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The identification and correction of negative factors, such as 4-ethylphenol and ethanethiol, is important to comply with food safety regulations and avoid economic losses to wineries. A simple amperometric measurement procedure that facilitates the simultaneous quantification of both compounds in the gas phase has been developed using fullerene and cobalt (II) phthalocyanine-modified dual screen-printed electrodes coated with a room temperature ionic liquid-based gel polymer electrolyte. The replacement of the typical aqueous supporting electrolyte by low-volatility ones improves both operational and storage lifetime. Under the optimum conditions of the experimental variables, Britton Robinson buffer pH 5 and applied potentials of + 0.86 V and + 0.40 V for each working electrode (vs. Ag ref. electrode), reproducibility values of 7.6% (n = 3) for 4-ethylphenol and 6.6% (n = 3) for ethanethiol were obtained, as well as capability of detection values of 23.8 µg/L and decision limits of 1.3 µg/L and 9.2 µg/L (α = ß = 0.05), respectively. These dual electrochemical devices have successfully been applied to the headspace detection of both compounds in white and red wines, showing their potential to be routinely used for rapid analysis control in wineries.

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4-ethylphenol and 4-ethylguaicol levels in wine are associated to organoleptic defects that cause consumer rejection accompanied by significant economic losses for producers. Thus, electrochemical sensors based on screen-printed carbon electrodes (SPCEs) modified with activated fullerene C60 (AC60) have been developed for the analysis of both phenols by direct headspace amperometric measurements. Upon optimization of the experimental variables affecting the sensors performance, the AC60/SPCE sensors presented linearity ranges from 9.9 to 65.4 µg/L and from 19.6 to 107.1 µg/L for 4-ethylphenol and 4-ethylguaicol, respectively. The achieved detection capacities were 10.3 µg/L (4-ethylphenol) and 19.6 µg/L (4-ethylguaicol), with a reproducibility of 6.3 % and 9.1 % (n = 3), respectively. In addition, dual-working AC60/SPCE devices were developed for the simultaneous analysis of both phenols using different working potentials for each electrode. The dual systems were successfully applied in the analysis of different spiked wine samples, obtaining good recoveries ranging from 94 to 108 %.

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Gut-microbiome-derived metabolites, such as 4-Ethylphenol [4EP], have been shown to modulate neurological health and function. Although the source of such metabolites is becoming better understood, knowledge gaps remain as to the mechanisms by which they enter host circulation, how they are transported in the body, how they are metabolised and excreted, and the way they exert their effects. High blood concentrations of host-modified 4EP, 4-ethylphenol sulfate [4EPS], are associated with an anxiety phenotype in autistic individuals. We have reviewed the existing literature and discuss mechanisms that are proposed to contribute influx from the gut microbiome, metabolism, and excretion of 4EP. We note that increased intestinal permeability is common in autistic individuals, potentially explaining increased flux of 4EP and/or 4EPS across the gut epithelium and the Blood Brain Barrier [BBB]. Similarly, kidney dysfunction, another complication observed in autistic individuals, impacts clearance of 4EP and its derivatives from circulation. Evidence indicates that accumulation of 4EPS in the brain of mice affects connectivity between subregions, particularly those linked to anxiety. However, we found no data on the presence or quantity of 4EP and/or 4EPS in human brains, irrespective of neurological status, likely due to challenges sampling this organ. We argue that the penetrative ability of 4EP is dependent on its form at the BBB and its physicochemical similarity to endogenous metabolites with dedicated active transport mechanisms across the BBB. We conclude that future research should focus on physical (e.g., ingestion of sorbents) or metabolic mechanisms (e.g., conversion to 4EP-glucuronide) that are capable of being used as interventions to reduce the flux of 4EP from the gut into the body, increase the efflux of 4EP and/or 4EPS from the brain, or increase excretion from the kidneys as a means of addressing the neurological impacts of 4EP.

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The aroma profile of industrial Sichuan paocai is formed and regulated by complex physiological and biochemical reactions and microbial metabolism, but little is known so far. In this study, we comprehensively analyzed the changes of metabolic profile and gene expression profile, mainly explored the formation pathways of two skeleton aroma-active compounds, 4-ethylphenol and 4-ethylguaiacol, and verified the pathways at multiple levels. The results showed that a total of 136 volatile metabolites and 560 non-volatile metabolites were identified in the whole fermentation process. The types and concentrations of metabolites in paocai were higher than those in brine, and gradually converged with fermentation. Differential analysis of metabolism and transcription levels were both enriched in three pathways: amino acid metabolism, phenylpropanoid metabolism and lipid metabolism. Among them, 4-ethylphenol and 4-ethylguaiacol, the products of the phenylpropanoid metabolism, were converted from p-coumaric acid and ferulic acid in plant cell walls, respectively. Under the action of decarboxylase produced by yeast (such as Debaryomyces Hansenii) and lactic acid bacteria (such as Lactobacillus versmoldensis), intermediate metabolites vinylphenols were produced, and the intermediate metabolites further produce the final products under the action of vinylphenol reductase. The key gene copy number, enzyme activity, and metabolite concentration in the pathways were detected to provide stronger evidence for the formation pathways. This study provided meaningful new insights for the development of aroma-producing enzymes and further guidance for the flavor improvement of industrial paocai.

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Microbial spoilage of olive fruits is among the most frequent reasons for two types of off-flavors in olive oils, assigned as musty and fusty/muddy sediment. To characterize both off-flavors on a molecular level by means of the sensomics approach, the key aroma compounds in a premium extra virgin olive oil (PreOO1) eliciting the typical sensory properties were compared to those identified in two off-flavor olive oils obtained from the International Olive Council (IOC). A comparative aroma extract dilution analysis (cAEDA) followed by identification experiments revealed 53 odorants in the musty reference olive oil (MusOO1) and 48 odorants in the fusty/muddy sediment one (FusOO1). Odorants, differing in flavor dilution (FD) factors or showing a high FD factor in at least one of the olive oils, were quantitated by stable isotope dilution analysis (SIDA), followed by the calculation of odor activity values (OAVs; ratio of concentration of an odorant to the respective odor threshold in odorless refined sunflower oil). Aroma recombination and omission experiments revealed 13 key aroma compounds in MusOO1 and 12 in FusOO1. To demonstrate the importance of volatile phenols, 10 phenolic smelling odorants were quantitated in further 13 extra virgin olive oils, in 3 musty and in 13 fusty/muddy sediment defective olive oils, and in 8 olive oils with other off-flavors. Both sensory defects could successfully be discriminated from extra virgin olive oils by applying either a principal component analysis or a hierarchical cluster analysis. Considering possible reaction pathways and all results obtained including Pearson coefficients between the odorant concentrations and the intensities of the defects, specifically 2-methoxyphenol and 4-ethylphenol were proposed as marker compounds for the quality assignment of both types of off-flavors induced by microbial spoilage among the identified key aroma compounds.

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Oomycetes, represented by Phytophthora, are seriously harmful to agricultural production, resulting in a decline in grain quality and agricultural products and causing great economic losses. Integrated management of oomycete diseases is becoming more challenging, and plant derivatives represent effective alternatives to synthetic chemicals as novel crop protection solutions. Biologically active secondary metabolites are rapidly synthesized and released by plants in response to biotic stress caused by herbivores or insects, as well as pathogens. In this study, we identified groups of volatile organic compounds (VOCs) from soybean plants inoculated with Phytophthora sojae, the causal agent of soybean root rot. 4-Ethylphenol was present among the identified VOCs and was induced in the incompatible interaction between the plants and the pathogen. 4-Ethylphenol inhibited the growth of P. sojae and Phytophthora nicotianae and had toxicity to sporangia formation and zoospore germination by destroying the pathogen cell membrane; it had a good control effect on soybean root rot and tobacco black shank in the safe concentration range. Furthermore, 4-Ethylphenol had a potent antifungal activity against three soil-borne phytopathogenic fungi, Rhizoctonia solani, Fusarium graminearum, and Gaeumannomyces graminis var tritici, and four forma specialis of Fusarium oxysporum, which suggest a potential to be an eco-friendly biological control agent.

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The adoption of two-phase olive oil extraction processes has led to a significant increase in the amounts of two-phase olive pomace produced each year. This material is typically led to kernel oil extraction facilities that are forced to store the excessive amounts until treatment. During storage, malodorous compounds, like 4-ethylphenol, are formed that are then released to the atmosphere during drying, causing serious problems in a radius of several kilometers. At the same time, increased microbial activity in the stored pomace deteriorates kernel oil, diminishing its value. This deterioration is expressed as increased kernel oil acidity. In this work, the evolution of 4-ethylphenol concentration and kernel oil acidity as a function of storage duration and waste acidification were examined. The concentration of 4-ethylphenol in the unmodified two-phase olive pomace seems to be maximized after 23 d of storage, while kernel oil acidity reached a plateau of 10% after 70 d. Acidification at pH 2 prevented the production of 4-ethylphenol and kept kernel oil acidity at 5% for more than 100 d of storage. The results presented herein are a step towards understanding the processes taking place during two-phase olive pomace storage and exploring ways of minimizing their effects.

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The use of non-conventional yeast species to obtain interesting flavors and aromas has become a new trend in the fermented beverages industry. Among such species, Brettanomyces bruxellensis (B. bruxellensis) has been reported as capable of producing desirable or at least singular aromas in fermented beverages like beer and wine. However, this yeast can also produce an aromatic defect by producing high concentrations of phenolic compounds like, 4-ethylguaiacol and particularly 4-ethylphenol (4-EP). In the present study, we designed a mutant screening method to isolate B. bruxellensis mutants with reduced 4-EP production. More than 1000 mutants were screened with our olfactory screening method, and after further sensory and chemical analysis we were able to select a B. bruxellensis mutant strain with a significant reduction of 4-EP production (more than threefold) and less phenolic perception. Notably, the selected strain also showed higher diversity and concentration of ethyl esters, the most important group of odor active compounds produced by yeasts. Based on these results, we consider that our selected mutant strain is a good candidate to be tested as a non-conventional yeast starter (pure or in co-inoculation) to obtain wines and beers with novel aromatic properties.

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4-Ethylphenol (4-EP) and 4-ethylguaiacol (4-EG) formation in red wines by Dekkera/Brettanomyces yeasts reduce significantly wine consumer's acceptability. Polymers with specific adsorption for volatile phenols (VPs) could be a valuable tool for wine producers for removing this negative sensory defect. In this work, a new molecularly imprinted polymer (MIP) was synthesised using ethylene glycol dimethacrylate (EDMA) as cross-linker and ethylene glycol methyl ether acrylate as functional monomers. Although there was observed a competitive binding of the more abundant structurally related phenolic compounds of the wine matrix, it was still able to reduce 38 to 63% the wine VPs, depending on the wine VPs levels, presenting higher performance than the respective non-imprinted polymers (NIP). Sensory analysis of the MIP treated wine resulted in a significant decrease in the phenolic attribute and significant increase of the fruity and floral attributes, with no significant differences in the wine colour perceived by the expert panel. The sensory improvement of the MIP was significantly higher than that observed for the correspondent NIP.

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Anaerobic degradation of p-cresol (4-methylphenol) by the denitrifying betaproteobacterium Aromatoleum aromaticum EbN1 is regulated with high substrate specificity, presumed to be mediated by the predicted σ54-dependent two-component system PcrSR. An unmarked, in-frame ΔpcrSR deletion mutant showed reduced expression of the genes cmh (21-fold) and hbd (8-fold) that encode the two enzymes for initial oxidation of p-cresol to p-hydroxybenzoate compared to their expression in the wild type. The expression of cmh and hbd was restored by in trans complementation with pcrSR in the ΔpcrSR background to even higher levels than in the wild type. This is likely due to ∼200-/∼30-fold more transcripts of pcrSR in the complemented mutant. The in vivo responsiveness of A. aromaticum EbN1 to p-cresol was studied in benzoate-limited anaerobic cultures by the addition of p-cresol at various concentrations (from 100 µM down to 0.1 nM). Time-resolved transcript profiling by quantitative reverse transcription-PCR (qRT-PCR) revealed that the lowest p-cresol concentrations just affording cmh and hbd expression (response threshold) ranged between 1 and 10 nM, which is even more sensitive than the respective odor receptors of insects. A similar response threshold was determined for another alkylphenol, p-ethylphenol, which strain EbN1 anaerobically degrades via a different route and senses by the σ54-dependent one-component system EtpR. Based on these data and theoretical considerations, p-cresol or p-ethylphenol added as a single pulse (10 nM) requires less than a fraction of a second to reach equilibrium between intra- and extracellular space (∼20 molecules per cell), with an estimated Kd (dissociation constant) of <100 nM alkylphenol (p-cresol or p-ethylphenol) for its respective sensory protein (PcrS or EtpR).IMPORTANCE Alkylphenols (like p-cresol and p-ethylphenol) represent bulk chemicals for industrial syntheses. Besides massive local damage events, large-scale micropollution is likewise of environmental and health concern. Next to understanding how such pollutants can be degraded by microorganisms, it is also relevant to determine the microorganisms' lower threshold of responsiveness. Aromatoleum aromaticum EbN1 is a specialist in anaerobic degradation of aromatic compounds, employing a complex and substrate-specifically regulated catabolic network. The present study aims at verifying the predicted role of the PcrSR system in sensing p-cresol and at determining the threshold of responsiveness for alkylphenols. The findings have implications for the enigmatic persistence of dissolved organic matter (escape from biodegradation) and for the lower limits of aromatic compounds required for bacterial growth.

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This work describes the development of an electrochemical sensor based on a molecularly imprinted polymer (MIP) for sensitive and selective determination of 4-ethylphenol in wine. The sensor has been built by means of the electrosynthesis of the MIP on a glassy carbon electrode surface using cyclic voltammetry. The electropolymerization has been performed in the presence of 4-ethylphenol and pyrrole as template molecule and functional monomer, respectively. The influence of the molar ratios of template molecules to functional pyrrole monomers and the time needed to remove the template have been optimized taking into account the differential pulse voltammetric response of 4-ethylphenol. Under the optimal experimental conditions the developed MIP/GCE sensor shows good capability of detection (0.2 µM, α = ß = 0.05) and reproducibility (3.0%) in the concentration range from 0.2 to 34.8 µM. The influence of possible interfering species in the analytical response has been studied and the sensor has successfully been applied to the determination of 4-ethylphenol in different wine samples.

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The trans to cis isomerization of the azobenzene chromophore in most azobenzene-based photoresponsive molecularly imprinted polymers (MIPs) is initiated by UV irradiation. This limits the application of these materials in cases where UV light toxicity is an issue, such as in biological systems, food monitoring, and drug delivery. Herein we report a tetra-ortho-methyl substituted azobenzene, (4-[(4-methacryloyloxy)-2,6-dimethyl phenylazo]-3,5-dimethyl benzenesulfonic acid (MADPADSA). The photoswitching of MADPADSA could be induced by visible-light irradiation (550 nm for trans to cis and 475 nm for cis to trans) in 4-hydroxyethylpiperazineethanesulfonic acid (HEPES) buffer-ethanol (4:1, v/v) at pH 7.0, however, the photoisomerization was slow. With the use of MADPADSA as a functional monomer, NaYF4:Yb3+,Er3+ as a substrate, 4-ethylphenol (4-EP) as a template, a novel photoresponsive surface molecularly imprinted polymer NaYF4:Yb3+,Er3+@MIP was obtained. The NaYF4:Yb3+,Er3+@MIP displayed rapid visible-light-induced photoswitching. The NaYF4:Yb3+,Er3+ substrate could efficiently increase the trans to cis isomerization rate of the photoresponsive MIP on its surface, which was faster than that of the corresponding azobenzene monomer MADPADSA. Possible reasons for this effect were investigated by fluorescence spectroscopy. NaYF4:Yb3+,Er3+@MIP displayed good specificity toward 4-EP with a specific binding constant (Kd) of 3.67 × 10-6 mol L-1 and an apparent maximum adsorption capacity (Qmax) of 10.73 µmol g-1, respectively. NaYF4:Yb3+,Er3+@MIP was applied to determine the concentration of 4-EP in red wine with good efficiency and a limit of detection lower than the value that could cause an unpleasant off-flavor.

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In the Albanian winemaking industry, there is little awareness of the potential detrimental effect of Brettanomyces in wines. The aim of this study was to detect and quantify Brettanomyces cells in 22 Albanian bottled wines, representing all the viticultural areas of Albania. A combined approach, including culture-dependent (viable plate counting) and culture-independent (qPCR) methods, was applied. Spoilage indicators (ethylphenols and total and volatile acidity), as well as the primary factors known to influence the growth of Brettanomyces in wine (pH, SO2 , and ethanol concentration), were also investigated. Brettanomyces was detected in only five (one Merlot, four Sheshi i Zi) out of 22 samples analyzed using viable counting, with loads ranging from 1.30 ± 0.03 log CFU/mL to 3.99 ± 0.00 log CFU/mL, whereas it was never detected in the Kallmet samples. When qPCR was applied, Brettanomyces cells were detected and quantified in all of the samples with a generally low load ranging from 0.47 ± 0.13 to 3.99 ± 0.01 log cells/mL. As a general trend, the loads of spoilage by this yeast were low (≤1.92 log cells/mL), with the exception of five samples that were also positive by plate counting. A positive correlation between the growth of this spoilage yeast on Dekkera/Brettanomyces differential media and its detection at high levels by qPCR was observed. A significant positive correlation between Brettanomyces and the concentration of ethylphenols and volatile acidity was also found. In summary, the results of this study demonstrated the low incidence of Brettanomyces spoilage yeasts in Albanian red wines. PRACTICAL APPLICATION: The awareness of Brettanomyces spoilage in the Albanian winemaking industry is very low. This study represents the first contribution to understand the extent of this spoilage yeast in Albanian autochthonous cultivars, which tend to have high economic value, to ensure product quality and safety. qPCR is confirmed to be a very sensitive method to rapidly detect Brettanomyces spoilage in wine samples.

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Data in this article presents the changes on phenolic compounds and headspace aroma abundance of a red wine spiked with 4-ethylphenol and 4-ethylguaiacol and treated with a commercial crustacean chitin (CHTN), two commercial crustacean chitosans (CHTB, CHTD), one fungal chitosan (CHTF), one additional chitin (CHTNA) and one additional chitosan (CHTC) produced by alkaline deacetylation of CHTN and CHTB, respectively. Chitin and chitosans presented different structural features, namely deacetylation degree (DD), average molecular weight (MW), sugar and mineral composition ("Reducing the negative sensory impact of volatile phenols in red wine with different chitosan: effect of structure on efficiency" (Filipe-Ribeiro et al., 2018) [1]. Statistical data is also shown, which correlates the changes in headspace aroma abundance of red wines with the chitosans structural features at 10 g/h L application dose.

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The adsorption and desorption characteristics of seven macroporous resins on the antioxidants in soy sauce were investigated. SP-207 and SP-825 resins possessing good adsorption and desorption capacities were studied further. The pseudo-second-order kinetics and Langmuir isotherm models were demonstrated to be appropriate to describe the whole exothermic and physical adsorption processes of antioxidants onto resins. The 60% ethanol eluted fraction from soy sauce purified by SP-825 resin column possessed the strongest antioxidant activity. The antioxidant activities and contents of typical soy isoflavones, furanones, pyranones, and phenolic acids in soy sauce were determined. These compounds contributed to 50.02% of the total antioxidant activity of the SP-60% fraction. The key small molecule antioxidant compounds in soy sauce were identified as 4-ethylguaiacol, catechol, daidzein, and 4-ethylphenol by the antioxidants omission experiments. Additionally, the purified active fraction with high contents of antioxidants from soy sauce could be applied as bioactive ingredient in food industry.

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"Brett character" is a negative sensory attribute acquired by red wines when contaminating Dekkera/Brettanomyces yeasts produce 4-ethylphenol and 4-ethylguaiacol, known as volatile phenols (VPs), from cinnamic acid precursors. In this study, chitins and chitosans with different structural features, namely deacetylation degree (5-91%) and molecular weight (24-466kDa) were used for the reduction of this sensory defect. Chitins and chitosans decreased 7-26% of the headspace abundance of VPs without changing their amounts in wines. The efficiency of reduction increased with the deacetylation degree and applied dose. Reduction of headspace abundance of VPs by chitosans enabled significant decreases in the negative phenolic and bitterness attributes and increased positive fruity and floral attributes. Results show that chitosan with high deacetylation degrees, including fungal chitosan, which is already approved for use in wines, is an efficient approach for reducing the negative sensory impact of VPs in red wines.

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Activated carbon (AC) could be a solution to remove 4-ethylphenol (4-EP) and 4-ethylguaiacol (4-EG) off-flavours from Dekkera/Brettanomyces contaminated red wines. The relation between AC physicochemical characteristics and removal efficiency of these compounds is unknown. The impact of ACs characteristics on 4-EP and 4-EG removal, phenolic and headspace aroma composition was studied. All ACs reduced significantly 4-EP and 4-EG levels (maximum 73%). Their efficiency was related to their surface area and micropores volume. A higher surface area of mesopores and total pore volume were detrimental for anthocyanins and colour intensity, while a higher surface area and micropores volume were important for removing phenolic acids. Volatile phenols reduction was more important for the positive fruity attribute perception than the abundance of headspace aroma compounds. With an optimal selection of the AC physicochemical characteristics it was possible to remove efficiently the volatile phenols without impacting negatively on the wine sensory quality.

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In-vial filtration with dispersive solid-phase extraction (d-SPE) clean-up of QuEChERS (quick, easy, cheap, effective, rugged and safe) extracts is proposed for the determination of ethylphenols (EPs) in red wines. Analytes were extracted from 5mL wine sample (previously alkalinized with 0.5% sodium hydroxide) using 5mL acetonitrile. For phase separation, 1.5g NaCl and 4g anhydrous MgSO4 were added. Then, a 0.5mL aliquot of the partitioned supernatant was cleaned-up using d-SPE and in-vial filtration with a combination of anhydrous CaCl2 (100mg) and primary-secondary amine (PSA, 25mg) as sorbents. The proposed method provided limits of quantification (LOQs) ranging from 0.024 to 0.04mgL-1. Considering matrix-matched calibration as quantification technique, the recoveries (accuracy) ranged between 73% and 116%. The method was applied for the determination of EPs in 15 commercial wines of Argentina, where 4-EP was quantified at concentrations ranging from 0.25 to 3.01mgL-1.

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Data in this article presents the changes on phenolic compounds, headspace aroma composition and sensory profile of a red wine spiked with 4-ethylphenol and 4-ethylguaiacol and treated with seven activated carbons with different physicochemical characteristics, namely surface area, micropore volume and mesopore volume ("Reduction of 4-ethylphenol and 4-ethylguaiacol in red wine by activated carbons with different physicochemical characteristics: impact on wine quality" Filipe-Ribeiro et al. (2017) [1]). Data on the physicochemical characteristics of the activated carbons are shown. Statistical data on the sensory expert panel consistency by General Procrustes Analysis is shown. Statistical data is also shown, which correlates the changes in chemical composition of red wines with the physicochemical characteristics of activated carbons used.

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Brettanomyces/Dekkera produces 4-ethylphenol (4-EP) and 4-ethylguaiacol (4-EG) from hydroxycinnamic acids that affect the wine aroma and overall quality. A simple, cheap, fast and reliable quantitation method is needed for routine quality control of wines. In this work a simple method based on one simple liquid-liquid extraction with pentane/diethyl ether (2:1) and analysis by GC-MS allow to obtain very good recoveries (98-102%) and low quantification limits (24 and 11µg/L for 4-EP and 4-EG, respectively), well below the sensory threshold for these volatile phenols and with an adequate measurement uncertainty: 70, 1.75 and 78, 1.95 and 1.35µg/L for levels of 1000, 25µg/L for 4-EP and 1000, 25 and 10µg/L for 4-EG, respectively. In addition a screening of eight fining agents (mineral, protein and polysaccharide based) for reducing the levels of these volatile phenols in red wines was performed, and the impact on the physicochemical characteristics of red wines was evaluated. At the levels used, activated carbon was the most efficient fining agent in removing 4-ethylphenol and 4-ethylguaiacol from red wines (57%) resulting in a 75% decrease of headspace concentration of these volatile phenols. Lower reductions were observed when using egg albumin (19%) resulting in a 30% decrease in the headspace concentration. Other fining agents although not reducing the total amount of the volatile phenols present in wine decreased their concentrations in the headspace like isinglass (27%), carboxymethylcellulose (15%) and chitosan (27%). All of these fining agents could be a possibility for treating wine contaminated with 4-ethylphenol and 4-ethylguaiacol.

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