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Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavourings, vitamin B 1, and vitamin B 6.
Malonic acid is the precursor in mitochondrial fatty acid synthesis (mtFASII), in which it is converted to malonyl-CoA by acyl-CoA synthetase family member 3 (ACSF3). [ 30 ] [ 31 ] Additionally, the coenzyme A derivative of malonate, malonyl-CoA, is an important precursor in cytosolic fatty acid biosynthesis along with acetyl CoA .
A notable method for synthesizing acetamidomalon ester is described in a 1950 patent, [1] which cites a procedure previously featured in Organic Syntheses. [2] The synthesis procedure involves the preparation of malonic acid diethyl ester in acetic acid combined with sodium nitrite (NaNO 2), resulting in diethyl isonitrosomalonate (also known as α-oximinomalonic acid diethyl ester).
Dimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide. [2]
Disodium malonate is a sodium salt of malonic acid with the chemical formula CH 2 (COONa) 2. It is a white crystal soluble in water but not in alcohols, esters or benzene. It can be prepared from the reaction of sodium hydroxide and malonic acid: CH 2 (COOH) 2 + 2 NaOH → CH 2 (COONa) 2 + 2 H 2 O
Diethyl oxomalonate is the diethyl ester of mesoxalic acid (ketomalonic acid), the simplest oxodicarboxylic acid and thus the first member (n = 0) of a homologous series HOOC–CO–(CH 2) n –COOH with the higher homologues oxalacetic acid (n = 1), α-ketoglutaric acid (n = 2) and α-ketoadipic acid (n = 3) (the latter a metabolite of the amino acid lysine).
Dihydroxymalonic acid can be obtained synthetically by hydrolysis of alloxan with baryta water, [2] by warming caffuric acid [7] with lead acetate solution, [4] by electrolysis of tartaric acid in alkaline solution, [8] or from glycerin diacetate and concentrated nitric acid in the cold. The product can be obtained also by oxidation of ...
On heating, the di-ester undergoes thermal decarboxylation, yielding an acetic acid substituted by the appropriate R group. [1] Thus, the malonic ester can be thought of being equivalent to the − CH 2 COOH synthon. The esters chosen are usually the same as the base used, i.e. ethyl esters with sodium ethoxide.