Methanol d4

Manufactured by Eurisotop

Sourced in France

Methanol-d4 is a deuterated form of methanol, a chemical compound with the molecular formula CH3OD. It is used as a solvent and reagent in various analytical and research applications.

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6 protocols using methanol d4

Iridium-Catalyzed Organic Transformations

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Chemicals (1a–1c and 2a–2d) and deuterated
solvents (methanol-d₄, CD₃OD,
99.8 atom %D, Eurisotop, and dimethyl sulfoxide-d₆, CD₃SOCD₃, 99.8 atom %D, Eurisotop)
were also used in the form obtained. In the experiment, pre-catalysts
{[Ir(IMes) (COD)Cl] and [Ir(COD) (PCy₃) (py)]PF₆)] (2 mg, 3.1 μmol)} and substrates (1a–1c, 3a–3b, and 4a-4b, 31 μmol) were dissolved in a deuterated solvent (900 μL).

Jeong H.J., Min S., Baek J., Kim J., Chung J, & Jeong K. (2023). Real-Time Reaction Monitoring of Azide–Alkyne Cycloadditions Using Benchtop NMR-Based Signal Amplification by Reversible Exchange (SABRE). ACS Measurement Science Au, 3(2), 134-142.

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Sample Preparation for NMR Analysis

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A stock solution of methanol-d₄ (99.8% D, Euriso-Top GmbH, Saarbrücken, Germany) with 0.02% v/v HMDSO (NMR grade, ≥ 99.5%, Sigma-Aldrich Corporation, St. Louis, MO, USA) as an IS and a line-shape indicator was prepared. Each sample was dissolved within the eppendorf in 700 μL of the deuterated stock solution, sonicated for 30 s and centrifuged (MIKRO 200R, Andreas Hettich GmbH & Co. Tuttlingen, Germany) at 14,000 rpm for 5 min. The supernatant (550 μL) was transferred via a 1-mL Hamilton glass syringe and placed in a 5 mm NMR tube (D400-5-7) with a PTFE cap (both obtained by Deutero GmbH, Kastellaun, Germany).

Beteinakis S., Papachristodoulou A., Gogou G., Katsikis S., Mikros E, & Halabalaki M. (2020). NMR-Based Metabolic Profiling of Edible Olives—Determination of Quality Parameters. Molecules, 25(15), 3339.

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Enzyme Inhibition Assay for Antioxidants

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Pyridine (99.8%), glutaraldehyde, hydroxylamine hydrochloride, sodium cyanoborohydride, ammonium acetate, methanol, acetonitrile, quercetin, kaempferol, myricetin, luteolin, caffeine, ferulic acid, acarbose, p-nitrophenyl α-d-glucopyranoside (p-NPG), and α-glucosidase type I (EC 3.2.20, from Saccharomyces cerevisiae, lyophilized powder) were obtained from Sigma-Aldrich (St. Louis, MO, USA). BcMag amine-terminated magnetic beads (30 mg/mL, 1 μm) were purchased from Bioclone (San Diego, CA, USA). methanol-d₄ was purchased from Eurisotop (Gif-Sur-Yvette Cedex, France). Water was purified by deionization and 0.22 μm membrane filtration using a Millipore system (Billerica, MA, USA), and other solvents were all analytical grade.

Wubshet S.G., Brighente I.M., Moaddel R, & Staerk D. (2015). Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: α-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae. Journal of natural products, 78(11), 2657-2665.

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Characterization of Bioactive Compounds by NMR Spectroscopy

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Deuterated water (D₂O) 99.97% D, methanol-D₄ 99.80% D, chloroform-D 99.80% D + 0.03% Tetramethylsilane (TMS), and 3-(trimethylsilyl)-propionic-2,2,3,3-d₄ acid sodium salt (TSP) were purchased from Euriso–Top (Saclay, France). Anhydrous sodium carbonate (Na₂CO₃), anhydrous potassium phosphate dibasic, anhydrous potassium phosphate monobasic and HPLC chemical standards (chlorogenic acid, caffeic acid, ferulic acid, gallic acid, and galacturonic acid) were purchased from Sigma–Aldrich (St. Louis, MO, USA). Methanol (HPLC-grade), chloroform (HPLC-grade), and glacial acetic acid were purchased from Carlo Erba Reagenti (Milan, Italy). Double-distilled water was obtained using a Millipore Milli-Q Plus water treatment system (Millipore Bedford Corp., Bedford, MA, USA).

Ingallina C., Spano M., Sobolev A.P., Esposito C., Santarcangelo C., Baldi A., Daglia M, & Mannina L. (2020). Characterization of Local Products for Their Industrial Use: The Case of Italian Potato Cultivars Analyzed by Untargeted and Targeted Methodologies. Foods, 9(9), 1216.

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Deuterated Solvents for NMR Analysis

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Deuterated water (D₂O) 99.97% D, methanol-D4 99.80% D, chloroform-D 99.80% D + 0.03% tetramethylsilane (TMS), and 3-(trimethylsilyl)-propionic-2,2,3,3-d4 acid sodium salt (TSP) were purchased from Euriso–Top (Saclay, France). Anhydrous potassium phosphate dibasic (K₂HPO₄) and anhydrous potassium phosphate monobasic (KH₂PO₄) were purchased from Sigma–Aldrich (St. Louis, MO, USA). Methanol (HPLC-grade) and chloroform (HPLC-grade) were purchased from Carlo Erba Reagenti (Milan, Italy). Millipore grade water was purchased from Tito Menichelli S.r.l. (Rome, Italy).

Di Matteo G., Spano M., Esposito C., Santarcangelo C., Baldi A., Daglia M., Mannina L., Ingallina C, & Sobolev A.P. (2021). NMR Characterization of Ten Apple Cultivars from the Piedmont Region. Foods, 10(2), 289.

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Comprehensive HPLC-ESI-MS and NMR Analysis

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HPLC-ESI-MS analysis. HPLC-ESI-MS was carried out in switch (positive/negative) ion mode using an Agilent 1100 Series liquid chromatography HPLC system (Agilent, Palo Alto, CA, USA) coupled with a Thermo Finnigan LCQ Advantage ion trap mass spectrometer (Thermo Fisher Scientific, San Jose, CA, USA) and equipped with an ESI source. The HPLC system included a binary pump, a thermostated autosampler, a column oven, and a diode array detector. A Gemini C18 column (150 mm × 3 mm, 3 µm; Phenomenex, Torrance, CA, USA) was used with an injection volume of 5 L and a flow rate of 0.3 mL/min. All samples were filtered through 0.2 µm sterile membranes before HPLC-MS analysis. The HPLC gradient used water (A) and ACN (B) (both acidified with 0.1% formic acid) as follows: 10%-100% B in 10 minutes and 100%-100% B in 4 minutes. The MS instrument parameters were: nebulization gas, N 2 , 50 a.u. sheath and 10 a.u. auxiliary gas flow; spray voltage, ±4.5 kV; capillary temperature, 275 °C; capillary voltage, -10 V; tube lens offset, -50 V.
NMR Analysis. NMR spectra of daphnetin and daphnoretin were acquired on a Bruker 500 MHz Avance III spectrometer (Bruker Biospin, Rheinstetten, Germany). Methanol-d4 (Euriso-Top, Saint-Aubin, France) was used as a deuterated solvent and its protonated residual signals were used as an internal standard at 3.31 ppm relative to trimethylsilane.

Amari N.O., Razafimandimby B., Auberon F., Azoulay S., Fernández X., Berkani A., Bouchara J., & Landreau A. (2021). Antifungal and Antiaging Evaluation of Aerial Part Extracts ofThymelaea hirsuta(L.) Endl. Natural Product Communications, 16(2), 1934578X2098793-1934578X2098793.

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