Eicosapentaenoic Acid
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| Category | Raw Materials of Healthcare Products |
| Catalog number | BBF-05819 |
| CAS | 10417-94-4 |
| Molecular Weight | 302.46 |
| Molecular Formula | C20H30O2 |
| Purity | 98% |
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Description
Eicosapentaenoic acid (EPA) is an omega-3 fatty acid found in fish oil. It acts as a precursor to prostaglandin-3 and thromboxane-3 families. EPA decreases serum lipid concentration, reduces the risk of cardiovascular disorders and suppresses platelet aggregation.
Nutritional supplement in health care products.
Specification
| Synonyms | Timnodonic acid; Icosapent; Icosapentaenoic acid; EPA; (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic Acid; (all-Z)-5,8,11,14,17-Eicosapentaenoic Acid; Incromega E 7010SR; Ropufa 70; cis-5,8,11,14,17-Eicosapentaenoic acid; 5Z,8Z,11Z,14Z,17Z-Eicosapentaenoic acid; (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid; all-cis-5,8,11,14,17-icosapentaenoic acid |
| Storage | -20 °C |
| IUPAC Name | (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid |
| Canonical SMILES | CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O |
| 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- |
| InChI Key | JAZBEHYOTPTENJ-JLNKQSITSA-N |
Properties
| Appearance | Colourless to Yellow Oily Matter |
| Application | Ingredient of health care products. |
| Boiling Point | 439.3±24.0°C at 760 mmHg |
| Melting Point | (-54)-(-53)°C |
| Flash Point | 336°C |
| Density | 0.943 g/mL at 25°C |
| Solubility | Soluble in Chloroform (Slightly), Ethyl Acetate (Sparingly), Methanol (Slightly) |
Reference Reading
1.Synthesis of the Conjugated Trienes 5E,7E,9E,14Z,17Z Eicosapentaenoic Acid and 5Z,7E,9E,14Z,17Z Eicosapentaenoic Acid, and Their Induction of Apoptosis in DLD-1 Colorectal Adenocarcinoma Cells
Tsuyoshi Tsuzuki, Kazumi Tanaka, Shigefumi Kuwahara, and Teruo Miyazawa,* Lipids, Vol. 40, no. 2 (2005)
To identify the specific cytotoxic FA, we have synthesized possible candidates for the active species. Here, we report the synthesis of (5E,7E,9E,14Z,17Z)-5,7,9,14,17-eicosapentaenoic acid (E-CEPA, Scheme 1) and its 5-(Z) isomer (Z-CEPA, Scheme. 1), which both exist naturally in the red alga (Ptilota filicina J. Agardh). We then examined the cytotoxicity of these molecules in human tumor cells and confirmed that both isomers have strong bioactivity.
2.Seasonal Transfer of the Pool of the Essential Eicosapentaenoic Acid along the Pelagic Trophic Chain of a Eutrophic Reservoir
N. N. Sushchik, M. I. Gladyshev, O. N. Makhutova. Doklady Biological Sciences, 2008, Vol. 422, pp. 355–356.
It is known that not only the amount of produced and consumed organic matter, but also its quality, i.e., its elementary and biochemical composition are important for functioning of trophic chains. In the past two decades, it has been demonstrated that interaction between producers and primary consumers (phyto- and zooplankton) in pelagic ecosystems substantially depends on the phytoplankton content of the essential eicosapentaenoic acid (20:5 w3, EPA). It is believed that the EPA content of seston, which ultimately determines the efficiency of interaction between trophic links, inversely depends on the trophicity level of water ecosystems. This statement is based on the analysis of summer phytoplankton, which is known to be mainly represented by diatom, cryptophyte, and other EPArich microalgae in oligotrophic water bodies, whereas cyanobacteria incapable of synthesizing this fatty acid dominate eutrophic water bodies.
3.Eicosapentaenoic acid increases lipolysis through up-regulation of the lipolytic gene expression and down-regulation of the adipogenic gene expression in 3T3-L1 adipocytes
Mak-Soon Lee, In-Sook Kwun, Yangha Kim. Genes Nutr (2008) 2:327–330
In the present study, we investigated the effects of eicosapentaenoic acid (EPA), known as one of the most critical components of n-3 PUFA, on lipid metabolism and the underlying mechanisms in 3T3-L1 adipocytes. We hypothesize that EPA stimulates lipolysis through induction of lipolytic gene expression and suppression of adipogenic gene expression. We measured the lipid accumulation and release of free fatty acids (FFAs) and glycerol into medium followed by EPA treatment. In addition, the mRNA levels of the adipogenic genes including peroxisome proliferator-activated receptor-c (PPAR-c) and acetyl-CoA carboxylase (ACC), and carnitine palmitoyltransferase I-a (CPT-Ia), one of lipolytic genes, were measured.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
