Pimelic acid

Structural formula
General
Surname	Pimelic acid
other names	Heptanedioic acid; 1,5-pentanedicarboxylic acid;
Molecular formula	C 7 H 12 O 4
Brief description	white crystals
External identifiers / databases
EC number	203-840-8
ECHA InfoCard	100.003.492
PubChem	385
ChemSpider	376
DrugBank	DB01856
Wikidata	Q414420
properties
Molar mass	160.17 g mol −1
Physical state	firmly
density	1.33 g cm −3
Melting point	102-105 ° C
boiling point	223 ° C
pK s value	pK s 1 = 4.47; pK s 2 = 5.52;
solubility	poor in water (50 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
Toxicological data	7000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pimelic acid (also heptanedioic acid or 1,5-pentanedicarboxylic acid ) belongs to the homologous series of dicarboxylic acids . The name is also derived from the Greek pimele (= fat). It lies between adipic acid and suberic acid ( suberic acid ). Their salts are called pimelates.

In contrast to adipic acid, pimelic acid has only a very limited area of application in the chemical industry.

properties

As a dibasic acid, pimelic acid dissociates in water in two stages of protolysis . Their octanol-water partition coefficient is log (K _OW ) = 0.61.

Biological importance

Pimeloyl-CoA is a component in the biosynthesis of biotin .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Data sheet pimelic acid (PDF) from Merck , accessed on February 13, 2010.
^ ^A ^b Fieser and Fieser, Organic Chemistry, 2nd Edition, Verlag Chemie 1982 ISBN 3-527-25075-1 .
↑ ^a ^b Data sheet Pimelic acid from Sigma-Aldrich , accessed on April 20, 2011 ( PDF ).
↑ Roempp Chemie Lexikon 9th Edition 1991 Keywords pimelic
↑ Paola Estrada, Miglena Manandhar, Shi-Hui Dong, Jaigeeth Deveryshetty, Vinayak Agarwal, John E. Cronan, Satish K. Nair: The pimeloyl-CoA synthetase BioW defines a new fold for adenylate-forming enzymes. In: Nature Chemical Biology. 13, 2017, pp. 668-674, doi : 10.1038 / nchembio.2359 .

[MERCK-1] ↑ ^a ^b ^c ^d ^e ^f ^g Data sheet pimelic acid (PDF) from Merck , accessed on February 13, 2010.

[Fieser_und_Fieser-2] A ^b Fieser and Fieser, Organic Chemistry, 2nd Edition, Verlag Chemie 1982 ISBN 3-527-25075-1 .

[Sigma-3] Data sheet Pimelic acid from Sigma-Aldrich , accessed on April 20, 2011 ( PDF ).

[4] Roempp Chemie Lexikon 9th Edition 1991 Keywords pimelic

[5] Paola Estrada, Miglena Manandhar, Shi-Hui Dong, Jaigeeth Deveryshetty, Vinayak Agarwal, John E. Cronan, Satish K. Nair: The pimeloyl-CoA synthetase BioW defines a new fold for adenylate-forming enzymes. In: Nature Chemical Biology. 13, 2017, pp. 668-674, doi : 10.1038 / nchembio.2359 .