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.
Nonoic acid; Nonylic acid;
C9:0 (Lipid numbers)
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||158.241 g·mol−1|
|Appearance||Clear to yellowish oily liquid|
|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|
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)
Refractive index (nD)
|Main hazards||Corrosive (C)|
|S-phrases (outdated)||(S1/2) S26 S28 S36/37/39 S45|
|NFPA 704 (fire diamond)|
|Flash point||114 °C (237 °F; 387 K)|
|405 °C (761 °F; 678 K)|
|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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Preparation, occurrence, and usesEdit
- 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.
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.
- 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)
- 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
- 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.