malonic

Malonic refers to malonic acid and its derivatives, including salts and esters, derived from propane-1,2-dicarboxylic acid. The core structure is HOOC-CH2-COOH, a dicarboxylic acid with a methylene group between two carbonyls. The term is used in organic chemistry and biochemistry to discuss reactions and compounds built around this motif.

Chemically, the methylene group between the two carbonyls is relatively acidic, allowing deprotonation to form the malonate anion. This acidity enables malonates to act as nucleophiles in carbon–carbon bond-forming reactions. Malonate esters, such as diethyl malonate, are common reagents and are used to introduce carbon units into molecules via alkylation at the methylene position, followed by hydrolysis and decarboxylation to yield substituted acetic acids. A widely used application is the malonic ester synthesis, which builds carbon skeletons by sequential alkylation and hydrolysis/decarboxylation steps.

In practical synthesis, malonate derivatives serve as versatile building blocks for pharmaceuticals and agrochemicals. Diethyl malonate and related esters can be employed to construct complex carbon frameworks, including α-substituted carboxylic acids, after appropriate manipulation. Decarboxylation of malonic derivatives upon heating or hydrolysis is a common step in these transformations.

In biochemistry, malonyl-CoA is a central intermediate in fatty acid biosynthesis, where the malonyl unit acts as an extender for growing fatty acyl chains. Malonyl groups also participate in polyketide biosynthesis, and malonyl-CoA can regulate fatty acid oxidation by inhibiting certain transport steps. The term malonyl can also describe related acyl groups attached to proteins or lipids in various biological contexts.