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6 protocols using 2 3 5 trimethylpyrazine

1

Characterization of Pyrazine Derivatives

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Pyrazine, 2-methylPyrazine (2M), 2,6-dimethylPyrazine (26DM), 2,3-dimethylPyrazine (23DM), 2-ethyl-3-methylPyrazine (2E3M), 2,3,5-trimethylPyrazine (235TM), 2,3-diethylPyrazine (23DE), 5-ethyl-2,3-dimethylPyrazine (5E23DM), 2,3,5,6-tetramethylPyrazine (2356TTM), 2-isobutyl-3-methylPyrazine (2I3M), 2,3-diethyl-5-methylPyrazine (23DE5M), 2-acetyl-3-methylPyrazine (2A3M), (3,5,6-trimethylpyrazin-2-yl)methanol (TM2YM) and 2-propylPyrazine were purchased from company Sigma-Aldrich (Shanghai, China). Meanwhile, 2-ethyl-6-methylPyrazine (2E6M), 2,6-diethylPyrazine (26DE) and 2-ethyl-3,5-dimethylPyrazine (2E35DM) were purchased from J&K Chemical Corp (Beijing, China). The above commercial standards (≥96% purity) were used. HPLC grade ethanol and LC–MS grade acetonitrile were purchased from Merck (Darmstadt, Germany). Ultra-pure water was obtained from a Milli-Q Gradient A10 system (Millipore, Billerica, MA, USA).
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2

Volatile Compound Identification in Potatoes

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Potato dextrose broth (PDB) was obtained from Becton Dickinson (Dickinson and Company, Sparks, MD, USA). Phenylalanine was purchased from Samchun Chemicals (Pyeongtaek-si, Gyeonggi-do, Korea). The 2,3,5-trimethyl pyrazine was purchased from Sigma-Aldrich (St. Louis, MO, USA). Methanol was obtained from J.T.Baker (Phillipsburg, NJ, USA). Authentic standard compounds for positive identification of volatile compounds were purchased as follows: N,N-dibutylformamide, 2-phenylpropan-1-ol, pentadecan-2-one, propan-2-yl hexadecanoate, 3,4-dimethylphenyl methanol, hexadecan-1-ol, and 3-phenylfuran-2,5-dione were purchased from Alfa Aesar (Haverhill, MA, USA); methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 3-methyl-2H-furan-5-one, and 6-methylheptan-2-one were obtained from SejinCI (Seoul, Korea), while all of the other authentic standards were purchased from Sigma-Aldrich (St. Louis, MO, USA).
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3

Compound Purchasing and Preparation

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The following compounds were purchased from Sigma-Aldrich (St. Louis, MO): piperonal (99.0%), 2,3,5-trimethylpyrazine (99.0%), menthone (99.0%), (E)-beta-damascone (99.0%), cinnamic acid methyl ester (99.0%), myosmine (99.0%), cotinine (98.5%), and the internal standard (ISTD) 6-methyl coumarin (99.0%). Hydroxyacetone (96.0%) was purchased from Santacruz Biotechnology (Dallas, TX). 200 proof ethanol was purchased from Pharmco-Aaper. Propylene glycol (PG) and vegetable glycerol (VG) were purchased from Spectrum (New Brunswick, NJ).
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4

Coffee Capsule Aroma Profile Analysis

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Capsules from sixty-five different types of coffee capsules belonging to five different brands (named A to E), together with their relative coffee machines, were purchased on local markets in Parma (Italy) or through online stores during 2016 (23 capsules from brand A; 15 capsules, brand B; 10 capsules, brand C; 10 capsules, brand D; and 7 capsules, brand E). Details on the type of coffee are fully described in reference [7 (link)].
Toluene, 2-methylbutanal, 3-methylbutanal, 2,3,5-trimethylpyrazine, and 1H-pyrrole-2-carbaldehyde were purchased from Sigma-Aldrich (St. Louis, MO, USA).
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5

Flavor Compounds Analytical Protocol

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The flavor standards, methanethiol (97 %), eucalyptol (99 %), 2,5-dimethyltetrahydrofuran (98 %), 2,5-dimethylpyrazine (98 %), hexanal (98 %), 2-ethyl-5-methylpyrazine (96 %), (E)-2-octenal (97 %), 3-ethyl-2,5-dimethylpyrazine (98 %), benzaldehyde (99.5 %), (Z)-2-octen-1-ol (97 %), 2-pentylfuran (98 %), carvone (96 %), methyleugenol (98 %), anethole (99 %), (E, E)-2,4-decadienal (97 %), 2,3,5-trimethylpyrazine (99 %), (Z)-3-phenylacrylaldehyde (97 %), p-cresol (99 %), 4-hydroxy-5-methyl-3(2H)-furanone (97 %), 2,3-dimethyl-5-ethylpyrazine (99 %), dimethyl trisulfide (98 %), 2(5H)-furanone (98 %), 1-octen-3-ol (98 %), 3-furaldehyde (97 %), and 2-furanmethanol (98 %) were commercially purchased from Sigma-Aldrich (Shanghai, China). And methyl pyrazine (98 %) and benzene acetaldehyde (98 %) were purchased from TCI (Shanghai, China). Meanwhile, 2-methyl-3-heptanone (99 %) from Dr. Ehrenstorfer (Beijing, China) as the internal standard and the n-alkanes external standard (C7-C40, ≥ 97 %) from o2si Smart Solutions (Shanghai, China) were purchased.
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6

Analytical Reagents for Organic Synthesis

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Petroleum ether (40-60°C; 95%) was purchased from Acros Organics (Geel, Belgium). 2,3-Hexanedione (94%) and 2,4,5-trimethyl oxazole (97%) were obtained from Alfa Aesar (Karlsruhe, Germany).
Benzaldehyde (99%) and hydrogen peroxide (30%) were obtained from AppliChem (Darmstadt, Germany). Acetic acid (100%), chloroform-d (99.8 atom% D, with 0.03 vol% TMS, stabilized with Ag), diethyl ether (99.5%), iron(II) sulphate heptahydrate (99.5%), sodium carbonate decahydrate (98%), sodium sulphate (p.a.) and sulfuric acid (96%) were purchased from Carl Roth (Karlsruhe, Germany). Pentanal (97%) was obtained from Fisher Scientific (Darmstadt, Germany), Silica gel 60 was purchased from Macherey-Nagel (Düren, Germany) and 2,3-butanedione (97%) from Merck (Darmstadt, Germany). Acetoin (96%), 2,3-pentanedione (97%), 2,3,5,6-tetramethylpyrazine (98%) and 2,3,5-trimethylpyrazine (99%) were purchased from Sigma-Aldrich (Taufkirchen, Germany). 5-Ethyl-2,3-dimethylpyrazine (98%) was obtained from TCI (Eschborn, Germany). Butanal (97%) and propanal (97%) were purchased from Th. Geyer (Renningen, Germany) and ethyl acetate (98%) from VWR (Darmstadt, Germany). Helium (5.0) was obtained from Praxair (Düsseldorf, Germany) and nitrogen (5.0) from Air Liquide (Düsseldorf, Germany). All numbers given in parentheses represent the minimum purity.
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