Ethyl pyruvate
Ethyl Pyruvate ball and stick model
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Names | |
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Other names
ethyl 2-oxopropanoate
Ethyl-2-oxopropanoat Propanoic acid, 2-oxo-, ethyl ester Pyruvic acid, ethyl ester (8CI) [1] | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.009.557 |
EC Number |
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PubChem CID
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UNII | |
UN number | 3272 |
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) 760 |
10 g L−1 (at 20 °C) [2] | |
log P | 0.048 |
Hazards[3] | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Flammable/Irritant |
GHS labelling: | |
Warning | |
H226 | |
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 45 °C |
Safety data sheet (SDS) | External MSDS |
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 molecule with both
Research and applications
Three independent studies of ethyl pyruvate were performed, with rats as their test subjects, and each produced an optimistic result. The first study showed that ethyl pyruvate has a protective role against phosgene-induced pulmonary edema.[6]
The second study showed the therapeutic effects of ethyl pyruvate against severe acute
The effects of ethyl pyruvate as an antioxidant were compared to that of its sodium salt in a recent study. Ethyl pyruvate has a greater lipophilicity than sodium pyruvate, which allows it to be a more effective scavenger in the reaction. This study was done using a liver homogenate as the model for cell membrane transport deletion.[9] Hypochlorous acid was used as the oxidant, and the focus of the study was on the capacity of the pyruvates to scavenge the reactive oxygen species. Ethyl pyruvate is a good antioxidant due to its α-ketocarboxylate structure, which allows it to reduce hydrogen peroxide to water and scavenge the hydroxyl radical through decarboxylation.
Amino-2H-imidazoles are a new class of BACE-1 inhibitors for the treatment of Alzheimer's disease. Amino-2H-imidazoles were introduced because current treatments of Alzheimer's disease only treat the symptoms, but do not correct the underlying neuropathology. Ethyl pyruvate is used as a reactant in the synthesis of many of these new BACE-1 inhibitors.[10]
Overall, ethyl pyruvate has been found to be beneficial in
Preparation and reactions
Ethyl pyruvate can be synthesized in a simple, one-step reaction from the oxidation of
Ethyl pyruvate can undergo
Enantioselective reactions are extremely important in chemistry, as the formation of optically pure products is especially useful in the food,
References
- ^ "2457 | C5H8O3 | ChemSpider".
- ^ "Ethyl Pyruvate, 98%". Acros Organics. Retrieved 21 March 2013.
- ^ "Ethyl pyruvate natural, 95%". Sigma Aldrich. Retrieved 21 March 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>.
- ^ "Chem Spider". Chem Spider. Retrieved 4 October 2013.
- ^ 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.
- ^ Therapeutic treatment with ethyl pyruvate attenuates the severity of liver injury in rats with severe acute pancreatitis. Luan, Zheng-Gang; Zhang, Hao; Ma, Xiao-Chun; Zhang, Cheng; Guo, Ren-Xuan. Department of Intensive Care Unit, The First Hospital, China Medical University, Shenyang, China.
- ^ Beneficial effects of sodium or ethyl pyruvate after traumatic brain injury in the rat. Nobuhiro Moro, Richard L. Sutton. Department of Neurosurgery, David Geffen School of Medicine, University of California, Los Angeles, CA, USA. Copyright © 2010 Elsevier Inc.
- ^ Olek, Robert Antonini; Ziolkowski, Wieslaw; Kaczor, Jan Jacek; Wierzba, Tomasz Henryk; Antosiewicz, Jedrzej."Higher Hypochlorous Acid Scavenging Activity of Ethyl Pyruvate Compared to its Sodium Salt" Biosci, Biotechnol, Biochem., 75 (3),(2011). 500-504.
- ^ Gravenfors, Ylva, et al. "New Aminoimidazoles as β-Secretase (BACE-1) Inhibitors Showing Amyloid-β (Aβ) Lowering in Brain." Journal of Medicinal Chemistry 55.21 (2012): 9297-9311.
- ^ "ethyl pyruvate - Compound Summary". Retrieved 11 April 2013.
- ^ "Ethyl lactate". sigmaaldrich.com. Retrieved 15 May 2023.
- ^ "Ethyl pyruvate". sigmaaldrich.com. Retrieved 15 May 2023.
- ^ 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.
- ^ Ibanez, M.F.; Vetere, V.; Santori, G.F.; Casella, M.L.; Ferretti, O.A."Enantioselective Hydrogenation of Ethyl Pyruvate with Cinchonidine Modified Pt/SiO2 and PtSn/SiO2 Catalysts" The Journal of the Argentine Chemical Society. Vol. 91 (2003). 63-72.