54845-95-3

Basic information

• Product Name: 15(S)-HETE
• Synonyms: 15(S)-HYDROXY-(5Z,8Z,11Z,13E)-EICOSATETRAENOIC ACID;15(S)-HYDROXYEICOSA-5Z,8Z,11Z,13E-TETRAENOIC ACID;15(S)-HETE;(15s,5z,8z,11z,13e)-15-hydroxyeicosatetraenoic acid;(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid;Icomucret;(5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-icosatetraenoic acid;(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoate
• CAS NO: 54845-95-3
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.47
• Mol File: 54845-95-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 487.7 °C at 760 mmHg
• Flash Point: 14℃
• Appearance: /
• Density: 0.984 g/cm³
• Vapor Pressure: 1.48E-11mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: −20°C
• PKA: 4.75±0.10(Predicted)
• BRN: 2470466
• CAS DataBase Reference: 15(S)-HETE(CAS DataBase Reference)
• NIST Chemistry Reference: 15(S)-HETE(54845-95-3)
• EPA Substance Registry System: 15(S)-HETE(54845-95-3)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 7-16-26-36
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 54845-95-3(Hazardous Substances Data)

Usage

Description

15(S)-HETE is a major arachidonic acid metabolite from the 15-lipoxygenase pathway. In mammals, 15(S)-HETE is synthesized in the respiratory epithelium, leukocytes, and reticulocytes. 15(S)-HETE is present in μg/ml concentrations in the nasal secretions of allergic rhinitis.

Uses

Different sources of media describe the Uses of 54845-95-3 differently. You can refer to the following data:
1. 15(S)-HETE is a major arachidonic acid metabolite from the 15-lipoxygenase pathway. In mammals, 15(S)-HETE is synthesized in the respiratory epithelium, leukocytes, and reticulocytes. 15(S)-HETE is present in μg/ml concentrations in the nasal secretions of allergic rhinitis.
2. 15(S)-HETE is an arachidonic acid metabolite with immunosuppressive activity.

Definition

ChEBI: An optically active form of 15-HETE having 15(S)-configuration..

General Description

15(S)-HETE is a product of the arachidonic acid pathway. It is synthesized by the human lungs and airway epithelial cells. 15(S)-HETE is a potent mucosecretagogue in human airways. It is a metabolite of 15-lipoxygenase. 15(S)-HETE is an endogenous ligand for peroxisome proliferator-activated receptor γ (PPARγ).

Biochem/physiol Actions

Metabolite of arachidonic acid via the 15-lipoxygenase pathway that may be involved in pulmonary anti-inflammatory responses through the inhibition of 5-lipoxygenase. 15(S)-HETE suppresses the incorporation of thymidine and biosynthesis of prostaglandin E2 in tumor cell cultures. Treatment of colon cancer cells with 15(S)-HETE inhibited cell proliferation and induced apoptosis, which was preceded by an increase in TGF-beta-inducible early gene (TIEG) and a decrease in Bcl-2.

InChI:InChI=1/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

Upstream product

• 70981-96-3 (5Z,8Z,11Z,13E)-15(S)-hydroperoxyeicosa-5,8,11,13-tetraenoic acid 
• 97643-28-2 (5Z,8Z,11Z,13E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-icosa-5,8,11,13-tetraenoic acid methyl ester 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 70946-44-0 (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester 
• 928-90-5 5-hexyl-1-ol 
• 102228-23-9 (5Z,8Z,13E)-(S)-15-(tert-Butyl-dimethyl-silanyloxy)-icosa-5,8,13-trien-11-ynoic acid methyl ester 
• 102228-19-3 (Z)-12-(tert-Butyl-dimethyl-silanyloxy)-1-trimethylsilanyl-dodec-4-ene-1,7-diyne 
• 102279-39-0 (4Z,7Z)-12-(tert-Butyl-dimethyl-silanyloxy)-1-trimethylsilanyl-dodeca-4,7-dien-1-yne 
• 102228-21-7 (5Z,8Z)-12-Trimethylsilanyl-dodeca-5,8-dien-11-ynoic acid methyl ester 
• 102228-17-1 tert-Butyl-((Z)-10-chloro-dec-8-en-5-ynyloxy)-dimethyl-silane 
• 102228-18-2 tert-Butyl-((Z)-10-iodo-dec-8-en-5-ynyloxy)-dimethyl-silane 
• 102228-22-8 Methyl (5Z,8Z)-Dodeca-5,8-dien-11-ynoate 
• 73448-13-2 tert-butyldimethylsilyl hex-5-yn-1-yl ether 

Downstream Products

• 70946-44-0 (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid methyl ester 
• 81416-72-0 (5Z,8Z,11Z,13E)-15-oxo-5,8,11,13-eicosatetraenoic acid 
• 339046-14-9 (5Z,8Z,11Z,13E,15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid sodium salt 
• 119008-09-2 (2E,4S)-4-hydroxy-2-nonenal 
• 161744-53-2 15(S)-hydroxy-eicosa-5Z,8Z,11Z,13E-tetraenoyl-N-(2-hydroxyethyl)amine 

Relevant articles and documents

Stereocontrolled Total Synthesis of (5Z,8Z,11Z,13E)(15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic Acid (15S-HETE) and Analogues

A novel and stereoselective synthesis of 15S-HETE and a number of analogues based on a Cu(I)-Pd(0) coupling reaction is described.

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.

Manufacture of (5Z,8Z,11Z,13E)(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid sodium salt for clinical trials

A robust synthesis of (5Z,8Z,11Z,13E)(15S)-15-hydroxyeicosa-5,8,11,13- tetraenoic acid (15(S)-HETE) sodium salt was established, utilising a biooxidation process. Treatment of arachidonic acid with soybean lipoxidase in 0.1 M sodium tetraborate buffer under oxygen pressure resulted in formation of the hydroperoxide, 15(S)-HPETE. Addition of sodium borohydride to the reaction mixture reduced the hydroperoxide to 15(S)-HETE, which was then purified by column chromatography. 15(S)-HETE sodium salt was prepared by treatment of an ethanol solution of HETE with aqueous sodium hydrogen carbonate. Multiple 10-g batches of 15(S)-HETE sodium salt with >98% enantiomeric excess and >98% chemical purity were prepared to support clinical trials.

9-Hydroxy-10,12-octadecadienoic acid (9-HODE) and 13-hydroxy-9,11-octadecadienoic acid (13-HODE): Excellent markers for lipid peroxidation

Various conditions for conversion of (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9S-HPODE) and (13S,9Z,10E)-13-hydroperoxy-9,11-octadecadienoic acid (13S-HPODE) into the corresponding hydroxy acids, (9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid (9S-HODE) and (13S,9Z,10E)-13-hydroxy-9,11-octadecadienoic acid (13S-HODE), were investigated in vitro. 9S-HODE and 13S-HODE were subjected to lipid peroxidation under various conditions: oxidation was carried out in air only, and in air/Fe2+/ascorbate, air/H2O2/Fe2+, air/Fe2+, and air/Fe3+. In contrast to the corresponding hydroperoxides (9S-HPODE and 13S-HPODE), 9-HODE and 13-HODE proved to be stable in all these oxidation experiments. Unexpectedly, hydroxy compounds obtained by reduction of hydroperoxides derived from arachidonic acid were not attacked by air/Fe2+/ascorbate or air/Fe2+. Thus, for instance, (15S,5Z,8Z,11Z,13E)-15-hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE) remained unchanged in spite of possessing the structural prerequisites for attack by radicals, i.e. a CH2-group located between two double bonds. Consequently, metal-induced air oxidation reactions of these systems seem to be restricted to hydroperoxides of unsaturated acids (LOOH) and not to corresponding hydroxy compounds (LOH). The reported experiments explain why hydroxy derivatives of unsaturated acids, especially 9-HODE and 13-HODE, are enriched in naturally occurring lipid peroxidation (LPO) processes to a greater extent than any other LPO product and why they are nearly ideal markers for LPO.