| Identification | Back Directory | [Name]
15(S)-HETE | [CAS]
54845-95-3 | [Synonyms]
C04742
AL12959
AL-12959
AL 12959
Icomucret
15(S)-HETE
(S)-15-HETE
JSFATNQSLKRBCI-VAEKSGALSA-N
15(S)-HETE MaxSpec Standard
15(S)-HETE Lipid Maps MS Standard
15(S)-HYDROXYEICOSA-5Z,8Z,11Z,13E-TETRAENOIC ACID
15(S)-HYDROXY-(5Z,8Z,11Z,13E)-EICOSATETRAENOIC ACID
(15s,5z,8z,11z,13e)-15-hydroxyeicosatetraenoic acid
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoate
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoate
(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
(5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-icosatetraenoic acid
5,8,11,13-Eicosatetraenoic acid, 15-hydroxy-, (5Z,8Z,11Z,13E,15S)- | [Molecular Formula]
C20H32O3 | [MDL Number]
MFCD00063590 | [MOL File]
54845-95-3.mol | [Molecular Weight]
320.47 |
| Chemical Properties | Back Directory | [Boiling point ]
487.7±45.0 °C(Predicted) | [density ]
0.984±0.06 g/cm3(Predicted) | [Fp ]
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 | [form ]
Liquid. | [pka]
4.75±0.10(Predicted) | [color ]
Colorless to light yellow | [BRN ]
2470466 |
| Hazard Information | Back Directory | [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. | [storage]
Store at -20°C | [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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