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P4904

Sigma-Aldrich

β-Acetyl-γ-O-hexadecyl-L-α-phosphatidylcholine hydrate

≥98%

Synonym(s):

1-Hexadecyl-2-acetyl-sn-glycero-3-phosphocholine, 1-O-Palmityl-2-acetyl-sn-glycero-3-phosphocholine monohydrate, 2-Acetyl-1-hexadecyl-sn-glycero-3-phosphocholine, 3-sn-Phosphatidylcholine, 1-hexadecyl-2-acetyl, PAF(C16), Platelet activating factor

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About This Item

Empirical Formula (Hill Notation):
C26H54NO7P · xH2O
CAS Number:
74389-68-7
Molecular Weight:
523.68 (anhydrous basis)
Beilstein/REAXYS Number:
3574588
MDL number:
MFCD00150679
UNSPSC Code:
12352211
PubChem Substance ID:
24898570
NACRES:
NA.77

assay

≥98%

form

powder

storage temp.

−20°C

SMILES string

O.CCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(C)=O

InChI

1S/C26H54NO7P.H2O/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21-31-23-26(34-25(2)28)24-33-35(29,30)32-22-20-27(3,4)5;/h26H,6-24H2,1-5H3;1H2/t26-;/m1./s1

InChI key

HFMSDOHEENWULV-UFTMZEDQSA-N

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Application

β-Acetyl-γ-O-hexadecyl-L-α-phosphatidylcholine has been used:
  • to study its effects on phagocytic activity and production of superoxide anion in equine alveolar macrophage and blood neutrophils
  • to study its protective effects against cisplatin-induced cell death in a human melanoma cell line in vitro
  • to determine its effects on cervical ripening and leukocyte infiltration in rat models

Biochem/physiol Actions

β-Acetyl-γ-O-hexadecyl-L-α-phosphatidylcholine or platelet-activating factor (PAF), is a phospholipid, and a pro-inflammatory lipid mediator. It acts as a ligand for G protein-coupled platelet-activating factor (PAF) receptors and participates in several biological processes such as airway constriction, hypotension, platelet activation, and increased vascular permeability. PAF is released by various cells such as platelets, neutrophils, endothelial cells, and monocytes/macrophages. The levels of PAF are low in the blood due to its rapid metabolism by PAF acetylhydrolase and low production.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T Hiran et al.
Prostaglandins & other lipid mediators, 66(4), 305-315 (2002-01-12)
Platelet-activating factor (PAF) is an early product of the inflammatory environment, influencing development and resolution of inflammation. Its production is greater in neutrophils and macrophages, which predominantly synthesize 1-alkyl sn-2 acetyl glycerophosphocholine (GPC) than in nongranulocytes (B cells and endothelial
R N Pinckard et al.
Journal of leukocyte biology, 59(2), 219-228 (1996-02-01)
Alkyl-PAF induced two components of polymorphonuclear leukocyte (PMN) priming for enhanced fMLP- and rC5a-induced superoxide anion (O2-) production. Component A priming had a shallow, linear alkyl-PAF concentration-response slope (10 pM-1 nM), and component B priming had a significantly steeper concentration-response
Damien Garrido et al.
Frontiers in veterinary science, 4, 226-226 (2018-01-13)
Lipid mediators are known to play important roles in the onset and resolution phases of the inflammatory response in mammals. The phospholipid platelet-activating factor (PAF) is a pro-inflammatory lipid mediator which participates in vascular- and innate immunity-associated processes by increasing
S Grassi et al.
Neuroscience, 94(2), 549-559 (1999-12-01)
In rat brainstem slices, we investigated the interaction between platelet-activating factor and group I metabotropic glutamate receptors in mediating long-term potentiation within the medial vestibular nuclei. We analysed the N1 field potential wave evoked in the ventral portion of the
Katarina Mariann Jørgensen et al.
Archives of dermatological research, 302(3), 221-227 (2009-12-31)
Platelet activating factor (PAF, 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine) is known to be present in excess in psoriatic skin, but its exact role is uncertain. In the present study we demonstrate for the first time the role of group VI PLA(2) in PAF-induced arachidonic
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