Nonadecanoic acid

Structural formula
General
Surname	Nonadecanoic acid
other names	n -Nonadecanoic acid
Molecular formula	C 19 H 38 O 2
Brief description	colorless leaflets
External identifiers / databases
EC number	211-472-4
ECHA InfoCard	100.010.431
PubChem	12591
Wikidata	Q412597
properties
Molar mass	298.50 g mol −1
Physical state	firmly
density	1.225 g cm −3 (25 ° C)
Melting point	106.5 ° C
boiling point	357.1 ° C
solubility	hardly soluble in water, benzene , ether ; soluble in ethanol ;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The nonadecanoic acid is a saturated long-chain fatty acid having an odd number of carbon atoms and belongs to the substance group of alkanoic acids . Their salts and esters are called nonadecanoates .

Occurrence

Like most long-chain fatty acids with an odd number of carbon atoms, nonadecanoic acid occurs only rarely and in low concentrations in nature.

At first it was isolated from natural sources only from the fat of the beef kidneys.

Dill ( anethum graveolens )

More recent studies have also found nonadecanoic acid in higher plants, such as 9.95% of the total fatty acids in the green parts of dill ( Anethum graveolens ), as well as in a red alga ( Hypnea musciformis ).

Microorganisms also form nonadecanoic acid, e.g. B. Streptomyces scabiei subsp. chosunensis .

In addition, it is important for termites in the insect world: The soldiers of the termite species Rhinotermes marginalis use, among other things, nonadecanoic acid in their defense secretions.

Extraction and presentation

Nonadecanoic acid can be produced by oxidizing 1-eicosene with potassium permanganate .

pharmacology

Just like other odd-numbered fatty acids, nonadecanoic acid is also increasingly accumulated in cases of vitamin B ₁₂ deficiency.

This fatty acid also acts as a cell poison against some human cancer cells .

use

Because of its rarity and its low occurrence in biological material, it - like tridecanoic acid and heneicosanoic acid - is often used as an internal standard in the gas chromatographic analysis of fatty acids .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-398.
↑ ^a ^b Datasheet Nonadecanoic acid from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
^ RP Hansen; FB Shorland, N. June Cooke: Occurrence of n-Nonadecanoic Acid in Ox Perinephric Fat , In: Nature 176. 1955, 882; doi : 10.1038 / 176882a0
↑ WM Amin, AA Sleem: Chemical And Biological Study Of Aerial Parts Of Dill (Anethum Graveolens L.) , In: Egyptian Journal of Biomedical Sciences , 23 2007, pp. 73-90.
↑ S. Siddqiui; SB Naqvi Shyum; K. Usmanghani; M. Shameel: Antibacterial activity and fatty acid composition of the extract from Hypnea musciformis (Gigartinales, Rhodophyta) , In: Pak J Pharm Sci , 6. 1993, pp. 45-51.
↑ ^a ^b J. C. Yoo; JM Han; SK Nam; OH Ko; CH Choi; KH Kee; J. K Sohng; JS Jo; CN Seong: Characterization and cytotoxic activities of nonadecanoic acid produced by Streptomyces scabiei subsp. chosunensis M0137 (KCTC 9927) , in: Journal of Microbiology 40. 2002, pp. 331-334.
↑ MS Blum; TH Jones; DE Howard; WL Overal: Biochemistry of termite defenses: Coptotermes, Rhinotermes and Cornitermes species , in: Comp. Biochem. Physiol. B. , 71, 1982, pp. 731-733.
↑ Donald G. Lee, Shannon E. Lamb, and Victor S. Chang: Carboxylic acids from the oxidation of terminal alkenes by permanganate: Nonadecanoic acid In: Organic Syntheses . 60, 1981, p. 11, doi : 10.15227 / orgsyn.060.0011 ; Coll. Vol. 7, 1990, p. 397 ( PDF ).
↑ EM Antolin; DM Delange; VG Canavaciolo; YT Diaz; MC Medina; RS Perez: Validation of a gas chromatographic method for determining fatty acids that compose D003 in 10 mg film-coated tablets , in: Il Farmaco , 59. 2004, pp. 543-547; doi : 10.1016 / j.farmac.2003.11.020
↑ DL Palmquist, TC Jenkins: Challenges with fats and fatty acid methods. In: Journal of animal science. Volume 81, Number 12, December 2003, pp. 3250-3254, PMID 14677882 (review).

Web links

Wiktionary: Nonadecanoic acid - explanations of meanings, word origins, synonyms, translations

[CRC90_3_398-1] ↑ ^a ^b ^c ^d ^e ^f David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-398.

[Sigma-2] Datasheet Nonadecanoic acid from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).

[3] RP Hansen; FB Shorland, N. June Cooke: Occurrence of n-Nonadecanoic Acid in Ox Perinephric Fat , In: Nature 176. 1955, 882; doi : 10.1038 / 176882a0

[4] WM Amin, AA Sleem: Chemical And Biological Study Of Aerial Parts Of Dill (Anethum Graveolens L.) , In: Egyptian Journal of Biomedical Sciences , 23 2007, pp. 73-90.

[5] S. Siddqiui; SB Naqvi Shyum; K. Usmanghani; M. Shameel: Antibacterial activity and fatty acid composition of the extract from Hypnea musciformis (Gigartinales, Rhodophyta) , In: Pak J Pharm Sci , 6. 1993, pp. 45-51.

[jmicrobiol-6] J. C. Yoo; JM Han; SK Nam; OH Ko; CH Choi; KH Kee; J. K Sohng; JS Jo; CN Seong: Characterization and cytotoxic activities of nonadecanoic acid produced by Streptomyces scabiei subsp. chosunensis M0137 (KCTC 9927) , in: Journal of Microbiology 40. 2002, pp. 331-334.

[7] MS Blum; TH Jones; DE Howard; WL Overal: Biochemistry of termite defenses: Coptotermes, Rhinotermes and Cornitermes species , in: Comp. Biochem. Physiol. B. , 71, 1982, pp. 731-733.

[8] Donald G. Lee, Shannon E. Lamb, and Victor S. Chang: Carboxylic acids from the oxidation of terminal alkenes by permanganate: Nonadecanoic acid In: Organic Syntheses . 60, 1981, p. 11, doi : 10.15227 / orgsyn.060.0011 ; Coll. Vol. 7, 1990, p. 397 ( PDF ).

[9] EM Antolin; DM Delange; VG Canavaciolo; YT Diaz; MC Medina; RS Perez: Validation of a gas chromatographic method for determining fatty acids that compose D003 in 10 mg film-coated tablets , in: Il Farmaco , 59. 2004, pp. 543-547; doi : 10.1016 / j.farmac.2003.11.020

[10] DL Palmquist, TC Jenkins: Challenges with fats and fatty acid methods. In: Journal of animal science. Volume 81, Number 12, December 2003, pp. 3250-3254, PMID 14677882 (review).