C16-PAF (PAF (C16)) is a phospholipid mediator, platelet activating factor, and ligand of the PAF G protein-coupled receptor (PAFR). C16-PAF displays anti-apoptotic effects and inhibits caspase-dependent death by activating PAFR. C16-PAF is a potent MAPK and MEK/ERK activator. C16-PAF induces increased vascular permeability.

Physicochemical Properties

Molecular Formula	C26H54NO7P
Molecular Weight	523.68
Exact Mass	523.363
CAS #	74389-68-7
PubChem CID	108156
Appearance	White to off-white solid powder
LogP	3.94
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	26
Heavy Atom Count	35
Complexity	546
Defined Atom Stereocenter Count	1
SMILES	CCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)C
InChi Key	HVAUUPRFYPCOCA-AREMUKBSSA-N
InChi Code	InChI=1S/C26H54NO7P/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/t26-/m1/s1
Chemical Name	[(2R)-2-acetyloxy-3-hexadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Human Endogenous Metabolite ERK MEK
ln Vitro	C16-PAF (PAF (C16); 0.5-1.5 μM; for 24 hours) triggers considerable concentration-dependent neuronal death in PAFR?/? but not PAFR+/+ cultures. C16-PAF (1 μM) triggers neuronal death in PAFR? /? cells infected with EGFP alone[1]. ?C16-PAF (1 μM; for 24 hours) activates caspase 7 but not caspase 3 in PAFR?/? neurons[1]. ?C16-PAF is generated by two separate processes ; the remodeling pathway and the de novo synthesis pathway. C16-PAF functions by interacting to a unique G-protein-coupled seven transmembrane receptor[2][3]. ?C16-PAF (1-25 μg/ml; 6, 12 , 24 h) inhibits M. smegmatis and M. bovis BCG growth in a time-dependent manner[3].
Cell Assay	Cell Viability Assay[1] Cell Types: Cerebellar granule neurons (CGNs) from PAFR−/− and PAFR+/+ mice Tested Concentrations: 0.5-1.5 μM Incubation Duration: 24 hrs (hours) Experimental Results: Elicited significant concentration-dependent neuronal loss in PAFR−/− but not PAFR+/+ cultures in serum-free media. Western Blot Analysis[1] Cell Types: CGNs Tested Concentrations: 1 μM Incubation Duration: 24 hrs (hours) Experimental Results: Activated caspase 7 but not caspase 3 in PAFR−/− neurons.
References	[1]. Heterogeneity in the sn-1 carbon chain of platelet-activating factor glycerophospholipids determines pro- or anti-apoptotic signaling in primary neurons. J Lipid Res. 2008 Oct;49(10):2250-8. [2]. Transfected platelet-activating factor receptor activates mitogen-activated protein (MAP) kinase and MAP kinase kinase in Chinese hamster ovary cells. J Biol Chem. 1994 Jan 21;269(3):2307-15. [3]. Direct Growth Inhibitory Effect of Platelet Activating Factor C-16 and Its Structural Analogs on Mycobacteria. Front Microbiol. 2018 Sep 11;9:1903. [4]. IGHG1 Regulates Prostate Cancer Growth via the MEK/ERK/c-Myc Pathway. Biomed Res Int. 2019 Jul 4;2019:7201562. [5]. RAP1-mediated MEK/ERK pathway defects in Kabuki syndrome. J Clin Invest. 2015 Sep;125(9):3585-99.
Additional Infomation	2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine is a 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis. It has a role as a beta-adrenergic antagonist, an antihypertensive agent, a bronchoconstrictor agent, a hematologic agent and a vasodilator agent. Platelet Activating Factor is a phosphatidylcholine derivative that modulates inflammation, vascular permeability, allergic responses and the functions of leukocytes and platelets. A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.

Solubility Data

Solubility (In Vitro)

DMSO: 50 mg/mL (95.48 mM) H2O: 33.33 mg/mL (63.65 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (4.77 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.77 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.9096 mL	9.5478 mL	19.0956 mL
	5 mM	0.3819 mL	1.9096 mL	3.8191 mL
	10 mM	0.1910 mL	0.9548 mL	1.9096 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.