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Butenoyl PAF

Cayman Chemical Item Number 60929

Butenoyl PAF

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Description

Butenoyl and butanoyl PAF are both products of the oxidative decomposition of 2-arachidonoyl phospholipids.1 Oxygenation of C-5 of the 5,6 double bond followed by cleavage of the hydroperoxide results in a PAF-like compound with a 4-carbon residue esterified in the sn-2 position; similar oxidized lipid products also act as ligands for oxidized lipid receptors and peroxisome proliferator-activated receptor.2 Although butenoyl PAF is 10-fold less potent than PAF as a PAF receptor agonist, it is present in amounts 100-fold greater than enzymatically generated PAF. Therefore, oxidation of LDL phospholipids generates physiologically relevant bioactive PAF-like molecules.

1 Marathe, G.K., Davies, S.S., Harrison, K.A., et al. Inflammatory platelet-activating factor-like phospholipids in oxidized low density lipoproteins are fragmented alkyl phosphatidylcholines. J Biol Chem 274 28395-28404 (1999).

2 Davies, S.S., Pontsler, A.V., Marathe, G.K., et al. Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor γ ligands and agonists. J Biol Chem 276 16015-16023 (2001).

Formal Name 1-​O-​hexadecyl-​2-​O-​(2E-​butenoyl)-​sn-​glyceryl-​3-​phosphocholine
Molecular Formula C28H56NO7P
Formula Weight 549.7
Formulation A solution in ethanol
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C(/C=C/C)​O[C@@H]​(COP([O-]​)​(OCC[N+]​(C)​(C)​C)​=O)​COCCCCCCCCCCCCCCCC

Background Reading

Davies, S.S., Pontsler, A.V., Marathe, G.K., et al. Oxidized alkyl phospholipids are specific, high affinity peroxisome proliferator-activated receptor γ ligands and agonists. J Biol Chem 276 16015-16023 (2001).

Kato, Y., Makino, Y., and Osawa, T. Characterization of a specific polyclonal antibody against 13-hydroperoxyoctadecadienoic acid-modified protein: Formation of lipid hydroperoxide-modified apoB-100 in oxidized LDL. J Lipid Res 38 1334-1346 (1997).

Butenoyl PAF is available in the following screening library:

Size Price Quantity Subtotal
1 mg $64.00 $0.00
5 mg $288.00 $0.00
10 mg $512.00 $0.00
50 mg $2,240.00 $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 2012-05-26. 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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