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5 protocols using 2 acetylfuran

1

Quantification of Furan Derivatives in Food

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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).
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2

Furan Derivatives Procurement and Analysis

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The furan standard was procured from Alfa Aesar Co. (Ward hill, MA, USA), while 3-methylfuran was from Acros Co., (Carlsbad, CA, USA), and 2-pentylfuran from Tokyo Chemical Industry Co. (Tokyo, Japan). The other furan derivative standards, including 2-methylfuran, 2,3-dimethylfuran, 2,5-dimethylfuran, 2-ethylfuran, furfural, furfuryl alcohol, 2-butylfuran, and 2-acetylfuran, were from Sigma-Aldrich (St. Louis, MO, USA). The internal standard d4-furan was from Dr. Ehrenstorfer GmbH Co. (Augsburg, Germany). The HPLC-grade methanol was from Merck (Darmstadt, Germany), and the sodium chloride was from Uni Region Bio-Tech (Los Altos, CA, USA). The sodium chloride was purchased from UNI-ONWARD CORP (New Taipei City, Taiwan).
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3

Flavor Compound Isolation and Synthesis

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The following compounds, 2-methylpropanal, 2,3-butanedione, 3-methylbutanal, methional, 2-acetylfuran, 1-octen-3-one, 1-octen-3-ol, (E)-2-nonenal, (E,Z)-2,6-nonadienal, 2-acetylpyrazine, 2-acetyl-2-thiazoline, 2-ethyl-3,5(and 6)-dimethylpyrazine, (E,E)-2,4-decadienal, 1-hexanol, 2-phenylethanol, salicylaldehyde, p-vinylguaiacol, ethyl nonanoate, and ethyl octanoate were purchased from Sigma Aldrich (St. Louis, MO, USA). 2-Ethyl-3,5-dimethylpyrazine and 2-ethyl-3,6-dimethylpyrazine were separated using preparative GC and [2H3]-2-Acetyl-1-pyrroline and [2H4]-2-acetyl-2-thiazoline were synthesized as previously described [37 (link)]. 3-Methyl-1-butanol, guaiacol, and 2-methyl-3-heptanone were purchased from Tokyo Chemical Industry (TCI; Portland, OR, USA). 2,3-Diethyl-5-methylpyrazine, butylated hydroxytoluene (BHT), ethanol (200 proof) and dichloromethane were purchased from Fisher Scientific (Pittsburgh, PA, USA). Sodium bicarbonate and anhydrous sodium sulfate were purchased from Avantor (Center Valley, PA, USA).
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4

Synthesis of 2-Acetylfuran Using Dichlorodimethylsilane

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Example 2

In a one-liter beaker, 100 g of 2-acetylfuran (Sigma-Aldrich) was stirred for a few minutes using a magnetic stirrer. Catalyst dichlorodimethylsilane, Si(CH3)2Cl2 (25 mL) (Sigma-Aldrich), was added slowly. Stirring was continued for 5 minutes and the stir bar was then removed. The mixture was transferred to a 500-mL (16 oz.) glass jar. The mouth of the jar was covered with Teflon tape before the jar cap was screwed on. The jar was allowed to stand at room temperature for 190 hours. A black solid formed.

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5

Quantification of Furan Derivatives

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Furan standard was purchased from Alfa Aesar Co. (Ward hill, MA, USA), while 3-methylfuran was from Acros Co., (Carlsbad, CA, USA), and 2-pentylfuran from Tokyo Chemical Industry Co. (Tokyo, Japan). The other furan derivative standards including 2-methylfuran, 2,3-dimethylfuran, 2,5-dimethylfuran, 2-ethylfuran, furfural, furfuryl alcohol, 2-butylfuran and 2-acetylfuran were from Sigma–Aldrich (St. Louis, MO, USA). Internal standard d4-furan was from Dr. Ehrenstorfer GmbH Co. (Augsburg, Germany). The HPLC-grade solvents methanol and petroleum ether were from Merck (Darmstadt, Germany). Deionized water was produced by a Milli-Q water purification system (Bedford, MA, USA). Sodium chloride, ninhydrin, 3,5-dinitrosalicylic acid, d-dextrose, potassium sodium tartrate 4-hydrate, and glycine was purchased from Sigma–Aldrich (St. Louis, MO, USA).
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