92008-51-0

Usage

Uses

Used in Pharmaceutical Industry:
5(S)-HEPE is used as a potential therapeutic agent for various inflammatory and immune-related disorders due to its anti-inflammatory and immunomodulatory properties. It has been shown to modulate the production of pro-inflammatory mediators and cytokines, as well as influence the activity of immune cells, making it a promising candidate for the treatment of conditions such as asthma, rheumatoid arthritis, and inflammatory bowel disease.
Used in Research Applications:
5(S)-HEPE is used as a research tool for studying the role of eicosanoids in various physiological and pathological processes. It is commonly used in in vitro and in vivo experiments to investigate the mechanisms of action of 5-lipoxygenase and its products, as well as to explore the potential therapeutic effects of 5(S)-HEPE in different disease models.

InChI:InChI=1/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+

Upstream product

• 375387-75-0 6-((1E,3Z,6Z,9Z,12Z)-pentadeca-1,3,6,9,12-pentaen-1-yl)tetrahydro-2H-pyran-2-one 
• 1553-41-9 5,8,11,14,17-eicosapentaenoic acid 
• 234087-56-0 6-[(3Z,6Z,9Z,12Z)-1-iodopentadeca-3,6,9,12-tetraen-1-yl]-tetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Synthesis of 5-(S)-HETE, 5-(S)-HEPE and (+)-zooxanthellactone: Three hydroxylated polyunsaturated fatty acid metabolites

Short and stereoselective syntheses of the two hydroxylated polyunsaturated fatty acid metabolites, namely 5-(S)-HETE and 5-(S)-HEPE, are reported in 23% and 30% overall yields, respectively. In addition, synthesis of the polyunsaturated fatty acid natura

Synthesis of oxidized fatty acid derivatives via an iodolactonization reaction

To study structure-activity relationships of oxidized fatty acids for the activation of peroxisome proliferator-activated receptors (PPARs), which are ligand-dependent transcription factors, we synthesized a series of oxidized fatty acids via iodolactone as a key intermediate.

Synthesis of polyconjugated fatty acids

The present invention relates to fatty acids. In particular, the present invention provides polyconjugated fatty acids, and methods of their synthesis and their use.

Synthesis of long chain n-3 and n-6 fatty acids having a photoactive conjugated tetraene group

Fatty acids of the n-3 and n-6 families containing a photoactive conjugated tetraene group near the carboxylate were prepared from several naturally occurring fatty acids by sequential iodolactonization and treatment with excess 1,8-diazabicyclo[5.4.0]undec-7-ene. The new conjugated fatty acids include 5E,7E,9E,11Z,14Z- and 5E,7E,9E,11E,14Z-eicosapentaenoic acids derived from arachidonic acid; 5E,7E,9E,11Z,14Z,17Z- and 5E,7E,9E,11E,14Z,17Z-eicosahexaenoic acids from eicosapentaenoic acid; and 4E,6E,8E,10Z,13Z,16Z,19Z- and 4E,6E,8E,10E,13Z,16Z,19Z-docosaheptaenoic acids from docosahexaenoic acid. All of the newly synthesized fatty acids were characterized by UV, 1H NMR and mass spectroscopy. These new products represent the first examples of directed conjugation of methylene interrupted double bond systems. The products can be synthesized in gram quantities and in high yields (>50%). Interestingly, it did not prove possible to synthesize fatty acids having a triene group near the carboxyl group even using mild conditions and different synthetic approaches. Once initiated, the isomerization always continued until a tetraene group was formed. Because of the sensitivity of the tetraene group to light, these fatty acids have the potential for being used in tracking fatty acid movements in cells employing fluorescence techniques and in UV light-induced cross linking to membrane proteins.