A 12-LO metabolite of arachidonic acid
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12(S)-HpETE

Item No. 44570

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12S-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
CAS Number
71774-10-2
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)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
237 nm
SMILES
CCCCC/C=C\C[C@H](OO)/C=C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+
InChi Key
ZIOZYRSDNLNNNJ-VXBMJZGYSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $145

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    50 µg

    $271

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    100 µg

    $513

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    250 µg

    $1,133

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    Product Description

    12(S)-HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of platelet or leukocyte 12-lipoxygenase (12-LO) on arachidonic acid.1,2 It activates human blood leukocyte 5-LO, resulting in the synthesis of 5(S)-HETE, leukotriene B4 (LTB4), and 5(S),12(S)-DiHETE.1 Rat lung metabolizes 12(S)-HpETE to 8,11,12- and 10,11,12-trihydroxyeicostrienoic acids.3 12(S)-HpETE is the mediator of many biological functions, including induction of c-fos and c-jun, activation of AP-1, and endothelium-dependent vasoconstriction.4,5 It mediates the inhibitory synaptic response to FMRF-amide in Aplysia sensory neurons6 and inhibits Ca2+/calmodulin-dependent protein kinase II from rat brain cortex.7,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Maclouf, J., Fruteau De Laclos, B., and Borgeat, P. Stimulation of leukotriene biosynthesis in human blood leukocytes by platelet-derived 12-hydroperoxy-eicosatetraenoic acid. Proc. Natl. Acad. Sci. USA 79, 6042-6046 (1982).

    2. Kishimoto, K., Nakamura, M., Suzuki, H., et al. Suicide inactivation of porcine leukocyte 12-lipoxygenase associated with its incorporation of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid derivative. Biochim. Biophys. Acta 1300, 56-62 (1996).

    3. Pace-Asciak, C.R., Granström, E., and Samuelsson, B. Arachidonic acid epoxides. Isolation and structure of two hydroxy epoxide intermediates in the formation of 8,11,12- and 10,11,12-trihydroxyeicosatrienoic acids. The Journal of Biological Chemisty 258, 6835-6840 (1983).

    4. Nishiyama, M., Okamoto, H., Watanabe, T., et al. Endothelium is required for 12-hydroperoxyeicosatetraenoic acid-induced vasoconstriction. Eur. J. Pharmacol. 341, 57-63 (1998).

    5. Rao, G.N., Glasgow, W.C., Eling, T.E., et al. Role of hydroperoxyeicosatetraenoic acids in oxidative stress-induced activating protein 1 (AP-1) activity. The Journal of Biological Chemisty 271, 27760-27764 (1996).

    6. Piomelli, D., Volterra, A., Dale, N., et al. Lipoxygenase metabolites of arachidonic acid as second messengers for presynaptic inhibition of Aplysia sensory cells. Nature 328, 38-43 (1987).

    7. Piomelli, D., Wang, J.K.T., Sihra, T.S., et al. Inhibition of Ca2+/calmodulin-dependent protein kinase II by arachidonic acid and its metabolites. Proc. Natl. Acad. Sci. USA 86, 8550-8554 (1989).