High-resolution mass spectrometry (HRMS) and liquid chromatography mass spectrometry (LCMS) were conducted on an Agilent 6545-QTOF W/1290 HPLC mass spectrometer at the University of Oklahoma Department of Chemistry and Biochemistry. NMR spectra were obtained on Varian VNMRS 400 or 500 MHz instruments at the NMR facility of the Department of Chemistry and Biochemistry of the University of Oklahoma using 99.9% DMSO-d6 with 0.05% v/v TMS or 99.9% D2O or 99.8% MeOH-d4 and 99.9% acetone-d6 (Cambridge Isotope Laboratories, MA, USA). 1H, 13C, and 31P chemical shifts were referenced to internal solvent resonances. Multiplicities are indicated by s (singlet), d (doublet), t (triplet), q (quartet), quin (quintet), m (multiplet), and br (broad). Chemical shifts are reported in parts per million (ppm) and coupling constants J are given in Hz. All NMR spectra were recorded at ambient temperature and processed using MestReNova software.
Acetone d6
Manufactured by Cambridge Isotopes
Sourced in United States
Acetone-d6 is a deuterated organic solvent manufactured by Cambridge Isotopes. It is used as a reference compound in nuclear magnetic resonance (NMR) spectroscopy.
Automatically generated - may contain errors
Lab products found in correlation
Dmso d6, by Cambridge Isotopes (3 mentions)
Dimethyl sulfoxide d6, by Cambridge Isotopes (2 mentions)
Nmr tube, by Wilmad (2 mentions)
Hplc spectro grade acetone, by Merck Group (2 mentions)
Vanb 1, by Thermo Fisher Scientific (2 mentions)
Methanol d4, by Cambridge Isotopes (2 mentions)
Meoh d4, by Cambridge Isotopes (1 mentions)
Vnmrs 400, by Agilent Technologies (1 mentions)
6545 qtof w 1290 hplc mass spectrometer, by Agilent Technologies (1 mentions)
Chloroform d, by Cambridge Isotopes (1 mentions)
Unity inova 500 mhz, by Agilent Technologies (1 mentions)
Benzene d6, by Cambridge Isotopes (1 mentions)
Dimethyl sulfoxide (dmso), by Thermo Fisher Scientific (1 mentions)
Acn d3, by Cambridge Isotopes (1 mentions)
Sudan 1, by Merck Group (1 mentions)
Ethanol, by Thermo Fisher Scientific (1 mentions)
Methanol, by Thermo Fisher Scientific (1 mentions)
Isopropanol, by Thermo Fisher Scientific (1 mentions)
Acetone, by Thermo Fisher Scientific (1 mentions)
N propanol, by Thermo Fisher Scientific (1 mentions)
12 protocols using acetone d6
1
High-Resolution Mass Spectrometry Protocols
2
NMR Characterization of Organic Compounds
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All NMR experiments
were performed
at 25 °C on a Varian Unity Plus 300 spectrometer or Varian Unity-Inova
500 MHz spectrometer equipped with a 5 mm triple-resonance 1H(13C/15N), z-axis pulsed-field
gradient probe head. For characterization purposes, samples consisted
of a ∼5 mM solution of each compound in chloroform-d (99.8% D, Cambridge Isotopes), dimethyl sulfoxide-d6 (99.9% D, Cambridge Isotopes), benzene-d6 (99.5%
D, Cambridge Isotopes) or acetone-d6 (99.9%
D, Cambridge Isotopes), and the spectra were referenced to residual
solvent peaks at 7.27, 2.50, 7.16, and 2.05 ppm, respectively. 1H-1D spectra were acquired at a resolution of 16k complex
points in the time domain with 32 accumulations each (sw = 6000 Hz,
d1 = 3 s).
were performed
at 25 °C on a Varian Unity Plus 300 spectrometer or Varian Unity-Inova
500 MHz spectrometer equipped with a 5 mm triple-resonance 1H(13C/15N), z-axis pulsed-field
gradient probe head. For characterization purposes, samples consisted
of a ∼5 mM solution of each compound in chloroform-d (99.8% D, Cambridge Isotopes), dimethyl sulfoxide-d6 (99.9% D, Cambridge Isotopes), benzene-d6 (99.5%
D, Cambridge Isotopes) or acetone-d6 (99.9%
D, Cambridge Isotopes), and the spectra were referenced to residual
solvent peaks at 7.27, 2.50, 7.16, and 2.05 ppm, respectively. 1H-1D spectra were acquired at a resolution of 16k complex
points in the time domain with 32 accumulations each (sw = 6000 Hz,
d1 = 3 s).
3
Extraction and Quantification of Sudan I in Paprika
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Sudan I (≥95% purity) was purchased from Sigma Aldrich (Oakville, Ontario). Reagent grade acetonitrile (ACN) and dimethyl sulfoxide (DMSO) was acquired from Fisher Scientific (Toronto, ON). Deuterated solvents including DMSO-d6, ACN-d3, and acetone-d6 were obtained from Cambridge Isotope Laboratories (Tewksbury, MA). Three bags of paprika powder samples of the same brand were purchased from local grocery stores in Vancouver, Canada. Sudan I stock solution at 2500 mg L−1 in ACN and DMSO were prepared using 50 mL volumetric flasks.
4
Isotopic Standards for Stable Isotope Analysis
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Acetone-d6, [13C2]ethanol and [13C2]acetic acid (both materials containing 0.99 mol/mol enrichment of 13C), and dimethyl sulfoxide-d6 were obtained from Cambridge Isotope Laboratories (Andover, MA, USA). Chromium acetylacetonate (Cr(Acac)3, 99%) and HPLC/Spectro grade acetone were obtained from Sigma-Aldrich (Oakville, ON, Canada). IRMS reference materials, IAEA‐CH‐6, USGS65, IAEA-600, NBS22, USGS61, IAEA-603, IAEA-610, IAEA-611, and IAEA-612 were obtained from the International Atomic Energy Agency.
NMR tubes (5 mm inner diameter) were obtained from Wilmad LabGlass (Buena, NJ, USA). Two high-purity synthetic vanillin materials were obtained from NRC [24 (link)]. Maleic acid (SRM grade, TraceCERT®, having a purity of 0.9989 ± 0.0031 g/g) was obtained from Fluka. VANA-1 and VANB-1 are both synthetic high-purity vanillin materials obtained from Fisher Scientific, Waltham, MA, USA) and from Sigma-Aldrich (St. Louis, MO, USA), respectively.
NMR tubes (5 mm inner diameter) were obtained from Wilmad LabGlass (Buena, NJ, USA). Two high-purity synthetic vanillin materials were obtained from NRC [24 (link)]. Maleic acid (SRM grade, TraceCERT®, having a purity of 0.9989 ± 0.0031 g/g) was obtained from Fluka. VANA-1 and VANB-1 are both synthetic high-purity vanillin materials obtained from Fisher Scientific, Waltham, MA, USA) and from Sigma-Aldrich (St. Louis, MO, USA), respectively.
5
Procurement of Chemical Standards
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Commercially available methanol, ethanol, isopropanol, n-propanol, and acetone were obtained from Fisher Scientific (Hampton, NH, USA) and acetaldehyde was obtained from Thermo Scientific (Waltham, MA, USA). Heavy isotopes were obtained from the following sources: methanol-d4, ethanol-d6, acetone-d6 (Cambridge Isotopes, Tewksbury, MA, USA), isopropanol-d8 (Thermo Chemicals, Waltham, MA, USA), and acetaldehyde-d4 (Fisher Scientific, Hampton, NH, USA).
6
Enzymatic Synthesis of Benzyloxybenzaldehyde Derivatives
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3,4-dibenzyloxybenzaldehyde (98%, Sigma-Aldrich, Milwaukee, WI, USA), methyl chloroacetate (99%, Sigma-Aldrich, USA), CDCl3 and acetone-d6 (D, 99.8%, Cambridge Isotope Laboratories, Inc. Andover, MA, USA) and dimethyl sulfoxide, DMSO (99.5%, Carlo Erba, Cornaredo, Italy) were used without further purification. Tetrahydrofuran, THF (anhydrous 99.9%), toluene (anhydrous, 99.8%), 2,5-dihydroxybenzoic acid, DHB (98%), lipase from Candida rugosa (≥700 U/mg), and Amano lipase G from Penicillium camemberti (≥5000 U/mg) were all purchased from Sigma-Aldrich, USA, and were used as received.
7
Purification and Characterization of Monomers
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The monomers, methyl methacrylate (MMA, 99%, Sigma-Aldrich, St. Louis, MO, USA) and ethylene glycoldimethacrylate (EGDMA, 98%, Sigma-Aldrich) were purified prior to the experiments by passing the neat liquids through a short column filled with basic alumina in order to remove the polymerization inhibitor. The radical initiator 2,2’-azobis(2,4-dimethyl-4-methoxyvaleronitrile (V-70) was purchased from Wako (Neuss, Germany), and acetone-d6 and chloroform-d1 (99.9% of D atoms) were purchased from Cambridge Isotope Laboratories (Tewksbury, MA, USA). Twenty five mg of a single diastereomer of the 1,4 diketone was kindly donated by the List group, and was a product of an asymmetric cross coupling catalysis reaction [34 (link)]. About 2 mg of “pseudo”-mandelalide and 11-epi-“pseudo”-mandelalide (recognized as isomers of mandelalide A as a result of its synthesis, following the inversion of the northern part) were obtained from the Fürstner group as the end product of a multistep synthesis by Willwacher et al. [41 (link)]
8
Synthesis and Characterization of Fluorinated Compounds
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Example 2
Overall Experimental
Bromoethane, copper(I) oxide, bromine, anhydrous N,N-dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), charcoal, and 1,4-dioxane were purchased from Sigma Aldrich. Phenothiazine and copper iodide were obtained from Acros Organics. Sodium hydride, sodium acetate, and acetic acid were purchased from Alfa Aesar. Pentafluorothiophenol and sodium pentafluoropropionate were purchased from Oakwood Chemical, iron powder from Mallinckrodt Pharmaceuticals, 2,3,4,5-tetrafluoroaniline from AK Scientific, potassium hydroxide and celite from Fisher Scientific, and ethanol from Decon Labs. All reagents were used without further purification.
Silica gel (65×250 mesh) was purchased from Sorbent Technologies, and solvents for purification were purchased from VWR International. 1H, 19F and 13C NMR spectra were obtained on 400 MHz Varian NMR spectrometers in DMSO-d6, acetone-d6 or CDCl3 purchased from Cambridge Isotope Laboratories. 19F NMR spectra were recorded in CDCl3 using hexafluorobenzene (Alfa Aesar) as an internal standard, and the chemical shifts are reported vs. CFCl3 at 0 ppm by adjusting the shift of hexafluorobenzene to −164.9 ppm. Mass spectra were obtained on an Agilent 5973 Network mass-selective detector attached to Agilent 6890N Network GC system. Elemental analyses were performed by Atlantic Microlab, Inc.
9
Vanillin Isotopic Characterization
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Acetone-d6 was
purchased from Cambridge Isotope Laboratories (Andover, MA, USA).
Chromium acetylacetonate Cr(Acac)3, 99% and HPLC/Spectro
grade acetone were obtained from Sigma-Aldrich (Oakville, ON, Canada).
IRMS reference materials IAEA-CH-6, USGS65, IAEA-600, NBS22, USGS61,
IAEA-603, IAEA-610, IAEA-611, and IAEA-612 were obtained from the
International Atomic Energy Agency. NMR tubes (5 mm diameter) were
obtained from Wilmad LabGlass (Buena, New Jersey, USA). Five vanillin
materials, VANA-1, VANB-1 (NMR analysis in previous study4 (link)), VAN-1, VAN-4, and VAN-8 (NMR analysis in this
study; GC-IRMS of all five vanillin samples in this study), are all
synthetic materials of high chemical purity (≥99%) obtained
from Fisher Scientific (Waltham, MA, USA), Sigma-Aldrich (St. Louis,
MO, USA), Alfa Aesar (product of USA), and Sigma-Aldrich (product
of China), respectively.
purchased from Cambridge Isotope Laboratories (Andover, MA, USA).
Chromium acetylacetonate Cr(Acac)3, 99% and HPLC/Spectro
grade acetone were obtained from Sigma-Aldrich (Oakville, ON, Canada).
IRMS reference materials IAEA-CH-6, USGS65, IAEA-600, NBS22, USGS61,
IAEA-603, IAEA-610, IAEA-611, and IAEA-612 were obtained from the
International Atomic Energy Agency. NMR tubes (5 mm diameter) were
obtained from Wilmad LabGlass (Buena, New Jersey, USA). Five vanillin
materials, VANA-1, VANB-1 (NMR analysis in previous study4 (link)), VAN-1, VAN-4, and VAN-8 (NMR analysis in this
study; GC-IRMS of all five vanillin samples in this study), are all
synthetic materials of high chemical purity (≥99%) obtained
from Fisher Scientific (Waltham, MA, USA), Sigma-Aldrich (St. Louis,
MO, USA), Alfa Aesar (product of USA), and Sigma-Aldrich (product
of China), respectively.
10
Kraft Pulping of Hardwood Feedstocks
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The KL used in this study was kindly provided by Moorim P&P Co., Ltd. (Ulsan, Korea), the only kraft pulp manufacturer in Korea. The wood chips used in kraft pulping were also provided by the same company. Two types of wood chips, namely, from Acacia spp. imported from Vietnam and mixed hardwood locally available in Korea (50% Quercus spp. + 50% other hardwoods), were ground and wood meals which passed through 40-mesh screen were prepared.
The reagents used were ethanol (HPLC grade), benzene (EP), and acetic anhydride (EP) from Duksan Pure Chemical (Ansan, Korea), 1,2-dichloroethane (GR) from Duksan Pharmaceutical (Ansan, Korea), anhydrous ethyl ether (EP) and acetic acid (EP) from Samchun Chemical (Pyeongtaek, Korea), 1,4-dioxane (HPLC grade) from Wako Chemical (Osaka, Japan), pyridine (GR) from Kanto Chemical (Tokyo, Japan), and toluene (HPLC grade) from Fisher-Scientific Korea (Seoul, Korea). The deuterated solvents used were D2O (Merck, Darmstadt, Germany), CDCl3 (Eurisotop, Saint-Aubin, France), and acetone-d6 (Cambridge Isotope Laboratories, Andover, MA, USA). All reagents were used without further purification.
The reagents used were ethanol (HPLC grade), benzene (EP), and acetic anhydride (EP) from Duksan Pure Chemical (Ansan, Korea), 1,2-dichloroethane (GR) from Duksan Pharmaceutical (Ansan, Korea), anhydrous ethyl ether (EP) and acetic acid (EP) from Samchun Chemical (Pyeongtaek, Korea), 1,4-dioxane (HPLC grade) from Wako Chemical (Osaka, Japan), pyridine (GR) from Kanto Chemical (Tokyo, Japan), and toluene (HPLC grade) from Fisher-Scientific Korea (Seoul, Korea). The deuterated solvents used were D2O (Merck, Darmstadt, Germany), CDCl3 (Eurisotop, Saint-Aubin, France), and acetone-d6 (Cambridge Isotope Laboratories, Andover, MA, USA). All reagents were used without further purification.
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