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E47808

Sigma-Aldrich

Ethyl pyruvate

98%

Synonym(s):

2-Oxopropanoic acid ethyl ester, Ethyl 2-oxopropanoate, Ethyl 2-oxopropionate, Ethyl methylglyoxylate, Methyl ethoxycarbonyl ketone

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About This Item

Linear Formula:
CH3COCOOC2H5
CAS Number:
617-35-6
Molecular Weight:
116.12
Beilstein:
1071466
EC Number:
210-511-2
MDL number:
MFCD00009123
UNSPSC Code:
12352100
PubChem Substance ID:
24894582
NACRES:
NA.22

Quality Level

200

Assay

98%

form

liquid

refractive index

n20/D 1.404 (lit.)

bp

144 °C (lit.)

density

1.045 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)C(C)=O

InChI

1S/C5H8O3/c1-3-8-5(7)4(2)6/h3H2,1-2H3

InChI key

XXRCUYVCPSWGCC-UHFFFAOYSA-N

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Application

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.

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

114.8 °F - closed cup

Flash Point(C)

46 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL1869
STBL0988
STBK6094
STBK3027
STBJ6410

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Highly Enantioselective Henry (Nitroaldol) Reaction of Aldehydes and ?-Ketoesters Catalyzed by N,N'-Dioxide-Copper (I) Complexes.
Qin B, et al.
The Journal of Organic Chemistry, 72(24), 9323-9328 (2007)
98% Enantioselectivity in the asymmetric synthesis of a useful chiral building block by heterogeneous method: Enantioselective hydrogenation of ethyl-benzoylformate over cinchona modified Pt/Al2 O3 catalysts in the acetic acid.
Sutyinszki M, et al.
Catalysis Communications, 3(3), 125-127 (2002)
Lin Sun et al.
Journal of neurotrauma, 36(3), 421-435 (2018-06-23)
High mobility group box-1 (HMGB1) could function as an early trigger for pro-inflammatory activation after spinal cord injury (SCI). Spinal cord edema contributes to inflammatory response mechanisms and a poor clinical prognosis after SCI, for which efficient therapies targeting the
M P Fink
Journal of internal medicine, 261(4), 349-362 (2007-03-30)
Ethyl pyruvate (EP) is a simple derivative of the endogenous metabolite, pyruvic acid. Treatment with EP has been shown to improve survival and/or ameliorate organ dysfunction in a wide variety of preclinical models of critical illnesses, such as severe sepsis
Kenneth K Kao et al.
Biochemical pharmacology, 80(2), 151-159 (2010-03-17)
Pyruvate is an important metabolic intermediate, and also is an effective scavenger of hydrogen peroxide and other reactive oxygen species (ROS). Pharmacological administration of pyruvate has been shown to improve organ function in animal models of oxidant-mediated cellular injury. However
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