24880-40-8Relevant articles and documents
Synthesis of Rare Polyunsaturated Fatty Acids: Stearidonic and ω-3 Arachidonic
Golovanov,Ivanov,Groza,Myagkova
, p. 1038 - 1041 (2016/02/18)
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.
Chemical C2-elongation of polyunsaturated fatty acids
Kuklev, Dmitry V.,Smith, William L.
, p. 172 - 177 (2007/10/03)
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.
