Eicosapentaenoic acid
EPA is the omega-3 fatty acid most directly relevant to skin inflammation. Where DHA’s primary role is structural – maintaining membrane fluidity and receptor mobility – EPA’s role is eicosanoid-competitive: it occupies the same membrane phospholipid positions as arachidonic acid (AA) and presents itself as an alternative substrate to cyclooxygenase (COX) and lipoxygenase (LOX), the enzymes that would otherwise convert AA to pro-inflammatory PGE₂ and LTB₄.
A 2019 lipidomics study separating EPA and DHA supplementation found EPA significantly superior to DHA at reducing AA-derived mediators specifically in epidermal phospholipids – elevating PGE₃, 12-HEPE, and EPEA as markers of a shifted, less inflammatory mediator profile. DHA did not produce the same epidermal shift. [1] This distinction matters for supplement selection: products providing DHA alone – some algae-derived omega-3 formulations – deliver less of the eicosanoid-competitive benefit relevant to inflammatory skin conditions.
EPA is also the precursor to E-series resolvins (RvE1, RvE2) – specialised pro-resolving mediators that actively terminate inflammation rather than simply competing with its amplification. This resolvin synthesis pathway is absent from the omega-6 arachidonic acid cascade entirely.
Dietary sources: oily fish (salmon, mackerel, sardines, herring), fish oil supplements, and combined EPA+DHA algae-derived supplements. ALA from plant sources converts to EPA at approximately 5–10% efficiency in healthy adults; insufficient to meaningfully shift membrane phospholipid composition.
References
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
- C₂₀H₃₀O₂
- Weight
- 302.50 g/mol
- IUPAC
- (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Computational Identifiers
| InChI | InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15- | |
|---|---|---|
| InChIKey | JAZBEHYOTPTENJ-JLNKQSITSA-N | |
| Canonical SMILES | CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O | |
| Isomeric SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O | |
Data sourced from: PubChem (NCBI) ↗ | ||
Also Known As
- EPA
Biological Relationships
Influenced By
- this Produced by Omega-3 fatty acids
Learn More
This topic is discussed in 4 articles:
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Active omega-3 fatty acid form (EPA) with anti-inflammatory properties, supporting skin health when combined with DHA.
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Active omega-3 fatty acid form beneficial for skin health
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Active omega-3 fatty acid form (EPA) with anti-inflammatory properties, supporting skin health when combined with DHA.
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