A product of 15-LO metabolism of arachidonic acid
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15(S)-HpETE

Item No. 44720

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15S-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
CAS Number
70981-96-3
Molecular Formula
C20H32O4
Formula Weight
336.5
Purity
≥95%
Formulation
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@H](OO)/C=C/C=C\C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,17-14+
InChi Key
BFWYTORDSFIVKP-USWFWKISSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $50

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    50 µg

    $75

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    100 µg

    $139

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    250 µg

    $323

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    Product Description

    15(S)-HpETE is a monohydroperoxy polyunsaturated fatty acid (PUFA) produced by the action of 15-lipoxygenase (15-LO) on arachidonic acid. It is either metabolized to 14,15-leukotriene A41 or reduced to 15(S)-HETE by peroxidases.2,1 15(S)-HpETE mediates a number of biological functions including the induction of c-fos and c-jun, and activation of AP-1.3 15(S)-HpETE inhibits prostacyclin synthesis in porcine aortic microsomes and bovine endothelial cells, and can cause the suicide inactivation of porcine 12-LO.2,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bryant, R.W., Schewe, T., Rapoport, S.M., et al. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14,15-leukotriene A4. The Journal of Biological Chemisty 260(6), 3548-3555 (1985).

    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. 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).

    4. Moncada, S., Gryglewski, R.J., Bunting, S., et al. A lipid peroxide inhibits the enzyme in blood vessel microsomes that generates from prostaglandin endoperoxides the substance (prostaglandin X) which prevents platelet aggregation. Prostaglandins 12, 715-737 (1976).

    5. Mayer, B., Moser, R., Gleispach, H., et al. Possible inhibitory function of endogenous 15-hydroperoxyeicosatetraenoic acid on prostacyclin formation in bovine aortic endothelial cells. Biochim. Biophys. Acta 875, 641-653 (1986).

    Product Citations

    Thollon, C., Iliou, J.P., Cambarrat, C., et al. Nature of the cardiomyocyte injury induced by lipid hydroperoxides. Cardiovasc. Res. 30, 648-655 (1995).