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Merck
CN

P6537

β-Acetyl-γ-O-octadecyl-L-α-phosphatidylcholine

≥98%

Synonym(s):

1-O-Octadecyl-2-acetyl-sn-glycero-3-phosphocholine, PAF(C18)

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About This Item

Empirical Formula (Hill Notation):
C28H58NO7P
CAS Number:
79549-26-1
Molecular Weight:
551.74
UNSPSC Code:
12352200
PubChem Substance ID:
24898776
MDL number:
MFCD00063528

Key Documents

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InChI

1S/C28H57NO8P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-28(31)34-24-27(37-26(2)30)25-36-38(32,33)35-23-22-29(3,4)5/h27H,6-25H2,1-5H3,(H,32,33)

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC(C)=O)COCCCCCCCCCCCCCCCCCC)=O

InChI key

WRNJZNCFXCBLTH-UHFFFAOYSA-N

assay

≥98%

solubility

chloroform: 10 mg/mL, aqueous base: decomposes

storage temp.

−20°C

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Biochem/physiol Actions

18-carbon analog of platelet activating factor (PAF); ligand for G protein-coupled PAF receptor. It is less potent than PAF C-16 for inducing platelet aggregation, hypotension, bronchosconstriction and chemotaxis, but more potent than PAF C-16 for inducing human neutrophil lysosomal secretion.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBD4343V
110M1440
051M1566V
090M1644
030M1677

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E J Carolan et al.
Journal of immunology (Baltimore, Md. : 1950), 145(8), 2561-2565 (1990-10-15)
Multiple molecular species of platelet activating factor (PAF) are produced as a result of inflammatory processes. PAF-induced neutrophil migration across endothelium is intrinsic to inflammatory responses. We therefore compared the ability of three naturally occurring PAF species (C16:0, C18:0, and
Kimberly D Dyer et al.
Journal of immunology (Baltimore, Md. : 1950), 184(11), 6327-6334 (2010-04-28)
Platelet-activating factor (PAF [1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine]) is a phospholipid mediator released from activated macrophages, mast cells, and basophils that promotes pathophysiologic inflammation. Eosinophil responses to PAF are complex and incompletely elucidated. We show in this article that PAF and its 2-deacetylated metabolite

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