15(S)-HETE Chemical Properties

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 Information

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

MSDS

• Language:English Provider:SigmaAldrich

15(S)-HETE Usage And Synthesis

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

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