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Key Documents

P4904

Sigma-Aldrich

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

≥98%

Synonyme(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

Formule empirique (notation de Hill):
C26H54NO7P · xH2O
Numéro CAS:
Poids moléculaire :
523.68 (anhydrous basis)
Numéro Beilstein :
3574588
Numéro MDL:
Code UNSPSC :
12352211
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Niveau de qualité

Pureté

≥98%

Forme

powder

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
Platelet-activating factor.
S M Prescott et al.
The Journal of biological chemistry, 265(29), 17381-17384 (1990-10-15)
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
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

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