A natural bioactive lipid
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5(S),12(S)-DiHETE

Item No. 35260

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid
CAS Number
79056-01-2
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
268 nm
SMILES
CCCCC/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7-,9-6-,14-10+,15-11+/t18-,19+/m0/s1
InChi Key
VNYSSYRCGWBHLG-RYYHSVJXSA-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

    $179

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    50 µg

    $337

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    100 µg

    $636

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    Product Description

    5(S),12(S)-DiHETE is a natural bioactive lipid derived from arachidonic acid (AA; Item No. 10006607). It is synthesized by glycogen-induced rabbit peritoneal polymorphonuclear leukocytes (PMNLs) incubated with AA.1 5(S),12(S)-DiHETE can be produced by successive oxygenation of AA by 5-lipoxygenase (5-LO) in platelets and 12-LO in leukocytes.2 It can also be synthesized from 12(S)-HETE by 5-LO, in the presence of 5-LO activating protein (FLAP), activated with calcium ionophore.3 5(S),12(S)-DiHETE is an epimer of leukotriene B4 (Item No. 20110) that is weakly chemotactic for PMNL.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Borgeat, P., and Samuelsson, B. Metabolism of arachidonic acid in polymorphonuclear leukocytes. The Journal of Biological Chemisty 254(16), 7865-7869 (1979).

    2. Borgeat, P., Fruteau De Laclos, B., Picard, S., et al. Studies on the mechanism of formation of the 5S,12S-dihydroxy-6,8,10,14 (E,Z,E,Z)-eicosatetraenoic acid in leukocytes. Prostaglandins 23, 713-724 (1982).

    3. Mancini, J.A., Waterman, H., and Riendeau, D. Cellular oxygenation of 12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid by 5-lipoxygenase is stimulated by 5-lipoxygenase-activating protein. The Journal of Biological Chemisty 273(49), 32842-32847 (1998).

    4. Lee, T.H., Mencia-Huerta, J.M., Shih, C., et al. Characterization and biologic properties of 5,12-dihydroxy derivatives of eicosapentaenoic acid, including leukotriene B5 and the double lipoxygenase product. The Journal of Biological Chemisty 259(4), 2383-2389 (1984).

    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).

    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).