Dihomo-γ-linolenic acid

Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω−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 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 (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product (Delta 6 desaturase) of linoleic 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.

Dihomo-γ-linolenic acid
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
PubChem CID
UNII
  • InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
    Key: HOBAELRKJCKHQD-QNEBEIHSSA-N
  • InChI=1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
    Key: HOBAELRKJCKHQD-QNEBEIHSBE
SMILES
  • CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O
Properties
C20H34O2
Molar mass 306.490 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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