Pelargonic acid

  (Redirected from Nonanoic acid)

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.

Pelargonic acid
Pelargonic acid.svg
Names
IUPAC name
Nonanoic acid
Other names
Nonoic acid; Nonylic acid;
1-Octanecarboxylic acid;
C9:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.574 Edit this at Wikidata
EC Number
  • 203-931-2
KEGG
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−1
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]
1.055 at 2.06 to 2.63 K (−271.09 to −270.52 °C; −455.96 to −454.94 °F)
1.53 at −191 °C (−311.8 °F; 82.1 K)
1.4322
Hazards
Main hazards Corrosive (C)
R-phrases (outdated) R34
S-phrases (outdated) (S1/2) S26 S28 S36/37/39 S45
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).
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Infobox references

Preparation, occurrence, and usesEdit

Pelargonic acid occurs naturally as esters in the oil of pelargonium. Together with azelaic acid, it is produced industrially by ozonolysis of oleic acid.[2]

H17C8CH=CHC7H14CO2H + 4O → HO2CC7H14CO2H + H17C8CO2H

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 an 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.

Pharmacological effectsEdit

Pelargonic acid may be more potent than valproic acid in treating seizures.[3] 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.[3]

ReferencesEdit

  1. ^ Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.CS1 maint: extra text: authors list (link)
  2. ^ David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
  3. ^ a b Chang, P.; Terbach, N.; Plant, N.; Chen, P. E.; Walker, M. C.; Williams, R. S. (2013). "Seizure control by ketogenic diet-associated medium chain fatty acids". Neuropharmacology. 69: 105–114. doi:10.1016/j.neuropharm.2012.11.004. PMC 3625124. PMID 23177536.

See alsoEdit

External linksEdit