3424-59-7

Usage

Uses

Used in Chemical Research:
ETHYL ACETATE (1-13C) is used as a research tool for studying chemical reactions and metabolic processes due to its 13C labeling, which facilitates the tracking of carbon atom movement and transformations in compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, ETHYL ACETATE (1-13C) is utilized as a key intermediate in the synthesis of various drugs, leveraging its properties to enhance the development of new medicinal compounds.
Used in Flavoring Agent for Food Products:
ETHYL ACETATE (1-13C) is employed as a flavoring agent in the food industry, where its sweet, fruity odor contributes to the sensory characteristics of food products.
Used in Production of Adhesives, Inks, and Coatings:
ETHYL ACETATE (1-13C) is used as a solvent in the manufacturing process of adhesives, inks, and coatings, capitalizing on its solvent properties to improve the performance and quality of these products.
Used in NMR Spectroscopy:
In analytical chemistry, ETHYL ACETATE (1-13C) is used as a reference compound in NMR spectroscopy, taking advantage of its 13C labeling to provide accurate spectral data for compound characterization.
Used in Metabolic Flux Analysis:
In the field of metabolic studies, ETHYL ACETATE (1-13C) is applied in metabolic flux analysis to trace the flow of metabolites and understand the dynamics of metabolic pathways within biological systems.

Upstream product

• 23424-28-4 sodium acetate 
• 75-03-6 ethyl iodide 
• 64-67-5 diethyl sulfate 
• 122-52-1 triethyl phosphite 
• 64-17-5 ethanol 
• 108-05-4 vinyl acetate 

Downstream Products

• 23424-28-4 sodium acetate 
• 868943-98-0 C₁₁⁽¹³⁾C₂H₂₄O₃ 
• 481036-67-3 1,4-dimethyl-[1-13C]cyclohexanol 
• 77504-73-5 ethyl acetoacetate-2,4-¹³C₂ 

Relevant academic research and scientific papers

Toward production of pure 13C hyperpolarized metabolites using heterogeneous parahydrogen-induced polarization of ethyl[1-13C]acetate

Here, we report the production of 13C-hyperpolarized ethyl acetate via heterogeneously catalyzed pairwise addition of parahydrogen to vinyl acetate over TiO2-supported rhodium nanoparticles, followed by magnetic field cycling. Importantly, the hyperpolarization is demonstrated even at the natural abundance of 13C isotope (ca. 1.1%) along with the easiest separation of the catalyst from the hyperpolarized liquid.

More Than 12 % Polarization and 20 Minute Lifetime of 15N in a Choline Derivative Utilizing Parahydrogen and a Rhodium Nanocatalyst in Water

Hyperpolarization techniques are key to extending the capabilities of MRI for the investigation of structural, functional and metabolic processes in vivo. Recent heterogeneous catalyst development has produced high polarization in water using parahydrogen with biologically relevant contrast agents. A heterogeneous ligand-stabilized Rh catalyst is introduced that is capable of achieving 15N polarization of 12.2±2.7 % by hydrogenation of neurine into a choline derivative. This is the highest 15N polarization of any parahydrogen method in water to date. Notably, this was performed using a deuterated quaternary amine with an exceptionally long spin-lattice relaxation time (T1) of 21.0±0.4 min. These results open the door to the possibility of 15N in vivo imaging using nontoxic similar model systems because of the biocompatibility of the production media and the stability of the heterogeneous catalyst using parahydrogen-induced polarization (PHIP) as the hyperpolarization method.

Efficient Synthesis of Molecular Precursors for Para-Hydrogen-Induced Polarization of Ethyl Acetate-1-13C and beyond

A scalable and versatile methodology for production of vinylated carboxylic compounds with 13C isotopic label in C1 position is described. It allowed synthesis of vinyl acetate-1-13C, which is a precursor for preparation of 13C hyperpolarized ethyl acetate-1-13C, which provides a convenient vehicle for potential in vivo delivery of hyperpolarized acetate to probe metabolism in living organisms. Kinetics of vinyl acetate molecular hydrogenation and polarization transfer from para-hydrogen to 13C via magnetic field cycling were investigated. Nascent proton nuclear spin polarization (%PH) of ca. 3.3 % and carbon-13 polarization (%P13C) of ca. 1.8 % were achieved in ethyl acetate utilizing 50 % para-hydrogen corresponding to ca. 50 % polarization transfer efficiency. The use of nearly 100% para-hydrogen and the improvements of %PH of para-hydrogen-nascent protons may enable production of 13C hyperpolarized contrast agents with %P13C of 20-50 % in seconds using this chemistry.

Heterogeneous 1H and 13C Parahydrogen-Induced Polarization of Acetate and Pyruvate Esters

Magnetic resonance imaging of [1-13C]hyperpolarized carboxylates (most notably, [1-13C]pyruvate) allows one to visualize abnormal metabolism in tumors and other pathologies. Herein, we investigate the efficiency of 1H and 13C hyperpolarization of acetate and pyruvate esters with ethyl, propyl and allyl alcoholic moieties using heterogeneous hydrogenation of corresponding vinyl, allyl and propargyl precursors in isotopically unlabeled and 1-13C-enriched forms with parahydrogen over Rh/TiO2 catalysts in methanol-d4 and in D2O. The maximum obtained 1H polarization was 0.6±0.2 % (for propyl acetate in CD3OD), while the highest 13C polarization was 0.10±0.03 % (for ethyl acetate in CD3OD). Hyperpolarization of acetate esters surpassed that of pyruvates, while esters with a triple carbon-carbon bond in unsaturated alcoholic moiety were less efficient as parahydrogen-induced polarization precursors than esters with a double bond. Among the compounds studied, the maximum 1H and 13C NMR signal intensities were observed for propyl acetate. Ethyl acetate yielded slightly less intense NMR signals which were dramatically greater than those of other esters under study.

Structural exploration of rhodium catalysts and their kinetic studies for efficient parahydrogen-induced polarization by side arm hydrogenation

Parahydrogen-induced polarization (PHIP) is a rapid and cost-effective hyperpolarization technique using transition metal-catalysed hydrogenation with parahydrogen. We examined rhodium catalysts and their kinetic studies, rarely considered in the research

Production of Pure Aqueous13C-Hyperpolarized Acetate by Heterogeneous Parahydrogen-Induced Polarization

A supported metal catalyst was designed, characterized, and tested for aqueous phase heterogeneous hydrogenation of vinyl acetate with parahydrogen to produce13C-hyperpolarized ethyl acetate for potential biomedical applications. The Rh/TiO2catalyst with a metal loading of 23.2 wt % produced strongly hyperpolarized13C-enriched ethyl acetate-1-13C detected at 9.4 T. An approximately 14-fold13C signal enhancement was detected using circa 50 % parahydrogen gas without taking into account relaxation losses before and after polarization transfer by magnetic field cycling from nascent parahydrogen-derived protons to13C nuclei. This first observation of13C PHIP-hyperpolarized products over a supported metal catalyst in an aqueous medium opens up new possibilities for production of catalyst-free aqueous solutions of nontoxic hyperpolarized contrast agents for a wide range of biomolecules amenable to the parahydrogen induced polarization by side arm hydrogenation (PHIP-SAH) approach.

PROCESS FOR THE PREPARATION OF HYPERPOLARIZED CARBOXYLATE COMPOUNDS

The present invention relates to a process for the preparation of aqueous solutions of [1-13C]-hyperpolarized carboxylate containing molecules of diagnostic interest that comprises parahydrogenating with molecular parahydrogen unsaturated alkenyl or alkynyl esters of the concerned 13C- carboxylate molecules.

A comprehensive mechanistic picture of the isomerizing alkoxycarbonylation of plant oils

Theoretical studies on the overall catalytic cycle of isomerizing alkoxycarbonylation reveal the steric congestion around the diphosphine coordinated Pd-center as decisive for selectivity and productivity. The energy profile of isomerization is flat with diphosphines of variable steric bulk, but the preference for the formation of the linear Pd-alkyl species is more pronounced with sterically demanding diphosphines. CO insertion is feasible and reversible for all Pd-alkyl species studied and only little affected by the diphosphine. The overall rate-limiting step associated with the highest energetic barrier is methanolysis of the Pd-acyl species. Considering methanolysis of the linear Pd-acyl species, whose energetic barrier is lowest within all the Pd-acyl species studied, the barrier is calculated to be lower for more congesting diphosphines. Calculations indicate that energy differences of methanolysis of the linear versus branched Pd-acyls are more pronounced for more bulky diphosphines, due to involvement of different numbers of methanol molecules in the transition state. Experimental studies under pressure reactor conditions showed a faster conversion of shorter chain olefin substrates, but virtually no effect of the double bond position within the substrate. Compared to higher olefins, ethylene carbonylation under identical conditions is much faster, likely due not just to the occurrence of reactive linear acyls exclusively but also to an intrinsically favorable insertion reactivity of the olefin. The alcoholysis reaction is slowed down for higher alcohols, evidenced by pressure reactor and NMR studies. Multiple unsaturated fatty acids were observed to form a terminal Pd-allyl species upon reaction with the catalytically active Pd-hydride species. This process and further carbonylation are slow compared to isomerizing methoxycarbonylation of monounsaturated fatty acids, but selective.

Synthesis of [1-13C]-para-xylene and [2-13C]-para-xylene

An efficient synthesis of [1-13C]-para-xylene (1a) and [2-13C]-para-xylene (1b) is described. The incorporation of the label has been achieved by cyclocondensation of suitable 1,5-bis(bromomagnesio)alkanes with either ethyl [1-1