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4 protocols using chloroform d1

1

Extraction and Isolation of Natural Compounds

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Solvents for different steps in analyses were partially denatured ethanol (AustrAlco, Spillern, Austria) for extraction, hexane, ethyl acetate (both Carl Roth, Karlsruhe, Baden-Württemberg, Germany) and methanol (VWR, Radnor, PA, USA) for open column chromatography and TLC, chloroform-d1 (VWR) and pyridine-d5 (Armar, Döttingen, Aargau, Switzerland) for NMR.
HPLC mobile phases consisted of ultrapure water prepared from deionized water with a Barnstead MicroPure system (Thermo Fisher Scientific, Waltham, MA, USA), HPLC-grade acetonitrile (VWR) and formic acid for LC-MS (Honeywell, Charlotte, NC, USA).
Reference substances were abietic acid contributed by the Department of Pharmaceutical Chemistry, University of Graz, Austria, apigenin (Sigma-Aldrich, St. Louis, MO, USA), chrysin, pinocembrin-7-methyl ether (pinostrobin), linoleic acid (all Carl Roth) and oleic acid (Fluka, Buchs, St. Gallen, Switzerland).
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2

NADES Preparation and Characterization

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For NADES preparation, chemicals choline chloride, 1,2-propanediol, DL-malic acid, malonic acid, D-sorbitol, urea (all Thermo Fisher Scientific, Waltham, MA, USA), citric acid monohydrate, glycerol, D(−)-fructose (all Carl Roth, Karlsruhe, Germany), D(+)-glucose (Merck, Darmstadt, Germany) and methylurea (Acros Organics, Geel, Belgium) were used. Methylurea had a specified purity of 97%, and all other reagents were at least 98% or higher. In HPLC mobile phases, ultrapure water prepared from deionized water with a Barnstead MicroPure system (Thermo Fisher Scientific, Waltham, MA, USA), HPLC-grade acetonitrile (VWR, Radnor, PA, USA) and formic acid (Honeywell, Charlotte, NC, USA) were used. The solvent for NMR analyses was chloroform-d1 (VWR). Other solvents used in this study were partly denatured ethanol (96% v/v, AustrAlco, Spillern, Austria) methanol (≥99.9%, Carl Roth) and dichloromethane (≥99.5%, Carl Roth). Reference substance spilanthol was isolated in the course of this work with a purity of 97% as determined by NMR.
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3

Extraction and Isolation of Natural Compounds

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Solvents for different steps in analyses were partially denatured ethanol (AustrAlco, Spillern, Austria) for extraction, hexane, ethyl acetate (both Carl Roth, Karlsruhe, Baden-Württemberg, Germany) and methanol (VWR, Radnor, PA, USA) for open column chromatography and TLC, chloroform-d1 (VWR) and pyridine-d5 (Armar, Döttingen, Aargau, Switzerland) for NMR.
HPLC mobile phases consisted of ultrapure water prepared from deionized water with a Barnstead MicroPure system (Thermo Fisher Scientific, Waltham, MA, USA), HPLC-grade acetonitrile (VWR) and formic acid for LC-MS (Honeywell, Charlotte, NC, USA).
Reference substances were abietic acid contributed by the Department of Pharmaceutical Chemistry, University of Graz, Austria, apigenin (Sigma-Aldrich, St. Louis, MO, USA), chrysin, pinocembrin-7-methyl ether (pinostrobin), linoleic acid (all Carl Roth) and oleic acid (Fluka, Buchs, St. Gallen, Switzerland).
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4

Synthesis of Ionic Liquids and Cellulose Composites

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The compounds used for the synthesis, 1-ethyl-3-methylimidazolium chloride (>99%), methyl iodide (99.5%), potassium carbonate (≥99%), silver benzoate (99%), and sodium salicylate (≥99.5%), were received from Sigma Aldrich. Silver nitrate (≥99.5%) was purchased from Carl Roth. 1,2,3-Triazole (98%) and ethyl bromide (98%) were purchased from abcr GmbH. The solvents tetrahydrofuran (≥99.9%), dimethyl sulfoxide–d 6 (99.8 atom-% D), acetone (≥99.5%), chloroform–d 1 (99.8 atom-% D), and methanol (≥99%) were received from VWR, Armar Europa GmbH, Sigma Aldrich, and Carl Roth (water content below 100 ppm in all cases). Microcrystalline cellulose with a particle size of 20 μ m and a molar mass of 37 kg mol 1 (as determined by viscosimetry) was purchased from Sigma Aldrich.
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