The deuterated internal standards of caffeic acid-d6 (CAS 2708298-33-1, ≥99%) and furfural-d4 (CAS 1219803-80-1, ≥98%) were purchased from CDN Isotopes (Pointe-Claire, QC, Canada). furfural ethyl ether (CAS 6270-56-0, ≥97%) was purchased from Fisher Scientific (Hampton, NH, USA). The following compounds were purchased from Sigma-Aldrich Inc. (Oakville, ON, Canada); caffeic acid (CAS 331-39-5, ≥98%), caftaric acid (CAS 67879-58-7, ≥97%), 3-acetyl-2,5-dimethylfuran (CAS 10599-70-9, ≥98%), 2-furanmethanethiol (CAS 98-02-2, ≥98%), 2,3-dihydrobenzofuran (CAS 496-16-2, ≥99%), 2-acetylfuran (CAS 1192-62-7, ≥99%), 5-methylfurfural (CAS 620-02-0, ≥98%), homofuraneol (CAS 27538-09-06, ≥96%), furfural (CAS 98-01-1, ≥99%), sodium chloride (NaCl, ≥99%) and ethyl-2-furoate (CAS 614-99-3, ≥99%). All solvents used were HPLC grade purity. Potassium metabisulphite (KMS) and potassium bitartrate (cream of tartar) were purchased from Scott Laboratories Ltd. (Niagara-on-the-Lake, ON, Canada). D-fructose (≥99%) was purchased from BioShop® Canada Inc. (Burlington, ON, Canada). Milli-Q water was obtained Millipore (Saint-Quentin-en-Yvelines, France).
5 methylfurfural
Manufactured by Merck Group
Sourced in United States
5-methylfurfural is a chemical compound that can be used as a laboratory reagent. It is a colorless to pale yellow liquid with a characteristic odor. The compound is soluble in organic solvents. 5-methylfurfural is used in various applications, including as an intermediate in organic synthesis and as a flavoring agent.
Automatically generated - may contain errors
Lab products found in correlation
Furfural, by Merck Group (7 mentions)
5 hydroxymethylfurfural, by Merck Group (4 mentions)
Furfuryl alcohol, by Merck Group (2 mentions)
4 pyridinecarboxaldehyde, by Merck Group (2 mentions)
Homofuraneol, by Merck Group (1 mentions)
Caftaric acid, by Merck Group (1 mentions)
Furfural d4, by CDN Isotopes (1 mentions)
3 acetyl 2 5 dimethylfuran, by Merck Group (1 mentions)
2 furanmethanethiol, by Merck Group (1 mentions)
2 3 dihydrobenzofuran, by Merck Group (1 mentions)
2 acetylfuran, by Merck Group (1 mentions)
Ethyl 2 furoate, by Merck Group (1 mentions)
Milli q water, by Merck Group (1 mentions)
Caffeic acid, by Merck Group (1 mentions)
Calcium carbonate, by Merck Group (1 mentions)
Sodium chloride (nacl), by Thermo Fisher Scientific (1 mentions)
Xylose, by Merck Group (1 mentions)
Acetic acid, by Thermo Fisher Scientific (1 mentions)
Sodium hydroxide (naoh), by Merck Group (1 mentions)
Formic acid, by Merck Group (1 mentions)
10 protocols using 5 methylfurfural
1
Quantification of Furan Derivatives in Food
2
Kraft Pulp Feedstock Preparation and Characterization
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Northern bleached hardwood kraft (NBHK) pulp was used as a model kraft pulp feedstock. Alberta Pacific Forest Industries Inc. (Al–Pac Inc., Edmonton, AB, Canada) generously supplied dried pressed sheets, which were cut in to ~6 mm × 8 mm by a pulp chopper (Pierret Cutting Machine G45L1, Corbion, LX, Belgium) at the InnoTech Alberta (Edmonton, AB, Canada).
Acetic acid (CH3COOH, 99.7%) and sodium chloride (NaCl, ≥99%) were procured from Fisher Scientific (Whitby, ON, Canada). Sulfuric acid (H2SO4, 72% and 95–98%), sodium hydroxide (NaOH, 98.8%), glucose (C6H12O6, ≥95%), xylose (C5H10O5, ≥99%), furfural (C5H4O2, 99%), 5–methyl furfural (C6H6O3, 99%), formic acid (CH2O2, >95%), and calcium carbonate (CaCO3, >99%), were purchased from Sigma–Aldrich (St. Louis, MO, USA). Deionized water (Milli–Q® water) was used to make solutions and suspensions in all experiments.
Acetic acid (CH3COOH, 99.7%) and sodium chloride (NaCl, ≥99%) were procured from Fisher Scientific (Whitby, ON, Canada). Sulfuric acid (H2SO4, 72% and 95–98%), sodium hydroxide (NaOH, 98.8%), glucose (C6H12O6, ≥95%), xylose (C5H10O5, ≥99%), furfural (C5H4O2, 99%), 5–methyl furfural (C6H6O3, 99%), formic acid (CH2O2, >95%), and calcium carbonate (CaCO3, >99%), were purchased from Sigma–Aldrich (St. Louis, MO, USA). Deionized water (Milli–Q® water) was used to make solutions and suspensions in all experiments.
3
Synthesis and Antimicrobial Evaluation
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Starting 1H-indole-3-carboxaldehyde (purity 97%), furfural (99%), 5-methylfurfural (99%), 2-thiophenecarboxaldehyde (98%), 4-pyridinecarboxaldehyde (97%), 2-naphthaldehyde (98%), cyclohexanecarbaldehyde (97%), Lawesson’s reagent (97%), morpholine (99%), benzoyl chloride (99%), iodomethane (99%), and 2-aminobenzenesulfonamide (98%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). The reagents for the analysis of the antimicrobial activity: Cefazolin—MP Biomedicals (Illkirch, France), Cefotaxime—PROMED (Saransk, Russia), Chloramphenicol—AppliChem (Darmstadt, Germany), Amikacin sulfate—Sigma-Aldrich (St. Louis, MO, USA), Fluconazole—Sigma-Aldrich (St. Louis, MO, USA), Amphotericin B—Sigma-Aldrich (St. Louis, MO, USA), Isoniazid—Sigma (St. Louis, MO, USA), LB-broth—VWR (Radnor, PA, USA), and LB-agar—Sigma (St. Louis, MO, USA).
4
Profiling Volatile Compounds in Green Coffee
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Green coffee beans (Coffea arabica, from Brazil) were bought from a commercial market in Seoul, Korea. The origin of green coffee beans was verified by the importers and experts. 2-Methylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2-ethyl-3-methylpyrazine, 2-ethyl-5-methylpyrazine, 3-ethyl-2,5-dimethylpyrazine, furfural, furfuryl acetate, furfuryl propionate, furfuryl alcohol, 1-furfurylpyrrole, 4-ethylguaiacol, 2-methoxy-4-vinylphenol, 5-methylfurfural, quinoxaline, and C7–C30 alkane standard were obtained from Sigma–Aldrich Chemical Co. (St. Louis, MO, USA). 2-Ethylpyrazine, 2,3-dimethylpyrazine, 1-methylpyrrole, guaiacol, and 2-acetylfuran were bought from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS, 50-μm film thickness) solid-phase microextraction (SPME) fiber was purchased from Supelco, Inc. (Bellefonte, PA, USA).
5
Synthesis of Heterocyclic Compounds
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Perinaphthenone (Sigma-Aldrich), new methylene blue (NMB, Sigma-Aldrich), anthracene (Sigma-Aldrich), naphthalene (Sigma-Aldrich), 1-methyl-2-pyrrolidone, (Sigma-Aldrich), 2-methylbenzo[1,2-d]oxazole (Sigma-Aldrich), 2-methylnaphtho[1,2-d]oxazole (AK Scientific, Inc.), 2-methylnaphtho[3,2-d]oxazole (TCI), 2-aminophenol (Sigma-Aldrich), 1-amino-2-naphthol hydrochloride (Sigma-Aldrich), 2-amino-3-naphthol (Sigma-Aldrich), furfural (Sigma-Aldrich), 5-methylfurfural, (Sigma-Aldrich), 5-bromofurfural (Sigma-Aldrich), 5-phenylfurfural (Sigma-Aldrich) and furoyl chloride (Sigma-Aldrich) were used as received. All solvents used were UV or HPLC grade.
6
Analytical Methods for Oxidative Stress Markers
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Glucose standard and acetic acid were purchased from Tianjin Yongda (Tianjin, PR China). 5-Hydroxymethylfurfural (HMF), 5-methylfurfural (MF), methyglyoxal (MGO; 40% solution in water), glyoxal (GO; 40% solution in water), o-phenylenediamine, 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,7-dichlorofluorescin, Folin-Ciocalteu reagent and gallic acid were purchased from Sigma-Aldrich, Merck (St. Louis, MO, USA). Test kits used for the determination of total superoxide dismutase (SOD), glutathione peroxidase (GPx), catalase (CAT), malondialdehyde (MDA) and serum biochemical markers (alanine transaminase (ALT) aspartate transaminase (AST), alkaline phosphatase (ALP) and total bilirubin) were purchased from Nanjing Jiancheng Bioengineering Institute (Nanjing, PR China). All reagents were of analytical grade.
7
HPLC Analysis of Furan Derivatives in Tetrahydrofuran
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Samples in tetrahydrofuran (THF, ≥99.9%, Sigma-Aldrich, St. Louis, MO, USA) were diluted with water 1 in 50, filtered through a 0.2 μm membrane and analysed by high-performance liquid chromatography (HPLC). HPLC was carried out on an Agilent 1290 system with diode array detection, using a YMC UltraHT Pro C18 100 mm × 2.1 mm I.D. column with 2 μm particle size and 12 nm pore. The mobile phases were A: water + 0.1% trifluoroacetic acid (TFA, ≥99.0, Sigma-Aldrich, St. Louis, MO, USA) and B: acetonitrile (≥99.9%, Sigma-Aldrich, St. Louis, MO, USA) + 0.1% TFA. A gradient from 20–60% B over 10 min followed by a 1.5-min re-equilibration to 20% B was used to separate the components at a flow rate of 0.2 mL/min. Detection was at 220 nm (furfuryl alcohol), 260 nm (2-furoic acid) and 280 nm (furfuraldehyde, 5-hydroxymethylfurfural, 5-methylfurfural). The injection volume was 1.0 μL. Analytical standards of furfuryl alcohol, furfuraldehyde, 2-furoic acid, 5-hydroxymethylfurfural and 5-methylfurfural from Sigma-Aldrich (St. Louis, MO, USA) were used to identify and quantify compounds.
8
Standardized Chemical Compound Acquisition
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Amitraz (97%) and N,N-diethyl-m-toluamide (DEET) (98%) were purchased from TCI (Tokyo, Japan). Benzyl benzoate (99%), 4,5-dimethylfurfural (97%), furfural (99%), furan (99%), α-guaiene (95%), (-)-α-gurjunene (97%), 5-hydroxymethylfurfural (97%), isovalerate (99%), 2-methylfuran (99%), 5-methylfurfural (99%), methyl 3-methylvalerate (97%), (-)-patchouli alcohol (98%), and viridiflorol (95%) were purchased from Sigma-Aldrich (St. Louis, MO, USA).
9
Synthesis of Chitosan-Arginine Conjugates
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Chitosan with a molecular weight of 8 kDa and 93% N-deacetylation was purchased from Golden-Shell Pharmaceutical Co., Ltd. (Zhejiang, China). l -Arginine and methanol were purchased from Sinopharm Chemical Reagent Co., Ltd., Shanghai, China. Furfural, 5-methylFurfural, 5-hydroxymethylFurfural, 5-chloro-Furfural, 5-bromo-Furfural, 2-pyridinecarboxaldehyde, 3-pyridinecarboxaldehyde, 4-pyridinecarboxaldehyde, 2-chloro-3-pyridinecarboxaldehyde, 2-bromo-3-pyridinecarboxaldehyde, 1,1′-carbonyldiimidazole (CDI) and dimethyl sulfoxide (DMSO) were purchased from Merck Life Science (Shanghai) Co., Ltd., Shanghai, China. Ethanol absolute was obtained from Fuyu Fine Chemicals Co., Ltd., Tianjin, China. Chloramphenicol and azithromycin were purchased from Aladdin Biochemical Technology Co., Ltd., Shanghai, China. Purified water was supplied by Wahaha Group Co., Ltd., Shandong, China.
10
Phenolic Compound Profiling in Red Wine
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Volatile phenols, furanic
compounds, lactones, phenolic aldehydes, and phenolic alcohols were
analyzed by gas chromatography–mass spectrometery (GC–MS).
The equipment used was an Agilent Technologies 6890N-MSD-5973N gas
chromatography–mass spectrometer. Chromatographic separation19 (link) was performed with the DB-WAX column (30 m ×
0.25 mm internal diameter × 0.25 μm film thickness) (J&W
Scientific, Folsom, CA, USA). The method was calibrated using the
following external standards: guaiacol, eugenol, furfural, furfuryl
alcohol, 5-methyl furfural, oak lactone, vanillin, syringaldehyde,
acetovanillone, ethyl vanillin, and vanillin alcohol (Merck, Hohenbrunn,
Germany).
Liquid extraction with dichloromethane was performed
before the chromatographic separation. A 2.5 mL volume of red wine
was mixed with 250 μL of dichloromethane and 25 μL of
3,4-dimethylphenol solution (10 mg/L) (Merck, Hohenbrunn, Germany)
as the internal standard; 0.37 g of NaCl was added and stirred in
a vortex for 5 min. After centrifugation at 7500 rpm for 15 min at
4 °C, the dichloromethane phase was extracted and injected into
the chromatograph (1 μL).
compounds, lactones, phenolic aldehydes, and phenolic alcohols were
analyzed by gas chromatography–mass spectrometery (GC–MS).
The equipment used was an Agilent Technologies 6890N-MSD-5973N gas
chromatography–mass spectrometer. Chromatographic separation19 (link) was performed with the DB-WAX column (30 m ×
0.25 mm internal diameter × 0.25 μm film thickness) (J&W
Scientific, Folsom, CA, USA). The method was calibrated using the
following external standards: guaiacol, eugenol, furfural, furfuryl
alcohol, 5-methyl furfural, oak lactone, vanillin, syringaldehyde,
acetovanillone, ethyl vanillin, and vanillin alcohol (Merck, Hohenbrunn,
Germany).
Liquid extraction with dichloromethane was performed
before the chromatographic separation. A 2.5 mL volume of red wine
was mixed with 250 μL of dichloromethane and 25 μL of
3,4-dimethylphenol solution (10 mg/L) (Merck, Hohenbrunn, Germany)
as the internal standard; 0.37 g of NaCl was added and stirred in
a vortex for 5 min. After centrifugation at 7500 rpm for 15 min at
4 °C, the dichloromethane phase was extracted and injected into
the chromatograph (1 μL).
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