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Pelargonic acid

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Pelargonic acid
Pelargonic acid.svg
Names
Preferred IUPAC name
Nonanoic acid
Other names
Nonoic acid; nonylic acid; 1-octanecarboxylic acid; C9:0 (lipid numbers)
Identifiers
3D model (JSmol)
1752351
ChEBI
ChemSpider
ECHA InfoCard 100.003.574
EC Number
  • 203-931-2
185341
KEGG
PubChem CID
UNII
  • InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) ☒N
    Key: FBUKVWPVBMHYJY-UHFFFAOYSA-N ☒N
  • InChI=1/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)
    Key: FBUKVWPVBMHYJY-UHFFFAOYAF
  • CCCCCCCCC(=O)O
Properties
C9H18O2
Molar mass 158.241 g/mol
Appearance Clear to yellowish oily liquid
Density 0.900 g/cm3
Melting point 12.5 °C (54.5 °F; 285.6 K)
Boiling point 254 °C (489 °F; 527 K)
Critical point (T, P) 439 °C (712 K), 2.35 MPa
0.3 g/L
Acidity (pKa)
  • 4.96
  • 1.055 at 2.06–2.63 K (−271.09 – −270.52 °C; −455.96 – −454.94 °F)
  • 1.53 at −191 °C (−311.8 °F; 82.1 K)
1.4322
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark
Warning
H315, H319, H412
P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P501
NFPA 704 (fire diamond)
3
1
0
Flash point 114 °C (237 °F; 387 K)
405 °C (761 °F; 678 K)
Related compounds
Related compounds
Octanoic acid, decanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.

The acid is named after the pelargonium plant, since oil from its leaves contains esters of the acid.

Preparation

Together with azelaic acid, it is produced industrially by ozonolysis of oleic acid.

Alternatively, pelargonic acid can be produced in a two-step process beginning with coupled dimerization and hydroesterification of 1,3-butadiene. This step produces a doubly unsaturated C9-ester, which can be hydrogenated to give esters of pelargonic acid.

A laboratory preparation involves permanganate oxidation of 1-decene.

Occurrence, and uses

Pelargonic acid occurs naturally as esters in the oil of pelargonium.

Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation of plasticizers and lacquers. The derivative 4-nonanoylmorpholine is an ingredient in some pepper sprays. The ammonium salt of pelargonic acid, ammonium pelargonate, is a herbicide. It is commonly used in conjunction with glyphosate, a non-selective herbicide, for a quick burn-down effect in the control of weeds in turfgrass.

The methyl form and ethylene glycol pelargonate act as nematicides against Meloidogyne javanica on Solanum lycopersicum, and the methyl against Heterodera glycines and M. incognita on Glycine max.

Esters of pelargonic acid are precursors to lubricants.

Pharmacological effects

Pelargonic acid may be more potent than valproic acid in treating seizures. Moreover, in contrast to valproic acid, pelargonic acid exhibited no effect on HDAC inhibition, suggesting that it is unlikely to show HDAC inhibition-related teratogenicity.

See also

External links


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