Nonadecylic acid

Nonadecylic acid
Names
	IUPAC name Nonadecanoic acid
Identifiers
CAS Number	646-30-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1786261
ChEBI	CHEBI:39246 ;
ChEMBL	ChEMBL1169674 ;
ChemSpider	12071 ;
ECHA InfoCard	100.010.431
EC Number	211-472-4;
PubChem CID	12591;
UNII	H6M3VYC62P ;
CompTox Dashboard (EPA)	DTXSID3060954 ;
	InChI 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) Key: ISYWECDDZWTKFF-UHFFFAOYSA-N ;
	SMILES O=C(O)CCCCCCCCCCCCCCCCCC;
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). verify (what is ?) Infobox references

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.^{[citation needed]}

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]

References

^ "Nonadecanoic acid". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ 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.
^ 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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[1] "Nonadecanoic acid". pubchem.ncbi.nlm.nih.gov.

[Blum-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.

[Smith-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.

[OS-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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[2]

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[4]

Nonadecylic acid

See also

References