24880-40-8

Usage

Uses

Used in Pharmaceutical Applications:
8Z,11Z,14Z,17Z-Eicosatetraenoic Acid is used as a therapeutic agent for promoting infant development and supporting overall health. Its essential role in growth and development makes it a crucial component in the diet of infants and young children.
Used in Cardiovascular Health:
8Z,11Z,14Z,17Z-Eicosatetraenoic Acid is used as a preventative measure for heart disease, hypertension, and thrombosis. Its presence in the diet helps to maintain a healthy cardiovascular system and reduce the risk of these conditions.
Used in Anti-Inflammatory and Autoimmune Applications:
8Z,11Z,14Z,17Z-Eicosatetraenoic Acid is used as a treatment for inflammatory and autoimmune disorders due to its ability to modulate the immune system and reduce inflammation.
Used in Platelet Membrane Function:
8Z,11Z,14Z,17Z-Eicosatetraenoic Acid is used as a regulator of platelet membrane function, as it inhibits arachidonoyl-CoA synthetase, which plays a role in the synthesis of eicosanoids, signaling molecules involved in various physiological processes, including blood clotting and inflammation.
Used in Research and Development:
8Z,11Z,14Z,17Z-Eicosatetraenoic Acid is used as a research tool for studying the role of ω-3 fatty acids in various biological processes and their potential applications in the development of new therapeutic strategies for a range of health conditions.

InChI:InChI=1/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h12-19H,2-11H2,1H3,(H,21,22)/b13-12-,15-14u,17-16u,19-18u

Upstream product

• 34498-25-4 1-bromo-2,5,8-undecatriyne 
• 35378-82-6 2,5,8-undecatriyne-1-ol 
• 1558-79-8 2,5-octadiynyl bromide 
• 35378-76-8 octa-2,5-diyn-1-ol 
• 309728-62-9 (all-Z)-Octadeca-2,6,9,12,15-pentaenal 
• 137682-11-2 (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenal 
• 121818-29-9 methyl 3-(3-((2Z,5Z,8Z,11Z,14Z)-heptadeca-2,5,8,11,14-pentaen-1-yl)oxiran-2-yl)propanoate 
• 84494-72-4 docosahexaenoic acid ethyl ester 
• 6217-54-5 docosahexaenoic acid 
• 181213-50-3 ((6Z,9Z,12Z,15Z)-2-Octadeca-6,9,12,15-tetraenyl)-malonic acid diethyl ester 
• 181213-43-4 (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-1-ol 
• 181213-46-7 1-bromo-6Z,9Z,12Z,15Z-octadecatetraene 
• 73097-00-4 6,9,12,15-cis-octadecanetetraenoic acid methyl ester 
• 122055-67-8 4,4-Dimethyl-2-((7Z,10Z,13Z,16Z)-nonadeca-7,10,13,16-tetraenyl)-4,5-dihydro-oxazole 

Relevant academic research and scientific papers

Synthesis of Rare Polyunsaturated Fatty Acids: Stearidonic and ω-3 Arachidonic

Total chemical syntheses of the rare natural ω-3 C18 and C20 fatty acids, which possess potential antiinflammatory activity, were elaborated for subsequent studies of their biological activity.

Concise syntheses of three ω-3 polyunsaturated fatty acids

The synthesis of the three ω-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials.

Chemical C2-elongation of polyunsaturated fatty acids

Three fatty acids were synthesized from commercially available α-linolenic, stearidonic and eicosapentaenoic acids by C2-elongation using a four step preparative technique. The parent fatty acid methyl esters were reduced to alcohols with LiAlH4, converted to bromides by treatment with triphenylphosphine dibromide, coupled with a lithiated C2-elongation block - 2,4,4-trimethyl-2-oxazoline - to form the corresponding 2,2-dimethyloxazolines of C2-elongated fatty acids, and finally, converted to the target polyunsaturated fatty acids by acidic alcoholysis. Yields of more than 60% were achieved on a gram scale. The resulting 11Z,14Z,17Z-eicosatrienoic, 8Z,11Z,14Z,17Z-eicosatetraenoic and 7Z,10Z,13Z,16Z,19Z-docosapentaenoic acids were obtained as colorless oils with >98% purity and could be used for biochemical investigations without additional purification. The elongated fatty acids were free of byproducts that could result from Z-E isomerization or migration of double bonds.

Synthesis of C2-elongated polyunsaturated fatty acids

The synthesis by a modified malonic ester procedure of C2-elongated polyunsaturated fatty acids from their natural precursors was described. Using the suggested Scheme 1, (7Z,11Z,14Z)-7,11,14-eicosatrienoic, (8Z,11Z,14Z,17Z)-8,11,14,17-eicosatetraenoic, (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic, (8Z,11Z,14Z,17Z)-8,11,14,17-docosatetraenoic, (7Z,10Z,13Z,16Z,19Z)-7,10,13,16,19-docosapentaenoic, and (6Z,9Z,12Z,15Z,18Z,21Z)-6,9,12,15,18,21-tetracosahexaenoic acids were synthesized. Their structures were confirmed by GC, UV, and MS data, which coincided with those of natural compounds. The target compounds were shown to be free from by-products, which could result from Z-E isomerization or migration of double bonds. The overall yields of the four-step synthesis of C2-elongated polyenoic acids were 25-30%.