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Phosphorylcholine

Cat No.:V40624 Purity: ≥98%
Phosphorylcholine is the major phospholipid component of eukaryotic membranes and is present in prokaryotes in those commensal or pathogenic bacteria associated with eukaryotes.
Phosphorylcholine
Phosphorylcholine Chemical Structure CAS No.: 3616-04-4
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
500mg
Other Sizes

Other Forms of Phosphorylcholine:

  • Phosphorylcholine
  • Calcium phosphorylcholine chloride, 98%
  • Phosphorylcholine chloride calcium salt tetrahydrate (phosphorylcholine chloride calcium salt tetrahydrate)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Phosphorylcholine is the major phospholipid component of eukaryotic membranes and is present in prokaryotes in those commensal or pathogenic bacteria associated with eukaryotes. Phosphorylcholine has Immune-modulatory properties.
Phosphorylcholine (CAS#: 3616-04-4) is a phospholipid widely present in biological systems, including eukaryotic biofilms and symbiotic or pathogenic bacteria associated with eukaryotes. It is the conjugate acid of phosphocholine. Phosphorylcholine has immunomodulatory properties and can be used to study atherosclerosis. It is recognized as an immunologically active epitope present on pathogens such as Streptococcus pneumoniae and certain helminths, where it modulates host-pathogen interactions and immune evasion.
Biological Activity I Assay Protocols (From Reference)
Targets
Phosphorylcholine targets multiple pathways and receptors. It stimulates the activation of α2-adrenergic receptors and increases plasma glucagon and choline concentrations, thereby stimulating peripheral autonomic nervous system activity. As an immunomodulatory epitope, it interacts with the immune system to modulate host-pathogen interactions. Phosphorylcholine is also an endogenous metabolite and a component of drug delivery micelles that improves cellular internalization efficiency.
ln Vitro
In vitro, phosphorylcholine is a component of drug delivery micelles that improves the efficiency of cellular internalization and increases the cytotoxicity of cytotoxins carried in micelles in HeLa cells. It stimulates the activation of α2-adrenergic receptors. Phosphorylcholine has immunomodulatory properties. It is used as a research tool for studying atherosclerosis and immune modulation. The compound's effects are typically evaluated in cell culture models of inflammation and immune response.
ln Vivo
In vivo, phosphorylcholine has been studied for its immunomodulatory properties. Calcium and magnesium phosphocholine salts can be used to treat hepatobiliary dysfunction. As an immunologically active epitope, phosphorylcholine modulates host-pathogen interactions and immune evasion. It has been reported in fruit flies, peppers, and other organisms. The compound's role in atherosclerosis and immune modulation is of research interest. However, specific in vivo efficacy data are not extensively detailed in the available literature.
Enzyme Assay
Cell-free assays for phosphorylcholine involve studying its biochemical properties and interactions. As a phospholipid, its chemical identity and purity are confirmed by HPLC and NMR analysis. Its ability to activate α2-adrenergic receptors can be assessed using receptor binding assays. The compound's immunomodulatory properties can be studied using cell-free immune assays. Its role as a component of drug delivery micelles can be evaluated using physicochemical characterization methods.
Cell Assay
In vitro cellular assays for phosphorylcholine typically involve treating cells with phosphorylcholine-containing micelles or formulations. HeLa cells are used to assess cellular internalization efficiency and cytotoxicity of drug-loaded micelles. Immune cells are used to study immunomodulatory effects. α2-adrenergic receptor activation is assessed using signaling assays. The compound is typically dissolved in appropriate buffers and diluted in cell culture medium. Cell viability and functional assays are performed to evaluate its effects.
Animal Protocol
In vivo animal studies for phosphorylcholine are conducted in models of atherosclerosis, inflammation, and hepatobiliary dysfunction. The compound is administered via various routes including oral or intravenous administration. Disease progression is monitored using appropriate endpoints. Inflammatory markers and immune responses are assessed. However, specific dosing regimens and experimental protocols are not extensively documented in the available literature. Standard protocols for evaluating immunomodulatory agents would typically be employed.
ADME/Pharmacokinetics
Pharmacokinetic properties of phosphorylcholine include a molecular weight of 183.14 g/mol and molecular formula C5H14NO4P. As a phospholipid, it has specific solubility and distribution properties. The compound is typically stored at appropriate conditions as a research reagent. Detailed ADME parameters such as half-life, Cmax, and AUC are not extensively reported in the available literature. The compound is used as a reference standard for analytical applications.
Toxicity/Toxicokinetics
The toxicity profile of phosphorylcholine has been characterized for research use. As a naturally occurring phospholipid and endogenous metabolite, it is generally considered safe at research concentrations. Calcium and magnesium phosphocholine salts have been used to treat hepatobiliary dysfunction. Standard safety precautions should be followed when handling this compound. It is intended for research and analytical use only, not for therapeutic applications.
References

[1]. Phosphorylcholine: friend or foe of the immune system? Immunol Today. 1999 Mar;20(3):125-9.

[2]. Enhancement of cellular uptake and antitumor efficiencies of micelles with phosphorylcholine. Macromol Biosci. 2011 Oct 10;11(10):1416-25.

[3]. 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.

[4]. Phosphorylcholine-targeting immunization reduces atherosclerosis. J Am Coll Cardiol. 2007 Aug 7;50(6):540-6.

Additional Infomation
Phosphocholine is the phosphate salt of choline and the parent compound of the phosphocholine family. It can function as an epitope, hapten, human metabolite, mouse metabolite, and allergen. It is the conjugate acid of phosphocholine (1-). Calcium and magnesium phosphocholine salts can be used to treat hepatobiliary dysfunction. Phosphocholine has been reported in fruit flies, peppers, and other organisms with relevant data. Phosphocholine is a metabolite found or produced in Saccharomyces cerevisiae. Calcium and magnesium phosphocholine salts can be used to treat hepatobiliary dysfunction.
Phosphorylcholine is a phospholipid widely present in biological systems with immunomodulatory properties. It stimulates α2-adrenergic receptors and increases plasma glucagon and choline concentrations. Phosphorylcholine is an immunologically active epitope on pathogens such as Streptococcus pneumoniae, modulating host-pathogen interactions. It is used in drug delivery micelles to improve cellular internalization. Phosphorylcholine is a research tool for studying immunology, atherosclerosis, and drug delivery.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C5H15NO4P+
Molecular Weight
184.1507
Exact Mass
184.074
CAS #
3616-04-4
Related CAS #
Phosphorylcholine chloride; 107-73-3; Calcium phosphorylcholine chloride, 98%; 4826-71-5; Phosphorylcholine chloride calcium salt tetrahydrate; 72556-74-2; Phosphorylcholine; 3616-04-4
PubChem CID
1014
Appearance
Colorless to light yellow oil
Source
Endogenously produced metabolite: Human Gut Microbiota Metabolites
Originated from microorganisms: a variety of prokaryotic and eukaryotic pathogens
LogP
-1.5
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
11
Complexity
158
Defined Atom Stereocenter Count
0
SMILES
C[N+](C)(C)CCOP(=O)(O)O
InChi Key
YHHSONZFOIEMCP-UHFFFAOYSA-O
InChi Code
InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1
Chemical Name
trimethyl(2-phosphonooxyethyl)azanium
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)
Solubility Data
Solubility (In Vitro)
H2O : ~100 mg/mL (~546.03 mM)
Ethanol : ~4 mg/mL (~21.84 mM)
DMSO : ~1 mg/mL (~5.46 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (546.03 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.4304 mL 27.1518 mL 54.3036 mL
5 mM 1.0861 mL 5.4304 mL 10.8607 mL
10 mM 0.5430 mL 2.7152 mL 5.4304 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration: mg/mL;

Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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