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5-OxoETE

Cayman Chemical Item Number 34250

5-KETE (CAS 106154-18-1)

5-OxoETE (CAS 106154-18-1)

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Description

5-OxoETE is a polyunsaturated keto acid formed by the oxidation of 5-HETE in human neutrophils by a specific dehydrogenase.1 It stimulates cytosolic calcium levels in neutrophils with an EC50 value of 2 nM.2 5-OxoETE selectively stimulates the migration and degranulation of eosinophils and activates the MAPK pathway in stimulated neutrophils via a specific G protein-coupled receptor.3,4,5,6

1 Powell, W.S., Gravelle, F., and Gravel, S. Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes. J Biol Chem 267 19233-19241 (1992).

2 Powell, W.S., Zhang, Y., and Gravel, S. Effects of phorbol myristate acetate on the synthesis of 5-oxo-6,8,11,14-eicosatetraenoic acid by human polymorphonuclear leukocytes. Biochemistry 33 3927-3933 (1994).

3 O'Flaherty, J.T., Kuroki, M., Nixon, A.B., et al. 5-Oxo-eicosanoids and hematopoietic cytokines cooperate in stimulating neutrophil function and the mitogen-activated protein kinase pathway. J Biol Chem 271 17821-17828 (1996).

4 O'Flaherty, J.T., Kuroki, M., Nixon, A.B., et al. 5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes. J Immunol 157 336-342 (1996).

5 Hosoi, T., Koguchi, Y., Sugikawa, E., et al. Identification of a novel human eicosanoid receptor coupled to Gi/o. J Biol Chem 277 (35) 31459-31465 (2002).

6 Jones, C.E., Holden, S., Tenaillon, L., et al. Expression and characterization of a 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils. Mol Pharmacol 63(3) 471-477 (2003).

Synonyms
  • 5-KETE
Formal Name 5-​oxo-​6E,​8Z,​11Z,​14Z-​eicosatetraenoic acid
CAS Number 106154-18-1
Molecular Formula C20H30O3
Formula Weight 318.5
Formulation A solution in ethanol
Purity ≥95%
λmax 279 nm
ε 22
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C=C/C(=O)​CCCC(=O)​O

Background Reading

Powell, W.S., Zhang, Y., and Gravel, S. Effects of phorbol myristate acetate on the synthesis of 5-oxo-6,8,11,14-eicosatetraenoic acid by human polymorphonuclear leukocytes. Biochemistry 33 3927-3933 (1994).

O'Flaherty, J.T., Kuroki, M., Nixon, A.B., et al. 5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes. J Immunol 157 336-342 (1996).

Jones, C.E., Holden, S., Tenaillon, L., et al. Expression and characterization of a 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils. Mol Pharmacol 63(3) 471-477 (2003).

O'Flaherty, J.T., Kuroki, M., Nixon, A.B., et al. 5-Oxo-eicosanoids and hematopoietic cytokines cooperate in stimulating neutrophil function and the mitogen-activated protein kinase pathway. J Biol Chem 271 17821-17828 (1996).

Powell, W.S., Gravelle, F., and Gravel, S. Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes. J Biol Chem 267 19233-19241 (1992).

Hosoi, T., Koguchi, Y., Sugikawa, E., et al. Identification of a novel human eicosanoid receptor coupled to Gi/o. J Biol Chem 277 (35) 31459-31465 (2002).

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Size Price Quantity Subtotal
25 µg $69.00 $0.00
50 µg $131.00 $0.00
100 µg $248.00 $0.00
250 µg $552.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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