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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:
74389-68-7
Poids moléculaire :
523.68 (anhydrous basis)
Beilstein:
3574588
Numéro MDL:
MFCD00150679
Code UNSPSC :
12352211
ID de substance PubChem :
24898570
Nomenclature NACRES :
NA.77
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

200

Essai

≥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[1]
  • to study its protective effects against cisplatin-induced cell death in a human melanoma cell line in vitro[2]
  • to determine its effects on cervical ripening and leukocyte infiltration in rat models[3]

Actions biochimiques/physiologiques

β-Acetyl-γ-O-hexadecyl-L-α-phosphatidylcholine or platelet-activating factor (PAF), is a phospholipid[4], and a pro-inflammatory lipid mediator.[5] 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.[5] 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.[6]

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)

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Certificats d'analyse (COA)

Lot/Batch Number
BCCG8643
BCCG4701
BCCB6898
BCBW2009
BCBV3299

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Platelet-activating factor.
S M Prescott et al.
The Journal of biological chemistry, 265(29), 17381-17384 (1990-10-15)
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
Luis Alexandre Muehlmann et al.
Research in veterinary science, 93(1), 393-397 (2011-08-09)
Phagocytosis exerted by alveolar macrophages and neutrophils is crucial in the clearance of exogenous particles deposited in the airways. Therefore, substances that activate these phagocytes in the airways can exert important effects on the particle clearance rate. PAF, particularly, was
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