A cytochrome P450 (CYP450) metabolite of arachidonic acid
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Active Metabolite(s)
1495020-hydroxy Prostaglandin E2
Labeled Version(s)
39003020-HETE-d6
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20-HETE

Item No. 90030

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
CAS Number
79551-86-3
Synonyms
  • 20-hydroxy Arachidonic Acid
  • 20-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
SMILES
OCCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChi Code
InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-
InChi Key
NNDIXBJHNLFJJP-DTLRTWKJSA-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

    $196

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    50 µg

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    100 µg

    $706

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    500 µg

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    Product Description

    20-HETE is a cytochrome P450 (CYP450) metabolite postulated to play an autacoid role in the renal and cerebral vasculature.1 In rat cerebral microvessels, 20-HETE is a vasoconstrictor that mediates pressure-induced autoregulatory vasoconstriction.2 20-HETE is excreted mainly as the glucuronide conjugate. The concentration of free 20-HETE (20-40 pg/ml in human urine) is about 10-fold lower than the corresponding concentration of the 20-glucuronide.3 20-HETE can be further metabolized by cyclooxygenase to 20-hydroxy PGG2 and 20-hydroxy PGH2.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McGiff, J.C., and Quilley, J. 20-HETE and the kidney: Resolution of old problems and new beginnings. Am. J. Physiol. 277(3), R607-R623 (1999).

    2. Gebremedhin, D., Lange, A.R., Lowry, T.F., et al. Production of 20-HETE and its role in autoregulation of cerebral blood flow. Circ. Res. 87(1), 60-65 (2000).

    3. Prakash, C., Zhang, J.Y., Falck, J.R., et al. 20-Hydroxyeicosatetraenoic acid is excreted as a glucuronide conjugate in human urine. Biochem. Biophys. Res. Commun. 185(2), 728-733 (1992).

    4. Schwartzman, M.L., Falck, J.R., Yadagiri, P., et al. Metabolism of 20-hydroxyeicosatetraenoic acid by cyclooxygenase. Formation and identification of novel endothelium-dependent vasoconstrictor metabolites. The Journal of Biological Chemisty 264(20), 11658-11662 (1989).

    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).

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    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).

    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).