{{Short description|Fatty acid}} {{chembox |ImageFile = Pelargonic acid.svg |ImageClass = skin-invert |PIN = Nonanoic acid |OtherNames = Nonoic acid; nonylic acid; 1-octanecarboxylic acid; C9:0 ([[fatty acid#Nomenclature|lipid numbers]]) |Section1={{Chembox Identifiers |CASNo_Ref = {{cascite|correct|CAS}} |CASNo = 112-05-0 |Beilstein = 1752351 |ChEBI_Ref = {{ebicite|correct|EBI}} |ChEBI = 29019 |ChEMBL = 108436 |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID = 7866 |EINECS = 203-931-2 |Gmelin = 185341 |KEGG_Ref = {{keggcite|correct|kegg}} |KEGG = C01601 |PubChem = 8158 |UNII_Ref = {{fdacite|correct|FDA}} |UNII = 97SEH7577T |InChI = 1/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) |InChIKey = FBUKVWPVBMHYJY-UHFFFAOYAF |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI = 1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = FBUKVWPVBMHYJY-UHFFFAOYSA-N |SMILES = CCCCCCCCC(=O)O }} |Section2={{Chembox Properties |C=9|H=18|O=2 |MolarMassUnit = g/mol |Appearance = Clear to yellowish oily liquid |Density = 0.900 g/cm<sup>3</sup> |MeltingPtC = 12.5 |BoilingPtC = 254 |CriticalTP = 439 °C (712 K), 2.35 MPa |Solubility = 0.3 g/L |pKa = {{ubli | 4.96<ref name=crc>{{cite book | author=Lide, D. R. (Ed.) | title=CRC Handbook of Chemistry and Physics (70th Edn.) | publisher=Boca Raton (FL):CRC Press | year=1990}}</ref> | 1.055 at {{convert|2.06–2.63|K|C F}} | 1.53 at {{convert|−191|C|F K}} }} |RefractIndex = 1.4322 }} |Section3={{Chembox Hazards |MainHazards = Corrosive |NFPA-H = 3 |NFPA-F = 1 |NFPA-R = 0 |GHSPictograms = {{GHS05}} {{GHS07}} |GHSSignalWord = Warning |HPhrases = {{H-phrases|315|319|412}} |PPhrases = {{P-phrases|264|273|280|302+352|305+351+338|321|332+313|337+313|362|501}} |FlashPtC = 114 |AutoignitionPtC = 405 }} |Section4={{Chembox Related |OtherCompounds = [[Octanoic acid]], [[decanoic acid]] }} }}
'''Pelargonic acid''', also called '''nonanoic acid''', is an [[organic compound]] with [[structural formula]] {{chem2|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 solvent]]s. The [[ester]]s and [[carboxylate salt|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== Together with [[azelaic acid]], it is produced industrially by [[ozonolysis]] of [[oleic acid]].<ref name=Ullmann>{{cite book | doi = 10.1002/14356007.a10_245.pub2 | chapter = Fatty Acids | title = Ullmann's Encyclopedia of Industrial Chemistry | date = 2006 | last1 = Anneken | first1 = David J. | last2 = Both | first2 = Sabine | last3 = Christoph | first3 = Ralf | last4 = Fieg | first4 = Georg | last5 = Steinberner | first5 = Udo | last6 = Westfechtel | first6 = Alfred | isbn = 978-3-527-30385-4 }}</ref>
:{{chem2 | CH3(CH2)7CH\dCH(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 give esters of pelargonic acid.<ref name=Ullmann2>{{Ullmann|title=Butadiene|author1=J. Grub|author2=E. Löser|year=2012|doi=10.1002/14356007.a04_431.pub2}}</ref>
:{{chem2 | 2 CH2\dCHCH\dCH2 + CO + CH3OH -> CH2\dCH(CH2)3CH\dCHCH2CO2CH3 }} :{{chem2 | CH2\dCH(CH2)3CH\dCHCH2CO2CH3 + 2 H2 -> CH3(CH2)7CO2CH3 }}
A laboratory preparation involves permanganate oxidation of [[1-Decene|1-decene]].<ref>{{cite journal |doi=10.15227/orgsyn.060.0011 |title=Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid |journal=Organic Syntheses |year=1981 |volume=60 |page=11 |first1=Donald G. |last1=Lee |first2=Shannon E. |last2=Lamb |first3=Victor S. |last3=Chang |doi-access=free}}</ref>
==Occurrence and uses== Pelargonic acid occurs naturally as esters in the oil of ''[[Pelargonium]]''.
Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation of [[plasticizer]]s and [[lacquer]]s. The derivative [[4-nonanoylmorpholine]] is an ingredient in some [[pepper spray]]s.
The [[ammonium salt]] of pelargonic acid, [[ammonium pelargonate]], is a [[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]]. 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.<ref>{{cite journal |last1=Lederer |first1=Barbara |last2=Fujimori |first2=Takane |last3=Tsujino |first3=Yasuko |last4=Wakabayashi |first4=Ko |last5=Böger |first5=Peter |title=Phytotoxic activity of middle-chain fatty acids II: peroxidation and membrane effects |journal=Pesticide Biochemistry and Physiology |date=November 2004 |volume=80 |issue=3 |pages=151–156 |doi=10.1016/j.pestbp.2004.06.010|bibcode=2004PBioP..80..151L }}</ref>
The methyl form and ethylene glycol pelargonate act as [[nematicide]]s against ''[[Meloidogyne javanica]]'' on ''[[Solanum lycopersicum]]'', and the methyl against ''[[soybean cyst nematode|Heterodera glycines]]'' and ''[[Meloidogyne incognita|M. incognita]]'' on ''[[Glycine max]]''.<ref name="Chitwood-2002">{{cite journal | last=Chitwood | first=David J. | title=Phytochemical Based Strategies for Nematode Control | journal=[[Annual Review of Phytopathology]] | publisher=[[Annual Reviews (publisher)|Annual Reviews]] | volume=40 | issue=1 | year=2002 | issn=0066-4286 | doi=10.1146/annurev.phyto.40.032602.130045 | pages=221–249| pmid=12147760 }} p.{{nbs}}229.</ref>
Esters of pelargonic acid are precursors to lubricants.
==Pharmacological effects== Pelargonic acid may be more potent than [[valproic acid]] in treating seizures.<ref name="PMC3625124">{{cite journal |title= Seizure control by ketogenic diet-associated medium chain fatty acids |pmc=3625124 | year=2013 |journal=Neuropharmacology |volume=69 |pages=105–114 |doi=10.1016/j.neuropharm.2012.11.004|pmid=23177536 |last1=Chang |first1=P. |last2=Terbach |first2=N. |last3=Plant |first3=N. |last4=Chen |first4=P. E. |last5=Walker |first5=M. C. |last6=Williams |first6=R. S. }}</ref> 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]].<ref name="PMC3625124" />
==See also== * [[List of saturated fatty acids]] * [[List of carboxylic acids]]
==References== <references/>
==External links== *[http://media.affymetrix.com/support/technical/usb/msds/19970A.pdf MSDS at affymetrix.com] {{Webarchive|url=https://web.archive.org/web/20200919194528/http://media.affymetrix.com/support/technical/usb/msds/19970A.pdf |date=2020-09-19 }}
{{Fatty acids}}
{{Authority control}}
[[Category:Alkanoic acids]] [[Category:Herbicides]] [[Category:Nematicides]] [[Category:Foul-smelling chemicals]]