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Cat. Number

652404778013520

Chemical Name

15(S)-HpETE Lipid Maps MS Standard

References

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%
Stability	1 year
Storage	-80°C
Shipping	Dry ice in continental US; may vary elsewhere
SMILES	CCCCCC(OO)C=CC=CC/C=CC/C=CCCCC(=O)O

Background Reading

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).

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).

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).

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).

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).

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Size	Global Purchasing
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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).

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