zhou Hui

Lignin, an abundant aromatic polymer in nature, has received significant attention for its potential in the production of bio-oils and chemicals owing to increased resource availability and environmental issues. The hydrodeoxygenation of guaiacol, a lignin-derived monomer, can produce cyclohexanol, a nylon precursor, in a carbon-negative and environmentally friendly manner. This study explored the porous properties and the effects of activation methods on the Ru-based catalyst supported by environmentally friendly and cost-effective hydrochar. Highly selective cleavage of C aryl -O bonds was achieved under mild conditions (160 °C, 0.2 MPa H 2 , and 4 h), and alkali activation further improved the catalytic activity. Various characterization methods revealed that hydrothermal treatment and alkali activation relatively contributed to the excellent performance of the catalysts and influenced their porous structure and Ru dispersion. X-ray photoelectron spectroscopy results revealed an increased formation of metallic ruthenium, indicating the effective regulation of interaction between active sites and supports. This synergistic approach used in this study, involving the valorization of cellulose-derived hydrochar and the selective production of nylon precursors from lignin-derived guaiacol, indicated the comprehensive and sustainable utilization of biomass resources.

研究领域: 化学工程 · 环境科学
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