Docosahexaenoic acid
DHA is the longer-chain omega-3 fatty acid, and its primary function in skin tissue is structural rather than eicosanoid-competitive. Incorporated into the phospholipid bilayers of keratinocytes, fibroblasts, 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 – EPA quiets the inflammatory signal; DHA-derived resolvins help clear it.
The 2019 epidermal lipidomics study that established EPA’s superior arachidonic acid displacement in the epidermis 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 retinal development, making it the omega-3 most critical during pregnancy – a consideration relevant to the nutritional counselling context when GLP-1 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.
References
Calder PC (2010). Omega-3 fatty acids and inflammatory processes. Nutrients, 2(3), 355-374 . doi.org/10.3390/nu2030355
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 . doi.org/10.1096/fj.201901501r
Molecular Structure
- 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
| 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- | |
|---|---|---|
| InChIKey | MBMBGCFOFBJSGT-KUBAVDMBSA-N | |
| Canonical SMILES | CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O | |
| Isomeric SMILES | CC/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
- this Produced by Omega-3 fatty acids
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