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Статті в журналах з теми "Ethylphenol"

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Автор: Grafiati

Опубліковано: 10 грудня 2022

Оновлено: 29 січня 2023

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1

Betz, Richard, Peter Klüfers, and Peter Mayer. "4-Ethylphenol." Acta Crystallographica Section E Structure Reports Online 65, no. 3 (February 18, 2009): o544. http://dx.doi.org/10.1107/s1600536809005108.

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2

Wöhlbrand, Lars, Heinz Wilkes, Thomas Halder, and Ralf Rabus. "Anaerobic Degradation of p-Ethylphenol by “Aromatoleum aromaticum” Strain EbN1: Pathway, Regulation, and Involved Proteins." Journal of Bacteriology 190, no. 16 (June 6, 2008): 5699–709. http://dx.doi.org/10.1128/jb.00409-08.

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ABSTRACT The denitrifying “Aromatoleum aromaticum” strain EbN1 was demonstrated to utilize p-ethylphenol under anoxic conditions and was suggested to employ a degradation pathway which is reminiscent of known anaerobic ethylbenzene degradation in the same bacterium: initial hydroxylation of p-ethylphenol to 1-(4-hydroxyphenyl)-ethanol followed by dehydrogenation to p-hydroxyacetophenone. Possibly, subsequent carboxylation and thiolytic cleavage yield p-hydroxybenzoyl-coenzyme A (CoA), which is channeled into the central benzoyl-CoA pathway. Substrate-specific formation of three of the four proposed intermediates was confirmed by gas chromatographic-mass spectrometric analysis and also by applying deuterated p-ethylphenol. Proteins suggested to be involved in this degradation pathway are encoded in a single large operon-like structure (∼15 kb). Among them are a p-cresol methylhydroxylase-like protein (PchCF), two predicted alcohol dehydrogenases (ChnA and EbA309), a biotin-dependent carboxylase (XccABC), and a thiolase (TioL). Proteomic analysis (two-dimensional difference gel electrophoresis) revealed their specific and coordinated upregulation in cells adapted to anaerobic growth with p-ethylphenol and p-hydroxyacetophenone (e.g., PchF up to 29-fold). Coregulated proteins of currently unknown function (e.g., EbA329) are possibly involved in p-ethylphenol- and p-hydroxyacetophenone-specific solvent stress responses and related to other aromatic solvent-induced proteins of strain EbN1.

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3

Majer, Sean H., and Joseph M. Tanski. "4-Chloro-3-ethylphenol." Acta Crystallographica Section E Structure Reports Online 70, no. 7 (June 21, 2014): o801. http://dx.doi.org/10.1107/s1600536814013919.

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The title compound, C8H9ClO, packs with two independent molecules in the asymmetric unit, without significant differences in corresponding bond lengths and angles, with the ethyl group in each oriented nearly perpendicular to the aromatic ring having ring-to-side chain torsion angles of 81.14 (18) and −81.06 (19)°. In the crystal, molecules form an O—H...O hydrogen-bonded chain extending along theb-axis direction, through the phenol groups in which the H atoms are disordered. These chains pack together in the solid state, giving a sheet lying parallel to (001),viaan offset face-to-face π-stacking interaction characterized by a centroid–centroid distance of 3.580 (1) Å, together with a short intermolecular Cl...Cl contact [3.412 (1) Å].

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4

Zhou, Peizheng, and Billy L. Crynes. "Thermolytic reactions of o-ethylphenol." Industrial & Engineering Chemistry Process Design and Development 25, no. 4 (October 1986): 898–907. http://dx.doi.org/10.1021/i200035a011.

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5

Reeve, C. D., M. A. Carver, and D. J. Hopper. "Stereochemical aspects of the oxidation of 4-ethylphenol by the bacterial enzyme 4-ethylphenol methylenehydroxylase." Biochemical Journal 269, no. 3 (August 1, 1990): 815–19. http://dx.doi.org/10.1042/bj2690815.

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The O2-independent hydroxylase 4-ethylphenol methylenehydroxylase (4EPMH) from Pseudomonas putida JD1 catalysed the complete conversion of 4-ethylphenol into 1-(4-hydroxyphenyl)ethanol together with a small amount of 4-hydroxyacetophenone, but with no formation of the side product 4-vinylphenol reported to be formed when the similar enzyme p-cresol methylhydroxylase (PCMH) catalyses this reaction. The enantiomer of 1-(4-hydroxyphenyl)ethanol produced by 4EPMH was R(+) when horse heart cytochrome c or azurin was used as electron acceptor for the enzyme. PCMHs from various bacterial strains produced the S(-)-alcohol. Both enantiomers of 1-(4-hydroxyphenyl)ethanol were substrates for conversion into 4-hydroxyacetophenone by 4EPMH, but the S(-)-isomer was preferred. The Km and kcat. were 1.2 mM and 41 s-1 respectively for the S(-)-alcohol and 4.7 mM and 22 s-1 for the R(+)-alcohol. In addition to the 1-(4-hydroxyphenyl)ethanol dehydrogenase activity of 4-EPMH, NAD(+)-linked dehydrogenase activity for both enantiomers of the alcohol was found in extracts of Ps. putida JD1.

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6

BAŠA ČESNIK, Helena, and Klemen LISJAK. "Volatile phenolics in Teran PTP red wine." Acta agriculturae Slovenica 107, no. 1 (April 6, 2016): 5. http://dx.doi.org/10.14720/aas.2016.107.1.01.

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The volatile phenolics, 4-ethylphenol, 4-vinylphenol, 4-ethylguaiacol and 4-vinylguaiacol were quantified in Teran PTP wines that were produced in the Kras winegrowing district. The compounds were determined by using gas chromatography coupled with mass spectrometry after extraction with diethylether. Three years monitoring (2011, 2012, 2013 vintages) showed that all four undesirable compounds were identified in Teran PTP wines, however their content did not influence significantly the sensory characteristics of the wine. The average contents gained over the three-year period (2011-2013; n=82) were 153±193 µg L<sup>-1</sup> for 4-ethylphenol, 1265±682 µg L<sup>-1</sup> for 4-vinylphenol, 69±94 µg L<sup>-1</sup> for 4-ethylguaiacol and 128±106 µg L<sup>-1</sup> for 4-vinylguaiacol. 7.3 % of samples showed contents of 4-ethylphenol above the odour threshold values. For 4-vinylphenol, 4-ethylguaiacol and 4-vinylguaiacol that percentage was 98.8 %, 25.6 % and 91.5 %, respectively.

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7

Jones, K. H., P. W. Trudgill, and D. J. Hopper. "4-Ethylphenol metabolism by Aspergillus fumigatus." Applied and Environmental Microbiology 60, no. 6 (1994): 1978–83. http://dx.doi.org/10.1128/aem.60.6.1978-1983.1994.

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8

Takahashi, Mika, Mutsuko Hirata-Koizumi, Nobuo Nishimura, Yoshihiko Ito, Masao Sunaga, Sakiko Fujii, Eiichi Kamata, Ryuichi Hasegawa, and Makoto Ema. "Susceptibility of newborn rats to 3-ethylphenol and 4-ethylphenol compared with that of young rats." Congenital Anomalies 46, no. 1 (March 2006): 26–33. http://dx.doi.org/10.1111/j.1741-4520.2006.00098.x.

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9

Qiu, Zegang, Ying Wang, Yali Di, Xiaoxiong Ren, Weiwei Liu, Zhiqin Li, and Guangyu Li. "One-step conversion of lignin-derived alkylphenols to light arenes by co-breaking of C–O and C–C bonds." New Journal of Chemistry 46, no. 6 (2022): 2710–21. http://dx.doi.org/10.1039/d1nj05793f.

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10

Renaud, Alexis, Yoann Paint, Alex Lanzutti, Leïla Bonnaud, Lorenzo Fedrizzi, Philippe Dubois, Marc Poorteman, and Marie-Georges Olivier. "Sealing porous anodic layers on AA2024-T3 with a low viscosity benzoxazine resin for corrosion protection in aeronautical applications." RSC Advances 9, no. 29 (2019): 16819–30. http://dx.doi.org/10.1039/c9ra01970g.

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11

Reeve, C. D., M. A. Carver, and D. J. Hopper. "The purification and characterization of 4-ethylphenol methylenehydroxylase, a flavocytochrome from Pseudomonas putida JD1." Biochemical Journal 263, no. 2 (October 15, 1989): 431–37. http://dx.doi.org/10.1042/bj2630431.

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The enzyme 4-ethylphenol methylenehydroxylase was purified from Pseudomonas putida JD1 grown on 4-ethylphenol. It is a flavocytochrome c for which the Mr was found to be 120,000 by ultracentrifuging and 126,000 by gel filtration. The enzyme consists of two flavoprotein subunits each of Mr 50,000 and two cytochrome c subunits each of Mr 10,000. The redox potential of the cytochrome is 240 mV. Hydroxylation proceeds by dehydrogenation and hydration to give 1-(4′-hydroxyphenyl)ethanol, which is also dehydrogenated by the same enzyme to 4-hydroxyacetophenone. The enzyme will hydroxylate p-cresol but is more active with alkylphenols with longer-chain alkyl groups. It is located in the periplasm of the bacterium.

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12

REEVE, CHRISTOPHER D., DAVID J. HOPPER, and MARK A. CARVER. "4-Ethylphenol methylenehydroxylase from Pseudomonas putida JD1." Biochemical Society Transactions 15, no. 5 (October 1, 1987): 934–35. http://dx.doi.org/10.1042/bst0150934.

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13

Hopper, David J., and Lisa Cottrell. "Alkylphenol Biotransformations Catalyzed by 4-Ethylphenol Methylenehydroxylase." Applied and Environmental Microbiology 69, no. 6 (June 2003): 3650–52. http://dx.doi.org/10.1128/aem.69.6.3650-3652.2003.

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ABSTRACT 4-Ethylphenol methylenehydroxylase from Pseudomonas putida JD1 acts by dehydrogenation of its substrate to give a quinone methide, which is then hydrated to an alcohol. It was shown to be active with a range of 4-alkylphenols as substrates. 4-n-Propylphenol, 4-n-butylphenol, chavicol, and 4-hydroxydiphenylmethane were hydroxylated on the methylene group next to the benzene ring and produced the corresponding chiral alcohol as the major product. The alcohols 1-(4′-hydroxyphenyl)propanol and 1-(4′-hydroxyphenyl)-2-propen-1-ol, produced by the biotransformation of 4-n-propylphenol and chavicol, respectively, were shown to be R(+) enantiomers. 5-Indanol, 6-hydroxytetralin, 4-isopropylphenol, and cyclohexylphenol, with cyclic or branched alkyl groups, gave the corresponding vinyl compounds as their major products.

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14

Morata, Antonio, Iris Loira, Carmen González, and Carlos Escott. "Non-Saccharomyces as Biotools to Control the Production of Off-Flavors in Wines." Molecules 26, no. 15 (July 28, 2021): 4571. http://dx.doi.org/10.3390/molecules26154571.

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Off-flavors produced by undesirable microbial spoilage are a major concern in wineries, as they affect wine quality. This situation is worse in warm areas affected by global warming because of the resulting higher pHs in wines. Natural biotechnologies can aid in effectively controlling these processes, while reducing the use of chemical preservatives such as SO2. Bioacidification reduces the development of spoilage yeasts and bacteria, but also increases the amount of molecular SO2, which allows for lower total levels. The use of non-Saccharomyces yeasts, such as Lachancea thermotolerans, results in effective acidification through the production of lactic acid from sugars. Furthermore, high lactic acid contents (>4 g/L) inhibit lactic acid bacteria and have some effect on Brettanomyces. Additionally, the use of yeasts with hydroxycinnamate decarboxylase (HCDC) activity can be useful to promote the fermentative formation of stable vinylphenolic pyranoanthocyanins, reducing the amount of ethylphenol precursors. This biotechnology increases the amount of stable pigments and simultaneously prevents the formation of high contents of ethylphenols, even when the wine is contaminated by Brettanomyces.

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15

Branco, Patrícia, Rute Coutinho, Manuel Malfeito-Ferreira, Catarina Prista, and Helena Albergaria. "Wine Spoilage Control: Impact of Saccharomycin on Brettanomyces bruxellensis and Its Conjugated Effect with Sulfur Dioxide." Microorganisms 9, no. 12 (December 7, 2021): 2528. http://dx.doi.org/10.3390/microorganisms9122528.

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The yeast Brettanomyces bruxellensis is one of the most dangerous wine contaminants due to the production of phenolic off-flavors such as 4-ethylphenol. This microbial hazard is regularly tackled by addition of sulfur dioxide (SO2). Nevertheless, B. bruxellensis is frequently found at low levels (ca 103 cells/mL) in finished wines. Besides, consumers health concerns regarding the use of sulfur dioxide encouraged the search for alternative biocontrol measures. Recently, we found that Saccharomyces cerevisiae secretes a natural biocide (saccharomycin) that inhibits the growth of different B. bruxellensis strains during alcoholic fermentation. Here we investigated the ability of S. cerevisiae CCMI 885 to prevent B. bruxellensis ISA 2211 growth and 4-ethylphenol production in synthetic and true grape must fermentations. Results showed that B. bruxellensis growth and 4-ethylphenol production was significantly inhibited in both media, although the effect was more pronounced in synthetic grape must. The natural biocide was added to a simulated wine inoculated with 5 × 102 cells/mL of B. bruxellensis, which led to loss of culturability and viability (100% dead cells at day-12). The conjugated effect of saccharomycin with SO2 was evaluated in simulated wines at 10, 12, 13 and 14% (v/v) ethanol. Results showed that B. bruxellensis proliferation in wines at 13 and 14% (v/v) ethanol was completely prevented by addition of 1.0 mg/mL of saccharomycin with 25 mg/L of SO2, thus allowing to significantly reduce the SO2 levels commonly used in wines (150–200 mg/L).

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16

de Castro, Antonio, Emilio Asencio, Maria Victoria Ruiz-Méndez, Concepción Romero, and Manuel Brenes. "Production of 4-ethylphenol in alperujo byLactobacillus pentosus." Journal of the Science of Food and Agriculture 95, no. 11 (October 31, 2014): 2222–27. http://dx.doi.org/10.1002/jsfa.6939.

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17

Botezatu, Andreea, and Gary James Pickering. "Novel Applications for Biomaterials: The Case of Remediation of Wine Taints Using Poly-Lactic Acid Polymer." Applied Mechanics and Materials 749 (April 2015): 70–73. http://dx.doi.org/10.4028/www.scientific.net/amm.749.70.

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Wine is the world’s oldest alcoholic beverage and the most consumed in at least 20 countries. However, taints detract from its quality and acceptance, significantly reducing the value of wine. In this study we investigated the capacity of a poly-lactic acid (PLA) biopolymer to reduce concentrations of four odorants responsible for tainting many red wines: isopropyl-methoxypyrazine (IPMP), isobutyl–methoxypyrazine (IBMP), 4-ethylphenol (4-EP) and 4-ethylguaiacol (4-EG). Red wine was spiked with either IPMP [20 ng/L] and IBMP [20 ng/L] (Study 1) or 4-EP [200 ug/L] and 4-EG [200 ug/L] (Study 2) and then treated with a PLA film [surface area 350 cm2/L]. Solid Phase Micro-Extraction Multi-Dimensional Gas Chromatography–Mass Spectrometry and Gas Chromatography-Mass Spectrometry were used to measure the methoxypyrazines and ethylphenols, respectively, both before and after treatment with PLA. Results showed significant reductions in all of the target odorants after 8hrs treatment: IPMP (51%), IBMP (26%), 4-EP (21%) and 4-EG (20%). Taken overall, the data suggest potential for the use of PLA in treating common wine faults, particularly ‘ladybug taint’, which is caused by elevated levels of IPMP.

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18

Wang, Hui, Yue Wang, Xiaopeng Hou, and Benhai Xiong. "Bioelectronic Nose Based on Single-Stranded DNA and Single-Walled Carbon Nanotube to Identify a Major Plant Volatile Organic Compound (p-Ethylphenol) Released by Phytophthora Cactorum Infected Strawberries." Nanomaterials 10, no. 3 (March 7, 2020): 479. http://dx.doi.org/10.3390/nano10030479.

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The metabolic activity in plants or fruits is associated with volatile organic compounds (VOCs), which can help identify the different diseases. P-ethylphenol has been demonstrated as one of the most important VOCs released by the Phytophthora cactorum (P. cactorum) infected strawberries. In this study, a bioelectronic nose based on a gas biosensor array and signal processing model was developed for the noninvasive diagnostics of the P. cactorum infected strawberries, which could overcome the limitations of the traditional spectral analysis methods. The gas biosensor array was fabricated using the single-wall carbon nanotubes (SWNTs) immobilized on the surface of field-effect transistor, and then non-covalently functionalized with different single-strand DNAs (ssDNA) through π–π interaction. The characteristics of ssDNA-SWNTs were investigated using scanning electron microscope, atomic force microscopy, Raman, UV spectroscopy, and electrical measurements, indicating that ssDNA-SWNTs revealed excellent stability and repeatability. By comparing the responses of different ssDNA-SWNTs, the sensitivity to P-ethylphenol was significantly higher for the s6DNA-SWNTs than other ssDNA-SWNTs, in which the limit of detection reached 0.13% saturated vapor of P-ethylphenol. However, s6DNA-SWNTs can still be interfered with by other VOCs emitted by the strawberries in the view of poor selectivity. The bioelectronic nose took advantage of the different sensitivities of different gas biosensors to different VOCs. To improve measure precision, all ssDNA-SWNTs as a gas biosensor array were applied to monitor the different VOCs released by the strawberries, and the detecting data were processed by neural network fitting (NNF) and Gaussian process regression (GPR) with high accuracy.

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19

Lee, K. M., and P. E. Lim. "Treatment of phenolic wastewater using agricultural wastes as an adsorbent in a sequencing batch reactor." Water Science and Technology 47, no. 10 (May 1, 2003): 41–47. http://dx.doi.org/10.2166/wst.2003.0534.

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The objective of this study is to investigate the potential of the activated rice husk to be used as an alternative adsorbent to powdered activated carbon (PAC) in the simultaneous adsorption and biodegradation processes under sequencing batch reactor (SBR) operation to treat synthetic wastewater containing phenol, p-methylphenol, p-ethylphenol and p-isopropylphenol. The rice husk (PRH) was activated by pyrolysis at 600°C for 5 hours in a nitrogen atmosphere. Using the Langmuir model, the limiting adsorption capacities of PRH for the phenols were found to vary from 0.015-0.05 of those of PAC. The SBR reactors with and without adsorbent addition were operated with fill, react, settle, draw and idle periods in the ratio of 4:6:1:0.75:0.25 for a cycle time of 12 hours. For phenolic wastewater containing, 1,200 mg/L phenol, 1,200 mg/L p-methylphenol, 800 mg/L p-ethylphenol and 650 mg/L p-isopropylphenol, it was found that the biodegradation process alone was unable to produce effluent of quality which would satisfy the discharge standards of COD ≤ 100 mg/L and phenol concentration ≤1 mg/L. The addition of PAC in the ratio of PAC/phenolic compound at 0.095 g/g for phenol, 0.119 g/g for p-methylphenol, 0.179 g/g for p-ethylphenol and 0.220 g/g for p-isopropylphenol, can improve the effluent quality to satisfy the discharge standards. Equivalent treatment performance was achieved with the use of PRH at dosages of 2-3 times higher than those of PAC for all the phenolic wastewater studied. The increased adsorption capacity of PRH shown in the treatment indicates bioregeneration of the adsorbed surface during the treatment process.

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20

Garcia-Mutio, D., A. Guerreiro, A. Gomez-Caballero, R. Gutierrez-Climente, S. Piletsky, M. A. Goicolea, and R. J. Barrio. "Molecularly Imprinted High Affinity Nanoparticles for 4-Ethylphenol Sensing." Procedia Engineering 120 (2015): 1132–36. http://dx.doi.org/10.1016/j.proeng.2015.08.821.

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21

Zhang, Ying, Liangkun Long, and Shaojun Ding. "Heterologous synthesis of 4-ethylphenol in engineered Escherichia coli." Process Biochemistry 96 (September 2020): 157–64. http://dx.doi.org/10.1016/j.procbio.2020.06.003.

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22

REEVE, CHRISTOPHER D., DAVID J. HOPPER, and MARK A. CARVER. "Reoxidation of the flavocytochrome 4-ethylphenol methylenehydroxylase by azurin." Biochemical Society Transactions 17, no. 5 (October 1, 1989): 924–25. http://dx.doi.org/10.1042/bst0170924.

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23

Suryanto, Edi, Mercy R. I. Taroreh, and Lydia Irma Momuat. "Purification and Characterization of Phenolic Antioxidant from Corncob Liquid Smoke." Asian Journal of Chemistry 32, no. 12 (2020): 2985–90. http://dx.doi.org/10.14233/ajchem.2020.22486.

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This study aimed to purify and characterize the antioxidant activity of liquid smoke acquired from corncobs. The smoke of crude liquids was generated through pyrolysis and was purified through fractional and simple distillation. The liquid smoke was analyzed using crude fibres, cellulose, hemicellulose, lignin, antioxidant activity and total phenolic compounds. Gas chromatography-mass spectrometry (GC-MS) was employed to analyze the volatile compounds of liquid smoke. Fractional distillation exhibited the higher carbonyl and phenol content than simple distillation, and the overall acid content of fractional distillation was relatively lower. Moreover, the liquid smoke obtained from fractional distillation exhibited the higher total antioxidant and free radical scavenging activity than simple distillation. The GC-MS results showed different derivatives and phenolic compounds as the most dominant components of the liquid smoke of corncobs. The major antioxidant components of fractional distillation include 2-methoxyphenol, phenol, 2,5-dimethylphenol, 2-methylphenol, 2-methoxy-4-methylphenol, 4-ethyl-2-methoxyphenol and 4-ethylphenol, and those of simple distillation include phenol, 2-methylphenol, 2-methoxy- phenol, 2,6-dimethoxyphenol and 3-ethylphenol.

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24

Yi, Qing, Wei-Peng Chen, Xiang-yang Zhang, Yan-Yang Wu, Bin Wu, Kui Chen, and Li-Jun Ji. "Isobaric Vapor–Liquid Equilibrium for the Binary Systems of 2-Phenylethanol + 2-Ethylphenol, 1-Phenyl-2-propanol + 2-Ethylphenol, 2-Phenylethanol + 1-Phenyl-2-propanol and 2-Phenyl-1-propanol + 2-Ethylphenol under 101.3 kPa." Journal of Chemical & Engineering Data 66, no. 12 (October 13, 2021): 4351–60. http://dx.doi.org/10.1021/acs.jced.1c00500.

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25

Yi, Qing, Wei-Peng Chen, Xiang-yang Zhang, Yan-Yang Wu, Bin Wu, Kui Chen, and Li-Jun Ji. "Isobaric Vapor–Liquid Equilibrium for the Binary Systems of 2-Phenylethanol + 2-Ethylphenol, 1-Phenyl-2-propanol + 2-Ethylphenol, 2-Phenylethanol + 1-Phenyl-2-propanol and 2-Phenyl-1-propanol + 2-Ethylphenol under 101.3 kPa." Journal of Chemical & Engineering Data 66, no. 12 (October 13, 2021): 4351–60. http://dx.doi.org/10.1021/acs.jced.1c00500.

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26

Tran, Viet T., Tan M. Le, Phu V. Vu, Hien M. Nguyen, Yen H. P. Duong, and Phung K. Le. "Depolymerization of Rice Straw Lignin into Value-Added Chemicals in Sub-Supercritical Ethanol." Scientific World Journal 2022 (May 20, 2022): 1–10. http://dx.doi.org/10.1155/2022/7872307.

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Depolymerization of lignin is an important step to obtain a lignin monomer for the synthesis of functional chemicals. In the context of more lignin produced from biomass and pulp industry, converting real lignin with low purity is still required more studies. In this study, the influence of solvent composition and reaction parameters such as binary solvents ratio, time, and temperature, the solvent-to-lignin ratio on the depolymerization of rice straw lignin was investigated carefully. Essential lignin-degraded products including liquid product (LP), char (solid), and gas were obtained, and their yields were directly influenced by reaction conditions. Results show that the maximum lignin conversion rate of 92% and LP yield of 66% was under the condition of 275°C, 30 min, 75 : 1 (mL solvent/1 g lignin), and ethanol 50%. Gas chromatography-mass spectroscopy (GC-MS) analysis was used for the analysis of the depolymerization products and identified 11 compounds which are mainly phenolic compounds such as 2-ethylphenol, 3-ethylphenol, phenol, methyl 2,4,6-trimethylbenzoate. The structure changes of LP and char in various conditions were analyzed using Fourier-transform infrared (FTIR).

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27

Pu, Dandan, Yuyu Zhang, Huiying Zhang, Baoguo Sun, Fazheng Ren, Haitao Chen, and Yizhuang Tang. "Characterization of the Key Aroma Compounds in Traditional Hunan Smoke-Cured Pork Leg (Larou, THSL) by Aroma Extract Dilution Analysis (AEDA), Odor Activity Value (OAV), and Sensory Evaluation Experiments." Foods 9, no. 4 (April 2, 2020): 413. http://dx.doi.org/10.3390/foods9040413.

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The key aroma compounds in smoke-cured pork leg were characterized by gas chromatography–olfactometry coupled with aroma extract dilution analysis (GC–O/AEDA), odor activity value (OAV), recombination modeling, and omission tests. Ranking analysis showed that pork leg smoke-cured for 18 days had the best sensory qualities, with strong meaty, smoky, roasty, woody, and greasy attributes. Thirty-nine aroma-active regions with flavor dilution (FD) factors ranging from 9 to 6561 were detected. Overall, 3-ethylphenol had the highest FD factor of 6561, followed by 2,6-dimethoxyphenol, 3,4-dimethylphenol, 4-ethylguaiacol, 4-methylguaiacol, 3-methylphenol, and 2-acetyl-1-pyrroline, with FD ≥243. Among 39 aroma compounds, 27 compounds with OAVs ≥1 and were potent odorants. A similarity of 90.73% between the recombination model and traditional Hunan Smoke-cured Pork Leg (THSL) sample was obtained. Omission tests further confirmed that (E)-2-nonenal, 2-methoxy-4-vinylphenol, guaiacol, 3-ethylphenol, 2,6-dimethylphenol, 2-acetyl-1-pyrroline, and methional were key odorants in smoke-cured pork leg. Additionally, 2-acetyl-1-pyrroline (38.88 μg/kg), which contributes to a roasty aroma, was characterized here as a key odorant of smoke-cured pork leg for the first time.

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28

Radonjic, Sanja, Helena Prosen, Vesna Maras, Lea Demsar, and Tatjana Kosmerl. "Incidence of volatile phenols in Montenegrin red wines: Vranac, Kratosija and Cabernet sauvignon." Chemical Industry and Chemical Engineering Quarterly, no. 00 (2020): 10. http://dx.doi.org/10.2298/ciceq190813010r.

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The main objective of this study was to determine the impact of three different commercial yeasts and two lactic acid bacteria, as well as the use of oak (chips and staves) on the volatile phenol (VP) formation in Montenegrin aged red wines (Vranac, Kratosija and Cabernet Sauvignon) of the 2013 vintage. Standard chemical parameters of the wines were determined in order to establish relationship with VP. After three years of bottle aging, chemical parameters of wines (alcohol content, residual sugars (RS), pH, free and total SO2, anthocyanins) and VP (4-ethylphenol and 4-ethylguaiacol) were determined. Volatile phenols were found in 18 samples of Kratosija and 5 samples of Vranac. Volatile phenols were not detected in Cabernet Sauvignon wines. Kratosija as a grape variety from the Montenegrin terroir during 2013 vintage had the highest potential for the VP formation, while the highest content of 4-ethylphenol (2.84 mg/L) and 4-ethylguaiacol (0.52 mg/L) was determined in Vranac wine. It was demonstrated that VP would be formed in wines even with high alcohol content (>12.50 v/v %), low pH (<3.30) and with free SO2 concentrations at bottling of 30-35 mg/L.

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29

ZHANG Qing, 张庆, 李鑫 LI Xin, 赵岩 ZHAO Yan, 杨勇刚 YANG Yong-gang, 李昌勇 LI Chang-yong, and 贾锁堂 JIA Suo-tang. "One Color Resonance Two-photon Ionization Spectra of p-ethylphenol." Acta Sinica Quantum Optica 22, no. 2 (2016): 115–20. http://dx.doi.org/10.3788/asqo20162202.0115.

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30

Das, Jagannath, and Anand B. Halgeri. "Selective synthesis of para-ethylphenol over pore size tailored zeolite." Applied Catalysis A: General 194-195 (March 2000): 359–63. http://dx.doi.org/10.1016/s0926-860x(99)00381-6.

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31

Wang, J., D. Montville, and K. E. Gonsalves. "Synthesis of polycarbonate-co-poly(p-ethylphenol) and CdS nanocomposites." Journal of Applied Polymer Science 72, no. 14 (June 28, 1999): 1851–68. http://dx.doi.org/10.1002/(sici)1097-4628(19990628)72:14<1851::aid-app7>3.0.co;2-n.

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32

Wang, J., and K. E. Gonsalves. "Synthesis and film formation of polycarbonate-co- poly(p-ethylphenol)." Journal of Polymer Science Part A: Polymer Chemistry 37, no. 2 (January 15, 1999): 169–78. http://dx.doi.org/10.1002/(sici)1099-0518(19990115)37:2<169::aid-pola7>3.0.co;2-a.

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33

de Albuquerque Fragoso, Danielle Munick, Henrique Fonseca Goulart, Antonio Euzebio Goulart Santana, and Samuel David Jackson. "Targeted Substituted-Phenol Production by Strategic Hydrogenolysis of Sugar-Cane Lignin." Biomass 1, no. 1 (June 18, 2021): 11–28. http://dx.doi.org/10.3390/biomass1010002.

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In this work, a waste-derived lignin with abundant uncondensed linkages, using accessible solvents (acetone/water mixture) and low-cost catalysts showed successful depolymerization for the production of target molecules 4-ethylphenol, 4-propyl-2,6-dimethoxyphenol and 4-propyl-2-methoxyphenol. Lignin samples were obtained from sugar-cane bagasse residue by an organosolv process. Four alumina-based catalysts (Pt/Al2O3, Rh/Al2O3, Ni/Al2O3 and Fe/Al2O3) were used to depolymerize the sugar cane lignin (SCL) in an acetone/water mixture 50/50 v/v at 573 K and 20 barg hydrogen. This strategic depolymerisation-hydrogenolysis process resulted in the molecular weight of the SCL being reduced by half while the polydispersity also decreased. Catalysts significantly improved product yield compared to thermolysis. Specific metals directed product distribution and yield, Rh/Al2O3 gave the highest overall yield (13%), but Ni/Al2O3 showed the highest selectivity to a given product (~32% to 4-ethylphenol). Mechanistic routes were proposed either from lignin fragments or from the main polymer. Catalysts showed evidence of carbon laydown that was specific to the lignin rather than the catalyst. These results showed that control over selectivity could be achievable by appropriate combination of catalyst, lignin and solvent mixture.

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34

Filipe-Ribeiro, L., F. Cosme, and F. M. Nunes. "Cork powder as a new natural and sustainable fining agent to reduce negative volatile phenols in red wine." BIO Web of Conferences 15 (2019): 02017. http://dx.doi.org/10.1051/bioconf/20191502017.

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In red winemaking, especially those aged in wood barrels, the contamination and growth of Dekkera/Brettanomyces yeasts results in the formation of 4-ethylphenol (4-EP) and 4-ethylguaiacol (4-EG). These volatile phenols (VPs) are responsible for negative aromatic notes like horsy, barnyard, smoky and medicine, decreasing significantly red quality and its commercial value. In this work, cork powder waste was especially prepared and used to remove these negative volatile phenols (4-EP and 4-EG) from spiked red wine. The optimisation of cork powder performance by removal of dichloromethane and ethanol cork extractives, air removal and ethanol impregnation, allowed to obtain 41 to 62% of 4-ethylphenol and 50 to 53% of 4-ethylguaiacol removal from VPs spiked red wine applied at 250 g/hL. There was no significant impact on phenolic acids and monomeric anthocyanins, although being observed a decrease in the headspace aroma abundance (40%). This optimised cork powder allowed to decrease significantly the wine negative phenolic character, bitterness and astringency, recovering the positive fruity and floral sensory attributes. Results show that optimised cork powder can be a good solution for VPs removal, presenting a great potential to be a new oenological fining agent, contributing to the wine industry sustainability.

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35

van den Heuvel, Robert H. H., Marco W. Fraaije, Colja Laane, and Willem J. H. van Berkel. "Regio- and Stereospecific Conversion of 4-Alkylphenols by the Covalent Flavoprotein Vanillyl-Alcohol Oxidase." Journal of Bacteriology 180, no. 21 (November 1, 1998): 5646–51. http://dx.doi.org/10.1128/jb.180.21.5646-5651.1998.

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ABSTRACT The regio- and stereospecific conversion of prochiral 4-alkylphenols by the covalent flavoprotein vanillyl-alcohol oxidase was investigated. The enzyme was active, with 4-alkylphenols bearing aliphatic side chains of up to seven carbon atoms. Optimal catalytic efficiency occurred with 4-ethylphenol and 4-n-propylphenols. These short-chain 4-alkylphenols are stereoselectively hydroxylated to the corresponding (R)-1-(4′-hydroxyphenyl)alcohols (F. P. Drijfhout, M. W. Fraaije, H. Jongejan, W. J. H. van Berkel, and M. C. R. Franssen, Biotechnol. Bioeng. 59:171–177, 1998). (S)-1-(4′-Hydroxyphenyl)ethanol was found to be a far better substrate than (R)-1-(4′-hydroxyphenyl)ethanol, explaining why during the enzymatic conversion of 4-ethylphenol nearly no 4-hydroxyacetophenone is formed. Medium-chain 4-alkylphenols were exclusively converted by vanillyl-alcohol oxidase to the corresponding 1-(4′-hydroxyphenyl)alkenes. The relative cis-transstereochemistry of these reactions was strongly dependent on the nature of the alkyl side chain. The enzymatic conversion of 4-sec-butylphenol resulted in two (4′-hydroxyphenyl)-sec-butene isomers with identical masses but different fragmentation patterns. We conclude that the water accessibility of the enzyme active site and the orientation of the hydrophobic alkyl side chain of the substrate are of major importance in determining the regiospecific and stereochemical outcome of vanillyl-alcohol oxidase-mediated conversions of 4-alkylphenols.

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36

Mirzayev, V. G., Ch K. Rasulov, S. G. Aliyeva, and E. M. Kuliyeva. "SYNTHESIS AND STUDY OF ANTIOXIDATIVE PROPERTIES OF AMINOMETHYLATED DERIVATIVES OF p-(CYCLOHEXENE3-YL-ETHYLPHENOL)." Chemical Problems 17, no. 3 (2019): 386–92. http://dx.doi.org/10.32737/2221-8688-2019-3-386-392.

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37

Pollnitz, Alan P., Kevin H. Pardon, and Mark A. Sefton. "Quantitative analysis of 4-ethylphenol and 4-ethylguaiacol in red wine." Journal of Chromatography A 874, no. 1 (March 2000): 101–9. http://dx.doi.org/10.1016/s0021-9673(00)00086-8.

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38

Matsumoto, M., T. Hakozaki, and T. Idai. "Industrial-scale method for separating m- and p-ethylphenol using zeolites." Zeolites 18, no. 2-3 (February 1997): 234. http://dx.doi.org/10.1016/s0144-2449(97)83995-4.

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39

Ye, Zhaolian, Zhenxiu Qu, Shuaishuai Ma, Shipeng Luo, Yantong Chen, Hui Chen, Yanfang Chen, Zhuzi Zhao, Mindong Chen, and Xinlei Ge. "A comprehensive investigation of aqueous-phase photochemical oxidation of 4-ethylphenol." Science of The Total Environment 685 (October 2019): 976–85. http://dx.doi.org/10.1016/j.scitotenv.2019.06.276.

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40

Gallardo-Chacón, Joan-Josep, and Thomas Karbowiak. "Sorption of 4-ethylphenol and 4-ethylguaiacol by suberin from cork." Food Chemistry 181 (August 2015): 222–26. http://dx.doi.org/10.1016/j.foodchem.2015.02.102.

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41

Larcher, R., C. Puecher, S. Rohregger, M. Malacarne, and G. Nicolini. "4-Ethylphenol and 4-ethylguaiacol depletion in wine using esterified cellulose." Food Chemistry 132, no. 4 (June 2012): 2126–30. http://dx.doi.org/10.1016/j.foodchem.2011.12.012.

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42

Philipp, Christian, Sezer Sari, Walter Brandes, Stefan Nauer, Elsa Patzl-Fischerleitner, and Reinhard Eder. "Reduction in Off-Flavors in Wine Using Special Filter Layers with Integrated Zeolites and the Effect on the Volatile Profile of Austrian Wines." Applied Sciences 12, no. 9 (April 25, 2022): 4343. http://dx.doi.org/10.3390/app12094343.

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In the course of the present study, filter layers with embedded zeolites (patented layer of the company Filtrox (Zwingen, Switzerland) with the brand name Fibrafix® TX) were tested for the elimination of the wine defects, cork taint (2,4,6-trichloroanisole), mouldy aroma (geosmin), and strong “animal” phenolic aromas (4-ethylphenol, 4-ethylguaiacol, 4-ethylcatechol). The test design allowed a comparison with conventional filter layers (sterile filter layers) in a small-scale trial (25 L) as well as in a large-scale trial (125 L). By means of gas chromatography-mass spectroscopy, not only the impact compounds of the wine faults were analysed, but also the loss of volatile substances such as 15 free monoterpenes, 34 ester compounds, and 24 wood flavours. Sensory analyses were carried out by means of expert panels. The Fibrafix® TX layers were satisfactory with regard to the reduction in 2,4,6-trichloroanisole (the lead substance of cork flavour; reduction > 90%) and geosmin (the lead substance of mould flavour; reduction > 75%), but not with regard to the reduction in 4-ethylphenol, 4-ethylguaicol, and 4-ethylcatechol. However, the reduction in these off-flavours was generally not specific enough to prevent a loss of volatile compounds, especially various ester compounds and free monoterpenes. The wines obtained after filtration (in case of contamination with geosmin or TCA) were sensory faultless, but for some of the tasters, the overall quality of these wines did not correspond to the quality wine clasification.

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43

Philipp, Christian, Sezer Sari, Walter Brandes, Stefan Nauer, Elsa Patzl-Fischerleitner, and Reinhard Eder. "Reduction in Off-Flavors in Wine Using Special Filter Layers with Integrated Zeolites and the Effect on the Volatile Profile of Austrian Wines." Applied Sciences 12, no. 9 (April 25, 2022): 4343. http://dx.doi.org/10.3390/app12094343.

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Анотація:

In the course of the present study, filter layers with embedded zeolites (patented layer of the company Filtrox (Zwingen, Switzerland) with the brand name Fibrafix® TX) were tested for the elimination of the wine defects, cork taint (2,4,6-trichloroanisole), mouldy aroma (geosmin), and strong “animal” phenolic aromas (4-ethylphenol, 4-ethylguaiacol, 4-ethylcatechol). The test design allowed a comparison with conventional filter layers (sterile filter layers) in a small-scale trial (25 L) as well as in a large-scale trial (125 L). By means of gas chromatography-mass spectroscopy, not only the impact compounds of the wine faults were analysed, but also the loss of volatile substances such as 15 free monoterpenes, 34 ester compounds, and 24 wood flavours. Sensory analyses were carried out by means of expert panels. The Fibrafix® TX layers were satisfactory with regard to the reduction in 2,4,6-trichloroanisole (the lead substance of cork flavour; reduction > 90%) and geosmin (the lead substance of mould flavour; reduction > 75%), but not with regard to the reduction in 4-ethylphenol, 4-ethylguaicol, and 4-ethylcatechol. However, the reduction in these off-flavours was generally not specific enough to prevent a loss of volatile compounds, especially various ester compounds and free monoterpenes. The wines obtained after filtration (in case of contamination with geosmin or TCA) were sensory faultless, but for some of the tasters, the overall quality of these wines did not correspond to the quality wine clasification.

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44

Füllemann, Daniela, Silva D. Neiens, and Martin Steinhaus. "Impact of processing on important cocoa off-flavour compounds." European Food Research and Technology 248, no. 1 (October 8, 2021): 197–205. http://dx.doi.org/10.1007/s00217-021-03873-0.

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AbstractThe compounds responsible for smoky and mouldy–musty off-flavours in fermented cocoa have recently been elucidated; however, their behaviour during further processing into chocolate was still unclear. The compounds 2-methoxyphenol, 3-methylphenol, 4-methylphenol, 3-ethylphenol, 4-ethylphenol, and 3-propylphenol known to contribute to smoky off-flavours showed a tendency towards a minor increase during roasting and processing into cocoa liquor. This increase amounted to 1.4-fold at the most, however, was clearly compensated by losses of 30–63% during further processing into chocolate mass and conching. Among the off-flavour compounds identified in mouldy–musty smelling cocoa, faecal, mothball-like 3-methyl-1H-indole showed a clear decrease during roasting and processing into cocoa liquor, at least at rather high roasting temperatures, and a further decrease during processing into chocolate mass and conching. In contrast, faecal, mothball-like 1H-indole substantially increased during roasting and processing into cocoa liquor, namely from concentrations below its odour threshold value to concentrations up to 8 times beyond its odour threshold value. During processing into chocolate mass and conching, 1H-indole remained virtually unchanged. The data suggested that the monitoring of off-flavour compounds at the incoming goods inspection in the chocolate industry should not be limited to the fermented beans as such but additionally include the analysis of a bean sample after test roasting to correctly assess the off-flavour potential of 3-methyl-1H-indole and 1H-indole.

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45

Bursell, E., A. J. E. Gough, P. S. Beevor, A. Cork, D. R. Hall, and G. A. Vale. "Identification of components of cattle urine attractive to tsetse flies, Glossina spp. (Diptera: Glossinidae)." Bulletin of Entomological Research 78, no. 2 (June 1988): 281–91. http://dx.doi.org/10.1017/s0007485300013043.

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AbstractThe attractiveness of cattle urine to Glossina morsitans morsitans Westwood and G. pallidipes Austen was shown to be entirely attributable to the phenolic components which it contains. Four of the eight naturally occurring phenol derivatives (3- and 4-methylphenol, 3-ethylphenol and 3-n-propylphenol) were electroantennographically active, induced upwind flight in wind-tunnel bioassays and increased trap catches in field tests in Zimbabwe. One of the minor components, 2-methoxyphenol, had little antennographic activity but induced upwind flight in the wind-tunnel and appeared to be repellent in field tests.

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46

Domínguez-Renedo, Olga, A. Marta Navarro-Cuñado, Victor Arnáiz-Lozano, and M. Asunción Alonso-Lomillo. "Molecularly imprinted polypyrrole based electrochemical sensor for selective determination of 4-ethylphenol." Talanta 207 (January 2020): 120351. http://dx.doi.org/10.1016/j.talanta.2019.120351.

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47

Torr, S. J., D. R. Hall, and J. L. Smith. "Responses of tsetse flies (Diptera: Glossinidae) to natural and synthetic ox odours." Bulletin of Entomological Research 85, no. 1 (March 1995): 157–66. http://dx.doi.org/10.1017/s000748530005210x.

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AbstractIn Zimbabwe, studies were made of the levels of known tsetse attractants present in natural ox odour. Typically an ox (400 kg) produced phenol (0.1 mg/h), 3-methylphenol (0.09 mg/h), 4-methylphenol (0.7 mg/h), 3-ethylphenol (0.01 mg/h), 4-ethylphenol (0.02 mg/h), 3- and 4-n-propylphenol (0.02 mg/h), l-octen-3-ol (0.01 mg/h), carbon dioxide (140 l/h), acetone (5 mg/h) and butanone (0.3 mg/h). Of these, only phenol, 4- and 3-methylphenol and carbon dioxide were always detected in ox odour. Studies were made of the numbers of Glossina pallidipes Austen and G. morsitans morsitans Westwood attracted to natural ox odour and synthetic odour, the latter consisting of blends of identified attractants dispensed at the doses naturally present in ox odour. Natural ox odour caught twice (P < 0.05) as many G. pallidipes and 1.5 (P < 0.05) times as many G. m. morsitans as the synthetic blend suggesting the presence of an unidentified attractant in ox odour. Passing ox odour through filters indicated that all attractants can be trapped on a combination of charcoal and sodalime filters but the unidentified attractant(s) may pass through a sodalime filter, and break through a charcoal filter used for more than 6 h. Increasing the dose of ketones in the synthetic odour from 2 to 100 mg/h doubled the catches at the source. Increases in ketone levels in hosts, induced by starvation or possibly trypanosomiasis, may increase attraction of tsetse to such animals.

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48

Biziks, Vladimirs, Marco Fleckenstein, Carsten Mai, and Holger Militz. "Suitability of a lignin-derived mono-phenol mimic to replace phenol in phenol-formaldehyde resin for use in wood treatment." Holzforschung 74, no. 4 (March 26, 2020): 344–50. http://dx.doi.org/10.1515/hf-2019-0061.

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AbstractThe goal of this study was to assess the suitability of a single mono-aromatic for substitution of petroleum-based phenol for phenol-formaldehyde (PF) resin synthesis and the usage of a new resin for wood treatment. After proper thermal decomposition of wood-based lignin, pyrolysis oil can be obtained. Due to the heterogeneity of the lignin macromolecule, oil contains large variety of organic-based compounds, mainly mono-aromatics, which are proposed to be used for replacement of phenol during PF resin synthesis. Therefore, for this purpose, nine of the most abundant mono-aromatic compounds in bio-oil were selected: ortho-, meta-, para-cresol, guaiacol, catechol, 4-methylcatechol, resorcinol, syringol, 4-ethylphenol and resol-type resin from each mono-aromatic were synthesized. Relevant features of the resin such as pH, viscosity, average molecular weight and curing behavior of resins using differential scanning calorimetry (DSC) were analyzed. Scots pine (Pinus sylvestris L.) sapwood samples were used to evaluate the suitability of resin for wood treatment in terms of dimensional stability and were compared with the PF resin-treated wood. From all tested resins, those made of guaiacol or ortho-, or meta-, or para-cresol and/or 4-ethylphenol proved to be suitable for wood treatment, whereas resins made of catechol or 4-methylguaiacol and syringol did not. Suitability of mono-aromatics for synthesis of resol-type resin depends on chemical structure, where the reactivity of the mono-aromatic (derivative of hydroxybenzene) is defined by the type, location and number of substituents.

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49

Api, A. M., D. Belsito, S. Biserta, D. Botelho, M. Bruze, G. A. Burton, J. Buschmann, et al. "RIFM fragrance ingredient safety assessment, p-ethylphenol, CAS Registry Number 123-07-9." Food and Chemical Toxicology 149 (March 2021): 111985. http://dx.doi.org/10.1016/j.fct.2021.111985.

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50

Zeng, Bo, Gui-Lan Chen, Nikoleta Daskoulidou, and Shang-Zhong Xu. "The ryanodine receptor agonist 4-chloro-3-ethylphenol blocks ORAI store-operated channels." British Journal of Pharmacology 171, no. 5 (February 27, 2014): 1250–59. http://dx.doi.org/10.1111/bph.12528.

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