Dihomogammalinolenic acid

Structural formula
General
Surname	Dihomogammalinolenic acid
other names	DGLA; (8 Z , 11 Z , 14 Z ) -Eicosa-8,11,14-trienoic acid; 20: 3 (ω − 6) ( lipid name ); 20: 3 ∆8,11,14 -eicosatrienoic acid;
Molecular formula	C 20 H 34 O 2
Brief description	colorless liquid
External identifiers / databases
EC number	217-233-0
ECHA InfoCard	100,015,667
PubChem	5280581
DrugBank	DB00154
Wikidata	Q415398
properties
Molar mass	306,50 g · mol -1
Physical state	liquid
boiling point	200 ° C
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 .

Dihomogammalinolenic acid [20: 3 (ω − 6)], often shortened to DGLA in the literature , is a triple unsaturated fatty acid , an omega-6 fatty acid . It is synthesized from gamma-linolenic acid in every animal and human organism . Dihomogammalinolenic acid is a basic material for the production of the "good" ones, because z. B. Anti-inflammatory, Series 1 eicosanoids . But it is also the precursor of (among other things) the inflammation-enhancing arachidonic acid . In this connection it would be desirable to keep the conversion of DGLA to arachidonic acid as low as possible in order to reduce the formation of arachidonic acid and thus of series 2 eicosanoids. DGLA is converted to arachidonic acid by the enzyme delta-5-desaturase.

The following substances inhibit this conversion and thus have an anti-inflammatory and anti-arteriosclerotic effect:

Sesamin , a substance in sesame seeds found
Curcumin , a substance found in turmeric and responsible for its anti-inflammatory properties
the omega-3 linolenic acid , occurs in linseed oil and a few other oils.

High levels of insulin in the blood activate the production of arachidonic acid.

Physical Properties

The flash point is 62 ° C.

Web links

Gamma-linolenic acid and dihomo-gamma-linolenic acid
Vital substances lexicon : gamma-linolenic acid and dihomo-gamma-linolenic acid

Individual evidence

↑ ^a ^b ^c ^d Entry on allcis-Eicosa-8,11,14-trienoic acid in the GESTIS substance database of the IFA , accessed on December 21, 2019(JavaScript required) .
^ 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).

[GESTIS-1] Entry on allcis-Eicosa-8,11,14-trienoic acid in the GESTIS substance database of the IFA , accessed on December 21, 2019(JavaScript required) .

[2] 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).