Pimelic acid

Pimelic acid

Names
IUPAC name heptanedioic acid
Identifiers
CAS Registry Number	111-16-0 Y
ChEBI	CHEBI:30531 N
ChemSpider	376 N
DrugBank	DB01856 N
EC number	203-840-8
InChI InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11) N Key: WLJVNTCWHIRURA-UHFFFAOYSA-N N InChI=1/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11) Key: WLJVNTCWHIRURA-UHFFFAOYAR
Jmol-3D images	Image
PubChem	385
SMILES OC(=O)CCCCCC(=O)O
Properties
Chemical formula	C7H12O4
Molar mass	160.17 g/mol
Density	1.28 g/cm3
Melting point	103 to 105 °C (217 to 221 °F; 376 to 378 K)
Boiling point	decomposes
Acidity (pKa)	4.71 pKa2 = 5.58 [1]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Pimelic acid is the organic compound with the formula HO₂C(CH₂)₅CO₂H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one CH
2 unit longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. It is the final member of the mnemonic used to aid recollection of the order of the first six dicarboxylic acids using their common (not IUPAC) nomenclature: Dicarboxylic acid

Pimelic acid has been synthesized from cyclohexanone and from salicylic acid.^[2] In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate.

See also

• Diaminopimelic acid

References