5-KETE

5-KETE Property

Boiling point:

495.0±45.0 °C(Predicted)

Density 

0.980±0.06 g/cm3(Predicted)

storage temp. 

Store at -80°C

solubility 

DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS pH 7.2: 0.8 mg/ml

form 

Liquid.

pka

4.59±0.10(Predicted)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

5-KETE Chemical Properties,Usage,Production

Description

5-OxoETE is a polyunsaturated keto acid formed by the oxidation of 5-HETE in human neutrophils by a specific dehydrogenase. It stimulates cytosolic calcium levels in neutrophils with an EC₅₀ value of 2 nM. 5-OxoETE selectively stimulates the migration and degranulation of eosinophils and activates the MAPK pathway in stimulated neutrophils via a specific G protein-coupled receptor.

5-OxoETE MaxSpec^® standard is a quantitative grade standard of 5-oxoETE that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This 5-oxoETE MaxSpec^® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

Uses

5-oxo-ETE is a compound that stimulates neutrophil degranulation.

Definition

ChEBI: 5-oxo-ETE is an oxoicosatetraenoic acid having a 5-oxo group; and (6E)-, (8Z), (11Z)- and (14Z)-double bonds. It has a role as a human metabolite, a mouse metabolite and an immunomodulator. It is functionally related to an icosa-6,8,11,14-tetraenoic acid. It is a conjugate acid of a 5-oxo-ETE(1-).

Biological Activity

Potent oxoeicosanoid (OXE) receptor agonist (EC 50 = 0.33 nM). Chemoattractant for both neutrophils and eosinophils and induces transendothelial migration of eosinophils.

References

[1] W S POWELL  S G  F Gravelle. Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes.[J]. The Journal of Biological Chemistry, 1992, 267 27: 19233-19241.
[2] WILLIAM S. POWELL  Sylvie G  Ying Zhang. Effects of Phorbol Myristate Acetate on the Synthesis of 5-Oxo-6,8,11,14-eicosatetraenoic Acid by Human Polymorphonuclear Leukocytes[J]. Biochemistry Biochemistry, 1994, 33 13: 3927-3933. DOI: 10.1021/bi00179a019
[3] J T O’FLAHERTY. 5-Oxo-eicosanoids and hematopoietic cytokines cooperate in stimulating neutrophil function and the mitogen-activated protein kinase pathway.[J]. The Journal of Biological Chemistry, 1996, 271 30: 17821-17828. DOI: 10.1074/jbc.271.30.17821
[4] J T O’FLAHERTY. 5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes.[J]. Journal of immunology, 1996, 157 1: 336-342.
[5] TAKESHI HOSOI. Identification of a Novel Human Eicosanoid Receptor Coupled to Gi/o *[J]. The Journal of Biological Chemistry, 2002, 64 1: 31459-31465. DOI: 10.1074/jbc.m203194200
[6] CAROL E JONES. Expression and characterization of a 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils.[J]. Molecular Pharmacology, 2003, 63 3: 471-477. DOI: 10.1124/mol.63.3.471