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Eicosapentaenoic acid

ChemicalSubstance Fatty Acid

EPA is the most directly relevant to . 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 (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 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 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 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.

Published
Updated
References
  1. 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 Eicosapentaenoic acid
Formula
C₂₀H₃₀O₂
Weight
302.50 g/mol
IUPAC
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
Computational Identifiers
Chemical 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-
InChIKeyJAZBEHYOTPTENJ-JLNKQSITSA-N
Canonical SMILESCCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
Isomeric SMILESCC/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

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