15(S)-HETE

15(S)-HETE Property

Boiling point:

487.7±45.0 °C(Predicted)

Density 

0.984±0.06 g/cm3(Predicted)

Flash point:

14℃

storage temp. 

-20°C

solubility 

0.1 M Na2CO3: 2 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS (pH 7.2): 0.8 mg/ml

pka

4.75±0.10(Predicted)

form 

Liquid.

color 

Colorless to light yellow

BRN 

2470466

Safety

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

7-16-26-36

RIDADR 

UN 1170 3/PG 2

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

15(S)-HETE Chemical Properties,Usage,Production

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

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

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.

References

[1] J A NADEL. Immunocytochemical localization of arachidonate 15-lipoxygenase in erythrocytes, leukocytes, and airway cells.[J]. Journal of Clinical Investigation, 1991, 87 4: 1139-1145. DOI: 10.1172/jci115110
[2] HUILING YUAN. 15-Lipoxygenases and its metabolites 15(S)-HETE and 13(S)-HODE in the development of non-small cell lung cancer.[J]. Thorax, 2010, 65 4: 321-326. DOI: 10.1136/thx.2009.122747
[3] WILLIAM S. POWELL  Joshua R. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2015, 1851 4: Pages 340-355. DOI: 10.1016/j.bbalip.2014.10.008
[4] GEORGE G. CHEN. 15-hydroxy-eicosatetraenoic acid arrests growth of colorectal cancer cells via a peroxisome proliferator-activated receptor gamma-dependent pathway[J]. International Journal of Cancer, 2003, 107 5: 837-843. DOI: 10.1002/ijc.11447
[5] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[6] NIKHLESH K SINGH  Gadiparthi N R  Venkatesh Kundumani Sridharan. 12/15-Lipoxygenase gene knockout severely impairs ischemia-induced angiogenesis due to lack of Rac1 farnesylation.[J]. Blood, 2011, 118 20: 5701-5712. DOI: 10.1182/blood-2011-04-347468
[7] MALWINA MAINKA . On the biosynthesis of specialized pro-resolving mediators in human neutrophils and the influence of cell integrity[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2022, 1867 3: Article 159093. DOI: 10.1016/j.bbalip.2021.159093
[8] WAN-YANG SUN. Phospholipase iPLA2β averts ferroptosis by eliminating a redox lipid death signal[J]. Nature chemical biology, 2021, 17 4: 465-476. DOI: 10.1038/s41589-020-00734-x
[9] ANETA DOBIERZEWSKA. Plasma cross-gestational sphingolipidomic analyses reveal potential first trimester biomarkers of preeclampsia.[J]. PLoS ONE, 2017: e0175118. DOI: 10.1371/journal.pone.0175118
[10] C. THOLLON. Nature of the cardiomyocyte injury induced by lipid hydroperoxides.[J]. Cardiovascular Research, 1995, 30 5 1: 648-655. DOI: 10.1016/s0008-6363(95)00075-5