Eicosapentaenoic Acid

For research use only. Not for therapeutic Use.

  • CAT Number: I000242
  • CAS Number: 10417-94-4
  • Molecular Formula: C20H30O2
  • Molecular Weight: 302.45
  • Purity: ≥95%
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Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3].
C/EBPβ phosphorylated form is evident in Eicosapentaenoic Acid (EPA; 100 μM; 24 h) treated cells, whereas it was barely detectable in control, and OA or LA treated U937[1].
Eicosapentaenoic Acid (100 μM; 1, 3, 24 h) causes a significant increase of H-Ras and N-Ras mRNA levels conditioning for 1 and 3 hours. K-Ras mRNA levels were not affected by Eicosapentaenoic Acid[1].


Catalog Number I000242
CAS Number 10417-94-4
Synonyms

(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

Molecular Formula C20H30O2
Purity ≥95%
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
SMILES CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O
Reference

[1]. Martins, J.G., EPA but not DHA appears to be responsible for the efficacy of omega-3 long chain polyunsaturated fatty acid supplementation in depression: evidence from a meta-analysis of randomized controlled trials. J Am Coll Nutr, 2009. 28(5): p. 525-42.
 [Content Brief]

[2]. Miaozhen Pan, et al. Dietary ω-3 polyunsaturated fatty acids are protective for myopia. Proc Natl Acad Sci U S A. 2021 Oct 26;118(43):e2104689118.
 [Content Brief]

[3]. Shun-he Wang, et al. Endogenous omega-3 long-chain fatty acid biosynthesis from alpha-linolenic acid is affected by substrate levels, gene expression, and product inhibition. RSC Adv., 2017, 7, 40946-40951.

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