Analytical grade volatile phenols (guaiacol, 4-methylguaiacol, 4-ethylguaiacol, 4-ethylphenol, o-cresol, m-cresol, p-cresol, and eugenol) and deuterated NMR solvents (d6-ethanol, D2O, and DCl) were purchased from Sigma-Aldrich (Castle Hill, NSW, Australia). Deuterium-labelled internal standards (d3-guaiacol, d3-4-methylguaiacol, and d4-4-ethylphenol) were sourced from CDN Isotopes (Pointe-Claire, Quebec, Canada). Analytical grade ethanol, tartaric acid, and sodium hydroxide were purchased from Thermo Fisher Scientific (Waltham, MA, USA). Food grade (>98% purity) α-, β-, and γ-CDs were supplied by IMCD Group (Adelaide, SA, Australia). Model wine was prepared by dissolving tartaric acid (5 g/L) in aqueous ethanol (12% alcohol by volume) and adjusting the pH to 3.5 by dropwise addition of 1 M sodium hydroxide. Stock solutions of internal standards and volatile phenols were prepared volumetrically in absolute ethanol and stored at −20 °C, with working solutions prepared in model wine and stored at 4 °C.
D6 ethanol
Manufactured by Merck Group
Sourced in Australia, Germany
D6-ethanol is a deuterated form of ethanol, a chemical compound with the molecular formula C2H6O. It is used primarily as a research tool in analytical chemistry and biochemistry, where it serves as a stable isotope label for the study of chemical and biological processes.
Automatically generated - may contain errors
Lab products found in correlation
Sodium hydroxide (naoh), by Thermo Fisher Scientific (1 mentions)
Tartaric acid, by Thermo Fisher Scientific (1 mentions)
Guaiacol, by Merck Group (1 mentions)
4 ethylguaiacol, by Merck Group (1 mentions)
4 ethylphenol, by Merck Group (1 mentions)
Eugenol, by Merck Group (1 mentions)
D3 4 methylguaiacol, by CDN Isotopes (1 mentions)
P cresol, by Merck Group (1 mentions)
D3 guaiacol, by CDN Isotopes (1 mentions)
D4 4 ethylphenol, by CDN Isotopes (1 mentions)
O cresol, by Merck Group (1 mentions)
Analytical grade ethanol, by Thermo Fisher Scientific (1 mentions)
4 methylguaiacol, by Merck Group (1 mentions)
M cresol, by Merck Group (1 mentions)
Penicillin, by Thermo Fisher Scientific (1 mentions)
Streptomycin, by Thermo Fisher Scientific (1 mentions)
Dichloromethane dcm, by Merck Group (1 mentions)
L glutamine, by Thermo Fisher Scientific (1 mentions)
Deuterium oxide d2o, by Merck Group (1 mentions)
4 protocols using d6 ethanol
1
Quantification of Volatile Phenols in Wines
2
SABRE-Mediated Cell Metabolic Profiling
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All chemicals were purchased from Sigma-Aldrich, Fisher or Alfa-Aesar. Deuterated solvents ([D6]ethanol, deuterium oxide (D2O) and dichloromethane (DCM) were purchased from Sigma. The following compounds were prepared according to literature procedures:methyl 4,6-d2 nicotinate, [25b] 4,6-d2-nicotinamide, [25b] methyl-5-d-pyrazinecarboxylate, methyl-6-d-pyrazinecarboxylate, 2,5-d2-isonicotinamide, [25b] 6-dpyrazinamide, 2,5-d2-isonaizid, [IrCl(COD)(IMes)] [40] [IrClCOD)(d2-IMes)], [25b] [IrClCOD)(d22-IMes)] [25b] and [IrClCOD)(d24-IMes)]. [25b] Cell culture and treatment A549 and MCF7 cells were grown in DMEM supplemented with 10% fetal bovine serum (FBS), penicillin (100 U/ml), streptomycin (100 µg/ml) and L-Glutamine (2mM) (all from Gibco, Life Technologies). The cells were maintained in a humidified atmosphere under standard conditions (37°C; 5% CO2). For treating cells with SABRE reaction mixture we followed the same method as illustrated previously [26] . Before treatment various volumes of the SABRE reaction mixture were diluted to a maximum of 10 µl in the same solvent from which the compounds were originally prepared. The final volume of the solvent or reaction mixture was always kept as 10% in the total volume of the cell growth medium (i.e. 10 µl in 100 µl).
3
Aspergillus niger Strain ES4 Isolation and Cultivation
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Aspergillus niger strain ES4 was isolated from a black spot on the outside upper wall of an ethanol tank of a petroleum company by the serial dilution method (Clark, Bordner, Galdrich, Kabler, & Huff,1958 ). It was identified based on morphological characteristics and then confirmed using molecular technique. The nucleotide sequence data were submitted into the DDBJ/EMBL/GenBank nucleotide sequence databases with accession number MK621333.
The fungus was grown on potato dextrose agar for 7 days, before three agar plugs were inoculated in 20 ml of potato dextrose broth and shaken at 180 rpm, room temperature for 3 days. The culture was then diluted 20‐fold into 20 ml of minimal medium (MM; per liter: 6 g NaNO3, 0.52 g KCl, 0.52 g MgSO4.7H2O, 1.52 g KH2PO4, 10 g glucose, 2 ml Hutner's trace elements, pH 6.8) (Barratt, Johnson, & Ogata,1965 ) with ethanol (Merck, absolute, ≥99.9%), water (as control), or ethanol‐d6 (Merck, deuteration degree ≥ 99%; for stable isotope labeling MS) at the indicated concentrations and shaken further until the predetermined time.
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Aspergillus niger strain ES4 was isolated from a black spot on the outside upper wall of an ethanol tank of a petroleum company by the serial dilution method (Clark, Bordner, Galdrich, Kabler, & Huff,
The fungus was grown on potato dextrose agar for 7 days, before three agar plugs were inoculated in 20 ml of potato dextrose broth and shaken at 180 rpm, room temperature for 3 days. The culture was then diluted 20‐fold into 20 ml of minimal medium (MM; per liter: 6 g NaNO3, 0.52 g KCl, 0.52 g MgSO4.7H2O, 1.52 g KH2PO4, 10 g glucose, 2 ml Hutner's trace elements, pH 6.8) (Barratt, Johnson, & Ogata,
4
Synthesis of Deuterated NADD Stereoisomers
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The (4-R)-(4-2H) and (4-S)-(4-2H) stereoisomers of reduced nicotinamide adenine dinucleotide (NADD) were prepared based on procedures described by Viola et al., 197840 (link). Ethanol-d6, glucose-1-d, Saccharomyces cerevisiae alcohol dehydrogenase, S. cerevisiae aldehyde dehydrogenase and Leuconostoc mesenteroides glucose-6-phosphate dehydrogenase were purchased from Merck KGaA (Darmstadt, Germany). Synthesized NADD was purified by anion exchange chromatography using a 6 mL Resource 15Q column (GE Healthcare). To this end, the complete reaction mixture was loaded onto the column equilibrated with buffer A (20 mM tris-HCl, pH 7.7) and eluted with a gradient to 40% buffer B (20 mM tris-HCl, 500 mM KCl, pH 7.7) over 60 ml at 1 ml min−1 flow. NADD eluted at approximately 8.5% buffer B. Purity was monitored by A260 to A340 absorbance ratio for all collected fractions. Fractions with a A260/A340 of ≤2.3, indicating fully reduced NADD, were pooled, assayed for deuterium content by LC/MS (Supplementary Fig. 14 ) and lyophilized.
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