A non-enzymatically derived oxylipin
Related Products
Isomer(s)
3450511(R)-HETE 3451011(S)-HETE
Labeled Version(s)
9002385(±)11-HETE-d8
Technical Support & Resources

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(±)11-HETE

Item No. 34500

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)11-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid
CAS Number
71030-38-1
Synonyms
  • (±)11-Hydroxyeicosatetraenoic Acid
Molecular Formula
C20H32O3
Formula Weight
320.5
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
CCCCC/C=C\C=C/C(O)C/C=C\C/C=C\CCCC(=O)O
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b9-6-,10-7-,14-11-,16-13+
InChi Key
GCZRCCHPLVMMJE-RLZWZWKOSA-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

    $103

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    50 µg

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    100 µg

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    Product Description

    (±)11-HETE is an oxylipin formed non-enzymatically from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1,2 Levels of (±)11-HETE are increased in an in vitro model of lipid peroxidation induced by ferrous ammonium sulfate (FAS) in rat brain homogenates.3 Levels are also increased in rat liver in an in vivo model of lipid peroxidation induced by carbon tetrachloride (CCl4). It has been found in skin extracts from individuals with psoriasis and in atherosclerotic plaques.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Powell, W.S., and Rokach, J. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochim. Biophys. Acta 1851(4), 340-355 (2014).

    2. Derogis, P.B.M.C., Chaves-Filho, A.B., and Miyamoto, S. Characterization of hydroxy and hydroperoxy polyunsaturated fatty acids by mass spectrometry. Bioactive lipids in health and disease 21-38 (2019).

    3. Guido, D.M., McKenna, R., and Mathews, W.R. Quantitation of hydroperoxy-eicosatetraenoic acids and hydroxy-eicosatetraenoic acids as indicators of lipid peroxidation using gas chromatography-mass spectrometry. Anal. Biochem. 209(1), 123-129 (1993).

    4. Camp, R.D.R., Mallet, A.I., Woollard, P.M., et al. The identification of hydroxy fatty acids in psoriatic skin. Prostaglandins 26(3), 431-447 (1983).

    5. Waddington, E., Sienuarine, K., Puddey, I., et al. Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high-performance liquid chromatography. Anal. Biochem. 292(2), 234-244 (2001).

    Product Citations

    Tufail, Y.Z., Guijas, C., Kummer, D.A., et al. Suppression of pain transmission and behavior by inhibition of peripheral diacylglycerol metabolism. Cell Chem. Bio. 33(1), 74-90.e19 (2025).

    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).

    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).

    Lahvic, J.L., Ammerman, M., Li, P., et al. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132. PNAS 115(37), 9252-9257 (2018).

    Gouveia-Figueira, S., Karlsson, J., Deplano, A., et al. Characterisation of (R)-2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide as a dual fatty acid amide hydrolase: Cyclooxygenase inhibitor. PLoS One 10(9), e0139212 (2015).

    Morgan, A.H., Hammond, V.J., Morgan, L., et al. Quantitative assays for esterified oxylipins generated by immune cells. Nat. Protoc. 5(12), 1919-1931 (2010).