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L5016

Sigma-Aldrich

1-O-Palmityl-sn-glycero-3-phosphocholine

≥99%, synthetic

Synonym(s):

1-Hexadecyl-sn-glycero-3-phosphocholine, 3-sn-Lysophosphatidylcholine, 1-hexadecyl, Lyso-PAF-C16, Lyso-platelet activating factor

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About This Item

Empirical Formula (Hill Notation):
C24H52NO6P
CAS Number:
52691-62-0
Molecular Weight:
481.65
MDL number:
MFCD00042932
UNSPSC Code:
12352211
PubChem Substance ID:
24896384
NACRES:
NA.77

biological source

synthetic

Quality Level

200

Assay

≥99%

storage temp.

−20°C

SMILES string

O[C@](COP([O-])(OCC[N+](C)(C)C)=O)([H])COCCCCCCCCCCCCCCCC

InChI

1S/C24H52NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h24,26H,5-23H2,1-4H3/t24-/m1/s1

InChI key

VLBPIWYTPAXCFJ-XMMPIXPASA-N

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Biochem/physiol Actions

Intermediate in the synthesis of platelet activating factor (PAF). Inactive form that can be used as a control in studies of PAF activity.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Sturk, A., et al.
Journal of Lipid Research, 23, 219-219 (1989)
J K Mickelson et al.
Journal of molecular and cellular cardiology, 20(6), 547-561 (1988-06-01)
Myocardial injury was produced in separated groups of anesthetized rabbits by occlusion of the left circumflex coronary artery for 1 h followed by reperfusion for 2, 4, or 6 h after release of the occlusive ligature. The ischemically-injured and reperfused
M Robinson et al.
Biochimica et biophysica acta, 837(1), 52-56 (1985-10-23)
1-Alkyl-2-acetyl-sn-glycero-3-phosphocholine (alkylacetyl-GPC; platelet-activating factor; PAF) is actively taken up and metabolized by rat alveolar macrophages maintained in culture. The major metabolic products are lyso-PAF (alkyllyso-GPC) and alkylacyl-GPC. Lyso-PAF accumulates primarily in the media, whereas alkylacyl-GPC is predominantly associated with cellular
C G Qian et al.
Journal of lipid mediators, 1(2), 113-123 (1989-03-01)
Suspensions of neonatal rat myocytes were used to investigate the metabolism of [3H]PAF (1-alkyl-2-acetyl-(sn-glycero-3-phosphocholine) (GPC] and [3H]alkyllyso-GPC. [3H]Alkylacyl-GPC consisting of molecular species with four or more double bonds (87%) was the major metabolite formed when either [3H]PAF (4 x 10(-6)
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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