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.[2]

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.[3]

Nonadecanoic acid has found applications in the field of metal lubrication.[4]

The compound can be prepared by permanganate oxidation of 1-eicosene.[5]

See also

References
  1. "Nonadecanoic acid". pubchem.ncbi.nlm.nih.gov.
  2. A.A. Warra (2015). "Physico-Chemical and GC/MS Analysis of Castor Bean (Ricinus communis L.) Seed Oil" (PDF). Chemistry and Materials Research. IISTE. 7 (2). ISSN 2224-3224. IISTE: CMR
  3. 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.
  4. 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.
  5. 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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