|Dihomo-gamma linolenic acid|
|Other names|| cis,cis,cis-8,11,14-Eicosatrienoic acid|
|SMILES|| CCCCCC=CCC=CCC=CCCCCCCC(=O)O (canonical)|
|Molar mass||306.483 g/mol|
| Except where noted otherwise, data are given for|
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
Dihomo-gamma-linolenic acid (DGLA) is a 20-carbon ω-6 fatty acid. In physiological literature, it is given the name 20:3(n-6). Chemically, DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of γ-linolenic acid [18:3(n-6)].
The eicosanoid metabolites of DGLA are:
- Series-1 thromboxanes (thromboxanes with 1 double-bond), via the COX-1 and COX-2 pathways.
- Series-1 prostanoids, via the COX-1 and COX-2 pathways.
- A 15-hydroxyl derivative that blocks the transformation of arachidonic acid to leukotrienes.
All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites of arachidonic acid (AA) which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA competes with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.
- Fan, Yang-Yi and Robert S. Chapkin (9 September 1998). "Importance of Dietary gamma -Linolenic Acid in Human Health and Nutrition". Journal of Nutrition 128 (9): 1411-1414. Retrieved on 2007-10-16.
- Belch, Jill JF and Alexander Hill (January 2000). Evening primrose oil and borage oil in rheumatologic conditions. Retrieved on February 12, 2006. PubMed cite
- Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP (1977). "Antithrombotic potential of dihomo-gamma-linolenic acid in man". British medical journal 2 (6100): 1441–4. PMID 338112.
- Johnson MM, Swan DD, Surette ME, et al (1997). "Dietary supplementation with gamma-linolenic acid alters fatty acid content and eicosanoid production in healthy humans". J. Nutr. 127 (8): 1435–44. PMID 9237935.
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