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)
• Uses: It can be used in the manufacture of pharmaceutical pindolol and pesticides thiabendazole. At the same time, it is an important intermediate of pharmaceutical and chemical industry. It is widely applied to various kinds of industries including medicine, pesticides, flavors and fragrances, food additives, air fresheners, fine chemicals and other industries. It can be used in the synthesis of cardiovascular drugs like expansion agent; it can also be applied to cosmetic of skin whitening and nutrition and can promote the healing of the wound, prevention and treatment of skin disease characterized by cracking, spalling and squamous metaplasia; it can be used as the high-efficiency active ingredients in the air fresheners and can effectively eliminate the ammonia and methyl mercaptan in the air; because itself has a special flavor, it can be applied to flavors, fragrance; it is also an important raw material for synthetic resins and plastics. Ethyl pyruvate is used as a flavoring agent in food and anti-inflammatory agent for the treatment of critical inflammatory conditions. It is used in the treatment of critical illnesses such as severe sepsis, acute respiratory distress syndrome, burn injury, acute pancreatitis and stroke. It plays an important role in cardiac function after coronary ischemia and reperfusion. Ethyl pyruvate (EP) has demonstrated neuroprotective effects against acute brain injury through its anti-inflammatory action. Ethyl pyruvate can undergo asymmetric Henry reaction with nitromethane to form α-hydroxy β-nitro esters. It can be used as the model compound for α-ketoesters to study the mechanism of enantioselective hydrogenation reactions.
• Production method: There are several methods for its preparation. Gas-phase oxidation of ethyl lactate Gas-phase oxidation of ethyl lactate is conducted in the presence of a catalyst with MoO3 catalyst exhibiting a higher selectivity than other kinds of metal oxides. In addition, binary oxide catalysts containing molybdenum oxide such as Fe2O3-MoO3 and TeO2-MoO3 also have a high selectivity on synthesis pyruvate ester (temperature 300 ℃, selectivity is higher than 90%), if using SnO2-MoO3 as the catalysts, it can be carried out at a relatively low temperature (for example, 250 ℃). SnO2-MoO3 catalysts can also be used as the catalyst of lactate liquid-phase oxidation with the reaction temperature being 130 ℃ and the reaction time being 3h. The conversion rate of ethyl lactate was 38.4% and the selectivity is 98.9% which produces ethyl pyruvate. Liquid phase oxidation of ethyl lactate Ethyl lactate is subject to liquid-phase oxidation in the presence of a small amount of bromine as the catalyst. Use H2O2 as the oxidant for performing the oxidation reaction, for example, 50% H2O2 was stirring added drop wise to a dichloromethane solution of ethyl lactate and the bromine upon sunshine. The reaction temperature is maintained at 25 ℃ and the addition time of H2O2 is controlled at about 1.5 h and the reaction was continued for 3 h after the completion of the dropping. The solution was neutralized with NaHCO3 and washed with Na2SO3 solution; destroy and remove the peroxide ethyl lactate, peroxide and then obtain the ethyl pyruvate through concentration and distillation under reduced pressure. The oxidation of acrylate Use H2O2 to oxidize the acrylate to generate pyruvate ester in the presence of Cr or V compound as the catalyst. For example, to make isopropyl acrylate, in the presence of chromium triacetylacetate as the catalyst, add H2O2 with stirring to the acetonitrile solvent; the reaction temperature is maintained at 50 ℃ with 8 h obtaining isopropyl acrylate with the selectivity being 99.1% and the conversion rate being 87.9%. Another example is that, methyl acrylate, in the presence of chromium triacetylacetate or chromic acid, is added of triethylamine for reaction of 20h with the temperature 40 ℃, the selectivity 72% and the conversion rate of 82% to give methyl pyruvate. In addition, methylglyoxal and methanol can be subject to gas phase reaction in the presence of nickel phosphate catalyst to obtain methyl pyruvate.

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-hydroxy-2-(2-oxocyclohexyl)propanoate

7,8-Dihydro-6,8-dimethyl-7-oxo-pteridin

6-methoxyquinoline-4-carboxylic acid ethyl ester

2-hydroxy-2-(5-methyl-2-oxo-cyclohexyl)-propionic acid ethyl ester

Refernces

• 1、 Wang, Dan,Liu, Wei,Xie, Zailai,Tian, Siyuan,Su, Dangsheng,Qi, Wei. "Oxidative dehydrogenation of ethyl lactate over nanocarbon catalysts: Effect of oxygen functionalities and defects". . p. 96 - 101. Retrieved 2020.
• 2、 Doke, Dhananjay S.,Khomane, Sonali B.,Pandhare, Swati L.,Dongare, Mohan K.,Dumeignil, Franck,Umbarkar, Shubhangi B.. "Vanadium-based highly active and selective catalysts for oxidative dehydrogenation of ethyl lactate to ethyl pyruvate". . . Retrieved 2019.
• 3、 Sugiyama, Shigeru,Shigemoto, Naoya,Masaoka, Naoki,Suetoh, Souichi,Kawami, Hideaki,et al.. "Vapor-Phase Oxidation of Ethyl Lactate to Pyruvate over Various Oxide Catalysts". . p. 1542 - 1547. Retrieved 1993.
• 4、 Crosby,Lienhard. "". . p. 5707,5708-5711, 5716. Retrieved 1970.
• 5、 Zhang, Wei,Ensing, Bernd,Rothenberg, Gadi,Raveendran Shiju. "Designing effective solid catalysts for biomass conversion: Aerobic oxidation of ethyl lactate to ethyl pyruvate". . p. 1866 - 1873. Retrieved 2018.
• 6、 Tao, Luyao,Bi, Xiuru,Zhang, Liping,Chen, Gexin,Zhao, Peiqing,Yang, Jun-Li,Meng, Xu. "Na-doped OMS-2-catalzyed highly selective aerobic oxidation of ethyl lactate to ethyl pyruvate under mild conditions". . . Retrieved 2020.
• 7、 Huchede,Morvan,Vera,Bellière-Baca,Millet. "Oxidative dehydrogenation of ethyl lactate to ethyl pyruvate over vanadium and iron antimonates catalysts". . . Retrieved 2021/05/04.