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3616-04-4

3616-04-4 Structure

3616-04-4 Structure
IdentificationBack Directory
[Name]

Phosphorylcholine
[CAS]

3616-04-4
[Synonyms]

Phosphorylcholine (Phosphocholine)
[Molecular Formula]

C5H15NO4P+
[MDL Number]

MFCD32689427
[MOL File]

3616-04-4.mol
[Molecular Weight]

184.15
Chemical PropertiesBack Directory
[storage temp. ]

Store at 4°C
[solubility ]

Water: 100 mg/mL (546.03 mM); Ethanol: 4 mg/mL (21.84 mM); DMSO: < 1 mg/mL (insoluble or slightly soluble)
[form ]

Oil
[color ]

Colorless to light yellow
Hazard InformationBack Directory
[Uses]

Phosphatidylcholine is the main phospholipid component in eukaryotic biofilms. Phosphatidylcholine exists in commensal or pathogenic bacteria associated with eukaryotes in prokaryotes. Phosphorylcholine exhibits a surprising range of immunomodulatory properties[1].
[Definition]

ChEBI: Phosphocholine is the phosphate of choline; and the parent compound of the phosphocholine family. It has a role as an epitope, a hapten, a human metabolite, a mouse metabolite and an allergen. It is a conjugate acid of a choline phosphate(1-).
[in vivo]

Phosphorylcholine (200-600 μmol/kg; ip; single dose) activates nicotinic and muscarinic cholinergic neurotransmission, stimulates the activation of α2-adrenergic receptors, and increases plasma glucagon and choline concentrations, thereby stimulating peripheral autonomic nervous system activity[3].
Phosphorylcholine (2 μg; ip; once every two weeks for 4 months) induces the production of anti-PC and anti-oxLDL antibodies, increases mature B cells in the spleen, and reduces atherosclerotic lesions in the aortic root in mouse models[4].

Animal Model:Sprague Dawley rats model[3]
Dosage:200-600 μmol/kg
Administration:ip; single dose
Result:Increased plasma glucagon and choline concentration.
Animal Model:apoE knockout mouse model[4]
Dosage:2 μg
Administration:ip; once every two weeks for 4 months
Result:Induced anti-PC and anti-oxLDL antibodies, reduced atherosclerotic lesions.
[IC 50]

Human Endogenous Metabolite; Microbial Metabolite
[storage]

Store at 4°C
[References]

[1] Harnett W, et al. Phosphorylcholine: friend or foe of the immune system? Immunol Today. 1999 Mar;20(3):125-9. DOI:10.1016/s0167-5699(98)01419-4
[2] Tu S, et al., Enhancement of cellular uptake and antitumor efficiencies of micelles with phosphorylcholine. Macromol Biosci. 2011 Oct 10;11(10):1416-25. DOI:10.1002/mabi.201100111
[3] Cansev M, et al., Choline, CDP-choline or phosphocholine increases plasma glucagon in rats: involvement of the peripheral autonomic nervous system. Eur J Pharmacol. 2008 Jul 28;589(1-3):315-22. DOI:10.1016/j.ejphar.2008.05.017
[4] Caligiuri G, et al., Phosphorylcholine-targeting immunization reduces atherosclerosis. J Am Coll Cardiol. 2007 Aug 7;50(6):540-6. DOI:10.1016/j.jacc.2006.11.054
Spectrum DetailBack Directory
[Spectrum Detail]

Phosphorylcholine(3616-04-4)1HNMR
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