Nonanoic acid
Nonanoic acid, also called pelargonic 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 nonanoic acid are called nonanoates.
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| IUPAC name
Nonanoic acid | |
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| ECHA InfoCard | 100.003.574 |
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| Properties | |
Chemical formula |
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) |
Solubility in water |
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) |
| Hazards | |
| Main hazards | Corrosive (C) |
| R-phrases (outdated) | R34 |
| S-phrases (outdated) | (S1/2) S26 S28 S36/37/39 S45 |
| NFPA 704 (fire diamond) | 
1
3
0 |
| Flash point | 114 °C (237 °F; 387 K) |
Autoignition temperature |
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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Its refractive index is 1.4322. Its critical point is at 712 K (439 °C) and 2.35 MPa.
Preparation, occurrence, and uses
Nonanoic acid occurs naturally as esters in the oil of pelargonium. Together with azelaic acid, it is produced industrially by ozonolysis of oleic acid.[2]
Synthetic esters of nonanoic acid, such as methyl nonanoate, are used as flavorings. Nonanoic 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 nonanoic acid, ammonium nonanoate, 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 effects
Nonanoic acid may be more potent than valproic acid in treating seizures.[3] Moreover, in contrast to valproic acid, nonanoic acid exhibited no effect on HDAC inhibition, suggesting that it is unlikely to show HDAC inhibition-related teratogenicity.[3]
References
- 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.