A vasodilator of renal arterioles
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(±)18-HETE

Item No. 10010638

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)18-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid
CAS Number
133268-58-3
Synonyms
  • (±)18-Hydroxyeicosatetraenoic Acid
Molecular Formula
C20H32O3
Formula Weight
320.5
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
SMILES
CCC(O)CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChi Code
InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-
InChi Key
PPCHNRUZQWLEMF-XBOCNYGYSA-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

    $165

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    50 µg

    $314

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    100 µg

    $594

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    Product Description

    (±)18-HETE is the racemic version of a cytochrome P450 (CYP450) metabolite of arachidonic acid. When formed by the CYP2E1 isoform, 18-HETE is comprised 100% of the (R) isomer.1 18(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, whereas 18(S)-HETE does not affect perfusion pressure.2 18-HETE has negligible effects on ATPase activity.2 18(R)-HETE at 1 µM completely blocks 20-HETE-induced vasoconstriction of renal arterioles.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Laethem, R.M., Balazy, M., Falck, J.R., et al. Formation of 19(S)-, 19(R)-, and 18(R)-hydroxyeicosatetraenoic acids by alcohol-inducible cytochrome P450 2E1. The Journal of Biological Chemisty 268(17), 12912-12918 (1993).

    2. Carroll, M.A., Balazy, M., Margiotta, P., et al. Cytochrome P-450-dependent HETEs: Profile of biological activity and stimulation by vasoactive peptides. Am. J. Physiol. 271(4 Pt 2), R863-R869 (1996).

    3. Zhang, F., Deng, H., Kemp, R., et al. Decreased levels of cytochrome P450 2E1-derived eicosanoids sensitize renal arteries to constrictor agonists in spontaneously hypertensive rats. Hypertension 45(1), 103-108 (2005).

    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).

    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).

    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).