(+/-)5-HEPE Chemical Properties

Boiling point:

488.0±45.0 °C(Predicted)

Density 

0.997±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

0.1 M Na2CO3: 2 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS pH 7.2: 0.8 mg/ml

form 

Clear to light-yellow liquid.

pka

4.67±0.10(Predicted)

(+/-)5-HEPE Usage And Synthesis

Description

(±)5-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 5(S)-HEPE and 5(R)-HEPE. The biological activity of (±)5-HEPE is likely mediated by one of the individual isomers, most commonly the 5(S) isomer in mammalian systems. EPA can be metabolized to 5-HEPE in human and bovine neutrophils, and human eosinophils, which is further metabolized to 5-oxoEPE and LTB₅. The 5-series metabolites of EPA, namely 5-HEPE, 5-oxoEPE, and LTB₅, have significantly decreased biological effects compared to the arachidonic acid-derived metabolites.

Uses

(±)5-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 5(S)-HEPE and 5(R)-HEPE. The biological activity of (±)5-HEPE is likely mediated by one of the individual isomers, most commonly the 5(S) isomer in mammalian systems. EPA can be metabolized to 5-HEPE in human and bovine neutrophils, and human eosinophils, which is further metabolized to 5-oxoEPE and LTB5. The 5-series metabolites of EPA, namely 5-HEPE, 5-oxoEPE, and LTB5, have significantly decreased biological effects compared to the arachidonic acid-derived metabolites.

Definition

ChEBI: 5-HEPE is a hydroxyicosapentaenoic acid that consists of 6E,8Z,11Z,14Z,17Z-icosapentaenoic acid with the hydroxy group located at position 5. It has a role as a mouse metabolite. It is a conjugate acid of a 5-HEPE(1-).

References

[1] Powell, et al. Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils. J. Lipid Res. 36, 2590-2598 (1995).

(+/-)5-HEPE(83952-40-3)Related Product Information

• (±)-5-HETE, (±)-(6E,8Z,11Z,14Z)-5-Hydroxyeicosatetraenoic acid solution
• dendrotoxin K
• (+/-)5-HEPE