# Pelargonic acid

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Fatty acid

Pelargonic acid Names Preferred IUPAC name Nonanoic acid Other names Nonoic acid; nonylic acid; 1-octanecarboxylic acid; C9:0 (lipid numbers) Identifiers CAS Number 112-05-0 Y 3D model (JSmol) Interactive image Beilstein Reference 1752351 ChEBI CHEBI:29019 Y ChEMBL ChEMBL108436 ChemSpider 7866 Y ECHA InfoCard 100.003.574 EC Number 203-931-2 Gmelin Reference 185341 KEGG C01601 Y PubChem CID 8158 UNII 97SEH7577T Y CompTox Dashboard (EPA) DTXSID3021641 InChI InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) Y Key: FBUKVWPVBMHYJY-UHFFFAOYSA-N Y InChI=1/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) Key: FBUKVWPVBMHYJY-UHFFFAOYAF SMILES CCCCCCCCC(=O)O Properties Chemical formula 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 Solubility in water 0.3 g/L Acidity (pKa) 4.96[1] 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) Refractive index (nD) 1.4322 Hazards Occupational safety and health (OHS/OSH): Main hazards Corrosive GHS labelling: Pictograms Signal word Warning Hazard statements H315, H319, H412 Precautionary statements 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) 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). Infobox references

Chemical compound

**Pelargonic acid**, also called **nonanoic acid**, is an [organic compound](/source/Organic_compound) with [structural formula](/source/Structural_formula) CH3(CH2)7CO2H. It is a nine-carbon [fatty acid](/source/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](/source/Organic_solvent). The [esters](/source/Ester) and [salts](/source/Carboxylate_salt) of pelargonic acid are called **pelargonates** or **nonanoates**.

The acid is named after the [pelargonium](/source/Pelargonium) plant, since oil from its leaves contains [esters](/source/Esters) of the acid.

## Preparation

Together with [azelaic acid](/source/Azelaic_acid), it is produced industrially by [ozonolysis](/source/Ozonolysis) of [oleic acid](/source/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](/source/Dimerization) and [hydroesterification](/source/Hydroesterification) of 1,3-[butadiene](/source/Butadiene). This step produces a doubly unsaturated C9-ester, which can be [hydrogenated](/source/Hydrogenated) to give 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](/source/1-Decene).[4]

## Occurrence and uses

Pelargonic acid occurs naturally as esters in the oil of *[Pelargonium](/source/Pelargonium)*.

Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation of [plasticizers](/source/Plasticizer) and [lacquers](/source/Lacquer). The derivative [4-nonanoylmorpholine](/source/4-nonanoylmorpholine) is an ingredient in some [pepper sprays](/source/Pepper_spray).

The [ammonium salt](/source/Ammonium_salt) of pelargonic acid, [ammonium pelargonate](/source/Ammonium_pelargonate), is a [herbicide](/source/Herbicide). It is commonly used in conjunction with [glyphosate](/source/Glyphosate), a non-selective herbicide, for a quick burn-down effect in the control of weeds in [turfgrass](/source/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.[5]

The methyl form and ethylene glycol pelargonate act as [nematicides](/source/Nematicide) against *[Meloidogyne javanica](/source/Meloidogyne_javanica)* on *[Solanum lycopersicum](/source/Solanum_lycopersicum)*, and the methyl against *[Heterodera glycines](/source/Soybean_cyst_nematode)* and *[M. incognita](/source/Meloidogyne_incognita)* on *[Glycine max](/source/Glycine_max)*.[6]

Esters of pelargonic acid are precursors to lubricants.

## Pharmacological effects

Pelargonic acid may be more potent than [valproic acid](/source/Valproic_acid) in treating seizures.[7] Moreover, in contrast to valproic acid, pelargonic acid exhibited no effect on [HDAC inhibition](/source/HDAC_inhibition), suggesting that it is unlikely to show HDAC inhibition-related [teratogenicity](/source/Teratogenicity).[7]

## See also

- [List of saturated fatty acids](/source/List_of_saturated_fatty_acids)

- [List of carboxylic acids](/source/List_of_carboxylic_acids)

## References

1. **[^](#cite_ref-crc_1-0)** Lide, D. R. (Ed.) (1990). *CRC Handbook of Chemistry and Physics (70th Edn.)*. Boca Raton (FL):CRC Press.

1. **[^](#cite_ref-Ullmann_2-0)** Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids". *Ullmann's Encyclopedia of Industrial Chemistry*. [doi](/source/Doi_(identifier)):[10.1002/14356007.a10_245.pub2](https://doi.org/10.1002%2F14356007.a10_245.pub2). [ISBN](/source/ISBN_(identifier)) [978-3-527-30385-4](https://en.wikipedia.org/wiki/Special:BookSources/978-3-527-30385-4).

1. **[^](#cite_ref-Ullmann2_3-0)** J. Grub; E. Löser (2012). "Butadiene". *[Ullmann's Encyclopedia of Industrial Chemistry](/source/Ullmann's_Encyclopedia_of_Industrial_Chemistry)*. Weinheim: Wiley-VCH. [doi](/source/Doi_(identifier)):[10.1002/14356007.a04_431.pub2](https://doi.org/10.1002%2F14356007.a04_431.pub2). [ISBN](/source/ISBN_(identifier)) [978-3-527-30673-2](https://en.wikipedia.org/wiki/Special:BookSources/978-3-527-30673-2).

1. **[^](#cite_ref-4)** Lee, Donald G.; Lamb, Shannon E.; Chang, Victor S. (1981). ["Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid"](https://doi.org/10.15227%2Forgsyn.060.0011). *Organic Syntheses*. **60**: 11. [doi](/source/Doi_(identifier)):[10.15227/orgsyn.060.0011](https://doi.org/10.15227%2Forgsyn.060.0011).

1. **[^](#cite_ref-5)** 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](/source/Bibcode_(identifier)):[2004PBioP..80..151L](https://ui.adsabs.harvard.edu/abs/2004PBioP..80..151L). [doi](/source/Doi_(identifier)):[10.1016/j.pestbp.2004.06.010](https://doi.org/10.1016%2Fj.pestbp.2004.06.010).

1. **[^](#cite_ref-Chitwood-2002_6-0)** Chitwood, David J. (2002). "Phytochemical Based Strategies for Nematode Control". *[Annual Review of Phytopathology](/source/Annual_Review_of_Phytopathology)*. **40** (1). [Annual Reviews](/source/Annual_Reviews_(publisher)): 221–249. [doi](/source/Doi_(identifier)):[10.1146/annurev.phyto.40.032602.130045](https://doi.org/10.1146%2Fannurev.phyto.40.032602.130045). [ISSN](/source/ISSN_(identifier)) [0066-4286](https://search.worldcat.org/issn/0066-4286). [PMID](/source/PMID_(identifier)) [12147760](https://pubmed.ncbi.nlm.nih.gov/12147760). p. 229.

1. ^ [***a***](#cite_ref-PMC3625124_7-0) [***b***](#cite_ref-PMC3625124_7-1) 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"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3625124). *Neuropharmacology*. **69**: 105–114. [doi](/source/Doi_(identifier)):[10.1016/j.neuropharm.2012.11.004](https://doi.org/10.1016%2Fj.neuropharm.2012.11.004). [PMC](/source/PMC_(identifier)) [3625124](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3625124). [PMID](/source/PMID_(identifier)) [23177536](https://pubmed.ncbi.nlm.nih.gov/23177536).

## External links

- [MSDS at affymetrix.com](http://media.affymetrix.com/support/technical/usb/msds/19970A.pdf) [Archived](https://web.archive.org/web/20200919194528/http://media.affymetrix.com/support/technical/usb/msds/19970A.pdf) 2020-09-19 at the [Wayback Machine](/source/Wayback_Machine)

v t e Lipids: fatty acids Saturated Acetic (C2) Propionic (C3) Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecylic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Carboceric (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38) Nonatriacontanoic (C39) Tetracontanoic (C40) ω−3 Unsaturated Octenoic (8:1) Decenoic (10:1) Decadienoic (10:2) Lauroleic (12:1) Laurolinoleic (12:2) Myristovaccenic (14:1) Myristolinoleic (14:2) Myristolinolenic (14:3) Palmitolinolenic (16:3) Palmitidonic (16:4) α-Linolenic (18:3) Stearidonic (18:4) α-Parinaric (18:4) Dihomo-α-linolenic (20:3) Eicosatetraenoic (20:4) Eicosapentaenoic (20:5) Clupanodonic (22:5) Docosahexaenoic (22:6) 9,12,15,18,21-Tetracosapentaenoic (24:5) 6,9,12,15,18,21-Tetracosahexaenoic (24:6) ω−5 Unsaturated Myristoleic (14:1) Palmitovaccenic (16:1) α-Eleostearic (18:3) β-Eleostearic (trans-18:3) Punicic (18:3) 7,10,13-Octadecatrienoic (18:3) 9,12,15-Eicosatrienoic (20:3) β-Eicosatetraenoic (20:4) ω−6 Unsaturated Obtusilic acid (10:1) 8-Tetradecenoic (14:1) 12-Octadecenoic (18:1) Linoleic (18:2) Linolelaidic (trans-18:2) γ-Linolenic (18:3) Calendic (18:3) Pinolenic (18:3) Dihomo-linoleic (20:2) Dihomo-γ-linolenic (20:3) Sciadonic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5) ω−7 Unsaturated Palmitoleic (16:1) Vaccenic (18:1) Rumenic (18:2) Paullinic (20:1) 7,10,13-Eicosatrienoic (20:3) ω−9 Unsaturated Hypogeic (16:1) Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) 8,11-Eicosadienoic (20:2) Mead (20:3) Ximenic (26:1) ω−10 Unsaturated Sapienic (16:1) ω−11 Unsaturated Gadoleic (20:1) Cetoleic (22:1) Lumequeic (30:1) ω−12 Unsaturated 4-Hexadecenoic (16:1) Petroselinic (18:1) 8-Eicosenoic (20:1)

Authority control databases GND

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Adapted from the Wikipedia article [Pelargonic acid](https://en.wikipedia.org/wiki/Pelargonic_acid) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Pelargonic_acid?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.