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4 protocols using 2 furanmethanethiol

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

Synthesis of FAM-tagged miR148b Oligonucleotides

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Custom-modified fluorescein amidites (FAM)-tagged oligonucleotides (miR148b: 5’ 6-FAM 2’OMe UCA GUG CAU CAC AGA ACU UUG U C6-NH2 3’) were acquired through Trilink Biotechnologies, LLC. (San Diego, CA). 6-Maleimidohexanoic acid (90%), 2-furanmethanethiol (98%), methanol (>99.9%), isopropanol (>99.9%), dichloromethane (99.8%), N-hydroxysuccinimide (NHS) (98%), silver nitrate (99%), formaldehyde (36.5%-38%), sodium hydroxide (98%, pellets), hydroxypropyl cellulose (HPC, Mn = 80,000, 99%), antifoam A (100%), tris(2-carboxyethyl)phosphine hydrochloride solution (TCEP) (0.5M), were all purchased and used without alteration from Sigma Aldrich (St. Louis, MO). EDC (1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride), was purchased from ThermoFisher Scientific (Waltham, MA). Mounted 415nm LED lights from ThorLabs, Inc. (Newton, NJ) were used for photo-release experiments.
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3

Quantification of Aroma Compounds by GC-MS

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The following reference compounds: acetic acid, acetoin, 2-methylbutanal, 2-methylpyrazine, 2,5-dimethylpyrazine, 2-furanmethanethiol, 2-acetyl-1-pyrroline, benzaldehyde, 1-octen-3-one, octanal, linalool, 2-acetylthiazole, 2-acetylpyridine, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 2-methoxyphenol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, hexadecanol, octadecanal, 2.3-pentanedione, butanoic acid, β-iso-methyl ionone, β-ionone, were from Sigma-Aldrich (St. Louis MO). Stock standard solutions 103 or 104 µg mL−1 of each compound was prepared as described earlier [21 (link)].
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4

Analytical Characterization of Volatile Thiols

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Mass spectrometry grade dichloromethane and methanol (MS SupraSolv®) were purchased by Merck (Darmstadt, Germany). Water was of ultrapure milli-Q grade. Ammonium formate was from Sigma. Nitrogen (Alphagaz, purity 99.999%, Air Liquid) was used in the Orbitrap-Exactive as the nebulization and fragmentation gas.
Ebselen (2-phenyl-1,2-benzisoselenazol-3(2H)-one, purity 98%), ethylenediaminetetraacetic acid (EDTA) (purity 98,5%);4-methoxy-α-toluenethiol (IS, purity 90%); 4-mercapto-1-butanol (4MB) (purity 95%); 3-mercapto-3-methylbutan-1-ol (3MMB) (purity 98%); 2-methyl-3tetrahydrofuranthiol (2MTHFT) (purity 97%); 3-mercaptohexanol (3MH) (purity 98%); ethanethiol (ET) (purity 97%); 3-mercapto-3-methylbutylformate (3MMBF) (purity 97.5%) and 2-furanmethanethiol (2FMT) (purity 97%) were purchased by Sigma-Aldrich (St Louis, MO, USA). Molecular structures of the reference thiols are shown in Fig. 1.
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