A dihydroxy hydrolysis product of LTA4
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5(S),6(R)-DiHETE

Item No. 35200

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,6R-dihydroxy-7E,9E,11Z,14Z-eicosatetraenoic acid
CAS Number
82948-88-7
Molecular Formula
C20H32O4
Formula Weight
336.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
273 nm
SMILES
CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19(22)16-14-17-20(23)24/h6-7,9-13,15,18-19,21-22H,2-5,8,14,16-17H2,1H3,(H,23,24)/b7-6-,10-9-,12-11+,15-13+/t18-,19+/m1/s1
InChi Key
UVZBUUTTYHTDRR-NSEFZGNTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $118

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    50 µg

    $219

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    100 µg

    $416

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    Product Description

    5(S),6(R)-DiHETE is a dihydroxy polyunsaturated fatty acid and a nonenzymatic hydrolysis product of leukotriene A4 (LTA4). Mouse liver cytosolic epoxide hydrolase catalyzes the conversion of LTA4 to 5(S),6(R)-DiHETE.1 It is a weak LTD4 receptor agonist in guinea pig lung membranes.2 It induces guinea pig ileum contraction with an ED50 value of 1.3 µM.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Haeggström, J., Wetterholm, A., Hamberg, M., et al. Enzymatic formation of 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid: Kinetics of the reaction and stereochemistry of the product. Biochim. Biophys. Acta 958(3), 469-476 (1988).

    2. Muller, A., Rechencq, E., Kugel, C., et al. Comparative biological activities of the four synthetic (5,6)-diHETE isomers. Prostaglandins 38(6), 635-644 (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).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Fulton, D., Falck, J.R., McGiff, J.C., et al. A method for the determination of 5,6-EET using the lactone as an intermediate in the formation of the diol. J. Lipid Res. 39(8), 1713-1721 (1998).