Eicosapentaenoic Acid
Eicosapentaenoic acid is a type of n-3 polyunsaturated fatty acids (n-3 PUFA) [1].
n-3 PUFA are widely used in cardiovascular medicine and lipid-lowering intervention. n-3 PUFA can change the fatty acid composition of the membranes and affect different types of membrane proteins [1].
In endothelial cell line H5V, eicosapentaenoic acid at 100 μM inhibited cell migration into a wound, triggered peripheral distribution of focal adhesions and caused partial disassembly of actin filaments [1]. In addition, at 1 ~ 5 μM, eicosapentaenoic acid inhibited oxidation of very large density lipoprotein in a dose-dependent manner over time [2].
In human subjects with diets high in eicosapentaenoic acid, either as a cod liver oil (40 ml = 4 g eicosapentaenoic acid daily) supplement to their normal Western diet for 24 days, or with mackerel (750 g = 10 ~ 15 g eicosapentaenoic acid daily) as the sole source of protein and lipids, for 3 days, eicosapentaenoic acid increased prostaglandin I3 formation in vivo, providing protection against heart diseases [3].
References:
[1]. Tonutti L, Manzi L, Tacconi M T, et al. Eicosapentaenoic acid inhibits endothelial cell migration in vitro. Journal of angiogenesis research, 2010, 2(12): 1-8.
[2]. Preston Mason R, Sherratt S C R. Eicosapentaenoic acid inhibits oxidation of very large density lipoprotein in a dose-dependent manner over time as compared to docosaheaenoic acid in vitro. Journal of the American College of Cardiology, 2020, 75(11): 2238.
[3]. Evidence of prostaglandin I3 formation in vivo from dietary eicosapentaenoic acid. Nutrition Reviews, 1984, 42(9): 317-318.
| Physical Appearance | A yellow oil |
| Storage | Store at -20°C |
| M.Wt | 302.45 |
| Cas No. | 10417-94-4 |
| Formula | C20H30O2 |
| Solubility | ≥116.8 mg/mL in DMSO; ≥49.3 mg/mL in H2O; ≥52.5 mg/mL in EtOH |
| Chemical Name | (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid |
| SDF | Download SDF |
| Canonical SMILES | CC/C([H])=C([H])\C/C([H])=C([H])\C/C([H])=C([H])\C/C([H])=C([H])\C/C([H])=C([H])\CCCC(O)=O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Chemical structure
