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5 protocols using l menthol

1

Menthol and Nicotine Solution Preparation

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L(−) menthol was used in all studies, the minty and cooling menthol isomer added to tobacco products 19 (link). Menthol solutions (10–200 μg/ml) were prepared by dissolving L(−)-menthol (Acros Organics) in distilled deionized H2O (ddH2O). Nicotine solutions (200μg/ml) were prepared fresh daily by dissolving nicotine base (Sigma) in dd H2O or 10–200 μg/ml menthol solutions. Drinking tubes with nicotine solutions were protected from light by covering with aluminum foil.
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2

Evaluating Natural Antioxidant Compounds

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Thymol of 99.5% purity (Sigma, Steinheim, Germany), 98% carvacrol, 99% eugenol, 98% syringaldehyde (Aldrich, Steinheim, Germany), 99% vanillin and 97% phythol (Sigma-Aldrich, Steinheim, Germany), 99% benzyl alcohol, 96% limonene, 98% α-pinene, 98% β-pinene, 98% D-carvone, 75% camphene, as well as α-fenchene, myrcene, 99.5% L-menthol, and 97% L-borneol (Acros Organics, Geel, Belgium) were used as standard antioxidants. Their 10 mM stock solutions were prepared by dissolving an accurately weighed portion in 5.0 mL of ethanol (rectificate). Less concentrated solutions were obtained with an exact dilution prior to measurements. Other reagents were of chemical purity and used as received.
The commercially available essential oils of various plant materials (Table 1) of different trademarks were studied. Their ten-fold dilution with ethanol was used exactly before the measurements.
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3

Synthesis and Characterization of GABA Derivatives

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The following chemicals and drugs were used as obtained from their commercial suppliers: l-menthol, DMAP, GABA (Acros Organics, Geel, Belgium; Darmstadt, Germany), carvacrol, guaiacol, DCC, di-tert-butyl dicarbonate (TCI, Philadelphia, PA, USA), thymol (Sigma-Aldrich, Schnelldorf, Germany). Boc-protected GABA was not obtained commercially and has been synthesized according to the literature procedure [21 (link)]. Structures of the obtained compound were established by 1H-NMR spectroscopy on a AVANCE DRX 500 (500 MHz) instrument (Bruker, Davis, CA, USA) using DMSO-d6 and CDCl3 as solvents and TMS as an internal standard. FAB mass spectrum was obtained on a VG 70-70EQ mass spectrometer (VG Analytical Ltd., Manchester, UK) equipped with Xe ion gun (8 kV); the sample was mixed with m-nitrobenzyl-alcohol matrix. High-resolution mass spectrometry (HRMS) was performed on a 6530 Accurate Mass quadrupole time of flight (Q-TOF) spectrometer (Agilent, Santa Clara, CA, USA) using ESI (electrospray ionization) coupled to an Agilent 1260 Infinity HPLC system. IR spectra were measured with a Frontier FT-IR spectrometer (Perkin-Elmer, Hopkinton, MA, USA) using KBr pellets. The purity and identity of the compound were monitored by TLC on Merck-made (TLC Silica gel 60 F254) plates (Darmstadt, Germany).
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Heavy Metal Ion Extraction Protocol

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Pb(II), Ni(II), Co(II), Zn(II), Mn(II), and Cd(II) solutions were prepared by dilution, starting from the stock solutions (1000 mg L−1) Merck (Darmstadt, Germany) to achieve the intended concentrations. Standard metal solutions used for calibration of the AAS spectrophotometer were prepared by diluting their respective 1000 mg L−1 stock solutions. For HDES preparation, L(-) menthol (CAS number: 2216-51-5; mass fraction purity: ≥99%), thymol (CAS number: 89-83-8; mass fraction purity: ≥99%), octanoic acid (CAS number: 124-07-2; mass fraction purity: ≥99%), dodecanoic acid (CAS number: 143-07-7; mass fraction purity: ≥99%), were obtained from Acros Organics (Antwerpen, Belgium) and decanoic acid (CAS number: 334-48-5; mass fraction purity: ≥99%) was procured from Alfa Aesar (Ward Hill, MA, USA). Disodium EDTA (CAS number: 6381-92-6; mass fraction purity: ≥99%) were obtained from Sigma-Aldrich (St. Louis, MO, USA).
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5

Cocrystal Formation via Intermolecular Interactions

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Lidocaine (purity: 97.5%; CAS 137-58-6), l-menthol (purity: 99.7%; CAS 2216-51-5) were purchased from Acros Organics (Morris Plains, NJ, USA), d-menthol (purity: 99%; CAS 15356-70-4) was obtained from Janssen Chimica (Geel, Belgium), and dl-menthol (purity: >98%; CAS 89-78-1) was provided by Alfa Aesar (Karlsruhe, Germany). No further purification steps were required since the cocrystals are directly obtained from the intermolecular interactions of the pure compounds. For the buffer preparation, Na2HPO4 and KH2PO4 were purchased from Acros Organics, and ultrapure water was prepared via filtration of distilled water through 2 ion-exchange membranes (resistivity = 18.2 MΩ·cm at 25 °C), with a final filtration through a 0.2 µm membrane (Milli-Q®, Merck, Darmstadt, Germany).
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