Ethyl pyruvate

Base Information

• Chemical Name: Ethyl pyruvate
• CAS No.: 617-35-6
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: H5 MOL WT. 116.12
• European Community (EC) Number: 210-511-2
• NSC Number: 48386
• UNII: 03O98E01OB
• DSSTox Substance ID: DTXSID2060674
• Nikkaji Number: J1.665I
• Wikipedia: Ethyl_pyruvate
• Wikidata: Q15632706
• RXCUI: 1539968
• Metabolomics Workbench ID: 124281
• ChEMBL ID: CHEMBL173373
• Mol file: 617-35-6.mol

Synonyms:Pyruvicacid, ethyl ester (6CI,7CI,8CI);2-Oxopropanoic acid ethyl ester;2-Oxopropionic acid ethyl ester;Ethyl 2-oxopropanoate;Ethyl 2-oxopropionate;Ethyl methylglyoxylate;NSC 48386;

Chemical Property of Ethyl pyruvate

Chemical Property:

• Appearance/Colour: clear pale yellow liquid
• Vapor Pressure: 3.09mmHg at 25°C
• Melting Point: -58 °C
• Refractive Index: 1.404 - 1.406
• Boiling Point: 154.999 °C at 760 mmHg
• Flash Point: 45.556 °C
• PSA: 43.37000
• Density: 1.04 g/cm³
• LogP: 0.13850
• Storage Temp.: 0-6°C
• Solubility.: 10g/l
• Water Solubility.: Miscible with water, ethanol and ether.
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

Ethyl pyruvate 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, F
• Hazard Codes: Xi,F
• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C(=O)C
• Recent ClinicalTrials: CTI-01 (Ethyl Pyruvate) Safety and Complication Prevention in Cardiac Surgery Patients on Cardiopulmonary Bypass (CPB)
• General Description: Ethyl pyruvate (EP) is a versatile keto ester that serves as a key reactant in the synthesis of biobased chemicals, such as itaconic acid ester analogues, via aldol condensation catalyzed by Lewis acidic zeolites like Hf-BEA. Ethyl pyruvate demonstrates high reactivity and selectivity in forming unsaturated dicarboxylic acid esters under optimized conditions, highlighting its utility in sustainable chemical production.

Technology Process of Ethyl pyruvate

There total 94 articles about Ethyl pyruvate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.6%

ethyl 2-hydroxypropionate (97-64-3,2676-33-7) → 2-oxo-propionic acid ethyl ester (617-35-6)

Guidance literature:

With dihydrogen peroxide; at 50 ℃; for 7h; Reagent/catalyst; Temperature; Catalytic behavior; Kinetics; Heating;

DOI:10.1021/acscatal.7b03558

Reference yield: 95.0%

2-methyl-1,3-dithiolane-2-carboxylic acid ethyl ester (76339-59-8) → 2-oxo-propionic acid ethyl ester (617-35-6)

Guidance literature:

With trichloroisocyanuric acid; silver nitrate; In water; acetonitrile; Ambient temperature;

Reference yield: 92.8%

ethanol (64-17-5) + 2-oxo-propionic acid (127-17-3) → 2-oxo-propionic acid ethyl ester (617-35-6)

Guidance literature:

2-oxo-propionic acid; With oxalyl dichloride; In dichloromethane; for 4h; Reflux;

ethanol; at 20 ℃;

upstream raw materials:

pyridine

tetrachloromethane

N-Bromosuccinimide

ethyl 2-hydroxypropionate

Downstream raw materials:

ethyl 2-[2-(4-nitrophenyl)hydrazinylidene]propanoate

2-(2,5-dimethyl-phenylhydrazono)-propionic acid ethyl ester

2-(methyl-phenyl-hydrazono)-propionic acid ethyl ester

ethyl 2-(diphenylphosphoryl)acrylate

Refernces

Synthesis of Itaconic Acid Ester Analogues via Self-Aldol Condensation of Ethyl Pyruvate Catalyzed by Hafnium BEA Zeolites

10.1021/acscatal.6b00561

The research investigates the use of Lewis acidic zeolites, specifically Hafnium-containing BEA (Hf-BEA) zeolites, to synthesize unsaturated dicarboxylic acid esters through the aldol condensation of keto esters, with a focus on producing itaconic acid ester analogs from ethyl pyruvate (EP). The purpose is to develop an efficient catalytic route for synthesizing valuable biobased chemicals, addressing issues like poor selectivity and catalyst deactivation in existing methods. The study found that Hf-BEA zeolites catalyze the condensation of EP into diethyl 2-methyl-4-oxopent-2-enedioate and diethyl 2-methylene-4-oxopentanedioate with high selectivity (around 80%) at a conversion rate of approximately 60%, demonstrating stability for 132 hours on stream in a packed-bed reactor. The catalyst's performance suggests that Hf(IV) open sites possess dual functionality for Lewis and Br?nsted acid catalysis. The research concludes that Hf-BEA zeolites are promising catalysts for this reaction, with potential for further optimization and application in biobased chemical production.