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Pelargonic acid

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Pelargonic acid
Names
IUPAC name
Nonanoic acid
Other names
  • Pelargonic acid
  • 1-Octanecarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.574 Edit this at Wikidata
EC Number
  • 203-931-2
KEGG
UNII
  • InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) ☒N
    Key: FBUKVWPVBMHYJY-UHFFFAOYSA-N ☒N
  • 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 158.241 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)
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
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive (C)
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 their standard state (at 25 °C [77 °F], 100 kPa).
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Nonanoic acid, also called pelargonic acid, is an organic compound composed of a nine-carbon chain terminating in a carboxylic acid with structural formula CH3(CH2)7COOH. The esters and salts of nonanoic acid are called nonanoates. Nonanoic acid is a clear, oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in chloroform, ether, and hexane. 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.

Its refractive index is 1.4322. Its critical point is at 712 K (439 °C) and 2.35 MPa.

Occurrence and uses

Nonanoic acid is a fatty acid which occurs naturally as esters in the oil of pelargonium. Synthetic esters, 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.

Potential pharmacological effects

Nonanoic acid may be more potent than valproic acid in treating seizures.[2] 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.[2]

References

  1. ^ Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
  2. ^ a b "Seizure control by ketogenic diet-associated medium chain fatty acids". 2013. PMC 3625124. {{cite web}}: Missing or empty |url= (help)
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