3oxohexanoyl

3-oxohexanoyl refers to the acyl substituent derived from the beta-keto acid 3-oxohexanoic acid. In structural terms the acid has the formula HOOC-CH2-CO-CH2-CH2-CH3, containing a carboxyl group and a ketone at the third carbon from the carboxyl. The corresponding 3-oxohexanoyl group attached to a molecule via the carbonyl is -CO-CH2-CO-CH2-CH2-CH3. The name reflects the position of the ketone (oxo) on the hexanoyl chain.

Beta-keto acids like 3-oxohexanoic acid are known to decarboxylate readily upon heating to yield a ketone; in this case 3-oxohexanoic acid decarboxylates to 2-pentanone (pentan-2-one). This reactivity is a common consideration in synthetic planning and in metabolic contexts.

In biochemistry and organic synthesis, 3-oxohexanoyl derivatives appear as intermediates in fatty acid and polyketide biosynthesis; they are typically generated as 3-oxoacyl-ACPs or thioesters and can undergo subsequent condensations to extend the carbon chain, or decarboxylation to give shorter ketones. They can be prepared by converting 3-oxohexanoic acid to the corresponding acyl chloride or anhydride, enabling acyl transfer to amines or alcohols to form amides or esters.

Because the beta-keto motif contains two carbonyl groups, these acyl groups are more reactive toward nucleophiles than simple alkyl acyl groups, and their chemistry is governed by keto-enol tautomers; conditions can favor decarboxylation or enolization.