106154-18-1

Basic information

• Product Name: 5-KETE
• Synonyms: 5-OXO-6E,8Z,11Z,14Z-EICOSATETRAENOIC ACID;5-OXOETE;5-KETE;5-KETOEICOSA-6E,8Z,11,Z14Z-TETRAENOIC ACID;5-Oxo-(6E,8Z,11Z,14Z)-6,8,11,14-eicosatetraenoicacid;5-OxoETE Lipid Maps MS Standard;MEASLHGILYBXFO-XTDASVJISA-N
• CAS NO: 106154-18-1
• Molecular Formula: C20H30O3
• Molecular Weight: 318.45
• Mol File: 106154-18-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 495.0±45.0 °C(Predicted)
• Appearance: /
• Density: 0.980±0.06 g/cm3(Predicted)
• Storage Temp.: Store at -80°C
• PKA: 4.59±0.10(Predicted)
• CAS DataBase Reference: 5-KETE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-KETE(106154-18-1)
• EPA Substance Registry System: 5-KETE(106154-18-1)

Safety Data

• Hazardous Substances Data: 106154-18-1(Hazardous Substances Data)

Usage

Description

5-OxoETE, also known as 5-oxo-ETE, is a polyunsaturated keto acid that is formed by the oxidation of 5-HETE in human neutrophils through the action of a specific dehydrogenase. It is characterized by its ability to stimulate 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. The compound is also available as a quantitative grade standard, 5-oxoETE MaxSpec, which is prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required.

Uses

1. Used in Pharmaceutical Applications:
5-OxoETE is used as a compound that stimulates neutrophil degranulation for various pharmaceutical applications. It plays a crucial role in the immune response by modulating the activity of neutrophils and eosinophils, which are essential components of the body's defense mechanism against infections and other diseases.
2. Used in Research and Development:
5-OxoETE is used as a research tool for studying the biological processes and pathways involving neutrophils and eosinophils. It helps researchers understand the molecular mechanisms underlying various immune responses and can be employed in the development of new therapeutic strategies for treating inflammatory and immune-related disorders.
3. Used in Mass Spectrometry and Related Applications:
The 5-oxoETE MaxSpec standard is used in mass spectrometry and related applications where quantitative reproducibility is required. It provides a reliable and accurate reference material for the analysis and identification of 5-oxoETE in various samples, ensuring the reliability and accuracy of experimental results.
4. Used in Quality Control and Validation:
The 5-oxoETE MaxSpec standard is used for quality control and validation purposes in the pharmaceutical and biotechnology industries. It helps ensure that the identity, purity, stability, and concentration of 5-oxoETE in various products and samples meet the required specifications, maintaining product quality and safety.
5. Used in Drug Development and Screening:
5-OxoETE can be used in drug development and screening processes to identify potential therapeutic agents that modulate the activity of neutrophils and eosinophils. By understanding the molecular targets and pathways involved in these immune cell functions, researchers can develop new drugs that can effectively treat various immune-related disorders and conditions.

Biological Activity

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

Upstream product

• 74785-00-5 methyl (6E,8Z,11Z,14Z)-5-oxo-6,8,11,14-eicosatetraenoate 
• 201273-29-2 4-[((1E,3Z,6Z,9Z)-2-Pentadeca-1,3,6,9-tetraenyl)-[1,3]dithiolan-2-yl]-butyric acid 
• 356070-86-5 (7Z,10Z,13Z)-6-Hydroxy-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-7,10,13-trien-4-one 
• 35378-79-1 undeca-2,5-diyn-1-ol 
• 13221-40-4 1,1-diethoxy-tetradeca-2,5,8-triyne 
• 3128-06-1 5-ketohexanoic acid 
• 10160-94-8 1,1-diethoxy-tetradeca-2c,5c,8c-triene 
• 57342-30-0 Toluene-4-sulfonic acid undeca-2,5-diynyl ester 
• 264601-59-4 5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-2-pentanone 
• 264601-56-1 3-methyloxetan-3-yl-carbinyl 5-oxohexanoate 
• 18495-27-7 1-bromooct-2-yne 
• 65090-68-8 dodeca-3,6-diyn-1-ol 
• 29125-78-8 (Z,Z)-3,6-dodecadien-1-ol 
• 83606-41-1 ((3Z,6Z)-dodeca-3,6-dien-1-yl)triphenylphosphonium bromide 

Relevant articles and documents

Pharmacokinetics and Metabolism of Selective Oxoeicosanoid (OXE) Receptor Antagonists and Their Effects on 5-Oxo-6,8,11,14-eicosatetraenoic Acid (5-Oxo-ETE)-Induced Granulocyte Activation in Monkeys

The potent eosinophil chemoattractant 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a 5-lipoxygenase product that acts via the selective OXE receptor, which is present in many species, but not rodents. We previously reported that the indole 230 is

Total Synthesis of a Potent Proinflammatory 5-Oxo-ETE and Its 6,7-Dihydro Biotransformation Product

The first total synthesis of a potent inflammatory mediator 5-oxo-6(E),8(Z),11(Z),14(Z)-eicosatetraenoic acid (5-oxo-ETE) 2 and its biotransformation product 6,7-dihydro-5-oxo-ETE 5 is reported. A convergent synthesis for the unstable title compounds is a

Inhibitory and mechanistic investigations of oxo-lipids with human lipoxygenase isozymes

Oxo-lipids, a large family of oxidized human lipoxygenase (hLOX) products, are of increasing interest to researchers due to their involvement in different inflammatory responses in the cell. Oxo-lipids are unique because they contain electrophilic sites that can potentially form covalent bonds through a Michael addition mechanism with nucleophilic residues in protein active sites and thus increase inhibitor potency. Due to the resemblance of oxo-lipids to LOX substrates, the inhibitor potency of 4 different oxo-lipids; 5-oxo-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid (5-oxo-ETE), 15-oxo-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid (15-oxo-ETE), 12-oxo-5,8,10,14-(Z,Z,E,Z)-eicosatetraenoic acid (12-oxo-ETE), and 13-oxo-9,11-(Z,E)-octadecadienoic acid (13-oxo-ODE) were determined against a library of LOX isozymes; leukocyte 5-lipoxygenase (h5-LOX), human reticulocyte 15-lipoxygenase-1 (h15-LOX-1), human platelet 12-lipoxygenase (h12-LOX), human epithelial 15-lipoxygenase-2 (h15-LOX-2), soybean 15-lipoxygenase-1 (s15-LOX-1), and rabbit reticulocyte 15-LOX (r15-LOX). 15-Oxo-ETE exhibited the highest potency against h12-LOX, with an IC50 = 1 ± 0.1 μM and was highly selective. Steady state inhibition kinetic experiments determined 15-oxo-ETE to be a mixed inhibitor against h12-LOX, with a Kic value of 0.087 ± 0.008 μM and a Kiu value of 2.10 ± 0.8 μM. Time-dependent studies demonstrated irreversible inhibition with 12-oxo-ETE and h15-LOX-1, however, the concentration of 12-oxo-ETE required (Ki = 36.8 ± 13.2 μM) and the time frame (k2 = 0.0019 ± 0.00032 s-1) were not biologically relevant. These data are the first observations that oxo-lipids can inhibit LOX isozymes and may be another mechanism in which LOX products regulate LOX activity.

METHOD OF SYNTHESIZING A 5-OXO-CONJUGATED FATTY ACID

There is provided a novel chemical synthetic method for the preparation of a 5-oxo-ETE and related compounds. The method is based on a short and efficient synthesis of 5-oxo-ETE from commercially available Arachidonic acid. The method is based on the surprising discovery that a 5-oxo-conjugated fatty acid may be efficiently converted into the corresponding 5-oxo-conjugated fatty acid by reaction with the Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one)in the presence of pyridine or a substituted pyridine.