68378-49-4

Usage

Uses

Used in Pharmaceutical Industry:
(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid is used as a pharmaceutical agent for its potential health benefits. It is known to have anti-inflammatory properties and may play a role in maintaining the structural integrity of cell membranes.
Used in Nutraceutical Industry:
(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid is used as a nutraceutical ingredient for its potential health-promoting effects. It is a rich source of omega-3 fatty acids, which are essential for maintaining heart and brain health.
Used in Food Industry:
(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid is used as a food additive to enhance the nutritional value of various food products. It can be incorporated into supplements, oils, and other food items to provide a source of essential fatty acids.
Used in Cosmetic Industry:
(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid is used as an ingredient in cosmetic products for its potential skin health benefits. It may help improve skin hydration, elasticity, and overall appearance.
Used in Research:
(6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid is used as a research compound to study its biological properties and potential applications in various fields, such as medicine, nutrition, and cosmetics.

Upstream product

• 21944-83-2 (3Z,6Z)-nona-3,6-dienal 
• 1638153-00-0 (3Z,6Z)-9,9-dimethoxy-nona-3,6-dien-1-yl 4-methylbenzenesulfonate 
• 696-86-6 cis,cis,cis-1,4,7-cyclononatriene 
• 50889-29-7 (5-carboxypentyl)triphenylphosphonium bromide 
• 137682-11-2 (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenal 
• 234087-66-2 (3Z,6Z,9Z,12Z,15Z)-1,1-dimethoxyoctadeca-3,6,9,12,15-pentaene 
• 1638153-04-4 [(3Z,6Z)-9,9-dimethoxynona-3,6-dien-1-yl]triphenylphosphonium iodide 
• 1638152-99-4 (3Z,6Z)-9,9-dimethoxynona-3,6-dien-1-ol 
• 1312442-35-5 methyl (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoate 
• 339570-70-6 ((5Z,8Z,11Z,14Z)-2-Icosa-5,8,11,14-tetraenyl)-malonic acid diethyl ester 
• 108803-63-0 (5Z,8Z,11Z,14Z)-1-bromoeicosa-5,8,11,14-tetraene 
• 13487-46-2 arachidonyl alcohol 
• 2566-89-4 methyl arachidonate 
• 1022976-32-4 (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaen-1-yl 4-methylbenzenesulfonate 

Downstream Products

• 1312442-35-5 methyl (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoate 

Relevant academic research and scientific papers

A nine carbon homologating system for skip-conjugated polyenes

Ozonolysis of Z,Z,Z-cylonona-1,4,7-triene leads to a 1,9-difunctionalised Z,Z-3,6-nonadiene which is readily converted into a range of polyunsaturated pheromones and fatty acids.

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.

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.

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%.