Gamma linolenic acid

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Structural formula
GLAnumbering.png
General
Surname Gamma linolenic acid
other names
  • (6 Z , 9 Z , 12 Z ) -Octadeca-6,9,12-trienoic acid ( IUPAC )
  • Gamolenic acid
  • 18: 3 (ω − 6) ( lipid name )
Molecular formula C 18 H 30 O 2
Brief description

light yellow liquid

External identifiers / databases
CAS number 506-26-3
EC number 624-740-4
ECHA InfoCard 100.107.263
PubChem 5280933
DrugBank DB13854
Wikidata Q415885
properties
Molar mass 278.44 g · mol -1
Physical state

liquid

density

0.91 g cm −3

Melting point

−11 ° C

boiling point

230–232 ° C (1.3 h Pa )

solubility

almost insoluble in water

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Gamma-linolenic acid (18: 3), often called GLA for short in the literature, is a triple-unsaturated omega-6 fatty acid . It is synthesized in every animal and human organism from the essential omega-6 fatty acid linoleic acid or it is ingested directly from food. Gamma-linolenic acid is the precursor of dihomogammalinolenic acid and arachidonic acid and is therefore the basis for the production of both the less inflammatory series-1 and the more inflammatory series-2 eicosanoids .

The intake of gamma-linolenic acid (for example from borage oil , evening primrose oil or hemp oil ) can have a positive effect on inflammatory processes in the body . In addition, gamma-linolenic acid is essential for the brain, especially for the conduction of nerve stimuli, and lowers blood pressure.

Occurrence

The following foods are good sources of gamma linolenic acid:

  • Borage oil (approx. 20%)
  • Evening primrose oil (approx. 10%)
  • Hemp oil (approx. 3%)

proof

The detection and determination of the content of linolenic acid is usually carried out by gas chromatography of the methyl ester; In addition, the unsaturated isomers can be separated using silver nitrate thin-layer chromatography.

Web links

Individual evidence

  1. a b c data sheet γ-Linolenic acid from Sigma-Aldrich , accessed on February 12, 2019 ( PDF ).
  2. a b c d Datasheet Linolenic acid at Acros, accessed on February 12, 2019.
  3. ^ X. Wang, H. Lin, Y. Gu: Multiple roles of dihomo-γ-linolenic acid against proliferation diseases. In: Lipids in health and disease. Volume 11, February 2012, p. 25, doi : 10.1186 / 1476-511X-11-25 , PMID 22333072 , PMC 3295719 (free full text) (review).
  4. T. Coste, M. Pierlovisi, J. Leonardi, D. Dufayet, A. Gerbi, H. Lafont, P. Vague, D. Raccah: Beneficial effects of gamma linolenic acid supplementation on nerve conduction velocity, Na +, K + ATPase activity , and membrane fatty acid composition in sciatic nerve of diabetic rats. In: J. Nutr. Biochem. 10 (7), 1999, pp. 411-420, PMID 15539317 .
  5. MM Engler, MB Engler, SK Erickson, SM Paul: Dietary gamma-linolenic acid lowers blood pressure and alters aortic reactivity and cholesterol metabolism in hypertension. In: J. Hypertens. , 10 (10), 1992, pp. 1197-1204, PMID 1335001 .
  6. B. Breuer, T. Stuhlfauth, HP Fock: Separation of fatty acids or methyl esters including positional and geometric isomers by alumina thin-layer chromatography. In: J. of Chromatogr. Science. 25, 1987, pp. 302-306