108437-64-5

Basic information

• Product Name: 12-KETE
• Synonyms: 12-OXOETE;12-OXO-5Z,8Z,10E,14Z-EICOSATETRAENOIC ACID;12-KETE;12-OxoETE Lipid Maps MS Standard;GURBRQGDZZKITB-VXBMJZGYSA-N
• CAS NO: 108437-64-5
• Molecular Formula: C20H30O3
• Molecular Weight: 318.45
• Mol File: 108437-64-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 494.9°Cat760mmHg
• Flash Point: 267.2°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 3.82E-11mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: 12-KETE(CAS DataBase Reference)
• NIST Chemistry Reference: 12-KETE(108437-64-5)
• EPA Substance Registry System: 12-KETE(108437-64-5)

Safety Data

• Hazardous Substances Data: 108437-64-5(Hazardous Substances Data)

Usage

Description

12-KETE, also known as 12-oxoETE, is an oxoicosatetraenoic acid with a 12-oxo group and (5Z)-, (8Z), (10E)-, and (14Z)-double bonds. It is synthesized by human platelets and Aplysia nervous tissue after incubation with arachidonic acid and plays a role in various biological processes.

Uses

Used in Biological Research:
12-KETE is used as a research compound for studying its effects on cytoplasmic free calcium levels. It induces a rapid, dose-dependent increase in cytoplasmic free calcium via a Leukotriene B4 receptor or a common activation sequence.
Used in Platelet and Nervous Tissue Studies:
12-KETE is used as a biomarker in the study of human platelets and Aplysia nervous tissue, as it is synthesized after incubation with arachidonic acid. This application helps researchers understand the role of 12-KETE in these tissues and its potential involvement in various physiological processes.
Used in Enzyme Conversion Studies:
12-KETE is used as a substrate in the study of microsomal fractions of various tissues, which can reduce 12-oxoETE to 12(S)-HETE or a mixture of 12(S)and 12(R)-HETE. This application aids in understanding the enzymatic conversion processes and the role of these enzymes in the metabolism of 12-KETE.
Used in Pharmaceutical Development:
12-KETE may be used as a starting point for the development of new pharmaceuticals targeting the Leukotriene B4 receptor or other related pathways. Its ability to modulate cytoplasmic free calcium levels could potentially be exploited for therapeutic purposes in various diseases and conditions.

InChI:InChI=1/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+

Upstream product

• 158359-25-2 (5Z,8Z,10E)-11-[((Z)-2-Oct-2-enyl)-[1,3]dithian-2-yl]-undeca-5,8,10-trienoic acid 
• 18495-27-7 1-bromooct-2-yne 
• 6026-86-4 methyl 4-formylbutanoate 
• 83606-22-8 (Z)-8-hydroxyoct-5-enoic acid methyl ester 
• 91097-63-1 ((3Z)-7-methoxycarbonyl-3-heptenyl)-triphenylphosphonium iodide 
• 91173-04-5 methyl (5Z)-8-iodooct-5-enoate 
• 85924-40-9 (Z)-8-bromooct-5-enoic acid methyl ester 
• 158359-19-4 2-(2-octenyl)-1,3-dithiane 
• 158359-18-3 2-Oct-2-ynyl-[1,3]dithiane 
• 158359-20-7 2,2-(Trimethylenedithio)dec-4(Z)-enal 
• 158359-22-9 (E)-3-[((Z)-2-Oct-2-enyl)-[1,3]dithian-2-yl]-prop-2-en-1-ol 
• 158359-23-0 (E)-3-[((Z)-2-Oct-2-enyl)-[1,3]dithian-2-yl]-propenal 
• 158359-21-8 (E)-3-[((Z)-2-Oct-2-enyl)-[1,3]dithian-2-yl]-acrylic acid methyl ester 
• 158359-24-1 (5Z,8Z,10E)-11-[((Z)-2-Oct-2-enyl)-[1,3]dithian-2-yl]-undeca-5,8,10-trienoic acid methyl ester 

Relevant articles and documents

Synthesis of 12-KETE and its 8,9-trans-isomer

The first total synthesis of the highly unstable biological mediator 12-ketoeicosatetraenoic acid (12-KETE) 3 and its 8,9-trans-isomer 20 is presented. The strategy focusses on the stable precursor dithiane 13 and its conversion to 3 and 20. Biochemical e

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.