Nonadecylic acid

Nonadecylic acid, or nonadecanoic acid, is a 19-carbon saturated fatty acid with the chemical formula CH3(CH2)17COOH. It forms salts called nonadecylates. Nonadecylic acid can be found in fats and vegetable oils, although it is rare.

Nonadecylic acid
Names
IUPAC name
Nonadecanoic acid
Identifiers
3D model (JSmol)
1786261
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.431
EC Number
  • 211-472-4
UNII
  • InChI=1S/C19H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21/h2-18H2,1H3,(H,20,21) checkY
    Key: ISYWECDDZWTKFF-UHFFFAOYSA-N checkY
  • O=C(O)CCCCCCCCCCCCCCCCCC
Properties
CH3(CH2)17COOH
Molar mass 298.50382 g/mol
Appearance White flakes or powder
Melting point 68 to 70 °C (154 to 158 °F; 341 to 343 K)
Boiling point 236 °C (457 °F; 509 K) (10 mmHg)
297 °C (100 mmHg)
Insoluble
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It is also present in the world of insects as the major constituent of the substance secreted by soldiers of the termite Rhinotermes marginalis for defence purposes.[2]

Nonadecanoic acid has found applications in the field of metal lubrication.[3]

The compound can be prepared by permanganate oxidation of 1-eicosene.[4]

See also

References
  1. "Nonadecanoic acid". pubchem.ncbi.nlm.nih.gov.
  2. Blum MS, Jones TH, Howard DF, Overal W (1982). "Biochemistry of termite defenses: Coptotermes, Rhinotermes and Cornitermes species". Comparative Biochemistry and Physiology Part B: Comparative Biochemistry. 71 (4): 731–733. doi:10.1016/0305-0491(82)90489-8.
  3. Smith, Hilton A.; McGill, Robert M. (1957). "The Adsorption of n-Nonadecanoic Acid on Mechanically Activated Metal Surfaces". The Journal of Physical Chemistry. 61 (8): 1025–1036. doi:10.1021/j150554a001.
  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.


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