Non-enzymatic oxidation product of EPA
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(±)18-HEPE

Item No. 32840

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)-18-hydroxy-5Z,8Z,11Z,14Z,16E-eicosapentaenoic acid
CAS Number
141110-17-0
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥97%
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
CCC(O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H30O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,15,17,19,21H,2-3,8-9,14,16,18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-,17-15+
InChi Key
LRWYBGFSVUBWMO-UXNZXXPISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $142

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    50 µg

    $270

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    100 µg

    $511

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    250 µg

    $1,065

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    Product Description

    (±)18-HEPE is produced by non-enzymatic oxidation of eicosapentaenoic acid (EPA; Item Nos. 90110 | 90110.1 | 21908).1 18-HEPE levels are increased in the plasma and heart, as well as in the supernatant of cultured peritoneal macrophages isolated from fat-1 transgenic mice that are capable of endogenously producing ω-3 fatty acids from ω-6 fatty acids.2,3,4 It reduces increases in cardiac fibrosis and the expression of Nppa, Col1a1, Tgfb1, Cx3cl1, and Adgre1 induced by transverse aortic constriction in a mouse model of cardiac hypertrophy when administered at doses of 1 and 5 µg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Onodera, T., Fukuhara, A., Shin, J., et al. Eicosapentaenoic acid and 5-HEPE enhance macrophage-mediated Treg induction in mice. Sci. Rep. 7(1), 4560 (2017).

    2. Li, J., Chen, C.-Y., Arita, M., et al. An omega-3 polyunsaturated fatty acid derivative, 18-HEPE, protects against CXCR4-associated melanoma metastasis. Carcinogenesis 39(11), 1380-1388 (2018).

    3. Endo, J., Sano, M., Isobe, Y., et al. 18-HEPE, an n-3 fatty acid metabolite released by macrophages, prevents pressure overload-induced maladaptive cardiac remodeling. J. Exp. Med. 211(8), 1673-1687 (2014).

    4. Kang, J.X. Fat-1 transgenic mice: A new model for omega-3 research. Prostaglandins Leukot. Essent. Fatty Acids 77(5-6), 263-267 (2007).

    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).

    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).

    Roberts, L.M., Schwarz, B., Speranza, E., et al. Pulmonary infection induces persistent, pathogen-specific lipidomic changes influencing trained immunity. iScience 24(9), 103025 (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).