// Workers AI · dad joke modeWhat did pelargonic acid say? I'm a fatty decision.
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| 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 | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.574 |
| EC Number |
|
| 185341 | |
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| 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) |
|
Refractive index (nD) |
1.4322 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Corrosive |
| GHS labelling: | |
  | |
| Warning | |
| H315, H319, H412 | |
| P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 114 °C (237 °F; 387 K) |
| 405 °C (761 °F; 678 K) | |
| Related compounds | |
Related compounds |
Caprylic acid, Capric 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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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
[edit]Pelargonic acid, similarly to azelaic acid, is produced industrially by the ozonolysis of oleic acid.[2]
- CH3(CH2)7CH=CH(CH2)7CO2H + O3 → CH3(CH2)7CO2H + HO2C(CH2)7CO2H
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 produce esters of pelargonic acid.[3]
- 2 CH2=CHCH=CH2 + CO + CH3OH → CH2=CH(CH2)3CH=CHCH2CO2CH3
- CH2=CH(CH2)3CH=CHCH2CO2CH3 + 2 H2 → CH3(CH2)7CO2CH3
A laboratory preparation involves permanganate oxidation of 1-decene.[4]
Occurrence and uses
[edit]
Pelargonic acid is found naturally in many species of animals and plants including numerous fruits and vegetables such as apples, grapes, oranges, potatoes and also milk.[5][6] The esters occur in the oil of Pelargonium. It was first isolated in 1845 by Austrian chemist H. Pless from the essential oil of Pelargonium roseum.[7] It was officially synthesized and named by Joseph Redtenbacher.[7] Pelargonic acid was also discovered in several essential oils of French lavender, hops and rose.[8]
As a contact herbicide, pelargonic acid acts through rapid membrane disruption.[9] From an environmental perspective its low accumulation and rapid degradation in soil make it a promising alternative for sustainable weed management.[8][9] In 1995, the Mycogen Corporation introduced the first pelargonic acid herbicide under the brand name Scythe, containing 57% pelargonic acid.[9]
In the United States, pelargonic acid is not a certified organic herbicide.[10] This is because it is manufactured using a synthetic process including ozonation which makes the material ineligible for use in organic agriculture under United States Department of Agriculture (USDA) criteria.[11]
Ammonium pelargonate (also known as ammonium nonanoate), is a naturally derived compound created by combining pelargonic acid with ammonia. It is commonly used as a non-selective herbicide, for a quick burn-down effect in the control of weeds in turfgrass. It works by causing leaks in plant cell membranes, allowing chlorophyll molecules to escape the chloroplast. Under sunlight, these misplaced molecules cause immense oxidative damage to the plant.[12] Ammonium pelargonate is approved for organic use by the USDA as it qualifies as an ammoniated soap salt of a fatty acid, whereas standalone pelargonic acid is not a soap and thus not eligible for use in USDA organic production.[11][13]
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.[14]
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.
Esters of pelargonic acid are precursors to lubricants.
Pharmacological effects
[edit]Pelargonic acid may be more potent than valproic acid in treating seizures.[15] 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.[15]
See also
[edit]References
[edit]- ↑ Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
- ↑ Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_245.pub2. ISBN 978-3-527-30385-4.
- ↑ J. Grub; E. Löser (2012). "Butadiene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_431.pub2. ISBN 978-3-527-30673-2.
- ↑ Lee, Donald G.; Lamb, Shannon E.; Chang, Victor S. (1981). "Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid". Organic Syntheses. 60: 11. doi:10.15227/orgsyn.060.0011.
- ↑ "Pelargonic Acid" (PDF). ICF International for the USDA National Organic Program. 2006.
- ↑ "Herbicides based on pelargonic acid: Herbicides of the bioeconomy" (PDF). Society of Chemical Industry. 2019.
- 1 2 "Biobased herbicides based on pelargonic acid" (PDF). Chemistry Today. 2019.
- 1 2 "PETITION FOR THE LISTING OF PELARGONIC ACID AND RELATED C6-C12 FATTY ACIDS ON THE USDA NATIONAL LIST OF ALLOWED AND PROHIBITED SUBSTANCES" (PDF). USDA National Organic Program. 2005.
- 1 2 3 Preisler AC, Campos EVR, Takeshita V, Rodrigues JS, de Freitas ASM, Cintra Cardoso B, Battaglini LD, Fraceto LF (2026). "Pelargonic Acid: From Historical Uses to Future Perspectives in Sustainable Agriculture". J Agric Food Chem. 74 (12): 9903–9915. doi:10.1021/acs.jafc.5c14438.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ↑ "Going natural: Effective weed control in squash with pelargonic acid". United States Department of Agriculture. 2026.
- 1 2 Baker, Brian (2021). "Pelargonic Acid". OMRI.
- ↑ Lederer, Barbara; Fujimori, Takane; Tsujino, Yasuko; Wakabayashi, Ko; Böger, Peter (November 2004). "Phytotoxic activity of middle-chain fatty acids II: peroxidation and membrane effects". Pesticide Biochemistry and Physiology. 80 (3): 151–156. Bibcode:2004PBioP..80..151L. doi:10.1016/j.pestbp.2004.06.010.
- ↑ "Organic herbicide update". United States Department of Agriculture. 2026.
- ↑ Chitwood, David J. (2002). "Phytochemical Based Strategies for Nematode Control". Annual Review of Phytopathology. 40 (1). Annual Reviews: 221–249. doi:10.1146/annurev.phyto.40.032602.130045. ISSN 0066-4286. PMID 12147760. p. 229.
- 1 2 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.
External links
[edit]- MSDS at affymetrix.com Archived 2020-09-19 at the Wayback Machine