102783-20-0

Usage

Uses

Used in Nutritional Supplements:
DHA is used as a nutritional supplement to support brain health and cognitive development in infants and to maintain normal brain function in adults. The inclusion of DHA in the diet has been shown to improve learning ability, while deficiencies are associated with learning deficits.
Used in Pharmaceutical Applications:
DHA has potential therapeutic benefits in a range of medical conditions. It is used as a pharmaceutical agent for the treatment and prevention of various diseases, including cancer, cardiovascular disease, and neurodegenerative disorders.
Used in Food and Beverage Industry:
DHA is incorporated into food and beverage products to enhance their nutritional value and promote brain health. It is commonly added to infant formulas, dietary supplements, and functional foods to ensure adequate intake of this essential fatty acid.
Used in Cosmetics and Personal Care Products:
DHA is used in cosmetics and personal care products for its moisturizing and anti-aging properties. It helps to maintain the skin's elasticity and hydration, promoting a healthy and youthful appearance.
Used in Animal Nutrition:
DHA is also used in animal nutrition to support the cognitive development and overall health of pets and livestock. It is added to pet food and animal feed to ensure a balanced diet and optimal health benefits.

InChI:InChI=1/C22H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23/h3-4,6-7,9-10,12-13,15-16,18-19,23H,2,5,8,11,14,17,20-22H2,1H3

Upstream product

• 81926-94-5 all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate 
• 6217-54-5 docosahexaenoic acid 
• 2566-90-7 all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester 
• 2734-47-6 (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester 

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 
• 105517-82-6 (14Z,17Z,20Z,23Z,26Z,29Z)-dotriaconta-14,17,20,23,26,29-hexaenoic acid 
• 1022976-32-4 (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaen-1-yl 4-methylbenzenesulfonate 
• 68378-49-4 (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-6,9,12,15,18,21-hexaenoic acid 

Relevant academic research and scientific papers

The synthesis of the very long chain polyunsaturated fatty acid (VLC-PUFA) 32:6 n-3

This article describes the synthesis of VLC-PUFA 32:6 n-3, D2-labeled 32:6 n-3, and the uptake of 32:6 n-3 into mouse retinal tissue.

Omefibrates for Treating Dyslipidemia and Cardiovascular Disease

The present invention relates to the fibric acid derivatives of omega-3 fatty acids and their use in treating Type2 diabetes, obesity, hypertriglyceridemia, cardiovascular diseases, metabolic syndrome, cancer, Alzheimer's disease; and their use for modulating activity of peroxisome proliferator-activated receptors (PPARs).

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.

SYNTHESIS AND USE OF OMEGA-3 AND OMEGA-6 VERY LONG CHAIN POLYUNSATURATED FATTY ACIDS (VLC-PUFA)

The invention provides methods of synthesizing omega-3 and omega-6 very long chain polyunsaturated fatty acids (VLC- PUFAs, C28-C42:4,5 and 6), analogs and derivatives thereof, pharmaceutical compositions containing these isolated VLC-PUFA compounds and therapeutic uses therefor.

LIPID COMPOSITIONS CONTAINING DERIVATIVES OF EPA AND DHA AN THEIR USE THEREOF

The present invention relates to a lipid composition comprising at least pro-drugs of omega-3 polyunsaturated alcohols, which pro-drugs of omega-3 polyunsaturated alcohols comprise at least one pro-drug of (all-Z) 5,8,11,14,17-eicosapentaen-1-ol, and at least one pro-drug of (all-Z)-4,7,10,13,16,19-docosahexaen-1-ol and their use as a pharmaceutical, in particular for the treatment of elevated triglyceride levels. The invention also relates to methods for the preparation of these pro-drugs from marine oils.

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.

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%.