sn-Glycero-3-phosphocholineNootropic phospholipid CAS# 28319-77-9 |
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Quality Control & MSDS
3D structure
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| Cas No. | 28319-77-9 | SDF | Download SDF |
| PubChem ID | 71920 | Appearance | Powder |
| Formula | C8H20NO6P | M.Wt | 257.22 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Choline Alfoscerate; Alpha-GPC; L-α-GPC | ||
| Solubility | H2O : 500 mg/mL (1943.86 mM; Need ultrasonic) DMSO : ≥ 125 mg/mL (485.97 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | [(2S)-2,3-dihydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | ||
| SMILES | C[N+](C)(C)CCOP(=O)([O-])OCC(CO)O | ||
| Standard InChIKey | SUHOQUVVVLNYQR-QMMMGPOBSA-N | ||
| Standard InChI | InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | L-Alpha glycerylphosphorylcholine (alpha-GPC, choline alfoscerate) is a natural choline compound found in the brain and in milk. It is also a parasympathomimetic acetylcholine precursor which may have potential for the treatment of Alzheimer's disease and dementia.
IC50 value:
Target: Anti-AD
Alpha-GPC rapidly delivers choline to the brain across the blood–brain barrier and is a biosynthetic precursor of the acetylcholine neurotransmitter. It is a non-prescription drug in most countries due to its Generally Recognised As Safe (GRAS) status [1]. Studies have investigated its efficacy for cognitive disorders including stroke and Alzheimer’s disease. An Italian multicentre clinical trial on 2,044 patients suffering from recent stroke were supplied alpha-GPC in doses of 1,000 mg/day for 28 days and 400 mg three times per day for the five ensuing months. The trial confirmed the therapeutic role of alpha-GPC on the cognitive recovery of patients based on four measurement scales, three of which reached statistical significance [2]. References: | |||||
sn-Glycero-3-phosphocholine Dilution Calculator
sn-Glycero-3-phosphocholine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.8877 mL | 19.4386 mL | 38.8772 mL | 77.7545 mL | 97.1931 mL |
| 5 mM | 0.7775 mL | 3.8877 mL | 7.7754 mL | 15.5509 mL | 19.4386 mL |
| 10 mM | 0.3888 mL | 1.9439 mL | 3.8877 mL | 7.7754 mL | 9.7193 mL |
| 50 mM | 0.0778 mL | 0.3888 mL | 0.7775 mL | 1.5551 mL | 1.9439 mL |
| 100 mM | 0.0389 mL | 0.1944 mL | 0.3888 mL | 0.7775 mL | 0.9719 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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L-Alpha glycerylphosphorylcholine (alpha-GPC, choline alfoscerate) is a natural choline compound found in the brain and in milk. It is also a parasympathomimetic acetylcholine precursor which may have potential for the treatment of Alzheimer's disease and
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Oxidative Degradation of the Monolayer of 1-Palmitoyl-2-Oleoyl-sn-Glycero-3-Phosphocholine (POPC) in Low-Level Ozone.[Pubmed:26463524]
J Phys Chem B. 2015 Nov 5;119(44):14188-99.
Ambient ozone is a common pollutant in the atmosphere that has an extremely high oxidative ability, can dramatically change the structure and functionality of biomolecules, and is harmful to public health. However, the knowledge about the influence of low-level ozone is still very limited at a molecular level. In the present study, the monolayer of 1-palmitoyl-2-oleoyl-sn-Glycero-3-phosphocholine (POPC, 16:0-18:1 PC) as well as its binary mixed monolayer with 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine (DPPC, 16:0 PC), which are widely found in many biological systems, have been systematically investigated in a low-level ozone environment (20 +/- 10 ppb), by pi-A isotherm, sum frequency generation (SFG) vibrational spectroscopy, and atomic force microscopy (AFM). Our results demonstrate that the POPC monolayer is unstable and the C horizontal lineC moieties in the oleyl chain are selectively oxidized by the low-level ozone. The oxidized lipids from POPC initially remain and reorientate the hydrophilic portion to the water surface and gradually dissolve into the aqueous solution. One should take great caution when using unsaturated lipid molecules to avoid their possible oxidation in the ambient environment. The present study expands and deepens our insights into the oxidation mechanism of unsaturated lipids at a molecular level.
Effect of Sterol Structure on the Physical Properties of 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine Membranes Determined Using (2)H Nuclear Magnetic Resonance.[Pubmed:27341069]
Langmuir. 2016 Aug 2;32(30):7654-63.
The effect of a series of phytosterols on lipid chain ordering in 1-palmitoyl((2)H31)-2-oleoyl-sn-Glycero-3-phosphocholine (POPC-d31) multibilayer vesicles was examined by (2)H NMR spectroscopy at 25 degrees C. These results, along with existing data for other sterols, indicate that the ordering power of sterols in POPC-d31 depends on subtle aspects of sterol structure. Cholesterol, 7-dehydrocholesterol (7-DHC), campesterol, beta-sitosterol, ergosterol, brassicasterol, and stigmasterol all increase the lipid chain order as sterol concentration is increased. However, saturation of the ordering occurs at different sterol concentrations for ergosterol (as previously reported), brassicasterol, beta-sitosterol, and stigmasterol. Here our interest lies in finding which part of the sterol structure is responsible for the observed saturation of the palmitoyl chain order as a function of sterol concentration. In particular, we propose that the saturation of the ordering of POPC-d31/brassicasterol and POPC-d31/stigmasterol membranes at quite low sterol concentrations is due to the presence of a double bond at C22. We also discuss how the structural differences between the sterols affect their ability to intercalate between the POPC acyl chains. Furthermore, the effective solubility of sterols in POPC is discussed in relation to the dependence of maximum POPC-d31 chain order vs sterol concentration.
Interaction of curcumin with 1,2-dioctadecanoyl-sn-glycero-3-phosphocholine liposomes: Intercalation of rhamnolipids enhances membrane fluidity, permeability and stability of drug molecule.[Pubmed:27716529]
Colloids Surf B Biointerfaces. 2017 Jan 1;149:30-37.
Stability of curcumin in neutral and alkaline buffer conditions has been a serious concern for its medicinal applications. We demonstrate that the stability of curucmin can be improved in 1,2-Dioctadecanoyl-sn-Glycero-3-phosphocholine (DSPC) liposomes. Curcumin strongly partition into liquid crystalline phase compared to solid gel phase of DSPC liposomes. Variation of fluorescence intensity of curcumin associated with liposomes with temperature successfully determines phase transition temperature of DSPC liposomes. However, at higher molar ratio curcumin can influence phase transition temperature by intercalating into deep hydrophobic layer of liposomes and facilitating fusion of two membrane phases. Rhamnolipids (RLs) are recently being applied for various biomedical applications. Here, we have explored new insight on intercalation of rhamnolipids with DSPC liposomes. Intercalation of rhamnolipids exceptionally increases partition of curcumin into solid gel phase of DSPC liposomes, whereas this increase is moderate in liquid crystalline phase. Fluorescence quenching study establishes that permeability and fluidity of the DSPC liposomes are enhanced in the presence of RLs. Membrane permeability and fluidity can be improved further by increasing the percentage of RLs in DSPC liposomes. The phase transition temperature of DSPC liposomes decreases with increase in percentage of RLs in DSPC liposomes by encouraging fusion between solid gel and liquid crystalline phases. Intercalation of RLs is found to further boost stability of drug, curcumin, in DSPC liposomes. Thus, mixing RLs with DSPC liposomes could potentially serve as a good candidate for drug delivery application.
Phase diagram of a polyunsaturated lipid mixture: Brain sphingomyelin/1-stearoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine/cholestero l.[Pubmed:26525664]
Biochim Biophys Acta. 2016 Jan;1858(1):153-61.
Phospholipids having a polyunsaturated acyl chain are abundant in biological membranes, but their behavior in lipid mixtures is difficult to study. Here we elucidate the nature of such mixtures with this report of the first ternary phase diagram containing the polyunsaturated lipid SDPC in mixtures of BSM/SDPC/Chol (brain sphingomyelin/1-stearoyl-2-docosahexaenoyl-sn-Glycero-3-phosphocholine/cholestero l). These mixtures show coexisting macroscopic liquid-disordered (Ld) and liquid-ordered (Lo) phase separation, with phase boundaries determined by FRET and by fluorescence microscopy imaging of giant unilamellar vesicles (GUVs). Surprisingly, SDPC mixes with BSM/Chol similarly to how DOPC and POPC mix with BSM/Chol. Notably, intermediate states are produced within the Ld+Lo liquid-liquid immiscibility region upon addition of fourth component POPC. These mixtures of BSM/SDPC/POPC/Chol exhibit nanoscopic Ld+Lo domains over a very large volume of composition space, possibly because Ld/Lo line tension is not high.
