A 5-LO metabolite of arachidonic acid
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Contained In
342305(S)-HETE
Labeled Version(s)
3342305(S)-HETE-d8
Technical Support & Resources

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5(S)-HETE

Item No. 34230

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid
CAS Number
70608-72-9
Synonyms
  • 5(S)-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\C/C=C\C=C/[C@@H](O)CCCC(=O)O
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
InChi Key
KGIJOOYOSFUGPC-JGKLHWIESA-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

    $125

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    50 µg

    $223

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    100 µg

    $393

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    250 µg

    $922

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    Product Description

    5(S)-HETE is produced by the action of 5-LO on arachidonic acid to give 5(S)-HpETE, followed by reduction of the hydroperoxide. 5(S)-HETE has proliferative and chemotactic effects on granulocytes.1 When further metabolized to 5-oxoETE, it is a more potent eosinophil chemoattractant than leukotriene B4.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dodge, W., and Thomas, M. The effect of 5-hydroxyeicosatetraenoic acid on the proliferation of granulocyte progenitors and embryonic fibroblasts of the chick. Biochem. Biophys. Res. Commun. 131(2), 731-735 (1985).

    2. Schwenk, U., and Schröder, J.M. 5-Oxo-eicosanoids are potent eosinophil chemotactic factors. Functional characterization and structural requirements. The Journal of Biological Chemisty 270(25), 15029-15036 (1994).

    3. Powell, W.S., Gravelle, F., and Gravel, S. Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes. The Journal of Biological Chemisty 267(27), 19233-19241 (1992).

    Product Citations

    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).

    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).

    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).

    Chavis, C., Fraissinet, L., Chanez, P., et al. A method for the measurement of plasma hydroxyeicosatetraenoic acid levels. Anal. Biochem. 271(1), 105-108 (1999).

    Rao, C.V., Desai, D., Rivenson, A., et al. Chemoprevention of colon carcinogenesis by phenylethyl-3-methylcaffeate. Cancer Res. 55(11), 2310-2315 (1995).