A racemic mixture of arachidonic acid metabolites
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(±)12-HETE

Item No. 34550

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)12-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
CAS Number
71030-37-0
Synonyms
  • (±)12-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
237 nm
SMILES
CCCCC/C=C\CC(O)/C=C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+
InChi Key
ZNHVWPKMFKADKW-VXBMJZGYSA-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

    $165

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    100 µg

    $313

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    250 µg

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    Product Description

    (±)12-HETE is a racemic mixture of the arachidonic acid metabolites 12(R)-HETE (Item No. 34560) and 12(S)-HETE (Item No. 34570). It is formed via non-enzymatic oxidation of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1,2 12(S)- and 12(R)-HETE are formed by 12S- and 12R-lipoxygenase-mediated oxidation of arachidonic acid, respectively.3,4,5 12(R)-HETE can also be formed by oxidation of arachidonic acid mediated by cytochrome P450 (CYP450) enzymes.1 (±)12-HETE (1 µM) induces aggregation of isolated human neutrophils.6 Production of (±)12-HETE by platelets isolated from spontaneously hypertensive rats is increased compared with platelets isolated from normotensive rats.7

    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. Kühn, H., Banthiya, S., and van Leyen, K. Mammalian lipoxygenases and their biological relevance. Biochim. Biophys. Acta 1851(4), 308-330 (2015).

    4. Bürger, F., Krieg, P., Marks, F., et al. Positional- and stereo-selectivity of fatty acid oxygenation catalysed by mouse (12S)-lipoxygenase isoenzymes. Biochem J. 348(Pt 2), 329-335 (2000).

    5. Hawkins, D.J., and Brash, A.R. Eggs of the sea urchin, Strongylocentrotus purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. The Journal of Biological Chemisty 262(16), 7629-7634 (1987).

    6. 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).

    7. Stern, N., Kisch, E.S., and Knoll, E. Platelet lipoxygenase in spontaneously hypertensive rats. Hypertension 27, 1149-1152 (1996).

    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., 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).

    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).

    Leiria, L.O., Wang, C.-H., Lynes, M.D., et al. 12-Lipoxygenase regulates cold adaptation and glucose metabolism by producing the omega-3 lipid 12-HEPE from brown fat. Cell Metab. 30(4), 768-783.e767 (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).

    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).

    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).