1022976-32-4

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 102783-20-0 (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaen-1-ol 
• 81926-94-5 all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate 
• 6217-54-5 docosahexaenoic acid 

Downstream Products

• 1312442-38-8 methyl (5Z,8Z,11Z,14Z,17Z,20Z)-tricosa-5,8,11,14,17,20-hexaenoate 
• 1095558-71-6 cis-4,7,10,13,16,19-docosahexaenoic acid 
• 68378-49-4 (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid 

Relevant academic research and scientific papers

A first synthesis of a phosphatidylcholine bearing docosahexaenoic and tetracosahexaenoic acids

The synthesis of phosphatidylcholine bearing docosahexaenoic and tetracosahexaenoic acids was presented. The method constituted two-carbon elongation of DHA ethyl ester to give an acid and synthesis of lysophosphatidylcholine starting from lipase catalyzed mono-acylation of 2-OoTBDMS-glycerol followed by the introduction of the silyl group. It was found that hydrogenolysis cannot be applied after acylation at the 1-position with unsaturated fatty acyl group because of the inevitable saturation of the olefinic bonds.

Efficient synthesis of the very-long-chain n-3 fatty acids, tetracosahexaenoic acid (C24:6n-3) and tricosahexaenoic acid (C 23:6n-3)

Tetracosahexaenoic acid (C24:6n-3, THA, 3) is an essential biosynthetic precursor in mammals of docosahexaenoic acid (C22:6n-3, DHA, 1), the end-product of the metabolism of n-3 fatty acids. THA 3 is present in commercially valuable fishes, such as flathead flounder. Tricosahexaenoic acid (C23:6n-3, TrHA, 2), an odd-numbered-chain fatty acid, has been identified from marine organisms such as the dinoflagellate, Amphidinium carterae. To date, few studies have examined THA 3 and TrHA 2 due to difficulties in detecting and identifying these compounds, so their chemical and biological properties remain poorly characterized. Only one methodology for the chemical synthesis of THA 3 has been presented, and no method for the synthesis of TrHA 2 has been reported. We report here the efficient synthesis of THA 3 in four steps in 56% overall yield, and the synthesis of TrHA 2 in six steps in 48% overall yield. We also present the synthesis of Δ2-THA 4, an intermediate of β-oxidation of THA 3 to DHA 1, in three steps in 73% overall yield.

ALPHA-SUBSTITUTED OMEGA-3 LIPIDS THAT ARE ACTIVATORS OR MODULATORS OF THE PEROXISOME PROLIFERATORS-ACTIVATED RECEPTOR (PPAR).

Omega-3 lipid compounds of the general formula (I): wherein R1 and R2 are the same or different and may be selected from a group of substitu- ents consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an al- kynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a car- boxy group, an alkylsulfmyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; - X represents a carboxylic acid or a derivative thereof, a carboxylate, a carboxylic anhydride or a carboxamide; and - Y is a C16 to C22 alkene with two or more double bonds, having E and/or Z configuration, are disclosed. Also disclosed are pharmaceutical compositions and lipid compositions comprising such compounds, and to such compounds for use as medicaments in particular for the treatment of cardiovascular and metabolic diseases.