Pimelic acid

Pimelic acid
Names
	IUPAC name heptanedioic acid
Identifiers
CAS Number	111-16-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30531 ;
ChemSpider	376 ;
DrugBank	DB01856 ;
ECHA InfoCard	100.003.492
EC Number	203-840-8;
PubChem CID	385;
UNII	BZQ96WX25F ;
CompTox Dashboard (EPA)	DTXSID5021598 ;
	InChI InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11) Key: WLJVNTCWHIRURA-UHFFFAOYSA-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;
	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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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

Synthesis

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.

In other syntheses, pimelic acid is made from cyclohexene-4-carboxylic acid,[3] and a fourth method also exists based on the 1,4 reaction of malonate systems with acrolein.[4]

Several patents exist for the production of pimelic acid.[5][6][7][8][9][10]

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References

CRC Handbook of Chemistry and Physics 83rd ed. p.8-52
H. R. Snyder, L. A. Brooks, S. H. Shapiro, A. Müller (1931). "Pimelic Acid". Organic Syntheses. 11: 42. doi:10.15227/orgsyn.011.0042.CS1 maint: uses authors parameter (link)
Werber, Frank X.; Jansen, J. E.; Gresham, T. L. (1952). "The Synthesis of Pimelic Acid from Cyclohexene-4-carboxylic Acid and its Derivatives". Journal of the American Chemical Society. 74 (2): 532. doi:10.1021/ja01122a075.
Warner, Donald T.; Moe, Owen A. (1952). "Synthesis of Pimelic Acid and α-Substituted Pimelic Acid and Intermediates1". Journal of the American Chemical Society. 74 (2): 371. doi:10.1021/ja01122a024.
U.S. Patent 2,826,609
U.S. Patent 2,800,507
U.S. Patent 2,698,339
U.S. Patent 3,468,927
U.S. Patent 4,888,443
U.S. Patent 2,673,219

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[1] CRC Handbook of Chemistry and Physics 83rd ed. p.8-52

[2] H. R. Snyder, L. A. Brooks, S. H. Shapiro, A. Müller (1931). "Pimelic Acid". Organic Syntheses. 11: 42. doi:10.15227/orgsyn.011.0042.CS1 maint: uses authors parameter (link)

[3] Werber, Frank X.; Jansen, J. E.; Gresham, T. L. (1952). "The Synthesis of Pimelic Acid from Cyclohexene-4-carboxylic Acid and its Derivatives". Journal of the American Chemical Society. 74 (2): 532. doi:10.1021/ja01122a075.

[4] Warner, Donald T.; Moe, Owen A. (1952). "Synthesis of Pimelic Acid and α-Substituted Pimelic Acid and Intermediates1". Journal of the American Chemical Society. 74 (2): 371. doi:10.1021/ja01122a024.

[5] U.S. Patent 2,826,609

[6] U.S. Patent 2,800,507

[7] U.S. Patent 2,698,339

[8] U.S. Patent 3,468,927

[9] U.S. Patent 4,888,443

[10] U.S. Patent 2,673,219

Pimelic acid

Synthesis

See also

References