Skip to the main content

Docosahexaenoic acid

ChemicalSubstance Fatty Acid

DHA is the longer-chain , and its primary function in tissue is structural rather than eicosanoid-competitive. Incorporated into the phospholipid bilayers of , , and immune cells, DHA’s six double bonds give the membrane exceptional fluidity – maintaining the lateral mobility of receptor proteins, ion channels, and signalling complexes that cell communication depends on. Membranes with adequate DHA are more responsive; membranes depleted of DHA become rigid in ways that impair cellular function before any other symptoms of deficiency become apparent.

DHA is the precursor to D-series resolvins (RvD1–RvD6) and protectins – including neuroprotectin D1, the best-characterised protectin – which are specialised pro-resolving mediators that actively signal the termination of the inflammatory cascade. [1] This resolvin and protectin synthesis is a distinct anti-inflammatory mechanism from EPA’s eicosanoid competition pathway, operating in series with it rather than in parallel – quiets the inflammatory signal; DHA-derived resolvins help clear it.

The 2019 epidermal lipidomics study that established EPA’s superior displacement in the confirmed that EPA and DHA are not interchangeable for this purpose – DHA supplementation did not produce the same shift in epidermal AA-derived mediators as EPA. [2] The practical implication: both are needed, but for specifically inflammatory skin presentations, an EPA-dominant combined supplement is preferable to a DHA-only formulation.

DHA is also essential for foetal brain and development, making it the omega-3 most critical during pregnancy – a consideration relevant to the nutritional counselling context when medication users or post-bariatric clients are planning conception.

Dietary sources: same marine sources as EPA – oily fish, fish oil, combined EPA+DHA algae supplements. DHA is present in breast milk; infants not breastfed require DHA-supplemented formula for adequate neural development.

Published
Updated
References
  1. Calder PC (2010). Omega-3 fatty acids and inflammatory processes. Nutrients, 2(3), 355-374 .

  2. Kendall AC, Pilkington SM, Murphy SA, et al. (2019). Dynamics of the human skin mediator lipidome in response to dietary ω-3 fatty acid supplementation. FASEB J, 33(11), 13014-13027 .

Molecular Structure

2D Molecular Structure of Docosahexaenoic acid
Formula
C₂₂H₃₂O₂
Weight
328.50 g/mol
IUPAC
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Computational Identifiers
Chemical Identifiers
InChI InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChIKeyMBMBGCFOFBJSGT-KUBAVDMBSA-N
Canonical SMILESCCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O
Isomeric SMILESCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
Data sourced from: PubChem (NCBI) ↗

Also Known As

  • DHA

Biological Relationships

Influenced By

Learn More

This topic is discussed in 5 articles: