Eicosapentaenoic Acid

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Cat.No. 5979 - Eicosapentaenoic Acid | C20H30O2 | CAS No. 10417-94-4
Description: Endogenous polyunsaturated fatty acid; stimulates ERK1/2 phosphorylation
Chemical Name: (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic acid
Purity: ≥99% (HPLC)
Datasheet
Citations
Literature
Pathways

Biological Activity

Endogenous polyunsaturated fatty acid. Stimulates ERK1/2 and C/EBPβ phosphorylation, and induces demethylation of CpG island B in U937 leukemia cells. Attenuates proliferation of U9137 cells, and induces cell cycle arrest and apoptosis in pancreatic cells in vitro. Also inhibits leukotriene B4 synthesis in rats.

Technical Data

M. Wt 302.45
Formula C20H30O2
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 10417-94-4
PubChem ID 446284
InChI Key JAZBEHYOTPTENJ-JLNKQSITSA-N
Smiles CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.25 100
ethanol 30.25 100

Preparing Stock Solutions

The following data is based on the product molecular weight 302.45. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.31 mL 16.53 mL 33.06 mL
5 mM 0.66 mL 3.31 mL 6.61 mL
10 mM 0.33 mL 1.65 mL 3.31 mL
50 mM 0.07 mL 0.33 mL 0.66 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Ceccarelli et al (2014) Eicosapentaenoic acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. PLoS One 9 e85025 PMID: 4454781

James et al (1993) Effect of dietary supplementation with n-9 eicosatrienoic acid on leukotriene B4 synthesis in rats: a novel approach to inhibition of eicosanoid synthesis. J.Exp.Med. 178 2261 PMID: 8245797

Lai et al (1996) Cell cycle arrest and induction of apoptosis in pancreatic cancer cells exposed to eicosapentaenoic acid in vitro. Br.J.Cancer 74 1375 PMID: 912532


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Keywords: Eicosapentaenoic Acid, supplier, endogenous, polyunsaturated, fatty, acids, stimulates, ERK, phosphorylation, leukotriene-B4, synthesis, inhibits, ERK, Leukotriene, and, Related, Receptors, ERK, Tocris Bioscience

Citations for Eicosapentaenoic Acid

Citations are publications that use Tocris products.

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Reviews

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Immunology

Immunology Product Listing

A collection of over 190 products for immunology research, the guide includes research tools for the study of:

  • Chemokine and Cytokine Signaling
  • Chemotaxis
  • Complement System
  • Immune Cell Signaling
  • Inflammation
Kinases

Kinases Product Listing

A collection of over 400 products for kinase research, the listing includes inhibitors of:

  • Receptor Tyrosine Kinases
  • Protein Kinases A, C, D and G
  • PI-3 Kinase, Akt and mTOR
  • MAPK Signaling
  • Receptor Serine/Threonine Kinases
Neurodegeneration

Neurodegeneration Product Guide

A collection of over 275 products for neurodegeneration research, the guide includes research tools for the study of:

  • Alzheimer's disease
  • Parkinson's disease
  • Huntington's disease
MAPK Signaling

MAPK Signaling Scientific Review

MAP kinase signaling is integral to the regulation of numerous cellular processes such as proliferation and differentiation, and as a result is an important focus of cancer and immunology research. Updated for 2016, this review discusses the regulation of the MAPK pathway and properties of MAPK cascades. Compounds available from Tocris are listed.

Pathways for Eicosapentaenoic Acid

MAPK

MAPK Signaling Pathway

The mitogen-activated protein kinase pathway evokes an intracellular signaling cascade in response to extracellular stimuli such as heat and stress. It can influence cell division, metabolism and survival.

Protocols

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