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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

15(S)-HpETE

Cayman Chemical Item Number 44720

(CAS 70981-96-3)

15(S)-HpETE (CAS 70981-96-3)

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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

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. J Biol Chem 260 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. J Biol Chem 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).

Formal Name 15S-​hydroperoxy-​5Z,​8Z,​11Z,​13E-​eicosatetraenoic acid
CAS Number 70981-96-3
Molecular Formula C20H32O4
Formula Weight 336.5
Formulation A solution in ethanol
Purity ≥98%
λmax 236 nm
ε 27
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC[C@H]​(OO)​/C=C/C=C\C/C=C\C/C=C\CCCC(O)​=O

Background Reading

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. J Biol Chem 260 3548-3555 (1985).

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).

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. J Biol Chem 271 27760-27764 (1996).

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).

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).

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15(S)-HpETE is available in the following screening library:

Size Price Quantity Subtotal
25 µg $29.00 $0.00
50 µg $55.00 $0.00
100 µg $104.00 $0.00
500 µg $512.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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