Tariric acid

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Structural formula
Structural formula of Tariricacid
General
Surname Tariric acid
other names

6-octadecinic acid ( IUPAC )

Molecular formula C 18 H 32 O 2
Brief description

White dust

External identifiers / databases
CAS number 544-74-1
PubChem 235711
ChemSpider 205669
Wikidata Q614708
properties
Molar mass 280.45 g mol −1
Physical state

firmly

Melting point

49-50 ° C

boiling point

178-180 ° C (40 Pa )

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The tariric acid is an unsaturated fatty acid in the group of alkynoic acids . It is the first proven natural product with a triple bond , an acetylene compound ; a triple unsaturated bond. Its systematic name is 6-octadecinic acid, the short notation is 18: 1-delta-6a, it is an isomer of linoleic acid .

Occurrence

Tariric acid occurs in specific vegetable oils and fats esterified with glycerine . It was first isolated from the seed oil of a species of Picramnia in 1892 . Further evidence was made in Picramnia camboita from Brazil, in Picramnia carpinterae from Guatemala and Picramnia lindeniana from Mexico. Tariric acid is biosynthesized from petroselinic acid ; both fatty acids were detected side by side in Picramnia and Alvaradoa species.

The occurrence of tariric acid as the main fatty acid is a characteristic of species of the Picramniaceae .

Extraction and presentation

Fatty acids can be obtained from the corresponding triacylglycerides by alkaline saponification by boiling the corresponding fats or oils with bases . The saponification itself initially supplies their salts. The free fatty acids are obtained by neutralization with (mineral) acids. Since the natural fats and oils always contain many different fatty acids, the resulting mixture is usually separated.

Tariric acid is synthetically produced from petroselinic acid, which is commercially available in pure form .

properties

Physical Properties

Pure tariric acid is solid at room temperature (melting point 40 ° C). The molar mass is 280.45 g mol −1 . The fatty acid is insoluble in water but soluble in methanol .

Chemical properties

The triple bond is the most reactive part of tariric acid. The acid and especially its salts are amphiphilic , that is, they contain both a polar, hydrophilic part (the carboxy group ) and a non-polar, lipophilic part (the hydrocarbon chain).

The synthesis of pure tariric acid takes place via bromination and dehydrohalogenation with potassium hydroxide from petroselic acid, the purity is proven by capillary gas chromatography, the identity by NMR spectroscopy, by selective hydrogenation and subsequent ozonolysis.

Biological properties

Tariric acid has a stronger inhibitory effect on microorganisms than petroselinic acid. In contrast to petroselinic acid, tariric acid cannot be completely broken down in mammalian catabolism.

proof

The detection and determination of the content of tariric acid as well as other fatty acids in fats is usually carried out by gas chromatography of the methyl ester ; In addition, the unsaturated fatty acids can be separated using silver nitrate thin-layer chromatography .

A second detection method would be the bromine water test for multiple bonds.

use

Tariric acid is not currently used commercially.

Individual evidence

  1. a b Xing-Cong Li, Melissa R. Jacob, Hala N. ElSohly, Dale G. Nagle, Troy J. Smillie, Larry A. Walker, Alice M. Clark: Acetylenic Acids Inhibiting azoles-Resistant from . In: Journal of Natural Products . tape 66 , no. 8 , August 2003, p. 1132-1135 , doi : 10.1021 / np030196r .
  2. JA Barve, FD Gunstone: Fatty acids, Part 33 The synthesis of all the octadecynoic acids and all the trans-octadecenoic acids . In: Chemistry and Physics of Lipids . tape 7 , no. 4 , December 1971, p. 311-323 , doi : 10.1016 / 0009-3084 (71) 90009-0 .
  3. ^ A b D. E. Ames, AN Covell, TG Goodburn: 164. Syntheses of long-chain acids. Part VI. Acetylenic acids and cis, cis-docosa-5,13-dienoic acid . In: Journal of the Chemical Society . 1965, p. 894 , doi : 10.1039 / JR9650000894 .
  4. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  5. M. Arnaud: Sur la constitution de l'acide taririque. In. Comt. Rend. 134, (1902), 473.
  6. ^ MA Arnaud: Sur un novel acid gras non saturé de la série CnH2n-4O2. In: Compt. Rend. 114, (1892), 79.
  7. B. Grützner: About a crystallized component of the fruits of Picramnia camboita. In: Chemiker Zeitung. 100, (1893), 1851.
  8. Cl. Grimme: About some rare oil fruits. In: Chemical review about the fat and resin industry. 17, (1910), 156.
  9. Cl. Grimme: About the fat of Picramnia lindeniana. In: Chemical review about the fat and resin industry. 19, (1912), 51.
  10. GF Spencer, R. Kleiman, FR Earle, IA Wolff: The Trans-6 fatty acids of Picramnia sellowii seed oil . In: Lipids . tape 5 , no. 3 , March 1970, p. 285-287 , doi : 10.1007 / BF02531458 .
  11. MB Pearl, R. Kleiman, FR Earle: Acetylenic acids of Alvaradoa amorphoides seed oil . In: Lipids . tape 8 , no. November 11 , 1973, pp. 627-630 , doi : 10.1007 / BF02533146 .
  12. R. Hansel: 22. Lipide In: R. Hansel, O. Sticher (Ed.): Pharmakognosie Phytopharmazie. 9th edition (2010), Springer, Heidelberg, ISBN 978-3-642-00962-4 , pp. 673–674, ( limited preview in the Google book search).
  13. ^ A b Karl Bernhard, Kushal Yekundi, Ekkehard Kaempf: The biological behavior of fatty acids with a triple bond: III. The breakdown of tariric acid . In: Helvetica Chimica Acta . tape 51 , no. 2 , January 1968, p. 373–376 , doi : 10.1002 / hlca.19680510217 .
  14. H. Lindlar: A new catalyst for selective hydrogenations. In: Helv. Chim. Acta. 35, (1952), 446.
  15. T. Stuhlfauth, H. Fock, H. Huber, K. Klug: The distribution of fatty acids including petroselinic and tariric acids in the fruit and seed oils of the Pittosporaceae, Araliaceae, Umbelliferae, Simarubaceae and Rutaceae. In: Biochemical Systematics and Ecology. 13, 1985, pp. 447-453, doi: 10.1016 / 0305-1978 (85) 90091-2 .
  16. Jon J. Kabara, Anthony J. Conley, Dennis M. Swieczkowski, IA Ismail, M. Lie Ken Jie, Frank D. Gunstone: Antimicrobial action of isomeric fatty acids on group A Streptococcus . In: Journal of Medicinal Chemistry . tape 16 , no. 9 , 1973, p. 1060-1063 , doi : 10.1021 / jm00267a028 .
  17. B. Breuer, T. Stuhlfauth, HP Fock: Separation of Fatty Acids or Methyl Esters Including Positional and Geometric Isomers by Alumina Argentation Thin-Layer Chromatography. In: Journal of Chromatographic Science . 25, 1987, pp. 302-306, doi: 10.1093 / chromsci / 25.7.302 .