A dihydroxy fatty acid synthesized by 15-LO from 5(S)-HETE
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5(S),15(S)-DiHETE

Item No. 35280

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,15S-dihydroxy-6E,8Z,10Z,13E-eicosatetraenoic acid
CAS Number
82200-87-1
Molecular Formula
C20H32O4
Formula Weight
336.5
Purity
≥95%
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
243 nm
SMILES
CCCCC[C@H](O)/C=C/C=C\C/C=C\C=C\[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C20H32O4/c1-2-3-9-13-18(21)14-10-7-5-4-6-8-11-15-19(22)16-12-17-20(23)24/h5-8,10-11,14-15,18-19,21-22H,2-4,9,12-13,16-17H2,1H3,(H,23,24)/b7-5-,8-6-,14-10+,15-11+/t18-,19+/m0/s1
InChi Key
UXGXCGPWGSUMNI-BVHTXILBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $107

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    50 µg

    $172

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    100 µg

    $321

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    Product Description

    5(S),15(S)-DiHETE is synthesized by 15-LO from 5(S)-HETE.1 It potentiates the degranulation of human PMNL in response to PAF, but not fMLP, calcium ionophore A23187, or LTB4.2 5(S),15(S)-DiHETE is chemotactic for eosinophils with an ED50 value of 0.3 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Green, F.A. Transformations of 5-HETE by activated keratinocyte 15-lipoxygenase and the activation mechanism. Lipids 25, 618-623 (1990).

    2. O'Flaherty, J.T., and Thomas, M.J. Effect of 15-lipoxygenase-deprived arachidonate metabolites on human neutrophil degranulation. Prostaglandins Leukot. Med. 17, 199-212 (1985).

    3. Morita, E., Schröder, J.M., and Christophers, E. Identification of a novel and highly potent eosinophil chemotactic lipid in human eosinophils treated with arachidonic acid. J. Immunol. 144, 1893-1900 (1990).

    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. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB J. 35(6), e21666 (2021).

    Roberts, L.M., Schwarz, B., Speranza, E., et al. Pulmonary infection induces persistent, pathogen-specific lipidomic changes influencing trained immunity. iScience 24(9), 103025 (2021).

    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).

    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).