ピルビン酸エチル

用途医農薬中間体、電子材料用溶剤、香料原料。

用途有機合成原料。

天然物の起源Reported found in Parmesan cheese, cognac, grape wines, cocoa and mushrooms.

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

一般的な説明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.

製造方法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

純化方法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.]