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5-hydroxymethylfurfural

5-Hydroxymethylfurfural (5-HMF) is a versatile platform chemical derived from the dehydration of hexose sugars, with applications in biofuels, polymers, and pharmaceuticals.
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Most cited protocols related to «5-hydroxymethylfurfural»

The phenolic compounds and furfurals were quantified by UHPLC following the method previously established by our research group [33 (link),34 (link)]. A Waters Acquity UPLC equipped with a PDA detector and an Acquity UPLC C18 BEH, 100 × 2.1 mm (i.d.) with 1.7 µm particle size (Waters Corporation, Milford, MA, USA) column was employed for the analysis. Nine phenolic compounds (gallic acid, ellagic acid, p-hydroxybenzaldehyde, vanillic acid, vanillin, syringic acid, syringaldehyde, sinapaldehyde, and coniferylaldehyde) and three furanic aldehydes (furfural, 5-methylfurfural, and 5-hydroxymethylfurfural) were identified.
The samples and standards were filtered through 0.22 µm nylon membranes, and they were injected in duplicate. The absorption was determined by UV scanning at between 250 and 400 nm, with a resolution of 1.2 nm. The linear standard curve ranges from 0.1 mg/L to 10 mg/L. The compounds were identified by comparing the retention times and UV-Vis spectra of the sample peaks against those previously obtained from the standards. The results were expressed in mg of compound per 100 mL of 100% vol. alcohol.
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Publication 2021
4-hydroxybenzaldehyde 5-hydroxymethylfurfural 5-methyl-2-furfural Aldehydes coniferaldehyde Ellagic Acid Ethanol Furaldehyde Gallic Acid Nylons Retention (Psychology) sinapaldehyde syringaldehyde syringic acid Tissue, Membrane Vanillic Acid vanillin
Milled samples (300 mg) were treated with 3 mL of a 12.0 M H2SO4 solution at room temperature for 2 h. Distilled water (40 mL) was then added to the slurry to achieve a 2.0 M H2SO4 final concentration, and the mixture was incubated for 3 h at 100 °C. Solid fraction was then recovered, thoroughly washed and oven dried at 105 °C to a constant weight (weight A). Finally, crucibles containing samples were calcinated in a muffle at 550 °C for 4 h. After cooling to room temperature inside a desiccator, the ash content was gravimetrically determined as well as the acid insoluble lignin content (AIL) by subtraction from A.
Acid soluble lignin was determined by absorbance measurements (280 nm) of the H2SO4 solution using a UV–Vis spectrophotometer (UV-2401PC, Shimadzu, Kyoto, Japan), and taking into account the interfering absorption of furfural and hydroxymethylfurfural [59 (link)].
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Publication 2017
5-hydroxymethylfurfural Acids Furaldehyde Lignin
Glucose in plasma and deproteinized fresh blood was measured with a glucose oxidase kit (Biosystems, Barcelona, Spain), supplemented with mutarotase (490 nkat/mL of reagent) (Calzyme, San Luis Obispo, CA, USA). Mutarotase was added to speed up epimerization equilibrium of α- and β-D-glucose and thus facilitate the oxidation of β-D-glucose by glucose oxidase (Miwa et al., 1972 (link)). The enzyme addition was complemented with a precise control of the time (15 min) and temperature (30 °C) conditions of development of the reaction, in order to make sure all glucose in the sample was oxidized to gluconate. Protein content was estimated with a variant of the Lowry method (Lowry et al., 1951 (link)) using fatty acid-free bovine serum albumin (Sigma, St Louis MO, USA) as standard.
RBC membranes were mineralized with perchloric acid (700 g/L) in 15 mL Teflon-stoppered glass tubes, in a dry block heater, at 150 °C for 24 h (Stein & Smith, 1982 ). Aliquots of the clear mineralized samples were used, after centrifugation, for the estimation of phosphate using the phosphomolybdate reaction using sodium mono-phosphate as standard (Gomori, 1942 ; Stein & Smith, 1982 ). A standard of phosphatidyl-choline (Sigma) was processed along with the samples. The measurements of phosphate from the phosphatidyl-choline standards proved that mineralization was complete (98–101%). Each batch of samples was corrected using their own standards, ran in parallel.
The degree of glycosylation was estimated by direct measurement of the 5-hydroxymethylfurfural (HMF) liberated by treatment of the samples with 1 N oxalic acid at 100 °C for 24 h (Gabbay et al., 1979 (link)) in 15 mL Teflon-stoppered tubes set in a dry heating block. After cooling, trichloroacetic acid was added (final concentration 100 g/L), and the tubes were shaken and centrifuged for 15 min at 5,000 × g. The precipitate was discarded. The amount of HMF released was measured through the condensation of HMF with 50 mM thiobarbituric acid (Sigma) (Gabbay et al., 1979 (link)). After 20 min at 37 °C for development of color, the OD was measured at 443 nm, using blanks and pure HMF (Sigma) standards, and was used to determine the HMF (i.e., unaltered glycosyl residues in proteins) in each sample.
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Publication 2015
5-hydroxymethylfurfural aldose 1-epimerase BLOOD Centrifugation Developmental Disabilities Enzymes Fatty Acids gluconate Glucose Oxalic Acids Oxidase, Glucose Perchloric Acid Phosphates Phosphatidylcholines phosphomolybdic acid Physiologic Calcification Plasma Protein Glycosylation Proteins Serum Albumin, Bovine sodium phosphate Specimen Handling Synapsin I Teflon thiobarbituric acid Tissue, Membrane Trichloroacetic Acid
Wheat straw, locally harvested in August 2013 and dried on field (Johan Håkansson Lantbruksprodukter, Lunnarp, Sweden), was chopped into pieces up to 50 mm long using a knife mill (Retsch GmbH, Haan, Germany). The dry matter (DM) content of the wheat straw was measured by drying the material in an oven at 105 °C until constant weight was obtained, and was found to be 90 %. The composition was determined using standardized analytical procedures from the National Renewable Energy Laboratory (NREL) [40 ], and is given in Table 1.

Composition of wheat straw expressed as percentage of dry matter (average and standard deviation of three measurements)

Ave. content (%)SD
Glucan29.31.2
Xylan21.61.9
Galactan0.30.0
Arabinan3.20.2
Mannan0.10.1
Lignina27.51.3

aAcid-soluble and -insoluble lignin and lignin ash are included

The wheat straw was soaked for 1 h in warm tap water with 1 % (by weight) acetic acid solution at room temperature in sealed buckets. The ratio between the wheat straw and the liquid was 1:20 by weight. After 1 h, the soaked material was dewatered to a DM content of 45–55 % (by weight) in a filter press (Tinkturenpressen HP5 M, Fischer Maschinen-fabrik GmbH, Burgkunstadt, Germany), and then stored at room temperature in sealed buckets overnight until pretreated. The impregnated material was steam pretreated in a steam pretreatment unit using a 10-L batch reactor described previously [8 (link)], at 190 °C for 10 min. The steam-pretreated slurry was thoroughly mixed and stored at 4 °C. The structural carbohydrates, lignin, and ash content in the water-insoluble solids and the sugars, by-products (acetic acid), and degradation products [furfural and HMF (5-hydroxymethyl-2-furaldehyde)] in the liquid fraction were determined using standardized NREL analytical procedures [40 , 41 ]. The total DM content was measured by drying the material in an oven at 105 °C until constant weight was obtained. The WIS content of the pretreated material was determined using the method developed by Weiss et al. [42 (link)]. The composition of the pretreated wheat straw is given in Table 2.

Composition of steam-pretreated wheat straw (average and SD of three measurements)

Ave. contentSD
DM (%)16.70.3
WIS (%)11.90.4
Content in solid fraction (% WIS)
 Glucan44.71.5
 Xylan11.90.8
 Lignina32.00.9
Content in liquid fraction (g/L)
 Glucoseb6.5 (1.0)0.0
 Xyloseb36.3 (9.9)0.1
 Acetic acid4.60.0
 Furfural1.50.0
 HMF0.20.0

aAcid-soluble and -insoluble lignin and lignin ash are included

bBoth monomeric and oligomeric forms are included; concentration of monomeric sugars are in parenthesis

Most of the pretreatment slurry was separated into a liquid and a solid fraction using a filter press. The rest of the slurry was used for batch SSCF experiments. The liquid fraction was then filtered using a vacuum filtration unit to remove the particles from the liquid. The particles were mixed with the solid fraction. The WIS content of the solid fraction was 40 %, and both the liquid and solid fractions were stored at 4 °C.
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Publication 2016
5-hydroxymethylfurfural Acetic Acid Carbohydrates Filtration Furaldehyde Lignin Steam Sugars Triticum aestivum Vacuum Vinegar
For hydrolysis by the enzyme of C. owensensis alone, each reaction system was prepared in 50 mM sodium acetate, pH 6.0 with the dry substrate of 2 % (w/v) and the enzyme loading of 15 mg protein per gram dry substrate. The reaction volume was 500 μl in a 2 ml Eppendorf tube, which was sealed by winding parafilm after closing the lip, and put in a water bath at 70 °C for 48 h.
For synergetic hydrolysis by the enzyme of C. owensensis and the commercial enzyme cocktail Cellic CTec2 (Novoyzmes), two trials were performed. One was that the lignocellulosic biomass (native corn stover or native corncob) was sequentially hydrolyzed (SH) by the enzyme of C. owensensis (the first step) and CTec2 (the second step). The first step was the same as described above (for hydrolysis by the enzyme of C. owensensis only). After 48 h hydrolysis by the enzyme of C. owensensis (the first step) the CTec2 and 500 μl of sodium acetate buffer, pH 5.0 were added, forming a reaction system of pH 5.0 with the dry substrate of 1 %, and then incubated in water bath at 50 °C for 72 h (the second step). The other was that the lignocellulosic biomass was co-hydrolyzed (CH) by the enzyme of C. owensensis and CTec2 in the sodium acetate buffer of pH 5.0 with the dry substrate of 1 % at 50 °C for 72 h. The loading rates of CTec2 (http://www.bioenergy.novozymes.com/) for synergetic hydrolysis were 30 mg/g glucan (high loading). These lignocellulosic biomasses were hydrolyzed by CTec2 alone in the sodium acetate buffer of pH 5.0 with the dry substrate of 1 % at 50 °C for 72 h as controls.
Reducing sugar assay was carried out by PHBAH method with xylose as the standard [51 (link), 52 (link)]. Glucose and xylose concentrations were measured on a HPLC system equipped with a Hi-Plex Ca column (7.7 × 300 mm, Agilent Technology, USA), LC-20AT pump (Shimadzu, Japan) and RID-10A refractive index detector (Shimadzu, Japan), using water at a flow rate of 0.6 ml/min as mobile phase. The amounts of released glucose and xylose were used for calculating glucan and xylan conversions, respectively. The furfural and 5-hydroxymethyl furfural (HMF) were analyzed by HPLC as described above. The phenolics in the hydrolysate were analyzed by ultraviolet spectra at 280 nm using p-hydroxy benzaldehyde as the standard.
The native corn stover morphologies before and after hydrolysis and after incubated in the acetate buffer (pH 6.0) at 70 °C for 48 h were examined by scanning electron microscopy (SEM). The specimens were mounted on stubs and sputter-coated with gold prior to imaging with a JEOL JSM-6700F scanning electron microscope using 5-kV accelerating voltage and 10-mm distance.
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Publication 2015
5-hydroxymethylfurfural Acetate Bath benzaldehyde Biological Assay Buffers Enzymes Furaldehyde Glucans Glucose Gold High-Performance Liquid Chromatographies Hydrolysis Maize Proteins Scanning Electron Microscopy Sodium Acetate Sugars Xylans Xylose

Most recents protocols related to «5-hydroxymethylfurfural»

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Publication 2023
5-hydroxymethylfurfural Acids Carbohydrates Centrifugation Glucose Hybrids Hydrochloric acid Phenol Polysaccharides Proteins Serum Albumin, Bovine Sugars Sulfuric Acids Technique, Dilution
Chloroauric acid (Strem
Chemicals, 99.8%); palladium chloride (Sigma-Aldrich, >99.9%);
poly(vinyl
alcohol) (Sigma-Aldrich, Mw 9000–10,000,
80% hydrolyzed); sodium borohydride (Sigma-Aldrich, 99.99%); 5-hydroxymethyl-2-furancarboxylic
acid (Carbosynth, >97.0%); distilled water millipore (18.2 MΩ·cm
at 25 °C); 5-hydroxymethylfurfural (Sigma-Aldrich, >99.0%);
5-formyl-2-furancarboxylic
acid (Fluorochem); 2,5-furandicarboxylic acid (Sigma-Aldrich, 97%);
molecular O2 (BOC, >99.95%); Nafion (Sigma-Aldrich,
5 wt
% in lower aliphatic alcohols and water, contains 15–20% water);
sodium hydrogen carbonate (Fisher Scientific, >99.5%); sodium hydroxide
(Fisher Scientific); Carbon Vulcan XC-72R (Cabot Corporation); ABTS
(2,2′-azinobis [3-ethylbenzothiazoline-6-sulfonic acid]-diammonium
salt) (Sigma-Aldrich, ≥98%); horseradish peroxidase (Sigma-Aldrich,
141.9 U/mg solid); hydrogen peroxide (Fisher Scientific, 30 wt %).
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Publication 2023
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 5-hydroxymethylfurfural Acids Alcohols Bicarbonate, Sodium Carbon gold tetrachloride, acid Horseradish Peroxidase Nafion palladium chloride Peroxide, Hydrogen Poly A sodium borohydride Sodium Hydroxide Sulfonic Acids
The as-prepared NiHC-pz-300 catalyst (12.5 mg) was dispersed in 968 μL absolute ethanol and 32 μL Nafion solution (5 wt%) accompanied by a continuous ultra-sonification to form a homogeneous catalyst ink. Then, 40 μL ink was pipetted onto the double sides of carbon paper, giving a catalyst loading of 1 mg cm−2. The catalyst with lower loadings was prepared by diluting the ink with ethanol. The electrochemical workstation (CHI 660E, Shanghai CH Instruments Co., China) was utilized for the electrochemical studies. The electrochemical measurements were carried out in a typical H-Type cell with three-electrode configuration, which consists of the as-prepared NiHC-pz-300 catalyst electrode as the working electrode, a platinum foil as the auxiliary electrode, and a Ag/AgCl (saturated KCl) as the reference electrode. All measured potentials were converted to the reversible hydrogen electrode (RHE) according to the following equation: E(RHE)=E(Ag/AgCl)+0.197+0.0591×pH
The electrochemical oxidation activity of 25 organic substrates (methanol, ethanol, 2,2,2-trifluoroethanol, benzyl alcohol, 2-propanol, 1,1,1-trifluoro-2-propanol, 1-phenylethanol, benzaldehyde, furfural, ethylene glycol, 1,4-butanediol, 1,6-hexanediol, ethylamine, 1-propylamine, 2,2,2-trifluoroethylamine, benzylamine, 2-propylamine, 1-phenylethylamine, cyclohexanol, cyclohexylamine, urea, glycerol, glucose, 5-hydroxymethylfurfural and 2-aminoethanol) were evaluated in 1 M KOH + 0.1 M substrate. The Linear sweep voltammetry (LSV) curves were scanned at a rate of 5 mV s−1 at room temperature after 5 cyclic voltammetry (CV) cycles at a scan rate of 50 mV s−1. All polarization curves were manually corrected with 90% iR-compensation. For obtaining accurate Tafel slope values, all Tafel plots were iR-corrected. Chronopotentiometric measurements were recorded at a current density of 20 mA cm−2. In order to reduce the impact on the stability of the catalyst due to the changes of substrate concentration, the electrolyte was refreshed every 12 h. Turnover frequencies (TOFs) were calculated from the following equation: TOF=InFc where I is the current density in the LSV curve (mA/mg), n is the number electrons needed for the oxidation of one urea molecule (n = 6 (N2) or 12 (NO2)), F is the Faraday constant of 96485 F/mol, c is the active Ni site density in the catalyst (mol/g).
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Publication 2023
1-phenylethanol 1-Propanol 2-propylamine 5-hydroxymethylfurfural benzaldehyde Benzyl Alcohol Benzylamines Butylene Glycols Carbon Cells Cyclohexanol Cyclohexylamines Electrolytes Electrons Ethanol Ethanolamine ethylamine Furaldehyde Glucose Glycerin Glycol, Ethylene Hydrogen Isopropyl Alcohol Methanol Nafion Phenethylamines Platinum Propylamines Radionuclide Imaging Trifluoroethanol trifluoroethylamine Urea
All reagents were used as received without further purification. Nickel chloride hexahydrate (NiCl2·6H2O), pyrazine, pyrimidine, 4,4-bipyridine, ethanol (≥ 99.7%), N,N-dimethylformamide, methanol, 2,2,2-trifluoroethanol, 2-phenylethanol, 1-propanol, 3-propanol, furfural, 1,4-butanediol, 1,6-hexanediol, ethylamine, 1-phenylethylamine, cyclohexanol, cyclohexylamine, 1-propylamine, 2-aminoethanol, urea, glycerol, glucose, 5-hydroxymethylfurfural (5-HMF), ethylene glycol and 1-hexanethiol were all purchased from Aladdin Industrial Corporation (China). Potassium hydroxide (KOH) was purchased from Sinopharm Chemical Reagent Co., Ltd. (China). 1,1,1-trifluoro-2-propanol, 1-phenylethanol, benzaldehyde and 2-propylamine were purchased from Innochem Alfa Acros (China). Methyl mercaptan was purchased from Macklin Biochemical Co., Ltd. (China). 2,2,2-trifluoroethylamine and benzylamine were purchased from Shanghai Titan Scientific Co., Ltd. (China). Ultrapure deionized water (18.2 MΩ·cm−1, 25 oC) was obtained from ELGA purification system (China). Anion exchange membrane was obtained from Fumatech (FAB-PK-130, Germany). Carbon fiber paper was purchased from Hesen Electric Co., Ltd. (HCP020N, China).
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Publication 2023
1-phenylethanol 1-Propanol 2-propylamine 5-hydroxymethylfurfural Anions benzaldehyde Benzylamines Butylene Glycols Carbon Fiber Cyclohexanol Cyclohexylamines Dimethylformamide Electricity Ethanol Ethanolamine ethylamine Furaldehyde Glucose Glycerin Glycol, Ethylene Methanol methylmercaptan nickel chloride hexahydrate Phenethylamines Phenylethyl Alcohol PK 130 potassium hydroxide Propylamines Pyrazines Pyrimidines Tissue, Membrane Trifluoroethanol trifluoroethylamine Urea
All reagents were analytically pure and were used immediately upon receipt. Glucose (99%), xylose (99%), tetrahydrofuran (99%), pyridine (99%), glutaraldehyde (50%), epichlorohydrin (98%), hexanediamine (99%), diphenylmethane diisocyanate (98%), and p-toluenesulfonic acid (99%) were purchased from Innochem (Shanghai, China). Dichloromethane (99%), lithium bromide (99%), furfural (99%), and phosphoric acid (75 wt%~80 wt%) were purchased from Aladdin® Chemicals (Shanghai, China); hydrochloric acid (37 wt%), acetone (99%), and ethanol (99%) were purchased from China National Pharmaceutical Group Corporation (Beijing, China). 5-hydroxymethylfurfural (HMF) was purchased from Bidepharm (Shanghai, China). Eucalyptus and masson pine (40–80 mesh) were provided by Qingshan Paper Co., Ltd. (Sanming, China), and the straw (40–80 mesh) was obtained from the State Key Laboratory of Bio-based Materials and Green Paper of Qilu University of Technology (Jinan, China).
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Publication 2023
4,4'-diphenylmethane diisocyanate 4-toluenesulfonic acid 5-hydroxymethylfurfural Acetone Epichlorohydrin Ethanol Eucalyptus Furaldehyde Glucose Glutaral Hydrochloric acid lithium bromide Methylene Chloride Pharmaceutical Preparations Phosphoric Acids Pinus pyridine tetrahydrofuran Xylose

Top products related to «5-hydroxymethylfurfural»

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5-Hydroxymethylfurfural is a chemical compound that can be used as a laboratory reagent. It is a colorless or pale yellow crystalline solid. The primary function of 5-Hydroxymethylfurfural is as a starting material for the synthesis of other organic compounds.
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Furfural is a colorless liquid organic compound derived from the hemicellulose fraction of various agricultural by-products, such as corn cobs, oat hulls, and sugarcane bagasse. It serves as a versatile industrial chemical with a wide range of applications, including the production of furan resins, solvents, and other specialty chemicals.
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D-glucose is a type of monosaccharide, a simple sugar that serves as the primary source of energy for many organisms. It is a colorless, crystalline solid that is soluble in water and other polar solvents. D-glucose is a naturally occurring compound and is a key component of various biological processes.
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Formic acid is a colorless, pungent-smelling liquid chemical compound. It is the simplest carboxylic acid, with the chemical formula HCOOH. Formic acid is widely used in various industrial and laboratory applications.
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Acetic acid is a colorless, vinegar-like liquid chemical compound. It is a commonly used laboratory reagent with the molecular formula CH3COOH. Acetic acid serves as a solvent, a pH adjuster, and a reactant in various chemical processes.
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Sulfuric acid is a highly corrosive, colorless, and dense liquid chemical compound. It is widely used in various industrial processes and laboratory settings due to its strong oxidizing properties and ability to act as a dehydrating agent.
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Levulinic acid is a chemical compound that can be used as a platform chemical in various industrial applications. It is a five-carbon organic acid that can be derived from the processing of carbohydrate-rich biomass. Levulinic acid serves as a versatile building block for the synthesis of other valuable chemicals and materials.
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Sodium hydroxide is a chemical compound with the formula NaOH. It is a white, odorless, crystalline solid that is highly soluble in water and is a strong base. It is commonly used in various laboratory applications as a reagent.
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Arabinose is a monosaccharide that is commonly used as a component in various laboratory equipment and supplies. It functions as a carbohydrate source and can be utilized in various biochemical and microbiological applications.
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5-hydroxymethylfurfural (5-HMF) is a chemical compound that can be used as a laboratory reagent. It is a heterocyclic compound derived from the dehydration of hexose sugars. 5-HMF serves as a versatile intermediate in the synthesis of various organic compounds.

More about "5-hydroxymethylfurfural"

5-Hydroxymethylfurfural (5-HMF) is a versatile and important chemical compound derived from the dehydration of hexose sugars, such as D-glucose.
It has a wide range of applications in the fields of biofuels, polymers, and pharmaceuticals. 5-HMF can be produced from various biomass sources, including agricultural and forestry waste, making it a valuable renewable resource.
In addition to 5-HMF, related compounds like furfural, formic acid, acetic acid, sulfuric acid, levulinic acid, and sodium hydroxide play important roles in the production and utilization of this platform chemical.
Furfural, for example, is another promising biomass-derived compound that can be converted into 5-HMF.
The dehydration of hexose sugars, such as D-glucose, is a key step in the production of 5-HMF.
This process can be facilitated by the use of various catalysts and reaction conditions, including the use of acids like sulfuric acid or bases like sodium hydroxide.
Beyond its application in biofuels and polymers, 5-HMF has also shown potential in the pharmaceutical industry, with possible uses in the development of new drugs and therapies.
Researchers are continually exploring ways to optimize the production and utilization of 5-HMF, leveraging advanced technologies like artificial intelligence (AI) to enhance reproducibility and accuracy in their experiments.
PubCompare.ai, for example, is an AI-driven tool that helps researchers identify the best publicly available protocols for 5-HMF studies, ensuring reliable and consistent results.
By utilizing this tool, researchers can take their 5-HMF research to new heights and unlock the full potential of this important biomass-derived compound.