Butenoyl PAF

Cayman Chemical Item Number 60929

(CAS 474944-25-7)

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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
CAS Number 474944-25-7
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
InCHI Code
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​1S/C28H56NO7P/c1-6-8-9-10-11-12-13-14-15-16-17-18-19-20-23-33-25-27(36-28(30)​21-7-2)​26-35-37(31,32)​34-24-22-29(3,4)​5/h7,21,27H,6,8-20,22-26H2,1-5H3/b21-7+/t27-/m1/s1
InCHI Key
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SRZBVCCSIMMDOV-UUUXUCBLSA-N

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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
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Cart Total $0.00

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Pricing updated 2015-03-29. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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Ann Arbor, Michigan 48108 USA

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