A portion of Mandelic acid (about 0.1 g) was dissolved in a solution of alkali metal hydroxide (LiOH, NaOH, KOH, RbOH, and CsOH) at a concentration of 0.1 M in a stoichiometric amount (1:1). The solution was heated to 50 °C and stirred for about 1 h. After the reaction, the mixture was filtered and slowly evaporated at room temperature. After the evaporation of water, crystalline substances were obtained, which were placed in an oven for 48 h at 120°C to get rid of the rest of the water. The synthesis was repeated three times, each time performing a preliminary FT-IRATR analysis of the salts obtained. Mandelic acid (98%) and alkaline metal hydroxides were purchased from Sigma Aldrich.
Mandelic acid
Manufactured by Merck Group
Sourced in United States
Mandelic acid is a chemical compound used in various laboratory applications. It is a crystalline solid with the molecular formula C6H6O3. Mandelic acid is commonly used as a precursor in organic synthesis and as a reagent in analytical chemistry.
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Lab products found in correlation
Sodium hydroxide (naoh), by Merck Group (3 mentions)
Hydroxybenzoic acid, by Merck Group (2 mentions)
Ascorbic acid, by Merck Group (2 mentions)
Quercetin, by Merck Group (2 mentions)
Chlorogenic acid, by Merck Group (2 mentions)
Rutin, by Merck Group (2 mentions)
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2 2 diphenyl 1 picrylhydrazyl (dpph), by Merck Group (2 mentions)
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Aluminum chloride, by Merck Group (1 mentions)
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2 2 diphenyle 1 picrylhydrazyle, by Merck Group (1 mentions)
5 5 dithio bis nitrobenzoic acid, by Merck Group (1 mentions)
Butyrylcholinesterase from equine, by Merck Group (1 mentions)
2 2 azino bis 3 ethylbenzothiazoline 6 sulfonic acid, by Merck Group (1 mentions)
Ethanol, by Merck Group (1 mentions)
Methanol, by Merck Group (1 mentions)
Sodium carbonate, by Merck Group (1 mentions)
Sodium nitrate, by Merck Group (1 mentions)
Phloroglucinol, by Merck Group (1 mentions)
9 protocols using mandelic acid
1
Synthesis of Alkali Metal Mandelic Salts
2
Mandelic Acid and its Metal Salts
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Mandelic acid (Sigma Aldrich, St. Louis, MI, USA) and its salts with alkali metals: lithium (Li), sodium (Na), and potassium (K) were used in this study. First, Mandelic acid and its derivatives were dissolved in sterile distilled water to prepare stock solutions at ten times greater than the target concentration. As a result, the final concentrations of Mandelic acid were 5.00; 3.00; 2.50; 2.25; 2.00; 1.75; 1.50; 1.25; 0.75 mg/mL; and 5.00 mg/mL for its salts with metals.
3
Phytochemical Screening and Antioxidant Assays
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Quercetin, morin, rutin, pyrogallol, mandelic acid, hydroxy benzoic acid, phloroglucinol and chlorogenic acid, Follin-ciocalteu reagent, sodium carbonate, 2,2-diphenyle-1 picrylhydrazyle [DPPH], aluminum chloride, sodium nitrate, sodium hydroxide, ethanol, methanol, ascorbic acid, distilled water, 5,5-dithio-bis-nitrobenzoic acid (DTNB), 2,2′-azino-bis-3 ethylbenzothiazoline-6-sulfonic acid (ABTS) were all purchased from Sigma Aldrich. Butyrylthiocholine iodide, acetylthiocholine iodide, acetyl cholinesterase from Electric eel (type-VI-S) and butyrylcholinesterase from Equine were obtained from Sigma-Aldrich USA and were used in enzyme inhibition assays. All solvents used in the assays were of HPLC grades purchased from Dae-Jung Korea.
4
Antimicrobial Activity of Essential Oils
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Essential oils (EO) were all obtained from Nobilis Tilia (Czech Republic): cinnamon (CEO), clove (CLEO), lemon (LEO), and thyme (TEO). The chemical composition of EOs is shown in Table S2 (Supplementary) . Data were obtained from Nobilis Tilia (Czech Republic). Mandelic acid (MA), 96% ethanol (Et), and NaOH were purchased from Sigma-Aldrich (MO, USA). All gels prepared in this study (GEOs—gels with EOs; GMAs—gels with Mandelic acid; GEO/MAs—gels with combination of EO and MA; GEts—gels with ethanol) were based on Carbomer (Polygel CA; Mica&Harasta, Czech Republic). SANYTOL with 60% ethanol (Marca, Czech Republic) and BALEA with 45% ethanol (dm-drogerie markt, Germany) were used as commercial ethanol-based hand sanitiser gels.
Diffusion methods were used for four bacterial and two yeast strains. Bacterial strains Escherichia coli CCM 3954, Staphylococcus aureus CCM 3953, Pseudomonas aeruginosa CCM 3955, Micrococcus luteus CCM 734, and yeast strains Candida albicans CCM 8275, and Candida parapsilosis CCM 8276 were supplied by Czech Collection of Microorganisms (Brno, Czech Republic). Bacteria were cultivated on Nutrient agar or Mueller Hinton agar; yeasts were grown on Sabouraud agar (Hi-Media Laboratories Ltd., Mumbai, India).
Diffusion methods were used for four bacterial and two yeast strains. Bacterial strains Escherichia coli CCM 3954, Staphylococcus aureus CCM 3953, Pseudomonas aeruginosa CCM 3955, Micrococcus luteus CCM 734, and yeast strains Candida albicans CCM 8275, and Candida parapsilosis CCM 8276 were supplied by Czech Collection of Microorganisms (Brno, Czech Republic). Bacteria were cultivated on Nutrient agar or Mueller Hinton agar; yeasts were grown on Sabouraud agar (Hi-Media Laboratories Ltd., Mumbai, India).
5
Acetylcholinesterase Inhibition Assay
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AChE (Electron eel type-VI-S) and Aquine BChE along with their substrates acetylthiocholine iodide and butyrylthiocholine iodide, and potassium phosphate buffer (pH 8.0) were purchased from Sigma Aldrich St. Louis, MO, USA. Antioxidant chemicals: DPPH, ABTS, ascorbic acid, malic acid, morin, epigallocatechin gallate, pyrogallol, rutin, quercetin, chlorogenic acid, mandelic acid, hydroxy benzoic acid, and gallic acid along with Folin–Ciocalteu regent were acquired from Sigma Aldrich, Darmstadt, Germany. Donepezil and scopolamine were also purchased from Sigma Aldrich (USA). All these chemicals used were of analytical grade; however, the HPLC solvents were of HPLC grade.
6
Optimized Gene Expression for Protein Studies
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PrimeSTAR® Max DNA polymerase (Takara Biotech, Dalian, China) was used for PCR amplification. The sequence information for AsLOV2-SsrA and SspB was acquired from the Protein Data Bank (4WF0 and 1YFN) and the genes and primers were synthesized (Generay, Shanghai, China) with codon optimized for expression in E. coli. FMN, mandelonitrile, and mandelic acid were purchased from Sigma-Aldrich (Shanghai, China). All other chemicals were purchased from SinopHarm Chemical Reagent Co., Ltd. (Shanghai, China). The BCNIT gene was acquired from our laboratory.
7
Synthesis and Characterization of Protic Ionic Liquids
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All chemical for PILs synthesis were used as purchased from the manufacturer, without further purification: 1-amino-2-propanol (Merck, mass fraction purity ω = 95%), formic acid (Sigma Aldrich, ω = 98%), acetic acid (Centrohem, ω = 99,8%), lactic acid (Sigma Aldrich ω = 98%), trifluoroacetic acid (Sigma Aldrich, ω = 98%), chloroacetic acid (Sigma Aldrich, ω = 99%), trichloroacetic acid (Merck, ω = 99,5%), 3-chloropropanoic acid (Sigma Aldrich, ω = 98%), 4-chlorobutyric acid (Sigma Aldrich, ω = 99%) and mandelic acid (Centrohem, ω = 98%). Nine different protic ionic liquids were synthesized according to the synthetic path presented in Fig. 1 .
In a typical preparation procedure of studied nine PILs, equal molar amount of anion was added dropwise to a 1-amino-2-propanol and cooled in an ice-bath. After addition of the corresponding acid, the reaction mixture was stirred at room temperature for 15 minutes. The obtained ionic liquid was dried under vacuum for the next 30 minutes to 3 hours to remove any traces of water. The obtained liquid products were kept under vacuum desiccator with P2O5 for the next 24 h. After drying, the water content in the PILs was determined by the Karl Fisher titration (using Metrohm 831 Karl Fischer coulometer). The water content was found to be less than 100 ppm in all prepared PILs.
In a typical preparation procedure of studied nine PILs, equal molar amount of anion was added dropwise to a 1-amino-2-propanol and cooled in an ice-bath. After addition of the corresponding acid, the reaction mixture was stirred at room temperature for 15 minutes. The obtained ionic liquid was dried under vacuum for the next 30 minutes to 3 hours to remove any traces of water. The obtained liquid products were kept under vacuum desiccator with P2O5 for the next 24 h. After drying, the water content in the PILs was determined by the Karl Fisher titration (using Metrohm 831 Karl Fischer coulometer). The water content was found to be less than 100 ppm in all prepared PILs.
8
Antioxidant Activity Determination Protocol
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Mandelic acid 98%, 3-hydroxyMandelic acid ≥ 97% and 3,4-dihydroxyMandelic acid 95% were purchased from Sigma Aldrich (Saint Louis, MO, USA), 4-hydroxy-3methoxyMandelic acid 98% was purchased from Alfa Aesor (Kandel, Germany), CuCl2 × 2H2O, FeCl3 × 6H2O, ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), Trolox and H2O2, were purchased from Sigma Aldrich and used without purification. KBr, DPPH (2,2-diphenyl-1-picrylhydrazyl), TPTZ (2,4,6—trypyridyl-s-tirazine), FeCl3, FeSO4 × 7H2O, neocuproine and ammonium acetate were purchased from Sigma Aldrich. Hydrochloric acid (35%), methanol and ethanol (analytical grade) were purchased from Chempur (Poland).
9
Synthesis and Purification of BEDT-TTF
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Synthesis and purification of starting materials BEDT-TTF was purchased from Sigma Aldrich and recrystallised from chloroform. 1,1,2-Trichloroethane, chlorobenzene R-(-)-mandelic acid, S-(+)-mandelic acid, mandelic acid, R-(-)-2-chloromandelic acid, S-(+)-2-chloromandelic acid, 2-chloromandelic acid, boric acid, sodium hydroxide, triethylamine and 18-crown-6 were purchased from Sigma Aldrich and used as received.
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