Pimelic acid

Synonym(s):Heptanedioic acid;Pimelic acid

CAS NO.：111-16-0
Empirical Formula: C7H12O4
Molecular Weight: 160.17
MDL number: MFCD00004425
EINECS: 203-840-8
Update Date: 2024-12-18 14:08:52

What is Pimelic acid?

Description

Pimelic acid is the organic compound with the formula HO₂C(CH₂)₅CO₂H which has been synthesized from cyclohexanone and from salicylic acid. In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate.
This acid (heptanedioic acid), from the Greek pimelh (pimele fat), as adipic acid, was isolated from oxidized fats. It was obtained in 1884 by Ganttner F et al. as a product of ricinoleic acid (hydroxylated oleic acid) from castor oil.

Chemical properties

white solid

The Uses of Pimelic acid

The major uses of pimelic acid are in plasticizers and polymers.

The Uses of Pimelic acid

Pimelic Acid is a metabolite found in four biofluids from dairy cows that may be used as biomarkers of milk.

Definition

ChEBI: An alpha,omega-dicarboxylic acid that is pentane with two carboxylic acid groups at positions C-1 and C-5.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 3425, 1956 DOI: 10.1021/ja01595a044
Organic Syntheses, Coll. Vol. 2, p. 531, 1943
Synthesis, p. 54, 1988

Purification Methods

Crystallise the acid from water or from *benzene containing 5% diethyl ether. [Beilstein 1 IV 2003.]

Properties of Pimelic acid

Melting point:	103-105 °C(lit.)
Boiling point:	212 °C10 mm Hg(lit.)
Density	1,329 g/cm³
refractive index	1.4352 (estimate)
Flash point:	212°C/10mm
storage temp.	Store below +30°C.
solubility	ethanol: 0.1 g/mL, clear to very faintly hazy
form	Powder
pka	4.71(at 25℃)
color	White to slightly beige
PH	3.77(1 mM solution);3.25(10 mM solution);2.74(100 mM solution)
Water Solubility	25 g/L (13 ºC)
Merck	14,7431
BRN	1210024
Stability:	Stable. Incompatible with oxidizing agents, bases. Combustible.
CAS DataBase Reference	111-16-0(CAS DataBase Reference)
NIST Chemistry Reference	Heptanedioic acid(111-16-0)
EPA Substance Registry System	Heptanedioic acid (111-16-0)

Safety information for Pimelic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.