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7 protocols using benzaldehyde

1

Extraction and Characterization of Japanese Cedar

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1-Methylimidazolium hydrogen sulfate ([MIM]HSO4) as shown in Fig. 5 was purchased from Sigma-Aldrich (St. Louis, MO USA). Japanese cedar (Cryptomeria japonica) was collected in our university forest with permission from our university and handled in accordance with relevant guidelines and regulations. Wood flours from Japanese cedar (Cryptomeria japonica) were extracted with ethanol/benzene (1/2, v/v) for 24 h in a Soxhlet apparatus. The wood flours were oven-dried at 105 °C for 24 h before use. 5-Hydroxymethylfurfrural (5-HMF), LiCl, MgCl2·6H2O, KCl, ethanol, acetonitrile, acetaldehyde, benzaldehyde, acetone, diethyl ether, tetrahydrofuran (THF), 1-butanol, methyl isobutyl ketone (MIBK), butyl acetate, benzene, and dichloromethane (DCM) were purchased from Wako Pure Chemicals Industries (Osaka, Japan). In this study, an electronic balance (ATX224, Shimadzu Corporation, Kyoto, Japan; Precision: below 0.1 mg) was used for all mass measurement.

Structural formula of 1-methylimidazolium hydrogen sulfate ([MIM]HSO4).

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2

Enzymatic Assays for Aromatic Aldehydes

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Vanillin (4-​hydroxy-​3-​methoxybenzaldehyde), vanillic acid (4-hydroxy-3-methoxybenzoic acid), ferulic acid (4-hydroxy-3-methoxycinnamic acid), isoVanillin (3-​hydroxy-​4-​methoxybenzaldehyde), protocatechualdehyde (3,​4-​dihydroxybenzaldehyde), benzaldehyde, p-hydroxybenzaldehyde, m-anisaldehyde (3-​methoxybenzaldehyde), veratraldehyde (3,​4-​dimethoxybenzaldehyde), syringaldehyde (4-​hydroxy-​3,​5-​dimethoxybenzaldehyde), and salicylaldehyde (2-​hydroxybenzaldehyde) were purchased from Wako Pure Chemicals (Osaka, Japan). NAD(P)+ and lactate dehydrogenase from the rabbit muscle were purchased from Oriental Yeast Co. Ltd. (Osaka, Japan). Oligonucleotides were purchased from Life Technologies Japan Ltd. (Tokyo, Japan).
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3

Comprehensive Volatile Compound Analysis

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n-Alkanes (C8–C40) were purchased from J&K Scientific, Beijing, China. Benzaldehyde, benzyl alcohol, (Z)-3-hexenyl acetate, methyl salicylate, and 2-phenylethanol were purchased from Wako Pure Chemical Industries Ltd, Osaka, Japan. Ethyl n-decanoate, geraniol, 1-hexanol, (Z)-3-hexenol, phenylacetaldehyde, α-farnesene, (E)-nerolidol, linalool, linalool oxide, polyvinylpolypyrrolidone (PVPP), and XAD-2 were purchased from Sigma-Aldrich Company Ltd., Louis, MO, USA. geraniol was purchased from TCI Development Co., Ltd, Shanghai, China. The Quick RNA isolation kit was purchased from Huayueyang Biotechnology Co., Ltd., Beijing, China. The 2× SYBR Green Universal PCR Mastermix was purchased from Bio-Rad Laboratories, Richmond, CA, USA.
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4

Benzaldehyde Synthesis from Benzylamine

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Benzaldehyde (compound 2) and super-dehydrated methanol were purchased from Fujifilm Wako Pure Chemical Industries, Ltd. (Japan) . Benzylamine (compound 1) was purchased from Tokyo Chemical Industry, Japan.
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5

Soy-based TVP Flavor Profiling

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Granule-type soy-based TVP was purchased from Marukome Co. Ltd. (Nagano, Japan). CGT (Amano Enzyme Inc., Nagoya, Japan) is a commercially available food-grade product. α-CD, β-CD, and γ-CD were obtained from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Potato starch was purchased from Nippon Star Chemical Co. Ltd. (Osaka, Japan). Hexanal, heptanal, octanal, nonanal, 2-octenal, 2-nonenal, benzaldehyde, 1-hexanol, 1-octen-3-ol, pyrazine, acetic acid, 2-pentylfuran, and furfural were obtained from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan).
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6

Functionalized Silica Nanoparticles Synthesis

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Cethyltrimethylammonium bromide (CTAB) and sodium silicate solution (∼27% SiO2) were purchased from Sigma-Aldrich and used without the purification. 3-Aminopropyltriethoxysilane (Shin-Etsu Chemical Co., Ltd.) and 3-(2-aminoethylamino)propyltrimethoxysilane (Tokyo Chemical Industries, Ltd.) were used as silane coupling agents. 2-Pyridinecarboxaldehyde, 3-pyridinecarboxaldehyde, 4-pyridinecarboxaldehyde, 2-quinolinecarboxaldehyde, cyclohexanecarboxaldehyde (Tokyo Chemical Industry Co., Ltd.), and benzaldehyde (Wako Pure Chemical Industries, Ltd.) as carbonyl compounds were used after purification. All other chemicals were reagent-grade materials and Milli-Q water was used throughout.
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7

Photosensitive DAAQ Compound Analysis

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Benzaldehyde, benzylamine, and glacial acetic acid were purchased from Wako Pure Chemical Industries (Osaka, Japan). Sodium dihydrogenphosphate dihydrate (NaH 2 PO 4 :2H 2 O) and disodium hydrogen phosphate (Na 2 HPO 4 ) were obtained from Nacalai Tesque (Kyoto, Japan). DAAQ and clorgiline were purchased from Sigma-Aldrich (St. Louis, MO, USA). Acetonitrile and methanol (HPLC grade) were obtained from Kanto Chemical Company (Tokyo, Japan). The water used was purified by a Simpli Lab UV (Millipore, Bedford, MA, USA). Phosphate buffer solution (PBS, 0.1 M, pH 7.8) was prepared by dissolving 0.13 g of Na 2 HPO 4 and 0.14 g of NaH 2 PO 4 :2H 2 O in 100 mL distilled water and a Horiba F22 pH-meter was used to check the pH of the buffer. Stock solution of Benzaldehyde (10 mM) was prepared in acetonitrile and stock solutions of clorgiline (0.2 mM) and benzylamine (5.6 mM) were prepared in PBS. 8.0 mM and 0.8 mM solutions of DAAQ were prepared in glacial acetic acid. Because of the expected photosensitivity of DAAQ, its solution was kept in amber-colored glass bottles.
It was found to be stable for at least 2 weeks when kept at 4 °C in the refrigerator.
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