(±)-5-HETE, (±)-(6E,8Z,11Z,14Z)-5-Hydroxyeicosatetraenoic acid solution Chemical Properties

Boiling point:

487.7±45.0 °C(Predicted)

Density 

0.984±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

0.1 M Na2CO3: 2 mg/ml
DMF: Miscible
DMSO: Miscible
Ethanol: MisciblePBS pH 7.2: 0.8 mg/ml

form 

Liquid

pka

4.67±0.10(Predicted)

color 

Colorless to light yellow

Safety Information

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

7-16

(±)-5-HETE, (±)-(6E,8Z,11Z,14Z)-5-Hydroxyeicosatetraenoic acid solution Usage And Synthesis

Uses

5-HETE ((±)-5-HETE), a fatty acid, is a oxidative derivative of Arachidonic acid. 5-HETE is a mixture of 5(S)-HETE and 5(R)-HETE. 5-HETE is a potent aggregating agent that induces the aggregation of neutrophils with an IC50 value of 200 nM[1].

Definition

ChEBI: 5-HETE is a HETE having a 5-hydroxy group and (6E)-, (8Z)-, (11Z)- and (14Z)-double bonds. It has a role as a mouse metabolite. It is a conjugate acid of a 5-HETE(1-).

References

[1] J T O'Flaherty, et al. Neutrophil-aggregating activity of monohydroxyeicosatetraenoic acids. Am J Pathol. 1981 Jul;104(1):55-62. PMID:7258296
[2] ZONGYUAN WU, FANG WEI*   Analytical Strategy for Oxylipin Annotation by Combining Chemical Derivatization-Based Retention Index Algorithm and Feature Tandem Mass Spectrometric Fragmentation as a Biomarker Discovery Tool[J]. Analytical Chemistry, 2023, 95 43: 15933-15942. DOI: 10.1021/acs.analchem.3c02789
[3] DONG CHENG. MGAT2 inhibitor decreases liver fibrosis and inflammation in murine NASH models and reduces body weight in human adults with obesity.[J]. Cell metabolism, 2022, 34 11: 1732-1748.e5. DOI: 10.1016/j.cmet.2022.10.007
[4] YILIN PANG . LC−MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products[J]. Free Radical Biology and Medicine, 2022, 193: Pages 363-372. DOI: 10.1016/j.freeradbiomed.2022.10.303
[5] ANNE-SOPHIE ARCHAMBAULT. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients[J]. FASEB Journal, 2021, 35 6. DOI: 10.1096/fj.202100540r
[6] DAVID MERIWETHER. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model.[J]. Journal of Clinical Investigation, 2019, 129 9: 3670-3685. DOI: 10.1172/jci123700
[7] JESMOND DALLI. Lipid Mediator Metabolomics Via LC-MS/MS Profiling and Analysis.[J]. Methods in molecular biology, 2018, 1730: 59-72. DOI: 10.1007/978-1-4939-7592-1_4
[8] CARLOS ARTÉRIO SORGI. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays[J]. Scientific Data, 2018, 5 1: 1-12. DOI: 10.1038/sdata.2018.167
[9] REBECA CAIRES. Omega-3 Fatty Acids Modulate TRPV4 Function through Plasma Membrane Remodeling.[J]. Cell reports, 2017, 21 1: 246-258. DOI: 10.1016/j.celrep.2017.09.029
[10] RYOHEI AOYAGI. Comprehensive analyses of oxidized phospholipids using a measured MS/MS spectra library.[J]. Journal of Lipid Research, 2017, 58 11: 2229-2237. DOI: 10.1194/jlr.d077123
[11] SWATHI BANTHIYA . Structural and functional basis of phospholipid oxygenase activity of bacterial lipoxygenase from Pseudomonas aeruginosa[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2016, 1861 11: Pages 1681-1692. DOI: 10.1016/j.bbalip.2016.08.002
[12] HAI-YAN QI. A cytosolic phospholipase A2-initiated lipid mediator pathway induces autophagy in macrophages.[J]. Journal of immunology, 2011, 187 10: 5286-5292. DOI: 10.4049/jimmunol.1004004

(±)-5-HETE, (±)-(6E,8Z,11Z,14Z)-5-Hydroxyeicosatetraenoic acid solution(71030-39-2)Related Product Information

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• CIS-8,11,14-EICOSATRIENOIC ACID
• Melatonine
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• dendrotoxin K
• DENDROTOXIN I
• C8 CERAMIDE-1-PHOSPHATE
• 4-[[(5Z,8Z,11Z,14Z)-1-OXO-5,8,11,14-EICOSATETRAENYL]AMINO]BUTANOIC ACID
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