126432-17-5

Basic information

• Product Name: 5-oxo-6,8,11,14-eicosatetraenoic acid
• Synonyms: 5-oxo-6,8,11,14-eicosatetraenoic acid
• CAS NO: 126432-17-5
• Molecular Formula: C20H30O3
• Molecular Weight: 318.45
• Mol File: 126432-17-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 495°Cat760mmHg
• Flash Point: 267.3°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 3.79E-11mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: 5-oxo-6,8,11,14-eicosatetraenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-oxo-6,8,11,14-eicosatetraenoic acid(126432-17-5)
• EPA Substance Registry System: 5-oxo-6,8,11,14-eicosatetraenoic acid(126432-17-5)

Safety Data

• Hazardous Substances Data: 126432-17-5(Hazardous Substances Data)

Usage

Definition

ChEBI: An oxoicosatetraenoic acid having a 5-oxo group; and (6E)-, (8Z), (11Z)- and (14Z)-double bonds.

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/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6+,10-9+,13-12+,16-14+

Upstream product

• 3128-06-1 5-ketohexanoic acid 
• 65090-68-8 dodeca-3,6-diyn-1-ol 
• 13221-40-4 1,1-diethoxy-tetradeca-2,5,8-triyne 
• 35378-79-1 undeca-2,5-diyn-1-ol 
• 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 
• 74785-00-5 methyl (6E,8Z,11Z,14Z)-5-oxo-6,8,11,14-eicosatetraenoate 
• 18495-27-7 1-bromooct-2-yne 
• 201273-29-2 4-[((1E,3Z,6Z,9Z)-2-Pentadeca-1,3,6,9-tetraenyl)-[1,3]dithiolan-2-yl]-butyric acid 
• 57342-30-0 Toluene-4-sulfonic acid undeca-2,5-diynyl ester 
• 10160-94-8 1,1-diethoxy-tetradeca-2c,5c,8c-triene 
• 29125-78-8 (Z,Z)-3,6-dodecadien-1-ol 
• 264601-56-1 3-methyloxetan-3-yl-carbinyl 5-oxohexanoate 
• 264601-59-4 5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-2-pentanone 
• 2566-89-4 methyl arachidonate 

Relevant articles and documents

Synthesis, molecular modelling studies and biological evaluation of new oxoeicosanoid receptor 1 agonists

The oxoeicosanoid receptor 1 (OXER1) is a member of the G-protein coupled receptors (GPCR) family, and is involved in inflammatory processes and oncogenesis. As such it is an attractive target for pharmacological intervention. The present study aimed to shed light on the molecular fundaments of OXER1 modulation using chemical probes structurally related to the natural agonist 5-oxo-ETE. In a first step, 5-oxo-ETE and its closely related derivatives (5-oxo-EPE and 4-oxo-DHA) were obtained by conducting concise and high-yielding syntheses. The biological activity of obtained compounds was assessed in terms of potency (EC50) and efficacy (Emax) for arrestin recruitment. Finally, molecular modelling and simulation were used to explore binding characteristics of 5-oxo-ETE and derivatives with the aim to rationalize biological activity. Our data suggest that the tested 5-oxo-ETE derivatives (i) insert quickly into the membrane, (ii) access the receptor via transmembrane helices (TMs) 5 and 6 from the membrane side and (iii) drive potency and efficacy by differential interaction with TM5 and 7. Most importantly, we found that the methyl ester of 5-oxo-ETE (1a) showed even a higher maximum response than the natural agonist (1). In contrast, shifting the 5-oxo group into position 4 results in inactive compounds (4-oxo DHA compounds (3) and (3a)). All in all, our study provides relevant structural data that help understanding better OXER1 functionality and its modulation. The structural information presented herein will be useful for designing new lead compounds with desired signalling profiles.

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.