98776-99-9

Usage

Uses

Used in Pharmaceutical Industry:
4,7,10,13,16,19-Docosahexaenoyl chloride, (4Z,7Z,10Z,13Z,16Z,19Z)is used as an intermediate in the synthesis of 1-Docosahexaenoyl-sn-glycero-3-phosphocholine (D494434), a potential molecular biomarker for the early detection of osteoarthritis. 4,7,10,13,16,19-Docosahexaenoyl chloride,
(4Z,7Z,10Z,13Z,16Z,19Z)can help in the development of diagnostic tools and therapies for this degenerative joint disease.
Additionally, due to its omega-3 fatty acid origin, 4,7,10,13,16,19-Docosahexaenoyl chloride, (4Z,7Z,10Z,13Z,16Z,19Z)may have potential applications in other areas of pharmaceutical research, such as the development of anti-inflammatory agents, neuroprotective drugs, or cardiovascular disease treatments, given the known health benefits of DHA and omega-3 fatty acids. However, more research would be needed to explore these potential applications.

Upstream product

• 6217-54-5 docosahexaenoic acid 
• 81926-94-5 all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate 
• 1235236-68-6 (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-aminoethyl)docosa-4,7,10,13,16,19-hexaenamide 

Downstream Products

• 1204317-83-8 2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy)benzoic acid 
• 1204317-85-0 3-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropyl 2-acetoxybenzoate 
• 92510-91-3 pyridin-3-ylmethyl all-Z-4,7,10,13,16,19-docosahexaeneoate 
• 946524-43-2 4,7,10,13,16,19-docosahexaenoyl ethanolamide-d4 
• 163656-44-8 N-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl)-L-phenylalanine 
• 1417784-13-4 C₃₆H₄₃NO₈ 
• 81926-94-5 all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate 

Relevant academic research and scientific papers

Antioxidative Properties and Chemical Changes of Quercetin in Fish Oil: Quercetin Reacts with Free Fatty Acids to Form Its Ester Derivatives

In this research, we studied the antioxidative properties and chemical changes of quercetin in fish oil during accelerated storage at 60 °C for 5 days. Gas chromatography (GC) analysis showed that quercetin inhibited aldehyde formation and unsaturated fatty acid oxidation in fish oil significantly; however, the inhibitory effects decreased gradually with prolonged heating time. Moreover, quercetin was consumed with increasing heating time. Some new phenolic derivatives were discovered in the fish oil with quercetin, with their structures fully elucidated by LC-MS/MS and comparison with newly synthesized ones (characterized by MS and NMR spectroscopy). Based on their chemical structures, we proposed that quercetin reacted with EPA and DHA to form the corresponding quercetin fatty acid esters in fish oil. In addition, the newly formed quercetin-3-O-eicosapentaenoate and quercetin-3-O-docosahexaenoate showed weaker DPPH and ABTS radical cation scavenging activity but much improved lipophilicity, higher cell membrane affinity, and hence enhanced cellular antioxidant activity compared with the parent quercetin. Overall, quercetin could be used as a safe dietary polyphenol to inhibit lipid oxidation. The newly formed quercetin-polyunsaturated fatty acid esters may render improved bioactivity to humans, which needs further investigation.

Epigallocatechin (EGC) esters as potential sources of antioxidants

Epigallocatechin (EGC) was acylated with selected fatty acids, namely propionic acid [C3:0], caprylic acid [C8:0], lauric acid [C12:0], stearic acid [C18:0]) and docosahexaenoic acid (DHA)[C22:6n-3] in order to increase its lipophilicity. Monoesters were

Preparation of Quercetin Esters and Their Antioxidant Activity

Quercetin, a polyphenolic compound, is widely distributed in plants and has numerous health benefits. However, its hydrophilicity can compromise its use in lipophilic systems. For this reason, quercetin was esterified with 12 different fatty acids as their acyl chlorides with varying chain lengths and degrees of unsaturation. Two monoesters (Q-3′-O-monoester and Q-3-O-monoester) and four diesters (Q-7,3′-O-diester, Q-3′,4′-O-diester, Q-3,3′-O-diester, and Q-3,4′-O-diester) were the major products as was shown by HPLC-MS and 1H-NMR data. The lipophilicity of quercetin derivatives was calculated; this was found to increase with fatty acid chain length. The antioxidant potential of quercetin and its derivatives was evaluated by using DPPH radical and ABTS radical cation scavenging activity; quercetin showed the highest radical scavenging activity among all tested samples. Despite the decrease of antioxidant activity in this study, the derivatives may show better antioxidant activity in lipophilic media and display improved absorption and bioavailability in the body once consumed.

Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration

N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.

A study of synthetic approaches to 2-acyl DHA lysophosphatidic acid

Lysophosphatidic acid (LPA) is a chemical mediator with a very simple glycerophospholipid structure. 1-Acyl LPA and 2-acyl LPA are biosynthesized in vivo. Unlike 1-acyl LPA, the biological function of 2-acyl LPA has been hardly elucidated and even organic synthesis of 2-acyl LPA had not been established. We suppressed acyl migration by formation of a salt with a phosphate group in order to synthesize 2-acyl LPA condensed with docosahexaenoic acid.

Lipophilization of resveratrol and effects on antioxidant activities

Resveratrol (R), a polyphenol, was structurally modified via esterification with selected fatty acids to expand its potential application in lipophilic foods, drugs, and cosmetics. The esterification was carried out using 12 different fatty acids with varying chain lengths and degrees of unsaturation (C3:0-C22:6). Two monoesters, two diesters, and one triester were identified by high-performance liquid chromatography-mass spectrometry, and the monoesters (R-3-O-monodocosahexaenoate and R-4'-O-monodocosahexaenoate) were structurally confirmed by nuclear magnetic resonance. The lipophilicity of resveratrol and its alkyl esters was calculated using ALOGPS 2.1. Resveratrol exhibited greater antioxidant activity in both 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation scavenging assays. Resveratrol esters with long-chain fatty acids (C18:0 and C18:1) showed higher antioxidant activity in the DPPH radical scavenging assay, whereas short-chain fatty acid (C3:0, C4:0, and C6:0) showed higher antioxidant activity in the ABTS radical cation scavenging assay. The results may imply that resveratrol derivatives could be used in lipophilic media as health beneficial antioxidants.

FATTY ACID ANTIVIRAL CONJUGATES AND THEIR USES

The invention relates to fatty acid antiviral conjugates; compositions comprising an effective amount of a fatty acid antiviral conjugate; and methods for treating or preventing a viral infection comprising the administration of an effective amount of a fatty acid antiviral conjugate.

DNA SYNTHASE INHIBITOR

PROBLEM TO BE SOLVED: To provide a compound having DNA synthase inhibitory activity, and a pharmaceutical composition comprising the compound as an active ingredient (DNA synthase inhibitor, anticancer agent and antiinflammatory agent). SOLUTION: A DNA synthase inhibitor comprises a compound represented by general formula (1) as an active ingredient. An example of the compound is carboxylate ester of plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone). COPYRIGHT: (C)2015,JPO&INPIT

FATTY ACID ANTIVIRAL CONJUGATES AND THEIR USES

The invention relates to fatty acid antiviral conjugates; compositions comprising an effective amount of a fatty acid antiviral conjugate; and methods for treating or preventing a viral infection comprising the administration of an effective amount of a fatty acid antiviral conjugate.

ASCORBATE ESTERS OF OMEGA-3 FATTY ACIDS

The present invention provides ascorbate esters of omega-3 fatty acids as their pharmaceutically-acceptable salts and pharmaceutically- acceptable formulations for use as dietary supplements with enhanced antioxidant properties, in improving the effectiveness of other drugs and in treatment of hypertriglyceridemia, hypercholestolemia, diabetes, psychiatric and neurological disorders, attention deficit and hyperactivity disorder, and as cosmeceuticals.