Ethyl pyruvate

Chemical properties

clear pale yellow liquid

Chemical properties

Ethyl pyruvate has a vegetable, caramel odor.

Occurrence

Reported found in Parmesan cheese, cognac, grape wines, cocoa and mushrooms.

The Uses of Ethyl pyruvate

Ethyl pyruvate (EP) has demonstrated neuroprotective effects against acute brain injury through its anti-inflammatory action.

The Uses of Ethyl pyruvate

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.

The Uses of Ethyl pyruvate

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.

Definition

ChEBI: Ethyl pyruvate is an oxo carboxylic acid.

Preparation

By direct esterification of pyruvic acid with absolute ethyl alcohol at the boil and subsequent vacuum distillation; by esterification via oxidation of vapors of ethyl lactate in the presence of V2O5 at 155°C

What are the applications of Application

Ethyl pyruvate is an organic building block that is a novel anti inflammatory in vitro

Taste threshold values

Taste characteristics at 60 ppm: sweet, rum-like with a fruity ethereal nuance.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 7191, 1993 DOI: 10.1016/S0040-4039(00)79284-7

General Description

Ethyl pyruvate is a volatile aliphatic ester of the pyruvate metabolite. It is present as a food additive/odor-active component in various food and beverage products. It is also used as an inhibitory odorant to repel the insects from human proximity.

Purification Methods

Shake the ester with 10mL portions of saturated aqueous CaCl2 solution (removes ethyl acetate) and the organic layer is removed by centrifugation, decantation and filtration, and is distilled under reduced pressure. Purification of small quantities is carried out via the bisulfite adduct: the ester (2.2mL) is shaken with saturated NaHSO3 (3.6mL), chilled in a freezing mixture when crystals separate rapidly (particularly if seeded). After 5minutes EtOH (10mL) is added and the crystals are filtered off, washed with EtOH and Et2O and dried. Yield ca 3g of bisulfite adduct. Then treat the adduct (16g) with saturated aqueous MgSO4 (32mL) and 40% formaldehyde (5mL) and shake, whereby the ester separates as an oil which is extracted with Et2O. The extract is dried (MgSO4), filtered, evaporated and the residue is distilled (b 56o/20mm), and then redistilled (b 147.5o/750mm) to give 5.5g of pure ester. [Cornforth Org Synth Coll Vol IV 467 1963, Beilstein 3 IV 1513.]