A racemic mixture of EPA derivatives
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(±)15-HEPE

Item No. 32700

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid
CAS Number
88852-33-9
Synonyms
  • (±)15-hydroxy Eicosapentaenoic Acid
  • (±)15-hydroxy EPA
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥98%
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
CC/C=C\CC(O)\C=C\C=C\C/C=C\C/C=C\CCCC(=O)O
InChi Code
InChI=1S/C20H30O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h3-5,8-11,13-14,17,19,21H,2,6-7,12,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,13-3-,17-14+
InChi Key
WLKCSMCLEKGITB-XWJJKCKWSA-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

    $65

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    50 µg

    $124

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    100 µg

    $234

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    250 µg

    $520

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    Product Description

    (±)15-HEPE is a racemic mixture of the monohydroxy fatty acids 15(R)-HEPE and 15(S)-HEPE (Item No. 32710). 15(S)-HEPE is formed from EPA via a 15(S)-HpEPE (Item No. 42710) intermediate, which is produced by 15-lipoxygenase (15-LO) and reduced by glutathione peroxidase (GPX).1,2 (±)15-HEPE is active against P. acnes and S. aureus (MICs = 128 and 512 mg/L, respectively).3 It inhibits aggregation of isolated rat neutrophils induced by the formyl peptide receptor agonist fMLP (IC50 = 4.7 µM).4 Bronchoalveolar lavage fluid (BALF) levels of (±)15-HEPE are increased in patients with allergic asthma or COVID-19.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miller, C., Yamaguchi, R.Y., and Ziboh, V.A. Guinea pig epidermis generates putative anti-inflammatory metabolites from fish oil polyunsaturated fatty acids. Lipids 24(12), 998-1003 (1989).

    2. Tan, L., Xin, X., Zhai, L., et al. Drosophila fed ARA and EPA yields eicosanoids, 15S-hydroxy-5Z,8Z, 11Z, 13E-eicosatetraenoic acid, and 15S-hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid. Lipids 51(4), 435-449 (2016).

    3. Desbois, A.P., and Lawlor, K.C. Antibacterial activity of long-chain polyunsaturated fatty acids against Propionibacterium acnes and Staphylococcus aureus. Mar. Drugs 11(11), 4544-4557 (2013).

    4. Lam, B., Marcinkiewicz, E., and Wong, P.Y.-K. Transformation of 15-hydroperoxyeicosapentaenoic acid into mono- and dihydroxyeicosapentaenoic acids by human platelets. Drugs affecting leukotrienes and other eicosanoid pathways 167-180 (1985).

    5. Lundström, S.L., Yang, J., Källberg, H.J., et al. Allergic asthmatics show divergent lipid mediator profiles from healthy controls both at baseline and following birch pollen provocation. PLoS One 7(3), e33780 (2012).

    6. 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).

    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., Brassard, J., Bernatchez, É., et al. Human and mouse eosinophils differ in their ability to biosynthesize eicosanoids, docosanoids, the endocannabinoid 2-arachidonoyl-glycerol and its congeners. Cells 11(1), 141 (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).

    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).

    Archambault, A.-S., Turcotte, C., Martin, C., et al. Comparison of eight 15-lipoxygenase (LO) inhibitors on the biosynthesis of 15-LO metabolites by human neutrophils and eosinophils. PLoS One 13(8), e0202424 (2018).

    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).