10551-58-3

Usage

Uses

Used in the Vinegar Industry:
5-Acetoxymethyl-2-furaldehyde is used as a flavor enhancer for reducing the off-taste of vinegar, providing a more pleasant and balanced taste to the final product.
Used in the Food and Beverage Industry:
5-Acetoxymethyl-2-furaldehyde is used as a sweet modulator to improve the taste and aroma of various food and beverage products, particularly those that utilize traditional balsamic vinegar of Modena as an ingredient. Its ability to enhance sweetness can contribute to a more enjoyable consumer experience.

InChI:InChI=1/C8H8O4/c1-6(10)11-5-8-3-2-7(4-9)12-8/h2-4H,5H2,1H3

Upstream product

• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 108-24-7 acetic anhydride 
• 39131-44-7 5-bromomethyl-furan-2-carbaldehyde 
• 563-63-3 silver(I) acetate 
• 68-12-2 N,N-dimethyl-formamide 
• 57471-93-9 2,1':4,6-di-O-isopropylidenesucrose tetraacetate 
• 57-50-1 Sucrose 
• 67-63-0 isopropyl alcohol 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 
• 14125-78-1 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-lyxo-hex-1-enitol 
• 64-19-7 acetic acid 
• 17460-45-6 tetra-acetyl glucosamine 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 623-17-6 furfurylacetate 

Downstream Products

• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 106-68-3 3-octanone 
• 1883-75-6 2,5-bis-(hydroxymethyl)furan 
• 104-80-3 tetrahydrofuran-2,5-dimethanol 
• 3238-40-2 furan-2,5-dicarboxylic acid 
• 6126-49-4 tetrahydro-5-methyl-2-furanmethanol 
• 90345-66-7 5-(acetoxymethyl)-furan-2-carboxylic acid 
• 6338-41-6 5-hydroxymethyl-furan-2-carboxylic acid 

Relevant academic research and scientific papers

Trienamines derived from 5-substituted furfurals: Remote ε-functionalization of 2,4-dienals

The selective ε-functionalization of 5-substituted furfurals via trienamine intermediates is reported herein. This methodology was successfully applied to several 5-substituted furfurals with different amines via formation of a trienamine through the furan ring. The rationalized reaction mechanism involves the addition of the trienamine intermediate to its corresponding iminium-ion producing new furan-containing scaffolds.

Structural identification of nonvolatile dimerization products of glucosamine by gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and nuclear magnetic resonance analysis

The degradation profile of glucosamine bulk form stressed at 100 °C for 2 h in an aqueous solution was studied. Column chromatography of acetylated product mixture led to isolation of two pure compounds (1 b and 2b) and a mixture of at least three isomers (3b). 1 a and 2a were identified as 5-(hydroxymethyl)-2-furaldehyde (5-HMF) and 2-(tetrahydroxybutyl)-5-(3′ ,4′-dihydroxy-1′-trans-butenyl)-pyrazine, respectively, by utilizing a variety of analytical techniques, such as GC-MS, LC-MS, on-line UV spectrum, 1H and 13C NMR, and DEPT, as well as 1H-1H COSY. 3a was identified as 2-(tetrahydroxybutyl)-5-(2′,3′,4′-trihydroxybutyl)pyrazine, commonly known as deoxyfructosazine. In addition, glucosamine solid dosage form was exposed to 40 °C/75% relative humility for 10 weeks. Methanol extract of glucosamine solid dosage form was analyzed after acetylation by LC-MS, resulting in degradants 3b and 4b. 3a and 4a were, therefore, determined as deoxyfructosazine and 2,5-bis-(tetrahydroxybutyl)pyrazine (fructosazine), respectively. Furthermore, the mechanisms of formation of identified degradation products are proposed and briefly discussed.

Selective oxidation of 5-Hydroxymethylfurfural to 2,5-Diformylfuran by polymer-supported IBX amide

5-Hydroxymethyl-2-furfural (HMF) was selectively converted to 2,5-diformylfuran (DFF) under mild conditions by polymer-supported IBX amide reagent, thus providing a new platform for the production of highly valuable chemicals from biomass. Georg Thieme Verlag Stuttgart New York.

Design, Synthesis, and Biological Evaluation of Ester and Ether Derivatives of Antisickling Agent 5-HMF for the Treatment of Sickle Cell Disease

Candidate drugs to counter intracellular polymerization of deoxygenated sickle hemoglobin (Hb S) continue to represent a promising approach to mitigating the primary cause of the pathophysiology associated with sickle cell disease (SCD). One such compound is the naturally occurring antisickling agent, 5-hydroxymethyl-2-furfural (5-HMF), which has been studied in the clinic for the treatment of SCD. As part of our efforts to develop novel efficacious drugs with improved pharmacologic properties, we structurally modified 5-HMF into 12 ether and ester derivatives. The choice of 5-HMF as a pharmacophore was influenced by a combination of its demonstrated attractive hemoglobin modifying and antisickling properties, well-known safety profiles, and its reported nontoxic major metabolites. The derivatives were investigated for their time- and/or dose-dependent effects on important antisickling parameters, such as modification of hemoglobin, corresponding changes in oxygen affinity, and inhibition of red blood cell sickling. The novel test compounds bound and modified Hb and concomitantly increased the protein affinity for oxygen. Five of the derivatives exhibited 1.5- to 4.0-fold higher antisickling effects than 5-HMF. The binding mode of the compounds with Hb was confirmed by X-ray crystallography and, in part, helps explain their observed biochemical properties. Our findings, in addition to the potential therapeutic application, provide valuable insights and potential guidance for further modifications of these (and similar) compounds to enhance their pharmacologic properties.

Lipase-catalyzed (Trans)esterification of 5-hydroxymethylfurfural and separation from HMF esters using deep-eutectic solvents

5-Hydroxymethylfurfural (HMF) is a valuable biomass-derived building block. Among possible HMF valorization products, a broad range of HMF esters can be synthesized. These HMF esters have found some promising applications, such as monomers, fuels, additives, surfactants, and fungicides, and thus several catalytic approaches for HMF (trans)esterifications have been reported. The intrinsic reactivity of HMF is challenging, forcing the use of mild reaction conditions to avoid by-product formation. This paper explores the lipase-catalyzed (trans)esterification of HMF with different acyl donors (carboxylic acids and methyl- and ethyl esters) mostly in solvent-free conditions. The results demonstrate that lipases may be promising alternatives for the synthesis of HMF esters - with high productivities and reactions at high substrate loadings - provided that robust systems for lipase immobilization are applied to assure an adequate reusability of the enzymes. Once (trans)esterifications have been conducted, the separation of unreacted HMF and HMF esters is performed by using deep-eutectic solvents (DES) as separation agents. DES are able to dissolve hydrogenbond donors (e.g., HMF), whereas non-hydrogen-bond donors (in this case HMF esters) form a second phase. By using this approach, high ester purities (>99%) and efficiencies (up to >90% HMF ester recovery) in separations were obtained by using choline chloride-based DES.

Cellulose acetate as a convenient intermediate for the preparation of 5-acetoxymethylfurfural from biomass

5-Acetoxymethylfurfural (AMF) is an important biomass derived platform chemical related to 5-hydroxymethylfurfural. Such furanic compounds can be produced via the hydrolysis of cellulose followed by dehydration of the resulting glucose units. However, the integration of these reactions in a single process remains technically challenging, and the direct use of monosaccharides is often preferred. In this work we report a new method for the synthesis of AMF based on the acetolysis of cellulose acetate in the presence of sulfuric acid. The strategy was optimized for both batch and continuous processing. Furthermore, cellulose acetate prepared by direct wood acetylation could be successfully applied as a precursor, proving the method as a robust solution for integrated biomass processing.

Transesterifications and peracid-assisted oxidations in aqueous media catalyzed by Mycobacterium smegmatis acyl transferase

Hydrolases catalyze synthetic reactions in nonaqueous media, whereas they perform hydrolysis under aqueous solutions. An acyl transferase from Mycobacterium smegmatis (MsAcT) is able to catalyze synthetic reactions in buffer because of its highly hydrophobic active site, which enables efficient transesterification reactions even at 99.9 % v/v buffer solution. This unique feature of MsAcT among hydrolases may open new opportunities to conduct synthetic (bio)catalysis in aqueous media. With these goals in mind, this paper explores some evidence of such potential: MsAcT can perform enantioselective transesterifications (e.g., (S)-2-octanol), which could be combined with other aqueous multistep (asymmetric) reactions; 5-hydroxymethylfurfural (HMF) can be esterified to produce more hydrophobic and easily extractable HMF esters (e.g., for downstream processing or wastewater treatment); and upon addition of dilute H2O2, MsAcT works efficiently as a perhydrolase to form in situ peracids - in bulk water - that can be used for oxidations (e.g., furfural to furoic acid oxidation). Overall, these and many other new applications can be envisaged by using MsAcT in aqueous solutions. Challenging thermodynamics? As a result of its highly hydrophobic active site, an acyl transferase from Mycobacterium smegmatis catalyzes synthetic reactions in buffer in which other hydrolases could only conduct hydrolysis. Among several options, opportunities for downstream processing, enantioselective (multistep) aqueous syntheses, and peracid-mediated epoxidations and oxidations are envisaged. Copyright

From lignocellulosic biomass to furans via 5-acetoxymethylfurfural as an alternative to 5-hydroxymethylfurfural

A facile pathway to furan derivatives from lignocellulosic biomass via 5-acetoxymethylfurfural (AMF) was developed. AMF possesses advantageous properties due to its less-hydrophilic acetoxymethyl group relative to the hydroxymethyl group of 5-hydroxymethylfurfural (HMF). The hydrophobicity and chemical stability of AMF allowed practical isolation and purification to afford a highly pure product of up to 99.9 %. AMF was produced in good to excellent yields under mild conditions from 5-chloromethylfurfural (CMF) and alkylammonium acetates, both of which could be obtained directly from lignocellulosic biomass. Heterogeneous reactions with polymer-supported alkylammonium acetates were also established; this showed the feasibility of a continuous process for this pathway. AMF could be transformed into various promising furanic compounds, such as 2,5-furandicarboxylic acid (FDCA), 2,5-furandimethanol (FDM), and 5-hydroxymethyl-2-furanoic acid (HFA), in high yields.

Silica-supported boric acid assisted conversion of mono- and poly-saccharides to 5-hydroxymethylfurfural in ionic liquid

Silica-supported boric acid has been prepared and applied as heterogeneous catalyst for the direct conversion of inexpensive and biorenewable mono- and polysaccharides to 5-hydroxymethylfurfural (HMF) in ionic liquid under much milder conditions. Fructose, glucose, sucrose, inulin, and cellulose were successfully converted to HMF with moderate to excellent conversion. The catalyst and the solvent system can be recycled for up to four consecutive cycles without a significant loss in conversion. This journal is the Partner Organisations 2014.

Diversified upgrading of HMF via acetylation, aldol condensation, carboxymethylation, vinylation and reductive amination reactions

Multiple sustainable methodologies were developed for the chemical upgrading of HMF: i) at 30–90 °C, highly selective base-catalyzed acetylation and carboxymethylation reactions of HMF with nontoxic reagents as isopropenyl acetate (iPAc) and dimethyl carbonate (DMC) were achieved to prepare the corresponding ester and carbonate products, (5-formylfuran-2-yl)methyl acetate (5-formylfuran-2-yl) methyl carbonate, respectively; ii) based on the combined use of iPAc/DMC with acetone, a tandem protocol of acetylation/transcarbonation and aldol condensation was designed to synthesize a variety of HMF-derived α,β-unsaturated carbonyl compounds; iii) in water as a solvent, a chemoselective Pd-catalysed reductive amination of HMF with amino-alcohols also including glycerol derivatives, was developed using H2 at atmospheric pressure; iv) finally, both HMF and its ester and carbonate products successfully underwent Wittig vinylation reactions promoted by a methyl carbonate phosphonium salt ( [Ph3PCH3] [CH3OCO2]), to obtain the corresponding olefins. The vinylation reagent (the salt) was a DMC derivative. In all cases i-iv), not only processes occurred under mild conditions, but post-reaction procedures (work-up and purification) were optimized to isolate final products in high yields of 85–98%.