54886-50-9

Basic information

• Product Name: 11(S)-HETE
• Synonyms: 11(S)-HYDROXYEICOSA-5Z,8Z,12E,14Z-TETRAENOIC ACID;11(S)-HETE;11S-HYDROXY-5Z,8Z,12E,14Z-EICOSATETRAENOIC ACID;11(S)-hydroxy-(5Z,8Z,12E,14Z)-*eicosatetraenoic A;11(S)-HETE Lipid Maps MS Standard;GCZRCCHPLVMMJE-YZGNWCGPSA-N
• CAS NO: 54886-50-9
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.47
• Mol File: 54886-50-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: 11(S)-HETE(CAS DataBase Reference)
• NIST Chemistry Reference: 11(S)-HETE(54886-50-9)
• EPA Substance Registry System: 11(S)-HETE(54886-50-9)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1170 3/PG 2
• Hazardous Substances Data: 54886-50-9(Hazardous Substances Data)

Usage

Lipid mediator

11(S)-HETE is a lipid mediator produced by the oxidation of arachidonic acid.

Potent chemoattractant

11(S)-HETE has been shown to be a potent chemoattractant, meaning it can attract cells to a specific location.

Implicated in inflammatory conditions

11(S)-HETE has been implicated in a variety of inflammatory conditions, including asthma, atherosclerosis, and cancer.

Stimulation of cancer cell growth

11(S)-HETE has been shown to stimulate the growth of certain cancer cells and is thought to play a role in tumor progression.

Contribution to atherosclerosis

11(S)-HETE has been shown to contribute to the development of atherosclerosis by promoting the adhesion of monocytes to the endothelium.

Biologically active

11(S)-HETE is a biologically active lipid mediator with implications in various pathophysiological processes.

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 

Relevant articles and documents

Crystal structure of a lipoxygenase in complex with substrate: The arachidonic acid-binding site of 8R-lipoxygenase

Lipoxygenases (LOX) play critical roles in mammalian biology in the generation of potent lipid mediators of the inflammatory response; consequently, they are targets for the development of isoform-specific inhibitors. The regio- and stereo-specificity of the oxygenation of polyunsaturated fatty acids by the enzymes is understood in terms of the chemistry, but structural observation of the enzyme-substrate interactions is lacking. Although several LOX crystal structures are available, heretofore the rapid oxygenation of bound substrate has precluded capture of the enzyme-substrate complex, leaving a gap between chemical and structural insights. In this report, we describe the 2.0 ? resolution structure of 8R-LOX in complex with arachidonic acid obtained under anaerobic conditions. Subtle rearrangements, primarily in the side chains of three amino acids, allow binding of arachidonic acid in a catalytically competent conformation. Accompanying experimental work supports a model in which both substrate tethering and cavity depth contribute to positioning the appropriate carbon at the catalytic machinery.

Production of hydroxy unsaturated fatty acids using crude lipoxygenase obtained from infected rice plants

In order to explore the oxidation mode of lipoxygenase (LOX) obtained from infected rice plants, typical unsaturated fatty acids (3-8) were treated with LOX and oxygen. It was observed that ω-10 and ω-6 positions of unsaturated fatty acids were oxidized predominantly in the cases of exotic ω-6 (4 and 5) and ω-3 (7 and 8) series, respectively. In the case of endogenous fatty acids (3 and 6), oxidation at ω-6 position predominated. All the allylic alcohols obtained by reduction of the oxidation products with NaBH4 possess S-configuration.