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Pimelic acid is the
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...
HO2C(CH2)5CO2H. Pimelic acid is one unit longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. However compared to adipic acid, pimelic acid is relatively small in importance industrially. Derivatives of pimelic acid are involved in the biosynthesis of the
amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha am ...
lysine Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. It contains an α-amino group (which is in the protonated form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −C ...
and the vitamin
biotin Biotin (or vitamin B7) is one of the B vitamins. It is involved in a wide range of metabolic processes, both in humans and in other organisms, primarily related to the utilization of fats, carbohydrates, and amino acids. The name ''biotin'', bor ...
.


Synthesis


Biosynthesis

The biosynthesis of pimelic acid is unknown but is speculated to start with
malonyl CoA Malonyl-CoA is a coenzyme A derivative of malonic acid. Functions It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis. Fatty acid biosynthesis Malonyl-CoA provides 2-carbon units to fatty acids and commi ...
.


Chemical and industrial routes

Like other simple dicarboxylic acids, many methods have been developed for producing pimelic acid. Pimelic acid is produced commercially by oxidation of
cycloheptanone Cycloheptanone, (CH2)6CO, is a cyclic ketone also referred to as suberone. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals. Synthesis In 1836, French chemist Jean-Baptiste Boussinga ...
with
dinitrogen tetroxide Dinitrogen tetroxide, commonly referred to as nitrogen tetroxide (NTO), and occasionally (usually among ex-USSR/Russia rocket engineers) as amyl, is the chemical compound N2O4. It is a useful reagent in chemical synthesis. It forms an equilibrium ...
. Other routes include the relatively unselective oxidation of palmitic acid and the
carbonylation Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbony ...
of
caprolactone ε-Caprolactone or simply caprolactone is a lactone (a cyclic ester) possessing a seven-membered ring. Its name is derived from caproic acid. This colorless liquid is miscible with most organic solvents and water. It was once produced on a large s ...
.


Niche methods

Many other methods exist. Pimelic acid has been synthesized from cyclohexanone and from salicylic acid. In the former route, the additional carbon is supplied by dimethyl
oxalate Oxalate (IUPAC: ethanedioate) is an anion with the formula C2O42−. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na2C2O4), and several esters such as dimethyl o ...
, which reacts with the enolate. In other syntheses, pimelic acid is made from cyclohexene-4-carboxylic acid, and a fourth method also exists based on the 1,4 reaction of malonate systems with
acrolein Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fa ...
. Several patents exist for the production of pimelic acid.


See also

*
Diaminopimelic acid Diaminopimelic acid (DAP) is an amino acid, representing an epsilon-carboxy derivative of lysine. DAP is a characteristic of certain cell walls of some bacteria. DAP is often found in the peptide linkages of NAM-NAG chains that make up the ce ...


References

{{Authority control Dicarboxylic acids