Furfuryl Acetate Research Articles

Selection and application of antifungal VOCs-producing yeasts as biocontrol agents of grey mould in fruits

Rotting caused by grey mould (Botrytis cinerea) is a concerning disease for numerous crops both pre- and postharvest stages. Application of antagonistic yeasts is a promising strategy for controlling grey mould incidence which could mitigate undesirable consequences of using synthetic fungicides. In this work, a screening for detection of yeasts isolated from figs producers of antifungal volatile organic compounds (VOCs) were performed by confrontation in double dishes systems. Eleven out of 34 yeasts confronted reduced B. cinerea growth parameter in vitro. This reduction was correlated (p ≤ 0.050) with the production of 10 volatile compounds: two acids (acetic acid and octanoic acid), 7 esters (Ethyl propionate, n-Propyl acetate, Isobutyl acetate, 2-methylbutyl acetate, furfuryl acetate, phenylmethyl acetate, 2-phenylethyl acetate) and one ketone (Heptan-2-one). In bases on in vitro assay, Hanseniaspora uvarum 793 was applied to in vivo assays with strawberries and cherries. The reduction of incidence of B. cinerea in strawberries at 7 °C and 25 °C was 54.9 and 72.1% after 6 and 3 days, respectively. The reduction of incidence of B. cinerea in cherries at 7 °C and 25 °C was 48.9 and 45.6% after 5 and 4 days, respectively. These results showed that VOCs produced by Hanseniaspora uvarum 793 are effective in the control of incidence of Botrytis cinerea in fruits, being a potential alternative to chemical fungicide.

Bifunctional rice husk-derived SiO2-Cu-Al-Mg nanohybrid catalyst for one-pot conversion of biomass-derived furfural to furfuryl acetate

Developing one-pot reaction methodologies, which typically require multifunctional catalyst systems, is crucial for sustainable production of bio-derived fuels and chemicals. This work reports one-pot hydrogenation-esterification of furfural to furfuryl acetate using a bifunctional metal-based nanohybrid catalyst, composed of rice husk (RH) derived SiO2, Cu, Al, and Mg species (RHSiO2-Cu-Al-Mg). For comparison, the catalytic efficiency of RHSiO2-Cu and RHSiO2-Cu-Al were tested under similar reaction conditions. Various analytical techniques were used to elucidate the physicochemical, textural, and acid-redox properties of the catalysts. It was found that the RHSiO2-Cu-Al-Mg catalyst contains an optimum amount of acid and redox sites, as illustrated by NH3-TPD and H2-TPR studies, respectively. Especially, Mg addition played a vital role in tailoring acidity of the RHSiO2-Cu-Al catalyst to promote in-situ esterification of furfuryl alcohol with acetic acid to yield furfuryl acetate. As a result, the RHSiO2-Cu-Al-Mg catalyst exhibited the best performance in one-pot conversion of furfural to furfuryl acetate, outperforming various noble metal/silica based catalysts. This study offers potential opportunities for the rational design of novel, bifunctional heterogeneous catalysts for efficient production of bio-derived fuels and value added chemicals.

Ruthenium triphos complexes [Ru(X(CH2PPh2)3-κ3-P)(NCCH3)3](OTf)2; X = H3C-C, N) as catalysts for the conversion of furfuryl acetate to 1,4-pentanediol and cyclopentanol in aqueous medium

The ruthenium complexes [Ru(H3CC(CH2PPh2)3-κ3-P)(NCCH3)3](OTf)2 (1, (H3CC(CH2PPh2)3 = triphos) and [Ru(N(CH2PPh2)3-κ3-P)(NCCH3)3](OTf)2 (2, N(CH2PPh2)3 = N-triphos) have been evaluated as homogeneous ionic hydrogenation catalysts for the catalytic hydrodeoxygenation of furfuryl alcohol and furfuryl acetate to 1,4-pentanediol and cyclopentanol in aqueous media reaction mixtures. For furfuryl alcohol, only marginal yields of 1,4-pentanediol could be achieved with mass balance deficiencies due to humin formation ranging from 67% to 90%. Attempts to improve the catalytic activity of 2 by enhancing its water solubility by nitrogen protonation and (or) methylation failed. Employing the less self-reactive furfuryl acetate as the substrate substantially diminishes humin formation, yielding up to 43% of 1,4-pentanediol and 19% of cyclopentanol (via Piancatelli rearrangement) with 1 and up to 33% of 1,4-pentanediol and 5% of cyclopentanol with 2. A design of experiments study was used to determine and compare the yield responses of the multiple parallel reaction channels with 1,4-pentanediol, cyclopentanol, and humins as a function of reaction temperature, time, catalyst load, and substrate concentration. This explores the correlations between these parameters and their impact on the reaction outcome and suggests an extremely complex overall reaction cascade of interdependent pathways of both acid- and metal-catalyzed steps with some significant differences emerging between the two catalysts.

Novelty of iron-exchanged heteropolyacid encapsulated inside ZIF-8 as an active and superior catalyst in the esterification of furfuryl alcohol and acetic acid

Metal-exchanged dodecatungstophosphoric acids encapsulated inside ZIF-8 framework were synthesized to produce a variety of active catalysts M-DTP@ZIF-8 for the formation of furfuryl acetate from the esterification of furfuryl alcohol and acetic acid.

Synthesis of 5-Methylene-2-pyrrolones.

A facile, one-pot synthetic method for the synthesis of 5-methylene-2-pyrrolones (5MPs) from inexpensive furfuryl acetate is described. Bromine oxidation and trapping of the in situ generated 1,4-dicarbonyl compound by a primary amine provided the corresponding 5MPs in 50-69% yield.

Theoretical study of the furfuryl benzoate and furfuryl acetate pyrolysis

AbstractIn the present work, the pyrolysis reaction mechanism of both furfuryl benzoate and furfuryl acetate was evaluated at the M06/6‐311++g(d,p) level. The uncommon methylenecyclobutenone compound and either the benzoic or the acetic acid were determined as the products of a multistep process consisting in two [3 + 3] rearrangements and a subsequent hydrogen α‐elimination step, through a cyclic 5‐membered transition state (TS), being the latter the rate‐limiting step for both reactants. Furthermore, a deeper analysis on the basis of the reaction force formalism showed that the TS is formed in two stages: The first one is characterized by the weakening of the C─O bond, and the second one is where the H atom is transferred from the C atom to its nearest O atom. The H─O bond formation was determined to contribute the most to the electronic activity occurring during the TS formation as suggested by a reaction electronic flux analysis. Accordingly, natural bond orbital calculations showed that the most significant changes occur in the charge distribution of the O and H atoms. Finally, a negligible effect of the substituting group on the reaction was determined since similar activation energies were obtained for the pyrolysis of furfuryl benzoate and furfuryl acetate; however, a minor difference was evidenced in the reaction force results. In this sense, the structural contribution to the activation energy is larger than the electronic one for the furfuryl benzoate reaction, , whereas the opposite is observed for the furfuryl acetate reaction, .

Accessing the HMF Derivatives from Furfural Acetate through Oxidative Carbonylation

AbstractExploring new bulky chemicals from furfural is greatly attractive since its raw biomass resources are not competitive with the food of human beings. Regarding the large market of the sub‐products of hydroxylmethyl furfural (HMF) with the current technical challenges in HMF production from cellulose, transforming furfural and its sub‐products to HMF derivatives may offer an alternative source of HMF sub‐products and a solution to narrow market of furfural. Here, we report a novel route to synthesize the sub‐chemicals of HMF from furfuryl acetate, a furfural based platform molecule, which realizes the transformation of renewable furfural to C6 chemicals through direct C−H oxidative carbonylation by Pd(OAc)2 catalyst.

Thermophysical Characterization of Furfuryl Esters: Experimental and Modeling

The use of compounds with high oxygen content in the fuels field is very promising because they can increase combustion engine efficiency and minimize pollution emissions. The study of the thermophysical properties of these compounds is essential in order to evaluate their possible applications. In this study, different thermodynamic and transport properties of three furfuryl esters—furfuryl acetate, furfuryl propionate, and furfuryl butyrate—have been determined and compared with those of fluids that are commonly used as fuels or additives. Finally, the thermophysical behavior of these compounds has been analyzed using different models such as PC-SAFT equation of state and density gradient theory. The results indicate that these compounds exhibit similar characteristics to those of the normafluid ISO4113 (standard fluid in diesel injectors) except the density, bulk modulus, and surface tension, which are higher in the esters studied. It can be concluded that, given their thermophysical properties, these ...

Safety and efficacy of furfuryl and furan derivatives belonging to chemical group 14 when used as flavourings for all animal species and categories

Following a request from the European Commission, the EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) was asked to deliver a scientific opinion on the safety and efficacy of 18 compounds belonging to chemical group 14 (furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms). They are currently authorised as flavours in food. This opinion concerns 13 compounds from this group. The FEEDAP Panel concludes that all compounds except 5‑methylfurfural are safe at the proposed maximum use level for all animal species: furfural and furfuryl alcohol at 5 mg/kg complete feed; methyl 2‑furoate and furfuryl acetate at 0.5 mg/kg complete feed; bis‑(2-methyl-3-furyl) disulfide, furanmethanethiol, S‑furfuryl acetothioate, difurfuryl disulfide, methyl furfuryl sulfide, 2‑methylfuran-3-thiol, methyl furfuryl disulfide and methyl 2‑methyl-3-furyl disulfide at 0.05 mg/kg complete feed. 5‑Methylfurfural is safe at the proposed use level of 0.5 mg/kg complete feed for cattle, salmonids and non-food producing animals and at the use level of 0.3 mg/kg complete feed for pigs and poultry. No safety concern would arise for the consumer from the use of these compounds up to the highest safe level in feeds. Hazards for skin and eye contact and respiratory exposure are recognised for the majority of the compounds under application. Most are classified as irritating to the respiratory system. The concentrations considered safe for the target species are unlikely to have detrimental effects on the terrestrial and freshwater environments. Since all the compounds under assessment are used in food as flavourings, and their function in feed is essentially the same as that in food, no further demonstration of efficacy is necessary. In the absence of data on the stability in water for drinking, the FEEDAP Panel is unable to conclude on the safety or efficacy of the substances under this mode of delivery.

Differentiation of Volatile Profiles and Odor Activity Values of Turkish Coffee and French Press Coffee

Volatile compositions of coffee obtained from two different coffee brewing methods, Turkish coffee (TC) and French press coffee (FPC), were analyzed by the gas chromatography-mass spectrometry technique. Liquid–liquid extraction with dichloromethane was used for extraction of volatile compounds. A total of 60 and 58 volatile compounds comprising furans, lactones, phenolic compounds, pyridines, pyrazines, acids, cyclopentenes, pyrroles, furanones, ketones, alcohols, aldehydes and thiols were identified and quantified in TC and FPC, respectively. Among the detected compounds, furans were present in the highest levels, followed by lactones. Furfuryl alcohol followed by ɣ-butyrolactone, pyridine, hexadecanoic acid, maltol, 2-methyl pyrazine and furfuryl acetate were found in large amounts in both coffee brews. It was observed that the volatile profiles of both samples were quite similar. Based on the odor activity values (OAVs), 13 volatile compounds presented OAVs greater than 1 and guaiacol, 2,3-butanedione and furfuryl acetate were the highest OAVs in both coffee samples. Practical Applications Coffee is one of the most widely consumed beverages in the world. The results of this first study provide valuable information for understanding the aroma and odor activity value differences between Turkish coffee and French press coffee. The liquid–liquid extraction technique for isolation followed by analysis and identification of those compounds by gas chromatography-mass spectrometry is an effective practical application tool for volatile description in coffee samples. It was observed that the volatile profiles of both samples were quite similar.

Kinetic modeling and docking study of immobilized lipase catalyzed synthesis of furfuryl acetate

The present work deals with the kinetic modeling and docking study for the furfuryl acetate synthesis using immobilized Burkholderia cepacia (BCL) lipase. Initially various lipases were immobilized on hydroxypropyl methyl cellulose (HPMC) and poly vinyl alcohol (PVA) base hybrid polymer matrix. After screening of various immobilized biocatalysts, HPMC:PVA:BCL was found to be a robust biocatalyst. Various reaction conditions were optimized using response surface methodology (RSM) based on a four-factor-three-level Box–Behnken design. The optimal conditions were obtained at molar ratio of 1:2 of furfuryl alcohol to acyl donor, temperature 50°C with catalyst loading of 30mg in 3mL of non-aqueous media toluene. Under these conditions 99.98% yield was obtained in 3h. The Arrhenius plot showed that the activation energy for furfuryl acetate synthesis was 10.68kcal/mol. The kinetics of reaction was studied close to optimized conditions which obey order bi–bi model. Molecular docking study was carried out to understand the active site of BCL which is responsible for the reaction. It was observed that the reaction proceeds via acylation of the active serine of BCL and demonstrating strong hydrogen bond between the substrate and histidine site. The catalyst recyclability study was carried up to five cycles.

Optimization and Application of a HS-SPME-GC-MS Methodology for Quantification of Furanic Compounds in Espresso Coffee

A headspace solid-phase microextraction gas chromatography (GC)-mass spectrometry (MS) method previously optimized for analyses of volatiles in coffee was used for simultaneous quantification of major furanic compounds (2-furfural, furfuryl alcohol, 5-methylfurfural and furfuryl acetate) and furan, in espresso coffee prepared from hermetically closed capsules. High sensitivity was achieved with low limits of detection and limits of quantification. Good linearity was observed with correlation coefficients higher than 0.999. Recovery percentages were 102 % for furan, 99.7 % for 2-furfural, 98.0 % for furfuryl alcohol, 99.8 % for 5-methylfurfural and 99.9 % for furfuryl acetate. The method was applied to the analyses of espresso coffee from hermetically closed capsules. A total of 69 volatiles for Blend Roast and Blend Dark Roast samples, 64 volatiles for Arabica Dark Roast samples, 91 volatiles for Arabica Light Roast samples, 96 volatiles for Caramel coffee, 90 volatiles for Vanilla coffee and 92 volatiles for Almond coffee. In general, furanic compounds were the major chemical family, ketones, aldehydes, acids, pyrazines, pyrroles, alcohols, pyridines, aromatic compounds, hydrocarbons, and ethers were also detected. Total content of these furanic compounds varied from 105 to 199 μg ml−1. The optimized method proved to be a reliable methodology for quantification of major furanic compounds and furan present in different types of espresso coffee. Although relative percentage of peak area is a good method for discriminate volatiles in different coffee brews with closer composition, the quantification of furanic compounds is more accurate for understand the real intake amount.

Furans and other volatile compounds in ground roasted and espresso coffee using headspace solid-phase microextraction: Effect of roasting speed

The profile of major classes of furanic compounds, as well as other volatile compounds, was evaluated by headspace solid-phase microextraction GC/MS in Arabica ground coffee roasted at three speeds, and in their respective espresso coffees. A total of 113 and 105 volatile compounds were respectively identified in ground coffee and espresso coffee. They were clustered in the following chemical classes: furans, pyrroles, pyridines, pyrazines, ketones, hydrocarbons, aldehydes and others. Results from Principal Component Analysis (PCA) using the data of major volatile class as variables showed that the levels (expressed as relative percentage of total peak area) of furans and pyrroles were higher in espresso samples, whereas those of pyrazines and ketones were higher in ground samples. Slow roasting speed favoured pyridines formation, while medium and fast roasting speed favoured ketones formation. The most representative furanic compound in ground samples was furfuryl alcohol, followed by furfuryl acetate, 2-furfural, 2-methylfuran and 5-methylfurfural. In espresso samples, the levels of 2-methylfuran, 2-furfural, furfuryl formate, 5-methylfurfural and furfuryl acetate were largely increased while the proportion of furfuryl alcohol was strongly reduced in comparison to ground coffee. High roast speed increased formation of 2-furfural and 5-methyl furfural in espresso coffee.

Response Surface Methodology Guided Release of Two Acetate Volatiles From an Oil-in-Water Emulsion

Optimization of the volatile release of two commonly used flavor compounds (isoamyl acetate and furfuryl acetate) from a food emulsion model system was evaluated using response surface methodology (RSM). Twenty-seven random order settings were established using a central composite face-centered (CCF) experimental design. The main and combined effects of four independent variables—concentration of isoamyl acetate (50–90 ppm), furfuryl acetate (20–30 ppm), salt (NaCl; 0.1–2%), and pH (5–7)—on the responses were examined. The main objective of the present study was to determine the optimal concentration level of the four variables leading to optimal release of the volatile compounds. Quantitative measurements were conducted using solid-phase microextraction (SPME) coupled with gas chromatography–mass spectrometry (GC-MS). Salt concentration and isoamyl acetate concentration were found to have significant positive effects (p ≤ 0.001) on the release of isoamyl acetate. The optimization procedure indicated that the optimal conditions leading to the desirable volatile release were isoamyl acetate 90 ppm, furfuryl acetate 30 ppm, salt 2% w/v, and pH 6.0176. The findings of this study can enable chefs and food manufacturers to optimize conditions for maximum flavor release from food emulsion products.

Hydroxymethyl-substituted furans: mutagenicity in Salmonella typhimurium strains engineered for expression of various human and rodent sulphotransferases

5-Hydroxymethylfurfural (HMF) and furfuryl alcohol (FFA) are present in numerous foodstuffs at high levels. FFA is also used for the production of polymers. Both compounds had demonstrated some evidence of carcinogenic activity in 2-year bioassays. We tested these compounds and four congeners for mutagenicity in Salmonella typhimurium TA100 and TA100-derived strains expressing human or rodent sulphotransferases (SULTs). 5-Hydroxymethylfuroic acid, a metabolite of HMF, was not mutagenic in any strain. 3-Hydroxymethylfuran was weakly mutagenic in all strains independently of SULT expression. HMF, 2,5-(bishydroxymethyl)furan (metabolite of HMF), FFA and 5-methyl-FFA were inactive in TA100 but strongly mutagenic when human SULT1C2 was expressed. This form has been detected in ovary, kidney and foetal tissues. Human SULT1A1, SULT1A2 and SULT1A3 as well as murine Sult1a1 and Sult1d1 also activated some hydroxymethyl-substituted furans to varying degrees. Whereas chemically synthesised 5-sulphooxymethylfurfural was mutagenic in TA100, furfuryl sulphate was bacteriotoxic, only leading to marginal increases in the number of revertants. Furfuryl acetate, an uncharged ester of FFA, used as fragrance and food flavouring, was clearly mutagenic. We determined half-life times of 120 min, 20 s and 10 h, respectively, for 5-sulphooxymethylfurfural, furfuryl sulphate and furfuryl acetate at 37°C in water. It is likely that the short lifespan of furfuryl sulphate, together with its charge, led to insufficient penetration of the bacteria when added externally, although it was mutagenic when generated by appropriate SULTs from FFA within the cell.

Reversible click chemistry at the service of macromolecular materials. Part 1: Kinetics of the Diels–Alder reaction applied to furan–maleimide model compounds and linear polymerizations

The model Diels–Alder reaction of furfuryl acetate with N-methylmaleimide and the linear polymerization of the corresponding difunctional monomers were followed by both UV and 1H NMR spectroscopy. The results obtained from this study provided clear-cut indications about the most appropriate conditions to be applied in the preparation of novel macromolecular materials based in part on renewable resources and possessing thermoreversible, mendable and recycling features, among other properties.

Synthesis of 5-Acetoxymethyl- and 5-Hydroxymethyl-2-vinyl-furan

5-Acetoxymethyl- and 5-hydroxymethyl-2-vinylfuran were synthesized by two routes. The first route starts from 2-methylfuran and the second from furfuryl acetate. The latter route, involving successive Vilsmeier-Haack and Wittig reactions, is suitable for producing 5-acetoxymethyl-2-vinylfuran and 5-hydroxymethyl-2 vinylfuran in 68% and 60%yields, respectively.

분석방법에 따른 시판 게향료의 휘발성 향기성분 비교

시판 수입 게향료 4종의 휘발성 향기성분을 SPME법과 LLCE법으로 비교 분석하였다. 동정된 86개의 휘발성 화합물 중 71개가 positive하게 동정되었으며, 이들은 함황화합물류 (13종), 알데히드류(3종), 케톤류(2종), 에스테르류(26종), 알콜류(5종), 방향족화합물류(3종), 테르펜류(8종), 산류(2종) 및 기타화합물류(9종)로 구성되었다. 인조 게향의 분석 및 동정에 있어서는 SPME법이 LLCE법에 비해 검출 감도가 매우 우수함을 알 수 있었고, 산류를 포함한 휘발성이 낮은 화합물들은 LLCE법에서만 검출되었다 제품 A-D의 특성에 따라 화합물의 조성에 차이가 있었으나 대체로 인조 게향에서는 함황 및 함질소화합물류 (dimethyl sulfide, dimethyl disulfide, depropyl disulfide, e(methylthio)propyl acetate, 3-(methylthio)propanal, 3-(methylthio)propanol, 2-methyl-3-(methylthio)pyrazine, 2-methyl-5-(methylthio)pyrazine)와 에스테르류 (styrallyl acetate, ethyl acetate, isoamyl acetate, benzyl acetate, ethyl pentanoate, butyl pentanoate, isoamyl pentanoate, furfuryl acetate) 등이 대표적인 물질로 추정되었다. Volatile flavor compounds in commercial crab-like flavorants were compared by mean of solid phase microextraction(SPME) and liquid continuous extraction (LLCE)/GC/MSD methods. A total of 86 volatile flavor compounds were detected. Of these, 71 were positively identified consisting mainly of sulfur-containing compounds (13), aldehydes (3), ketones (2), esters (26), alcohols (5), aromatic compounds (3), terpenes (8), acids (2) and miscellaneous compounds (9). SPME method was more effective than LLCE method in detection of volatile components in commercial crab-like flavorants. Eight S-, N-containing compounds such as dimethyl sulfide, dimethyl disulfide, dipropyl disulfide, 3-(methylthio)propyl acetate, 3-(methylthio) propanal, 3-(methylthio) propanol, 2-methyl-3-(methylthio) pyrazine and 2-methyl-5-(methylthio) pyrazine, 8 esters such as styrallyl acetate, ethyl acetate, isoamyl acetate, benzyl acetate, ethyl pentanoate, butyl pentanoate, isoamyl pentanoate and furfuryl acetate were considered as major components in crab-like flavorants.

7‐Oxanorbornane and Norbornane Mimics of a Distorted β‐D‐Mannopyranoside: Synthesis and Evaluation as β‐Mannosidase Inhibitors

AbstractThe racemic 7‐oxanorbornanyl and norbornanyl aminoalcohols 3, 4, 42, 45, and 46 were synthesized and tested as snail β‐mannosidase inhibitors. The amino tetraol 3 was obtained from the known sulfonyl acrylate 9 and furan 10. Esterification provided 11 that underwent an intramolecular Diels–Alder reaction to the 7‐oxanorbornene 12. Reduction of 12 to 13, desulfonylation, isopropylidenation, and cis‐dihydroxylation gave 16. A second isopropylidenation to 17, followed by debenzylation and a Mitsunobu–Gabriel reaction provided 19 that was deprotected via 20 to 3. Diels–Alder cycloaddition of furfuryl acetate and maleic anhydride to 21, followed by alcoholysis of the anhydride, cis‐dihydroxylation, isopropylidenation, and Barton decarboxylation gave the ester 25. Deacetylation to 26 and a Mitsunobu–Gabriel reaction led to 27 that was transformed into the N‐Boc analogue 29, reduced to the alcohol 30, and deprotected to 4. The 1‐aminonorbornane 5 was obtained from Thiele's Acid 31. Diels–Alder cycloaddition of the cyclopentadiene obtained by thermolysis of the diester 32, methanolysis of the resulting anhydride 33, dihydroxylation, isopropylidenation, Barton decarboxylation, and Curtius degradation led to the benzyl carbamate 39 that was reduced to the alcohol 40, transformed into the N‐Boc carbamate 41, and deprotected to 5. The alcohol 40 was also transformed into the benzylamine 42, aniline 45, and hydroxylamine 46. Snail β‐mannosidase was hardly inhibited by 3, 4, 42, 45, and 46. Only the amino triol 5 proved a stronger inhibitor. The inhibition by 5 depends on the pH value (at pH 3.5: Ki = 1900 μM; at pH 4.5: Ki = 340 μm; at pH 5.5: Ki = 110 μm). The results illustrate the strong dependence of the inhibition by bicyclic mimics upon the precise geometry and orientation of the amino group as determined by the scaffold. It is in keeping with the hypothesis that the reactive conformation imposed by snail β‐mannosidase is close to a 1,4B/1S3.

Furfuryl ethyl ether: important aging flavor and a new marker for the storage conditions of beer.

Recently, it was reported that furfuryl ethyl ether is an important flavor compound indicative of beer storage and aging conditions. A study of the reaction mechanism indicates that furfuryl ethyl ether is most likely formed by protonation of furfuryl alcohol or furfuryl acetate followed by S(N)2-substitution of the leaving group by the nucleophilic ethanol. For the reaction in beer, a pseudo-first-order reaction kinetics was derived. A close correlation was found between the values predicted by the kinetic model and the actual furfuryl ethyl ether concentration evolution during storage of beer. Furthermore, 10 commercial beers of different types, aged during 4 years in natural conditions, were analyzed, and it was found that the furfuryl ethyl ether flavor threshold was largely exceeded in each type of beer. In these natural aging conditions, lower pH, darker color, and higher alcohol content were factors that enhanced furfuryl ethyl ether formation. On the other hand, sulfite clearly reduced furfuryl ethyl ether formation. All results show that the furfuryl ethyl ether concentration is an excellent time-temperature integrator for beer storage.