Ethyl acetoacetate

Manufactured by Thermo Fisher Scientific

Sourced in United States, Germany

Ethyl acetoacetate is a chemical compound used in various laboratory applications. It serves as a versatile reagent and precursor in organic synthesis. Its core function is to provide a source of the acetoacetate moiety for various chemical transformations.

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Lab products found in correlation

9 protocols using ethyl acetoacetate

Enzymatic Conversion of Prochiral Ketones

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Acetobacter pasteurianus GIM1.158 was purchased from Guangdong Culture Collection Center. Other strains (Acetobacter sp. CCTCC M209061, Bacillus cereus AS1.126, Pseudomonas putica GIM1.193, Candida parapsilosis CCTCCM203011, Candia tropicalis CICC1316, Saccharomyces cerevisiae GIM 2.34, Rhodotorula sp. AS2.2241, Pseudomonas oleovorans GIM1.304) used in this work were kept in our laboratory (Lab of Applied Biocatalysis, South China University of Technology, China).
2-Octanone (99% purity) and ethyl acetoacetate were purchased from Alfa Aesar (USA). (R)-2-Octanol (98% purity) and (S)-2-octanol (98% purity) were from Sigma-Aldrich (USA). Other prochiral ketones and the corresponding alcohols were obtained from Aldrich-Fluka and were all over 97% purity. All other chemicals were from commercial sources and were of analytical grade.

Du P.X., Wei P., Lou W.Y, & Zong M.H. (2014). Biocatalytic anti-Prelog reduction of prochiral ketones with whole cells of Acetobacter pasteurianus GIM1.158. Microbial Cell Factories, 13, 84.

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Bioconversion of 2-Octanone to (R)-2-Octanol

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Acetobacter pasteurianus GIM1.158 was purchased from Guangdong Culture Collection Center. 2-Octanone (99% purity) and ethyl acetoacetate were purchased from Alfa Aesar (USA). (R)-2-Octanol (98% purity) and (S)-2-octanol (98% purity) were from Sigma-Aldrich (USA). The five ILs used in this work, shown in Table 1, were purchased from Lanzhou Institute of Chemical Physics (China). All other chemicals were from commercial sources and were of analytical grade.

Xu P., Du P.X., Zong M.H., Li N, & Lou W.Y. (2016). Combination of deep eutectic solvent and ionic liquid to improve biocatalytic reduction of 2-octanone with Acetobacter pasteurianus GIM1.158 cell. Scientific Reports, 6, 26158.

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Heterogeneous Catalytic Synthesis Protocol

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As received, ethyl acetoacetate, n-butylamine, resorcinol, acetonitrile, pyridine, cesium nitrate (CsNO₃), ammonium hydroxide (NH₄OH), zirconium oxynitrate (ZrO(NO₃)₂), 12-tungstophosphoric acid (H₃PW₁₂O₄₀:PW), methylene blue (MB), and sulfuric acid (H₂SO₄) were obtained from Alfa Aeser. Both cetyltrimethylammonium bromide (N-cetyl-N,N,N-trimethyl ammonium bromide, CTAB) and tetraethyl orthosilicate (TEOS) were analytical-grade reagents.

Ibrahim A.A., Kospa D.A., Hayes O.R., Khder A.S., El-Hakam S.A, & Ahmed A.I. (2023). Cesium salt of tungstophosphoric acid/mesoporous (zirconia–silica) composite for highly efficient synthesis of 7-hydroxy-4-methyl coumarin and removal of methylene blue. RSC Advances, 13(22), 15243-15260.

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Optimization and Characterization of Novel Compounds

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Ethyl acetoacetate, DPPH, ABTS, deuterated dimethyl sulfoxide, and salicylaldehyde and its hydroxylated derivatives were purchased from Alfa Aesar (Kandel, Germany). Absolute ethanol, piperidine, deuterated chloroform, thiosemicarbazide, and acetic acid were purchased from Merck (Milan, Italy). Reagents were used as received without further purification.
NMR spectra were acquired with a Bruker Advance III HD 600 spectrometer (Rheinstetten, Germany) at room temperature with tetramethylsilane (TMS) as the internal standard in DMSO-d6 or CDCl₃. ESI mass spectra were recorded with a triple quadrupole QqQ Varian 310-MS mass spectrometer (Palo Alto, CA, USA) using previously optimized parameters [5 (link)]. High-resolution ESI mass spectra were acquired on a Thermofisher ORBITRAP-ELITE (Waltham, MA, USA). Melting points were measured on a Kofler Hot Stage (Rochford, UK) and are uncorrected.

Masuri S., Era B., Pintus F., Cadoni E., Cabiddu M.G., Fais A, & Pivetta T. (2023). Hydroxylated Coumarin-Based Thiosemicarbazones as Dual Antityrosinase and Antioxidant Agents. International Journal of Molecular Sciences, 24(2), 1678.

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Surface Modification of Glass Coverslips

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Trichloroethylene (TCE) (99%), tetrahydrothiophene (98%), nitroethane (98%), nitromethane (98%), ethyl acetoacetate (EAA) (99%), and glycine (99.5%) were from Alfa Aesar. Chloroform (99.8%) was from BDH Chemicals. Dichloromethane (99.5%) was from Sigma-Aldrich. Ethyl acetate (99.9%) was from Fisher Chemical. Nile red (99%, Acros Organics) was dissolved in dimethyl sulfoxide to form a 3 mM stock solution and kept at −20 °C. Glass coverslips (25 mm circle, VWR) were cleaned with a heated piranha solution (75% sulfuric acid and 25% hydrogen peroxide), and then rinse with Milli-Q water (18.4 MΩ cm), thus rendering a highly hydrophilic surface. After blown dry with nitrogen, the coverslip was immersed into a chosen liquid for 3 hr, and then let dry in air.

Xiang L., Wojcik M., Kenny S.J., Yan R., Moon S., Li W, & Xu K. (2018). Optical characterization of surface adlayers and their compositional demixing at the nanoscale. Nature Communications, 9, 1435.

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Enzymatic Synthesis of NAD Cofactors

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Nicotinamide adenine dinucleotides (NAD⁺, NADH, NADP⁺ and NADPH) were purchased from Carbosynth (Berkshire, UK). Ethyl acetoacetate (EAA), ethyl 3-hydroxybutyrate, ethyl 2-chloroacetoacetate and ethyl 4-chloroacetoacetate were purchased from Alfa Aesar (Karlsruhe, Germany). Alcohols, ketones and aldehydes were supplied by Sigma-Aldrich (St. Louis, IL). Polyethyleneimine (PEI) (MW. 25–60 kDa) and polyallylamine (PAA) (MW. 17 kDa) were purchased from Sigma-Aldrich (St. Louis, IL, USA). Plain 6BCL agarose was purchased from Agarose Beads Technologies (Madrid, Spain). Protein concentrations were determined using BCA Protein Assay Kit from Pierce (Rockford, IL, USA). Enzymatic assays were carried out on a V-730 spectrophotometer from JASCO Analitica Spain S.L. (Madrid, Spain). Buffers, mediums and other reagents were obtained from Sigma-Aldrich Co. (St. Louis, IL, USA). Single particle experiments were carried out on a Cytation 5 cell image multi-mode reader from Biotek Instruments Inc. (Winooski, VT, USA). The gene from formate dehydrogenase (FDH) from Candida boidinii were synthetized and cloned in pET28b by GenScript (Piscataway, USA).

Orrego A.H., Andrés-Sanz D., Velasco-Lozano S., Sanchez-Costa M., Berenguer J., Guisan J.M., Rocha-Martin J, & López-Gallego F. (2021). Self-sufficient asymmetric reduction of β-ketoesters catalysed by a novel and robust thermophilic alcohol dehydrogenase co-immobilised with NADH. Catalysis Science & Technology, 11(9), 3217-3230.

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Determination of Free CaO in Fly Ash

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Free calcium oxide (CaO) (W_CaO) content was determined according to PN-EN 451-1:2017 [38 ]. In this method, 1 ± 0.001 g of fly ash was weighed in a 0.25 dm³ flask and refluxed with mixture containing 0.012 dm³ of ethyl acetoacetate (99% + pure, Acros Organics, Geel, Belgium) and 0.080 dm³ of butan-2-ol for 3 h. Next, the mixture was centrifuged and filtrated, and the residue was washed with 0.050 dm³ of propan-2-ol. The filtrate was titrated using 0.1 mol dm⁻³ HCl (Avantor, Gliwice, Poland) and bromophenol blue as indicator (yellow color of the solution indicates the end of titration). W_CaO content was calculated using Equation (1):

W_{C a O} = \frac{28.04 \times 0.1 \times V}{m} \times 100 %

where 28.04 (g mol⁻¹) is ½ mass of CaO; 0.1 (mol dm⁻³) is the concentration of HCl solution, V (dm³) is the volume of HCl solution used for titration, and m (g) is the mass of fly ash used for analysis.

Mokrzycki J., Baran P., Gazda-Grzywacz M., Bator J., Wróbel W, & Zarębska K. (2023). Decarbonatization of Energy Sector by CO2 Sequestration in Waste Incineration Fly Ash and Its Utilization as Raw Material for Alkali Activation. Materials, 16(18), 6094.

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Organic Solvents and Reagents Usage

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Common
organic solvents and reagents were
obtained from commercial suppliers and used as received. Sodium hydride
(60% in mineral oil), diethyl malonate (99%), acetylacetone (99%),
malononitrile (99%), and lithium hexamethyldisilazide (LiHMDS, 1M
in THF) were obtained from Aldrich Chemical Company, Inc., and were
used without further purification. Ethyl cyanoacetate (99%) and ethyl
benzoylacetate (99%) were obtained from TCI Chemicals and were used
without further purification. Ethyl acetoacetate (99%) was obtained
from Acros Organics and was used without further purification. Chloroform-d (CDCl₃, 99.9% D), acetonitrile-d₃ (CD₃CN, 99.9% D), and dimethyl sulfoxide-d₆ (DMSO-d₆, 99.9%
D) were obtained from Cambridge Isotope Laboratories, Inc., and were
used without further purification.

Shrinidhi A, & Perrin C.L. (2022). Nucleophilic Addition of Enolates to 1,4-Dehydrobenzene Diradicals Derived from Enediynes: Synthesis of Functionalized Aromatics. ACS Omega, 7(26), 22930-22937.

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Synthesis of Ionic Liquid-Catalyzed Organic Reactions

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The investigated ionic liquid (1-ethyl-3-methylimidazolium tetrafluoroborate) (Fig. 1) were supplied by Sigma Aldrich (South Africa), ethyl acetoacetate was supplied by Acros Organics New Jersey (USA) and benzaldehyde was supplied by Merck (South Africa) with stated purity of ≥99.5% (GC) for both chemicals and were used as received. The content of water of the ionic liquid used was removed by the use of vacuum treatment at 340 K under reduced pressure of 5 × 10⁻² Pa. The content of water was examined by the use of Karl-Fischer auto titrator before commencement of the experimental work. The ionic liquid mass percent water content was found to be 340 × 10⁻⁶ % and the purity was ≥98% (determined by HPLC).Fig. 1

Structure of the ionic liquid (1-ethyl-3-methylimidazolium tetrafluoroborate) used in this study.

Fig. 1

Kabane B., Chokkareddy R, & Redhi G.G. (2019). Molecular interaction studies of binary systems comprising [C2mim] [BF4] with ethyl acetoacetate or benzaldehyde. Heliyon, 5(5), e01548.

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