Ethyl pyruvate
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 Ethyl Pyruvate
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| Names | |
|---|---|
| Other names
ethyl 2-oxopropanoate
Ethyl-2-oxopropanoat Propanoic acid, 2-oxo-, ethyl ester Pyruvic acid, ethyl ester (8CI) [1] | |
| Identifiers | |
| ChemSpider | |
| ECHA InfoCard | 100.009.557 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C5H8O3 | |
| Molar mass | 116.12 g mol-1 |
| Appearance | colorless liquid |
| Density | 1.045 g cm-3 |
| Melting point | −58 °C (−72 °F; 215 K) |
| Boiling point | 142 °C (288 °F; 415 K) |
| log P | 0.048 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethyl Pyruvate is a colorless organic compound with a molecular formula of C5H8O3.
Structure
Ethyl pyruvate is small organic molecule with both ketone and ester functionality. The molecule has no hydrogen donors, but three atoms that are hydrogen receptors. Three of the bonds are rotatable and there are no stereocenters. [3]
Research/Applications
After studying ethyl pyruvate the results suggest that ethyl pyruvate has a protective role against phosgene-induced pulmonary edema. [4] In order to prove this, rats were given ethyl pyruvate incubated with RAW264.7 cells immediately after exposure to phosgene. Wet-to-dry lung weight ratio (W:D ratio), nitric oxide (NO) production, prostaglandin E2 (PGE2) production, cyclooxygenase2 (COX-2) expression, inducible nitric oxide synthase (iNOS) expression, and mitogen-activated protein kinases activities (MAPKs) were measured. The results reviled that the ethyl pyruvate treatment reduced phosgene-induced pulmonary edema and decreased the levels of NO and PGE2. The results also showed that ethyl pyruvate significantly reduced COX-2 expression, iNOS expression and MAPK activation induced by phosgene.
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Preparation and reactions
Ethyl pyruvate can be synthesized in a simple, one-step reaction from the oxidation of ethyl lactate. Since ethyl lactate [5] is slightly cheaper to buy than ethyl pyruvate, [6] this synthesis can be useful. There are many different reagents that can be used to push the reaction forward to yield in excess of 98%, such as using potassium permanganate and aluminum sulfate hydrate in dichloromethane solvent. [7]
Ethyl pyruvate can undergo reduction chemistry as well. For example, when reduced by sodium borohydride the ketone gets reduced to an alcohol, leaving the ester group untouched. But, when ethyl pyruvate is reduced by lithium aluminum hydride both the ketone and ester get completely reduced to alcohols.
References
- ^ http://www.chemspider.com/Chemical-Structure.11544.html?rid=e1ca4956-9c8d-4f40-b981-c0a169e18dfb
- ^ http://www.chemicalbook.com/ProductChemicalPropertiesCB3198366_EN.htm. Retrieved March 9, 2013
- ^ "Ethyl Pyruvate." ChemExper. N.p., n.d. Web. 13 Mar. 2013. <http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID=6445>.
- ^ Ethyl pyruvate protects rats from phosgene-induced pulmonary edema by inhibiting cyclooxygenase2 and inducible nitric oxide synthase expression. Chen, Hong-li; Bai, Hua; Xi, Miao-miao; Liu, Riu; Qin, Xu-jun; Liang, Xin; Zhang, Wei; Zhang, Xiao-di; Li, Wen-li; Hai, Chun-xu. Department of Toxicology, Fourth Military Medical University, Xi'an, 710032, China. Epub 2011 Aug 5.
- ^ http://www.sigmaaldrich.com/catalog/product/aldrich/W244015?lang=en®ion=US
- ^ http://www.sigmaaldrich.com/catalog/product/aldrich/W245712?lang=en®ion=US
- ^ Preparation of α-keto esters by oxidation of hydroxy esters. Kurata, Takeo; Kobayashi, Makoto; Arimura, Tomohiro; Sekiguchi, Takayuki. Musashino Chemical Laboratory Ltd., Japan. May 9, 2002.