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Phosphatidylethanolamine (Phosphatidylethanolamine)

Cat No.:V68723 Purity: ≥98%
Phosphatidylethano lamine is a biochemical compound that could be utilized as a biomaterial or organic/chemical reagent in biomedical research.
Phosphatidylethanolamine (Phosphatidylethanolamine)
Phosphatidylethanolamine (Phosphatidylethanolamine) Chemical Structure CAS No.: 90989-93-8
Product category: Biochemical Assay Reagents
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Phosphatidylethano lamine is a biochemical compound that could be utilized as a biomaterial or organic/chemical reagent in biomedical research.
Phosphatidylethanolamine (PE, CAS 90989-93-8) is a naturally occurring phospholipid derived from bovine sources, comprising approximately 15-25% of total mammalian phospholipids. With molecular formula C₉H₁₈NO₈P, it is the most abundant phospholipid in prokaryotes and the second most abundant in mammalian, plant, and yeast cell membranes. PE is a key component of biological membranes, particularly enriched in the brain where it constitutes nearly half of total phospholipids. It exists as a mixture of various fatty acyl groups at the sn-1 and sn-2 positions and is widely used in research to study membrane biophysics, lipid-protein interactions, and cell signaling pathways.
Biological Activity I Assay Protocols (From Reference)
Targets
Phosphatidylethanolamine targets the autophagy pathway and acts as a lipid anchor for autophagy-related proteins Atg8/LC3, participating in autophagosome membrane formation. It also serves as a substrate for phospholipid-modifying enzymes and plays a role in liposome formation and membrane fusion. PE enhances autophagic flux, promotes cell differentiation, regulates lipid droplet fusion, delays aging, and influences lipid metabolism and membrane integrity. Its interactions with various proteins and lipids are fundamental to its diverse biological functions.
ln Vitro
In vitro, phosphatidylethanolamine is used to study membrane biophysics, lipid-protein interactions, and cell signaling pathways. It enhances autophagic flux and promotes cell differentiation in cultured cells. PE is also utilized in liposome-based drug delivery systems and as a component of model membranes for biophysical studies. It serves as a substrate for phospholipases and other lipid-modifying enzymes in enzymatic assays.
ln Vivo
In vivo, phosphatidylethanolamine is essential for normal cellular function and membrane integrity. It plays a critical role in autophagy, lipid metabolism, and membrane fusion processes. PE is enriched in the brain and is crucial for neuronal function. In animal models, it has been shown to regulate lipid droplet fusion and delay aging. Its role as a lipid anchor for autophagy proteins is fundamental to cellular homeostasis.
Enzyme Assay
For in vitro enzyme/receptor binding assays, phosphatidylethanolamine is typically used as a substrate or membrane component. Standard protocols involve reconstituting PE into liposomes or model membranes and incubating with phospholipases or other lipid-modifying enzymes. Enzyme activity is measured by detecting reaction products using thin-layer chromatography (TLC), mass spectrometry, or fluorescence-based assays. PE-lipid interactions can be studied using surface plasmon resonance (SPR) or isothermal titration calorimetry (ITC).
Cell Assay
For in vitro cell-based experiments, cells are cultured in media containing phosphatidylethanolamine or PE-containing liposomes. Autophagic flux is assessed by measuring LC3-II levels via western blot or fluorescence microscopy. Cell differentiation and lipid droplet fusion are evaluated using appropriate markers and imaging techniques. PE's effects on membrane integrity and lipid metabolism can be studied using lipidomics and fluorescence-based membrane assays. Cytotoxicity is assessed using standard MTT or resazurin-based assays.
Animal Protocol
In vivo animal studies using phosphatidylethanolamine are conducted to evaluate its effects on lipid metabolism, autophagy, and aging. Standard protocols involve administering PE via oral gavage or intravenous injection to rodents. Tissue samples (liver, brain, adipose) are collected for lipidomics analysis, autophagy marker detection (LC3-II, p62), and histological examination. PE's effects on aging and lipid droplet fusion are assessed using appropriate biomarkers and imaging techniques.
ADME/Pharmacokinetics
Pharmacokinetic properties of phosphatidylethanolamine are not extensively characterized as a therapeutic agent. As a natural phospholipid, PE is absorbed and incorporated into cell membranes. It is metabolized by phospholipases and other lipid-modifying enzymes. PE is soluble in ethanol (1 mg/mL), chloroform, and methanol, but insoluble in water. When administered orally, it is expected to be digested and absorbed as lysophosphatidylethanolamine and fatty acids.
Toxicity/Toxicokinetics
Phosphatidylethanolamine is generally considered biocompatible and non-toxic as it is a natural component of cell membranes. It is not classified as hazardous under standard GHS criteria. However, standard laboratory safety practices should be followed when handling the compound. PE is for research use only and not for human therapeutic applications as a drug. Specific LD₅₀ values and acute toxicity classifications are not available.
References

[1]. Phosphatidylethanolamine positively regulates autophagy and longevity. Cell Death Differ. 2015 Mar;22(3):499-508.

[2]. Docosahexaenoic acid-containing phosphatidylethanolamine enhances HL-60 cell differentiation by regulation of c-jun and c-myc expression. Mol Cell Biochem. 2005 Jul;275(1-2):127-33.

[3]. Lipid Droplet Fusion in Mammary Epithelial Cells is Regulated by Phosphatidylethanolamine Metabolism. J Mammary Gland Biol Neoplasia. 2017 Dec;22(4):235-249.

[4]. Studies on the anorectic effect of N-acylphosphatidylethanolamine and phosphatidylethanolamine in mice. Biochim Biophys Acta. 2011 Sep;1811(9):508-12.

[5]. The ratio of phosphatidylcholine to phosphatidylethanolamine influences membrane integrity and steatohepatitis. Cell Metab. 2006 May;3(5):321-31.

[6]. The contrasting effect of dietary phosphatidylethanolamine and phosphatidylcholine on serum lipoproteins and liver lipids in rats. J Nutr. 1983 Dec;113(12):2403-11.

[7]. Effect of phosphatidylethanolamine and its constituent base on the metabolism of linoleic acid in rat liver. Biochim Biophys Acta. 1989 Oct 17;1005(3):253-9.

Additional Infomation
Cephalin is a phospholipid in which the polar ethanolamine is linked to diacylglycerol via a phosphate ester bond. It is a derivative of phosphatidic acid, in which the phosphate is partially bound to the ethanolamine via an ester bond. Complete hydrolysis yields 1 mole of glycerol, phosphate, ethanolamine, and 2 moles of fatty acid.
Phosphatidylethanolamine (CAS 90989-93-8) is a research-grade biochemical reagent, not an FDA-approved pharmaceutical drug. Its primary applications are in membrane biophysics, lipid-protein interaction studies, and cell signaling research. PE is also used in liposome-based drug delivery systems and as a component of model membranes. It plays a critical role in autophagy and lipid metabolism research. No clinical trials or approved therapeutic indications exist for this compound.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H18NO8P
Molecular Weight
299.21500
Exact Mass
299.077
CAS #
90989-93-8
PubChem CID
21668201
Appearance
Light yellow to yellow ointment
LogP
0.273
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
11
Heavy Atom Count
19
Complexity
347
Defined Atom Stereocenter Count
0
SMILES
CC(=O)OCC(COP(=O)([O-])OCC[NH3+])OC(=O)C
InChi Key
CFWRDBDJAOHXSH-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H18NO8P/c1-7(11)15-5-9(18-8(2)12)6-17-19(13,14)16-4-3-10/h9H,3-6,10H2,1-2H3,(H,13,14)
Chemical Name
[2-acetyloxy-3-[2-aminoethoxy(hydroxy)phosphoryl]oxypropyl] acetate
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

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)
Ethanol: 50 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween-80 + 45% Saline (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 ethanol stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Suspended solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of ethanol stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well.
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 3: ≥ 2.5 mg/mL (saturation unknown) in 10% EtOH + 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 EtOH stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3420 mL 16.7101 mL 33.4202 mL
5 mM 0.6684 mL 3.3420 mL 6.6840 mL
10 mM 0.3342 mL 1.6710 mL 3.3420 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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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

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.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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