 | |
| Names | |
|---|---|
| Preferred IUPAC name (8Z,11Z,14Z)-Icosa-8,11,14-trienoic acid | |
| Other names cis,cis,cis-8,11,14-Eicosatrienoic acid; DGLA; Diroleuton (INNTooltip International Nonproprietary Name) | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.015.667 |
| UNII | |
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| |
| Properties | |
| C20H34O2 | |
| Molar mass | 306.490 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Dihomo-γ-linolenic acid (DGLA) is a 20-carbonω−6 fatty acid (also called, cis,cis,cis-8,11,14-eicosatrienoic acid). In physiological literature, it is given the name 20:3 (ω−6). DGLA is acarboxylic acid with a 20-carbon chain and threecis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product ofγ-linolenic acid (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product (Delta 6 desaturase) oflinoleic acid (18:2, ω−6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.[1][2]
Theeicosanoid metabolites of DGLA are:
All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites ofarachidonic acid (AA), which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLAcompetes with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.
Taken orally in a small study, DGLA producedantithrombotic effects.[5] Supplementing dietary GLA increases serum DGLA, as well as serum AA levels.[6] Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.[7]
