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Pelargonic acid

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Pelargonic acid
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
ChemSpider
ECHA InfoCard 100.003.574Edit this at Wikidata
EC Number
  • 203-931-2
185341
KEGG
UNII
  • InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)checkY
    Key: FBUKVWPVBMHYJY-UHFFFAOYSA-NcheckY
  • InChI=1/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)
    Key: FBUKVWPVBMHYJY-UHFFFAOYAF
  • CCCCCCCCC(=O)O
Properties
C9H18O2
Molar mass 158.241g/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)
  • 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)
1.4322
Hazards
Occupational safety and health(OHS/OSH):
Main hazards
 Corrosive
GHSlabelling:
GHS05: CorrosiveGHS07: Exclamation mark
Warning
H315,H319,H412
P264,P273,P280,P302+P352,P305+P351+P338,P321,P332+P313,P337+P313,P362,P501
NFPA 704(fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 114 °C (237 °F; 387 K)
405 °C (761 °F; 678 K)
Related compounds
Related compounds
 Octanoic acid,decanoic acid
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Pelargonic acid,also callednonanoic acid,is anorganic compoundwithstructural formulaCH3(CH2)7CO2H.It is a nine-carbonfatty acid.Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble inorganic solvents.Theestersandsaltsof pelargonic acid are calledpelargonatesornonanoates.

The acid is named after thepelargoniumplant, since oil from its leaves containsestersof the acid.

Preparation[edit]

Together withazelaic acid,it is produced industrially byozonolysisofoleic acid.[2]

Alternatively, pelargonic acid can be produced in a two-step process beginning with coupleddimerizationandhydroesterificationof 1,3-butadiene.This step produces a doubly unsaturated C9-ester, which can behydrogenatedto give esters of pelargonic acid.[3]

A laboratory preparation involves permanganate oxidation of1-decene.[4]

Occurrence and uses[edit]

Pelargonic acid occurs naturally as esters in the oil ofpelargonium.

Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation ofplasticizersandlacquers.The derivative4-nonanoylmorpholineis an ingredient in somepepper sprays.

Theammonium saltof pelargonic acid,ammonium pelargonate,is aherbicide.It is commonly used in conjunction withglyphosate,a non-selective herbicide, for a quick burn-down effect in the control of weeds inturfgrass.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 asnematicidesagainstMeloidogyne javanicaonSolanum lycopersicum,and the methyl againstHeterodera glycinesandM. incognitaonGlycine max.[6]

Esters of pelargonic acid are precursors to lubricants.

Pharmacological effects[edit]

Pelargonic acid may be more potent thanvalproic acidin treating seizures.[7]Moreover, in contrast to valproic acid, pelargonic acid exhibited no effect onHDAC inhibition,suggesting that it is unlikely to show HDAC inhibition-relatedteratogenicity.[7]

See also[edit]

References[edit]

  1. ^Lide, D. R. (Ed.) (1990).CRC Handbook of Chemistry and Physics (70th Edn.).Boca Raton (FL):CRC Press.
  2. ^David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" inUllmann's Encyclopedia of Industrial Chemistry,2006, Wiley-VCH, Weinheim.doi:10.1002/14356007.a10_245.pub2
  3. ^J. Grub; E. Löser (2012). "Butadiene".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a04_431.pub2.ISBN978-3527306732.
  4. ^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.
  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.doi:10.1016/j.pestbp.2004.06.010.
  6. ^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.ISSN0066-4286.PMID12147760.p.229.
  7. ^abChang, 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.PMC3625124.PMID23177536.

External links[edit]

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