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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)
Numéro Beilstein :
3574588
Numéro MDL:
MFCD00150679
Code UNSPSC :
12352211
ID de substance PubChem :
24898570
Nomenclature NACRES :
NA.77

Niveau de qualité

200

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

Adriana Vieira-de-Abreu et al.
International immunopharmacology, 5(13-14), 1966-1974 (2005-11-09)
New therapeutic approaches for the treatment of allergic diseases can be aided by the development of agents capable of regulating eosinophilic leukocytes. Here, we evaluated the anti-allergic properties of a crude extract of the Brazilian bromeliaceae Nidularium procerum, focusing on
Naoki Okumura et al.
Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics, 22(5), 347-352 (2006-11-02)
The aim of this study was to examine the levels of platelet-activating factor (PAF) and lyso-PAF in tears from experimental animals developing allergic conjunctivitis (AC). AC was induced in guinea pigs by application of ovalbumin in eye drops. Tear samples
G Karlström et al.
Acta physiologica Scandinavica, 137(4), 521-533 (1989-12-01)
The renal medulla harbours powerful humoral antihypertensive mechanisms, as earlier explored in unclipping experiments on renal hypertensive rats or in normotensive isolated kidneys cross-circulated at increased perfusion pressures from 'donor rats', in which renal function also seemed to be affected.
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
E E Muirhead et al.
The American journal of the medical sciences, 298(2), 93-103 (1989-08-01)
Medullipin I causes a delayed onset depressor response when injected intravenously into rats. The glyceryl compounds selachyl alcohol (SA) and monoolein (MO) cause similar vasodepression. The neutral lipid 1-O-hexadecyl-2-acetyl-sn-glycerol (HAG) was suggested by Blank et al to be medullipin I
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