83952-40-3

Basic information

• Product Name: (+/-)5-HEPE
• Synonyms: (+/-)5-HEPE;(+/-)-5-HYDROXY-6E,8Z,11Z,14Z,17Z-EICOSAPENTAENOIC ACID;(+/-)5-HYDROXYEICOSA-6E,8Z,11Z,14Z,17Z-PENTAENOIC ACID;5-hydroxy-6,8,11,14,17-eicosapentaenoic acid;FTAGQROYQYQRHF-FCWZHQICSA-N
• CAS NO: 83952-40-3
• Molecular Formula: C20H30O3
• Molecular Weight: 318.45
• Mol File: 83952-40-3.mol

Chemical Properties

• Boiling Point: 488 °C at 760 mmHg
• Flash Point: 263.1 °C
• Appearance: /
• Density: 0.997 g/cm³
• Vapor Pressure: 1.42E-11mmHg at 25°C
• Refractive Index: 1.526
• PKA: 4.67±0.10(Predicted)
• CAS DataBase Reference: (+/-)5-HEPE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)5-HEPE(83952-40-3)
• EPA Substance Registry System: (+/-)5-HEPE(83952-40-3)

Safety Data

• Hazardous Substances Data: 83952-40-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(±)5-HEPE is utilized as a pharmaceutical agent for its anti-inflammatory and immunomodulatory properties. It is known to modulate the production of inflammatory mediators and cytokines, thereby reducing inflammation and promoting tissue repair.
Used in Nutraceutical Industry:
In the nutraceutical industry, (±)5-HEPE is employed as a dietary supplement to support cardiovascular health. Its consumption is believed to help maintain a healthy balance of eicosanoids, which are hormone-like substances derived from fatty acids that play a crucial role in various physiological processes, including blood clotting, immune response, and inflammation.
Used in Research Applications:
(±)5-HEPE is also used in research settings as a tool to study the metabolism and biological effects of EPA and its metabolites. This helps scientists better understand the role of omega-3 fatty acids in human health and disease, as well as develop new therapeutic strategies targeting the eicosanoid pathway.

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 
• 234087-56-0 6-[(3Z,6Z,9Z,12Z)-1-iodopentadeca-3,6,9,12-tetraen-1-yl]-tetrahydro-2H-pyran-2-one 

Relevant articles and documents

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.