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Furfuryl acetate

(Synonyms: 乙酸糠醇酯) 目录号 : GC68048

Furfuryl acetate可用于 5-乙酰氧基甲基-2-呋喃和 5-羟甲基-2-呋喃的合成。

Furfuryl acetate Chemical Structure

Cas No.:623-17-6

规格 价格 库存 购买数量
10mg
¥405.00
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25mg
¥644.00
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50mg
¥900.00
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100mg
¥1,260.00
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500mg
¥2,520.00
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1g
¥3,528.00
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5g
¥7,056.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

Furfuryl acetate can be used in the synthesis of 5-acetoxymethyl-2-vinylfuran and 5-hydroxymethyl-2-vinylfuran[1].

[1]. Mehner A, et al. Synthesis of 5-acetoxymethyl- and 5-hydroxymethyl-2-vinyl-furan. Molecules. 2007 Mar 26;12(3):634-40.

Chemical Properties

Cas No. 623-17-6 SDF Download SDF
别名 乙酸糠醇酯
分子式 C7H8O3 分子量 140.14
溶解度 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 7.1357 mL 35.6786 mL 71.3572 mL
5 mM 1.4271 mL 7.1357 mL 14.2714 mL
10 mM 0.7136 mL 3.5679 mL 7.1357 mL
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Research Update

Synthesis of 5-Methylene-2-pyrrolones

Org Lett 2018 Aug 17;20(16):4885-4887.PMID:30063360DOI:10.1021/acs.orglett.8b02030.

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.

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

Enzyme Microb Technol 2016 Mar;84:1-10.PMID:26827768DOI:10.1016/j.enzmictec.2015.12.003.

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.

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

J Agric Food Chem 2004 Mar 24;52(6):1661-8.PMID:15030227DOI:10.1021/jf035412g.

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.

Production of Hydroxymethylfurfural Derivatives From Furfural Derivatives via Hydroxymethylation

Front Bioeng Biotechnol 2022 Feb 15;10:851668.PMID:35242752DOI:10.3389/fbioe.2022.851668.

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.

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

Int J Food Microbiol 2022 Sep 2;376:109772.PMID:35667262DOI:10.1016/j.ijfoodmicro.2022.109772.

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.