A monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid
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(±)5-HETE

Item No. 34210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)5-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid
CAS Number
71030-39-2
Synonyms
  • (±)5-Hydroxyeicosatetraenoic Acid
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥95%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
236 nm
SMILES
CCCCC/C=C\C/C=C\C/C=C\C=C/C(O)CCCC(=O)O
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+
InChi Key
KGIJOOYOSFUGPC-XTDASVJISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $87

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    50 µg

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    100 µg

    $313

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    Product Description

    (±)5-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. It contains equal amounts of 5(S)-HETE and 5(R)-HETE. (±)5-HETE induces the aggregation of isolated neutrophils with an IC50 value of 200 nM.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. O'Flaherty, J.T., Thomas, M.J., Lees, C.J., et al. Neutrophil-aggregating activity of monohydroxyeicosatetraenoic acids. Am. J. Pathol. 104, 55-62 (1981).

    Product Citations

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    Cheng, D., Zinker, B.A., Luo, Y., et al. MGAT2 inhibitor decreases liver fibrosis and inflammation in murine NASH models and reduces body weight in human adults with obesity. Cell Metab. 34(11), 1732-1748 (2022).

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. The FASEB Journal 35(6), e21666 (2021).

    Brouwers, H., Jónasdóttir, H.S., Kuipers, M.E., et al. Anti-inflammatory and proresolving effects of the omega-6 polyunsaturated fatty acid adrenic acid. J. Immunol. 205(10), 2840-2849 (2020).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Dalli, J., Colas, R.A., Walker, M.E., et al. Lipid Mediator Metabolomics via LC-MS/MS Profiling and Analysis. Clinical Metabolomics 59-72 (2018).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    Caires, R., Sierra-Valdez, F.J., Millet, J.R.M., et al. Omega-3 fatty acids modulate TRPV4 function through plasma membrane remodeling. Cell Reports 21, 245-258 (2017).

    Aoyagi, R., Ikeda, K., Isobe, Y., et al. Comprehensive analyses of oxidized phospholipids using a measured MS/MS spectra library. J. Lipid. Res. 58(11), 2229-2237 (2017).

    Banthiya, S., Kalms, J., Yoga, E.G., et al. Structural and functional basis of phospholipid oxygenase activity of bacterial lipoxygenase from Pseudomonas aeruginosa. Biochim. Biophys. Acta 1861, 1681-1692 (2016).

    Qi, H.-Y., Daniels, M.P., Liu, Y., et al. A cytosolic phospholipase A2-initiated lipid mediator pathway induces autophagy in macrophages. J. Immunol. 187(10), 5286-5292 (2011).