Furfuryl Acetate Research Articles

Characterization and perceptual interaction of key aroma compounds in Rosa roxburghii Tratt by sensomics approach

Rosa roxburghii Tratt (RRT) is esteemed for its unique aroma and nutritional value. Analyzing RRT juice samples from four elevations using GC–MS and GC-O, 99 volatile compounds were identified with 37 exhibiting aroma activity. 29 compounds including aldehydes, alcohols, and terpenes, were key contributors to RRT's aroma, based on high OAVs. Aroma recombination and omission tests confirmed 18 key aroma compounds in RRT while 2,5-Dimethyl-4-methoxy-3(2H)-furanone, hexanal, furfuryl acetate, furaneol acetate, and benzaldehyde as critical aroma compounds. The σ-τ graph revealed additive interactions among primary aroma compounds, indicating synergistic effects on RRT's overall aroma profile. Longli produced the most fragrant RRT at the lowest elevation of the four producing areas.

Analysis of volatile compounds, α-dicarbonyl compounds, and acetic acid in Robusta coffee by soaking with D-xylose and D-ribose

BackgroundThe study investigated the impact of D-xylose and D-ribose soaking methods (autoclaved and non-autoclaved) on Robusta coffee's volatile compounds, α-dicarbonyl compounds (α-DCs), and acetic acid. Robusta coffees were soaked with D-xylose and D-ribose solutions, and the beans were dried until constant moisture content and lightly roasted.ResultsThe sugar treatment led to an 85.6% reduction in pyrazine levels and a 64.4% decrease in pyridine, while pyrroles and furans increased significantly by 84.4% and 16.4%, respectively (p < 0.05). The total concentration of α-DCs was decreased by 24.6–69.2%, with the autoclaved D-xylose sample exhibiting the lowest among all samples. Acetic acid concentration was lower in non-autoclaved samples compared to autoclaved samples (p < 0.05). Principal component analysis indicated autoclave-treated pentose pretreatment reduced pyrazines and increased in the levels of 1-furfurylpyrrole, methyl furfuryl disulfide, 4-ethyl-2-methoxy-phenol, 2-methoxyphenol, 2-acetylpyrrole, pyridine, furfuryl acetate, and acetic acid.ConclusionThis study, utilizing GC–MS, GC–NPD, and HPLC–UV for compound quantification, offers valuable insights into the changes of volatiles, α-DCs, and acetic acid in Robusta coffee soaking with D-xylose and D-ribose, suggesting potential applications in the coffee industry to modulate flavor profiles.Graphical

Assessing the influence of spontaneous fermentation on consumer emotional responses to roasted arabica coffee in a biometric approach

Beyond sensory quality, food-evoked emotions play a crucial role in consumers acceptance and willingness to try, which are essential for product development. The link between fermented coffee sensory characteristics and elicited emotional responses from consumers is underexplored. This study aimed to evaluate consumers’ acceptability of spontaneously fermented and unfermented roasted coffee through self-reported sensory evaluation and biometrics assessment. Self-reported liking in 15-cm non-structured scale, multiple choice of negative, neutral, and positive emojis, and subconscious emotional responses from 85 regular coffee consumers were analysed. Their relationship with the pattern of volatile aromatic compounds were also investigated. Fermented (F) and unfermented (UF) coffee beans with light- (L), dark- (D), and commercial dark (C) roasting levels were brewed and evaluated along with gas chromatography-mass spectrometry measurement. Multivariate data analysis was conducted to explore the inner relationships among volatile compounds, self-reported liking, and biometrics. Unfermented-dark roasted coffee (UFD) had highest overall consumer liking response ± standard error (8.68 ± 0.40), followed by the fermented-dark roasted (FD) at 7.73 ± 0.43 with no significant differences (p > 0.05). Fermented light-roasted coffee was associated with lower liking scores and negative emotional responses. In contrast, dark roasted coffee, which was linked to positive emojis and emotional responses, exhibited less detected peak area of volatile compounds contributing fruity and vegetative aromas, such as benzaldehyde, furfuryl acetate, 2-acetyl-1-methyl pyrrole, and isovaleric acid, potentially as negative drivers of consumer liking. Findings from this study could guide coffee manufacturers in developing specialty coffee if spontaneous fermentation is offered.

Systematic establishment of the relationship between skin absorption and toxicity of furanoids via in silico, in vitro, and in vivo assessments

Furanoids are a class of contaminants prevalent in both airborne and occupational environments, with potential health implications through inhalation, oral ingestion, and skin penetration. Given their diminutive molecular size, there is a presumption that furanoids can readily permeate the skin. To systematically explore this presumption, we investigated the skin absorption and toxicity of a series of furans (furfuryl alcohol, furfuryl acetate, furfural, methyl 2-furoate, and 5-methylfurfural) using in silico, in vitro, and in vivo models. The in vitro permeation test (IVPT) from neat and aqueous suspension (5 mM) of furans demonstrated a facile absorption through pig and nude mouse skins. The lipophilicity of furans significantly influenced skin deposition, with higher lipophilicity displaying greater deposition. However, an opposing trend emerged in the receptor compartment accumulation. In barrier-defective skin simulating atopic dermatitis (AD) and psoriasis, enhanced deposition occurred with more hydrophilic furans but not with the more lipophilic ones. In the cell-based study, furanoids induced the proliferation of keratinocytes and skin fibroblasts except for the compounds with the aldehyde group (furfural and 5-methylfurfural). Both furfuryl acetate and 5-methylfurfural activated keratinocytes via the overexpression of COX-2 and PGE2 by 1.5‒2-fold. This stimulation involved the mitogen-activated protein kinase (MAPK) signaling pathway. For the in vivo mouse skin treatment, we selected furfuryl acetate (hydrophilic) and 5-methylfurfural (lipophilic). Both furans showed different patterns of skin lesions, where repeated application of furfuryl acetate caused epidermal hyperplasia and scaling, while 5-methylfurfural predominantly evoked skin inflammation and barrier disintegration. Toxicokinetics analysis revealed a higher plasma concentration of topically applied furfuryl acetate than that of the 5-methylfurfural (5.04 versus 2.34 nmol/ml), resulting in the mild injury of furfuryl acetate-treated peripheral organs. Conversely, no notable adverse effects on organs were observed for the 5-methylfurfural. This study established the relationship between cutaneous absorption and the toxicity of furans following skin exposure.

Palladium-Catalyzed Cross-Coupling Reaction via C–H Activation of Furanyl and Thiofuranyl Substrates

The present study explores the potential of four NHC-palladium(II) complexes derived from (Z)- or (E)-styryl-N-alkylbenzimidazolium salts, namely trans-dichloro-[(Z)-1-styryl- 3-benzyl-benzimidazol-2-yliden]pyridine palladium(II) (6), trans-dichloro-[(E)-1-styryl-3-benzyl- benzimidazol-2-yliden]pyridine palladium(II) (7), trans-dichloro-[(Z)-1-styryl-3-(3-fluorobenzyl)- benzimidazol-2-yliden]pyridine palladium(II) (8) and trans-dichloro-[(E)-1-styryl-3- (3-fluorobenzyl)-benzimidazol-2-yliden]pyridine palladium(II) (9), to be use as pre-catalysts for the cross-coupling reactions between furanyl or thiofuranyl derivatives and arylbromides via the C–H activation of the heterocycles. The structures of the four Pd(II) complexes have been elucidated through the use of multinuclear NMR, FT-IR and mass spectroscopy. Furthermore, the cis or trans conformation of the styryl substituents and the geometry of two different compounds was substantiated by single-crystal X-ray diffraction, which was carried out on organometallic species 6, 8 and 9. After the optimization of catalytic conditions, which was carried out with 1 mol% of pre-catalyst with KOAc as a base in dimethylacetamide at 120 °C for 3 h, complex 6 proved to be the most effective pre-catalyst agent, with full or quasi full conversions being observed in the cross-coupling of 4-bromoacetophenone with 2-butylfuran, 1-(2-furanyl)-ethanone, furfuryl acetate, furfural, 1-(2-thienyl)-ethanone, thenaldehyde and 2-methylthiophene.

N-alkylbenzimidazolepalladium(II) complexes: Synthesis and their catalytic activities in direct C-H functionalization of pyrrole, furan and 2-acetylthiophene

Herein, we reported the synthesis of six new palladium complexes (2a-2f) containing benzimidazole core and examined their catalytic activities in the direct arylation of heteroaromatic species with aryl bromides. For this purpose, a new series of palladium(II) complexes bearing N-coordinated benzimidazole complexes have been synthesized and fully characterized by elemental analysis, FT-IR, 1H NMR and 13C NMR spectroscopies. Additionally, the structures of the complexes 2a-2e have been characterized by X-ray crystallography. Further, direct arylation reactions, using KOAc as base and DMAc as solvent under inert conditions, were carried out with the synthesized complexes in the presence of various aryl bromides, and 1-methylpyrrole-2-carboxaldehyde, furfuryl acetate, 2-acetylfuran and 2-acetylthiophene. Moreover, moderate to high yields were obtained in the direct arylation of heteroarenes and aryl bromides under 1 % mol catalyst loading conditions.

Profiling flavor characteristics of cold brew coffee with GC-MS, electronic nose and tongue: effect of roasting degrees and freeze-drying.

Roasting is an important process in the formation of coffee flavor characteristics, which determines the quality of coffee and consumer acceptance. However, the influence of roasting degree on the flavor characteristics of cold brew coffee has not been fully described. In the present study, the flavor characteristics of cold brew coffee with different roasting degrees were compared in detail by using chromatographic and electronic sensory approaches, and the flavor changes induced by freeze-drying were investigated. Pyrazine and heterocyclic compounds were the main aroma compounds in coffee, and gradually dominated with the increase of roasting. Pyridine was consistently present in cold brew coffees of different roasting degrees and showed significant gradient of quantity accumulation. Aroma compounds such as pyrazine, linalool and furfuryl acetate were the main contributors to coffee roasting, floral and fruity flavor. Freeze-drying preserved the fruity and floral aromas of medium-roasted cold brew coffee, whereas reducing the bitterness, astringency and acidity properties that are off-putting to consumers. The higher consumer acceptance and enjoyment in medium roast cold brew coffee may be related to its stronger floral and fruity aroma. The aroma profile qualities of freeze-drying processed medium roasted cold brewed coffee were more dominant and more suitable for freeze-drying processing than medium dark roasting. Application of freeze-drying for cold brew coffee will promote the convenience of drinking. The present study provides valuable technical guidance in improving the flavor and quality of cold brew coffee, and also promotes its commercialization process. © 2024 Society of Chemical Industry.

Characterization of yeast mutant strains for starter culture in Arabica coffee fermentation

Arabica coffee is the most popular and best-selling type of coffee. During coffee fermentation, microorganisms are essential for the production of metabolites and volatile compounds that affect coffee flavor quality. This work aimed to study the mutation, selection, and characterization of the Wickerhamomyces anomalus strain YWP1-3 as a starter culture to enhance the flavor quality of Arabica coffee. The results revealed that six mutants could produce relatively high levels of the pectinase enzyme on pectin agar media and exhibited high activity levels, ranging from 332.35 to 415.88 U/ml in mucilage broth. Strains UV22-2, UV22-3, UV41-1 and UV32-1 displayed higher levels of amylase activity than did the wild type. The UV22-2 and UV22-3 mutants exhibited the highest pectin degradation indices of 49.22% and 45.97%, respectively, and displayed significantly enhanced growth rates in nitrogen yeast base media supplemented with various sugars; thus, these mutants were evaluated for their ability to serve as a starter for fermentation of Arabica coffee. The cupping scores of coffees derived from UV22-2 and UV22-3 were 83.5 ± 1.5 and 82.0 ± 2.14, respectively. The volatile compounds in the roasted coffee fermented by UV22-2 were analyzed by GC‒MS, which revealed higher levels of furfuryl alcohol and furfuryl acetate than did the other samples. These findings suggested that UV22-2 could be an influential starter culture for Arabica coffee fermentation.

Influence of maturation and roasting on the quality and chemical composition of new conilon coffee cultivar by chemometrics

Coffee is one of the most consumed beverages worldwide. Espírito Santo is the largest Brazilian producer of conilon coffee, and invested in the creation of new cultivars, such as “Conquista ES8152”, launched in 2019. Therefore, the present study aimed to evaluate the effects of maturation and roasting on the chemical and sensorial composition of the new conilon coffee cultivar “Conquista ES8152”. The coffee was harvested containing 3 different percentages of ripe fruits: 60%, 80%, and 100%, and roasted at 3 different degrees of roasting: light, medium, and dark, to evaluate the moisture and ash content, yield of soluble extract, volatile compound profile, chlorogenic acid and caffeine content, and sensory profile. “Conquista ES8152” coffee has a moisture content between 1.38 and 2.62%; ash between 4.34 and 4.72%; and yield between 30.7 and 35.8%. Sensory scores ranged between 75 and 80 and the majority of volatile compounds belong to the pyrazine, phenol, furan, and pyrrole groups. The content of total chlorogenic acids was drastically reduced by roasting, with values between 2.40 and 9.33%, with 3-caffeoylquinic acid being the majority. Caffeine was not influenced by either maturation or roasting, with values between 2.16 and 2.41%. The volatile compounds furfural, 5-methylfurfural, and 2-ethyl-5-methylpyrazine were positively correlated with the evaluated sensory attributes and 5-methylfurfural was the only one significantly correlated with all attributes. Ethylpyrazine, furfuryl acetate, 1-furfurylpyrrole, 4-ethyl-2-methoxyphenol, and difurfuryl ether were negatively correlated. The stripping did not affect the quality and composition of this new cultivar, however, the roasting caused changes in both the chemical and sensorial profiles, appropriately indicated by the principal component analysis.

Synthesis of palladium complexes containing benzimidazole core and their catalytic activities in direct C[sbnd]H functionalization of five-membered heterocyclic bioactive motifs

Herein, we reported the synthesis of nine new PEPPSI-Pd(II)–N-heterocyclic carbene (NHC) complexes 3a-h containing benzimidazole core and examined their catalytic activities in the direct arylation of heteroaromatic species with aryl bromides and arylchlorides. Nine new Pd benzimidazole complexes were synthesized and their structures were elucidated by 1H and 13C NMR spectroscopy, FT-IR spectroscopy, and elemental analysis methods. In the 13C NMR spectra, NCHN peaks of Pd(II) complexes were observed between 159.7–161.5 ppm. Further, direct arylation reaction, using KOAc as base and DMAc as solvent under inert conditions, were carried out with the synthesized complexes in the presence of various aryl bromides and chlorides, and 2-acetyl furan, and furfuryl acetate 2-acetylthiophene and N-methylpyrrole-2- carboxaldehyde. Moreover, moderate to hig yields were obtained in the direct arylation of heteroarenes and aryl bromides under 1 mol% catalyst loading at 150 °C for 2 h loading conditions. The results showed that electron-donating and electron-withdrawing substituents on the aryl halides might produce coupling products in good yields in the presence of complexes 2a-d. Taken together, our findings are expected to contribute to the synthesis and design of palladium complexes containing benzimidazole core structures.

Influence of baking conditions and formulation on furanic derivatives, 3-methylbutanal and hexanal and other quality characteristics of lab-made and commercial biscuits

Biscuit baking can cause the formation of heat-related toxic compounds, mainly through the Maillard reaction, including some volatile organic compounds (VOCs) that are potentially carcinogenic to humans.This study investigates the effects of different baking conditions and recipes on quality characteristics (moisture, water activity, colour, texture) and on the concentration of some VOCs (furfural, furfuryl acetate, 5-methylfurfural, furfuryl alcohol, 3-methylbutanal, hexanal) in biscuits. Specifically, lab-made biscuits baked under static and ventilated conditions and three commercial biscuit types categorised as shortbreads with eggs, with chocolate chips and dry petits were evaluated.Concerning the lab-made biscuits, the ventilated mode resulted in faster baking and a slightly lower concentration of investigated VOCs compared to the static mode. Besides the process conditions, the recipe also played a role in the final quality and target volatiles, whose concentrations were lower in dry petits than in shortbreads, which are characterised by higher sugar and fat contents.

Plausible PEPPSI catalysts for direct C-H functionalization of furans and pyrroles

The worth of bi(hetero)arenes in ongoing medicinal and industrial research fields promotes their efficient synthesis by Pd-PEPPSI-bearing NHC spectator ligands encapsulated as site-selective direct C-H functionalization agents. Eight new asymmetric N-heterocyclic carbenes ligands and their plausible pyridine-assisted Pd (II) complexes are reported in this work. The synthesized compounds were thoroughly characterized by respective spectroscopic techniques, such as 1H, 13C, FTIR and elemental analysis. The structures of synthesized pro-ligand salts and complexes were determined by Single Crystal XRD. The on/off mechanism of pyridine assisted Pd-NHC complexes made them the best C-H functionalized catalysts for regioselective C5 arylated products. Five membered heterocyclic compounds such as 2-acetyl furan, furfuryl acetate and 1-methyl-2-pyrrole-carboxylaldehyde were treated with numerous aryl bromides under optimal catalytic reaction conditions. Furfuryl acetate was used for the first time as a substrate in the present research work. Interestingly, all the prepared catalysts possessed essential structural features that facilitated the formation of desired coupled products in quantitative yield with excellent selectivity.

Optimization of Coffee Oil Extraction from Defective Beans Using a Supercritical Carbon Dioxide Technique: Its Effect on Volatile Aroma Components.

Defective green coffee beans are typically discarded due to their negative impacts on coffee qualities compared to normal beans. However, there are some types of defective beans that can cause volatile aroma compounds after roasting similar to those produced by normal beans. This study aimed to optimize conditions for coffee oil extraction by supercritical carbon dioxide using the response surface methodology (RSM). Furthermore, the investigation assessed the aroma-active compounds and sensory quality in extracted coffee oil. Thus, operational temperatures (33.2-66.8 °C), pressure (10-30 MPa) and ethanol (g) to roasted coffee (g) ratio (0.25:1-1.5:1) were optimized for coffee oil extraction. As a result, different oil yields with different key volatile aroma compounds concentrations were obtained and it was found that the optimum conditions for extraction were a temperature of 50 °C, pressure of 30 MPa, and ethanol (g) to roasted coffee (g) ratio of 1:1 to obtain 6.50% (w/w) coffee oil yield. Key volatile aroma compounds, including furfuryl alcohol, 5-methyl furfural, 2,5-dimethylpyrazine, 4-vinylguaiacol, furfuryl acetate, 3-ethyl-2,5-dimethylpyrazine, thiazole, 1-furfurylpyrrole, pyridine, 2,3-butanediol, and 3-methyl-1,2-cyclopentanedione which contributed to the most preferable burnt, sweet, bready, chocolate-like, and roasted flavors, were quantified. Overall, the results suggested that coffee oil extracted from defective beans could be potentially used as a flavoring agent.

The Impact of Wet Fermentation on Coffee Quality Traits and Volatile Compounds Using Digital Technologies

Fermentation is critical for developing coffee’s physicochemical properties. This study aimed to assess the differences in quality traits between fermented and unfermented coffee with four grinding sizes of coffee powder using multiple digital technologies. A total of N = 2 coffee treatments—(i) dry processing and (ii) wet fermentation—with grinding levels (250, 350, 550, and 750 µm) were analysed using near-infrared spectrometry (NIR), electronic nose (e-nose), and headspace/gas chromatography–mass spectrometry (HS-SPME-GC-MS) coupled with machine learning (ML) modelling. Most overtones detected by NIR were within the ranges of 1700–2000 nm and 2200–2396 nm, while the enhanced peak responses of fermented coffee were lower. The overall voltage of nine e-nose sensors obtained from fermented coffee (250 µm) was significantly higher. There were two ML classification models to classify processing and brewing methods using NIR (Model 1) and e-nose (Model 2) values as inputs that were highly accurate (93.9% and 91.2%, respectively). Highly precise ML regression Model 3 and Model 4 based on the same inputs for NIR (R = 0.96) and e-nose (R = 0.99) were developed, respectively, to assess 14 volatile aromatic compounds obtained by GC-MS. Fermented coffee showed higher 2-methylpyrazine (2.20 ng/mL) and furfuryl acetate (2.36 ng/mL) content, which induces a stronger fruity aroma. This proposed rapid, reliable, and low-cost method was shown to be effective in distinguishing coffee postharvest processing methods and evaluating their volatile compounds, which has the potential to be applied for coffee differentiation and quality assurance and control.

Measurement of the critical temperatures, pressures, heat capacities, and thermal diffusivities of four furanic compounds involved in the production of second-generation biofuels

The critical temperatures, critical pressures, heat capacities, and thermal diffusivities have been measured for furfural, furfuryl alcohol, furfuryl acetate, and tetrahydrofurfuryl alcohol, the compounds of industrial importance because they are involved in the production of biofuels. The critical properties have been measured using the pulse-heating method applicable to thermally unstable compounds. The relative combined expanded uncertainties with the 0.95 level of confidence are 0.01 and 0.03 for the critical temperature and pressure of furfural and furfuryl acetate and 0.015 and 0.04 for furfuryl alcohol and tetrahydrofurfuryl alcohol. The acentric factors of the compounds have been calculated based on the experimental data. The critical properties of the compounds have also been calculated by the group contribution methods of Wilson and Jasperson, Nannoolal et al. Marrero and Gani, Hukkerikar et al. in two variants. The Wilson and Jasperson and Nannoolal et al. techniques provide the best estimation of the critical temperature; for the critical pressure, the Nannoolal et al. method gives the best results. The heat capacities in the liquid phase have been measured at atmospheric pressure in the temperature range from 298.15 to 451.15 K by DSC technique with relative combined expanded uncertainty 0.03. The data obtained have been approximated by third-order polynomials. The experimental heat capacities have been compared with those calculated by the group-contribution method of Kolska et al. The thermal diffusivities have been measured by laser flash method at atmospheric pressure in the temperature range from 313.15 to 373.15 K with relative combined expanded uncertainty 0.05. The experimental data have been approximated by first-order polynomials. The thermal conductivities have been calculated using the experimental data obtained.

Changes of volatile substance composition during processing of nine-processed tangerine peel (Jiuzhi Chenpi) determined by gas chromatography-ion mobility spectrometry.

Nine-processed tangerine peel (Jiuzhi Chenpi in Chinese) is a famous Chinese traditional snack. The composition and contents of volatile substances during its processing is unclear. Gas chromatography combined with ion mobility spectrometry (GC-IMS) was applied to determine the characteristic changes of volatile components throughout the production process. Four stages such as untreated dry tangerine peel (raw material), debittered tangerine peel, pickled tangerine peel, and final product were examined. A total of 110 flavor compounds including terpenes, alcohols, aldehydes, ketones, esters, acids, and two others were successfully detected in tangerine peel samples across the various production stages. There were abundant amounts of terpenes contributing to the flavor, including limonene, gamma-terpinene, alpha-pinene, myrcene, beta-pinene, and alpha-thujene which were reduced at the later stage of production. Large amounts of esters and alcohols such as methyl acetate, furfuryl acetate, ethyl acetate, benzyl propionate, 2-hexanol, linalool, and isopulegol, were diminished at the early stage of processing, i.e., soaking for debittering. One the other hand, the final product contained increased amount of aldehydes and ketones including pentanal, hexanal, 2-hexenal, 2-heptenal (E), 2-pentenal (E), 1-penten-3-one, 6-methyl-5-hepten-2-one, 2-methyl-2-propenal, and 2-cyclohexen-1-one, and very high level of acetic acid. Present findings help to understand the formation of the unique flavor of nine-processed tangerine peel and provide a scientific basis for the optimization of processing methods and quality control.

Synergistic catalytic activity of core-shell Pd@UiO-66(Hf) MOF catalyst for the one-pot hydrogenation-esterification of furfural

The development of new strategies for cascade reactions that demand composite catalysts with multifunctionality is imperative to advance bio-oil upgradation and its combustion properties. This work reports a model bio-oil-upgrading method of one-pot hydrogenation-esterification (OHE) of furfural for selective synthesis of furfuryl acetate using a bifunctional Pd@UiO-66(Hf) core-shell material. Additionally, the catalytic activity of Pd/UiO-66(Hf) and Pd@UiO-66(Zr) materials were evaluated in the OHE reaction for comparison. Various properties of the screened catalysts were elucidated by different characterization techniques. The Pd@UiO-66(Hf) hybrid material demonstrated high catalytic performance in the OHE reaction of furfural with acetic acid. The superior activity of Pd@UiO-66(Hf) over the other MOF-based hybrid materials is correlated with its surface acidic properties and the synergistic effect of Pd NPs with the acidic sites (on SBU of MOF). The excellent performance exhibited by Pd@UiO-66(Hf) in OHE of furfural with acetic acid is superior to the reported catalysts. The present study offers new opportunities for the efficient conversion of biomass-derived molecules into value-added products. This is the first-ever report on MOF-based catalyst studied for the OHE reaction of furfural with acetic acid for the selective synthesis of furfuryl acetate.

Control of toxigenic Aspergillus spp. in dried figs by volatile organic compounds (VOCs) from antagonistic yeasts

Aspergillus flavus and Aspergillus niger are fungi which can contaminate dried figs before and after harvest and consequently produce aflatoxins (AFs) and ochratoxin A (OTA). Many approaches have been applied to minimise the growth of these filamentous fungi, mainly involving the use of synthetic fungicides which are limited due to their negative impact on human health and the environment. In this context, biocontrol is a recent approach that needs to be explored. This study evaluated the potential of three volatile organic compounds (VOCs), octanoic acid (OA), 2-phenylethyl acetate (2PEA) and furfuryl acetate (FA), produced by Hanseniaspora uvarum and Hanseniaspora opuntiae yeasts on the growth, germination, gene expression and production of AFs and OTA by A. flavus M144 and A. niger M185 on dried fig-based agar and the incidence rates in dried figs. Two of the three VOCs evaluated (2PEA and FA) effectively controlled A. flavus M144 and A. niger M185 by using at least amounts of 50 μL (715 μL/L in the headspace) for FA and 100 μL (1430 μL/L in the headspace) for 2PEA in dried figs. One of the mode of actions of both compounds consists in early repressing the expression of genes involved in the biosynthesis of AFs (aflR) and OTA (pks) of A. flavus and A. niger, respectively. The results of this study support the application of 2PEA and FA at the early post-harvest stages of dried figs to control mycotoxin accumulation.

Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation.

Hydroxymethylfurfural (HMF) derivatives such as 2,5-bis(hydroxymethyl)furan (BHMF) and furandicarboxylic acid (FDCA) are promising alternative of fossil-based diols and dicarboxylic acids for synthesis of polyesters such as polyethylene terephthalate (PET). However, high cost for preparing HMF from biomass discourages the commercialization of HMF-derived polyesters. Since producing furfural (FUR) from five-carbon sugars (e.g., xylose) via dehydration is an inexpensive and commercialized process, we herein reported a method to synthesize BHMF derivatives (5-(ethoxymethyl)furan-2-methanol (EMFM), 2,5-bis(hydroxymethyl)furan monoacetate (BHMFM) and 2,5-bis(hydroxymethyl)furan diacetate (BHMFD) from furfural derivatives, i.e., (2-(ethoxymethyl)furan (EMF) and furfuryl acetate (FA)). To avoid strong acid-induced side reactions (e.g., furan ring opening, condensation and carbonization), two reaction systems, i.e., a low-concentration HCl aqueous solution combined with formaldehyde and anhydrous acetic acid combined with paraformaldehyde, were found to be suitable for such a hydroxymethylation reaction and could lead to decent product yields. In order to improve the carbon utilization, condensed furanic byproducts were further converted into hydrocarbon fuels via a reported two-step hydrodeoxygenation (HDO) process. This study not only validates the possibility of synthesizing functional HMF derivatives (EMFM, BHMFM, and BHMFD) from commercially-available FUR derivatives (EMF and FA), but also provide a new way to transform condensed furanics to value-added hydrocarbon fuels.

Selective synthesis of furfuryl acetate over solid acid catalysts and active site exploration using density functional theory

Sulfated zirconia is reported to be an efficient catalyst to make furfuryl acetateviaesterification. This study is an integration of experimental and DFT that correlates the hydrogen removal energy with catalytic activity.