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6 protocols using 4 vinylphenol

1

In Vitro Antioxidant Analysis

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Methanol (99.9%), formic acid, sodium hydroxide, sodium dihydrogen phosphate dehydrate, sodium carbonate and calcium chloride dehydrate (CaCl2(H2O)2) were purchased from Merck (Darmstadt, Germany). Folin–Ciocalteu reagent, 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•) reagent, 2,2-Azino-bis-3-etilbenzotiazolin-6-sulfonic acid (ABTS) reagent, Trolox, hydrochloric acid, p-coumaric acid, trans-ferulic acid, caffeic acid, p-hydroxybenzoic acid, gallocatechin, 4-vinylphenol, 4-vinylguaiacol, α-amylase (EC 232-565-6) from porcine pancreas (enzyme activity 5 U/mg solid), pepsin (EC 232-629-3) from porcine gastric mucosa (enzyme activity ≥ 2500 U/mg protein) and pancreatin (EC 232-468-9) from porcine pancreas (4 × USP specifications) were purchased from Sigma-Aldrich (Steinheim, Germany). Bile bovine (EC 232-369-0) was from Millipore (ZDA). Potassium chloride (KCl), potassium dihydrogen phosphate (KH2PO4), sodium bicarbonate (NaHCO3), sodium chloride (NaCl), and magnesium chloride hexahydrate (MgCl2(H2O)6) were purchased from Sigma-Aldrich (Steinheim, Germany). Ammonium carbonate ((NH4)2CO3) was from Honeywell/Riedel-de Haen (Seelze, Germany). All chemicals and reagents used were of analytical quality. For preparation of working solutions ultrapure water (Milli-Q; Millipore, Bedford, MA, USA) was used.
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2

Quantification of Phenolic Compounds

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Ethyl gallate, 4-hydroxybenzaldehyde, vanillin, tyrosol, protocatechuic aldehyde, syringaldehyde, pyrogallol, 4-hydroxy-3-methoxycinnamaldehyde, 4-methylcatechol, tryptophol, ethyl 3,4-dihydroxycinnamate, 2,6-dimethoxyphenol, ethyl vanillate, homovanillyl alcohol, eugenol, 4-hydroxy-3-methoxyphenylacetone, salicylaldehyde, coniferyl alcohol, epicatechin, catechin, scopoletin, p-coumaric acid, caffeic acid, resveratrol, syringic acid, rutin, gallic acid, salicylic acid, protocatechuic acid, 2-methoxy-4-vinylphenol, 4-vinylphenol, 4-ethylguaiacol were purchased from Sigma-Aldrich (Steinheim, Germany). All chemicals were used in the highest purity available. Acetonitrile and methanol (gradient grade for liquid chromatography) were also purchased from Sigma-Aldrich. Deionized water was produced by Mili-Q® Reference System (Merck KGaA, Darmstadt, Germany). Sodium chloride was purchased by Lach-Ner (Neratovice, Czech Republic). Standard solution of n-alkanes C8-C33 was purchased by CPAchem (Stara Zagora, Bulgaria). Technical gases, i.e., helium 4.6, hydrogen, and nitrogen, were purchased from Linde Gas (Prague, Czech Republic).
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3

Microbial Conversion of Hydroxycinnamic Acids

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Luria–Bertani (LB) medium was used for cell cultivation of E. coli. Hydroxycinnamic acids and the corresponding 4-vinylphenol derivatives, including FA, p-coumaric acid, caffeic acid, 4-vinylguaiacol, and 4-vinylphenol, were purchased from Sigma–Aldrich (St. Louis, MO, United States). Isopropyl-β-D thiogalactopyranoside (IPTG) was also obtained from Sigma–Aldrich. Yeast extract and tryptone were purchased from Oxoid (Basingstoke, England). Kanamycin was provided by Amresco (Solon, OH, United States). All the organic solvents used for whole-cell catalysis and high-performance liquid chromatography (HPLC) were of HPLC grade. The other chemicals used in this study were of analytical grade and were commercially available.
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4

Flavor Compound Procurement for Analysis

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Diethyl ether, dansyl chloride, and saturated
alkane standards were purchased from Sigma-Aldrich (Gillingham, Dorset,
UK). O-(2,3,4,5,6-Pentafluorobenzyl)-hydroxylamine
hydrochloride (PFBHA) was purchased from Fluka (Loughborough, UK).
The following food-grade aroma compounds were purchased from Sigma-Aldrich
(purity in parenthesis): acetaldehyde (≥99%), acetic acid (≥99.5%),
2,3-butanedione (97%), butanoic acid (≥99%), (E)-β-damascenone (≥98%), dimethyl sulfide (≥99%),
5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone (97%),
5(or 2)-ethyl-4-hydroxy-2(or 5)-methyl-3(2H)-furanone
(96%), (Z)-4-heptenal (≥98%), 3-hydroxy-4,5-dimethyl-2(5H)-furanone (10% in propylene glycol), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (≥98%), methional (≥97%), 2-methoxy-4-methylphenol
(≥98%), 2-methoxyphenol (≥99%), 2-methoxy-4-vinylphenol
(≥98%), 2-methylbutanal (≥95%), 3-methylbutanal (≥97%),
3-methylbutanoic acid (99%), 3-methyl-1-butanol (≥98%), methylpropanal
(≥98%), 2,3-pentanedione (≥96%), phenylacetaldehyde
(10% in ethanol), 2-phenylacetic acid (≥99%), 2-phenylethanol
(≥99%), vanillin (≥97%), and 4-vinylphenol (10% in propylene
glycol). Encapsulated 3-methyl-2-butene-1-thiol flavor standard (0.02–4
ng/g) was purchased from FlavorActiV (Aston Rowant, UK).
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5

Synthesis and Characterization of Boron-Containing Compounds

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All reactions were performed under an atmosphere of dinitrogen employing standard Schlenk techniques. Acetonitrile and dichloromethane were purchased from Merck and distilled from sodium benzophenone before use. Commercial grade acetone, hexane, ethyl acetate, tetrahydrofuran, and methanol were used without further purification. Compounds [Bu4N][B12H11(C4H8O2)] (2) [93 (link)] and [3,3′-Co(8-C4H8O2-1,2-C2B9H10)(1′,2′-C2B9H11)] (3) [94 (link)] and T8-COSAN [43 (link)] were synthesised according to the literature. Compounds [Bu4N]Br, Grubbs 1st generation catalyst [RuCl2(CHPh)-(PCy3)2], octavinylsilsesquioxane (OVS), 1,3,5-tris(4-hydroxyphenyl)benzene (1) and 4-vinylphenol solution 10 wt% in propylene glycol were purchased from Sigma-Aldrich (Merck Life Science, Madrid, Spain). K2CO3 was obtained from Labkem (Barcelona, Spain).
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6

Aroma Compound Analysis Protocol

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The following aroma compounds were purchased from Sigma-Aldrich (purity in parenthesis): acetaldehyde (≥99 %), acetic acid (≥99.5 %), 2,3-butanedione (97 %), butanoic acid (≥99 %), dimethyl sulfide (≥99 %), 5(or 2)-ethyl-4-hydroxy-2(or 5)-methyl-3(2H)-furanone (homofuraneol, 96 %), Z-4-heptenal (≥98 %), 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone, 10 % in propylene glycol), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol, ≥98 %), methional (≥97 %), 2'methoxyacetophenone (99 %), 2-methoxy-4-methylphenol (≥98 %), 2-methoxyphenol (≥99 %), 2methoxy-4-vinylphenol (≥98%), 2-methylbutanal (≥95 %), 3-methylbutanal (≥97 %), 3methylbutanoic acid (99 %), 3-methyl-1-butanol (≥98%), methylpropanal (≥98 %), 2methylthiophene (98 %), 2,3-pentanedione (≥96 %), phenylacetaldehyde (10 % in ethanol), 2phenylacetic acid (≥99 %), 2-phenylethanol (≥99 %), vanillin (≥97 %), 4-vinylphenol (10 % in propylene glycol). All were food grade except 2'-methoxyacetophenone and 2-methylthiophene.
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