| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
Sphingomyelins target lipid rafts and membrane microdomains. As a major component of cell membranes (particularly in myelin sheaths), sphingomyelin interacts with cholesterol to form liquid-ordered phases. It is a substrate for sphingomyelinase, which generates ceramide, a key signaling molecule involved in apoptosis, inflammation, and differentiation. The very-long-chain nervonic acid (C24:1) is enriched in the brain and myelin.
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| ln Vitro |
N-Nervonoyl-D-erythro-sphingosylphosphorylcholine is a biochemical reagent and is not used for biological activation. It can be incorporated into liposomes or supported lipid bilayers to study the biophysical properties of sphingolipid-rich membranes. It is also used as an internal standard for sphingolipid quantification by LC-MS/MS. In sphingomyelinase assays, it serves as a substrate for neutral and acidic sphingomyelinases.
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| ln Vivo |
Not applicable; the compound is a biochemical reagent and is not used in vivo. However, sphingomyelin levels are altered in Niemann-Pick disease, atherosclerosis, and neurodegenerative disorders. The nervonic acid-containing sphingomyelin is particularly relevant to multiple sclerosis and other demyelinating diseases.
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| Enzyme Assay |
For sphingomyelinase activity assays, recombinant human neutral sphingomyelinase (nSMase2, 0.1-1 U) is incubated with N-Nervonoyl-D-erythro-sphingosylphosphorylcholine (0.1-5 mM) in 100 mM Tris-HCl pH 7.4, 10 mM MgCl2, 0.1% Triton X-100 at 37degC for 30-60 min. The reaction is terminated by adding 2:1 chloroform/methanol (Folch extraction), and ceramide product is quantified by LC-MS/MS or by an Amplex Red-based assay. For kinetic parameters, Km and Vmax are calculated. For lipidomics, the compound is used as a reference standard. For model membrane studies, the lipid is incorporated into liposomes (e.g., with cholesterol and POPC) by dry-film hydration and extrusion. Liposome properties (size, lamellarity, phase transition) are characterized by DLS, DSC, and fluorescence anisotropy.
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| Cell Assay |
For cellular sphingomyelinase assays, cells are labeled with [14C]- or [3H]-sphingomyelin (1-2 uCi/mL, 24 h). After washing, cells are treated with test compounds (e.g., nSMase2 activators or inhibitors). [14C]-ceramide is extracted and quantified by scintillation counting or by TLC. Alternatively, the compound (as a standard) is spiked into lipid extracts for quantification. Not applicable; the compound is used as a lipid standard, not as a cell treatment.
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| Animal Protocol |
Not applicable; the compound is not administered to animals. For lipidomics studies, tissues (brain, liver, plasma) are collected from mice, lipids are extracted, and N-Nervonoyl-D-erythro-sphingosylphosphorylcholine levels are quantified using the compound as an internal standard by LC-MS/MS.
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| ADME/Pharmacokinetics |
The compound is lipophilic (logP ~10). It is soluble in chloroform, methanol, and DMSO. For liposome preparation, it is co-dissolved with other lipids in chloroform/methanol (2:1) and dried under N2. For LC-MS/MS, it is eluted on a C18 column with a gradient of water/methanol/isopropanol. Not for in vivo use.
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| Toxicity/Toxicokinetics |
Low toxicity as a lipid. Standard safety precautions. Not a drug.
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| Additional Infomation |
SM(d18:1/24:1(15Z)) is a sphingomyelin d18:1 in which the N-acyl group is designated as (15Z)-teicosenoyl. It is a mouse metabolite. It is a sphingomyelin d18:1, sphingomyelin 42:2, and N-teicosenoylsphingosine-1-phosphocholine. It is functionally associated with (15Z)-teicosenoic acid. C24:1 sphingomyelin has been reported in trypanosomes and black silkworms, and relevant data are available.
N-Nervonoyl-D-erythro-sphingosylphosphorylcholine (C24:1 sphingomyelin) is a research-grade lipid standard. It is not an FDA-approved drug. It is used in sphingolipid metabolism studies, lipidomics (LC-MS/MS), membrane biophysics, and myelin biology. For research use only. |
| Molecular Formula |
C47H93N2O6P
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|---|---|
| Molecular Weight |
813.22
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| Exact Mass |
812.677
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| CAS # |
94359-13-4
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| PubChem CID |
44260126
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| Appearance |
Typically exists as solids at room temperature
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| LogP |
14.136
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
43
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| Heavy Atom Count |
56
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| Complexity |
961
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| Defined Atom Stereocenter Count |
2
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| SMILES |
P(=O)([O-])(OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)NC(CCCCCCCCCCCCC/C=C\CCCCCCCC)=O)OCC[N+](C)(C)C
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| InChi Key |
WKZHECFHXLTOLJ-QYKFWSDSSA-N
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| InChi Code |
InChI=1S/C47H93N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-47(51)48-45(44-55-56(52,53)54-43-42-49(3,4)5)46(50)40-38-36-34-32-30-28-19-17-15-13-11-9-7-2/h20-21,38,40,45-46,50H,6-19,22-37,39,41-44H2,1-5H3,(H-,48,51,52,53)/b21-20-,40-38+/t45-,46+/m0/s1
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| Chemical Name |
[(E,2S,3R)-3-hydroxy-2-[[(Z)-tetracos-15-enoyl]amino]octadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
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| Synonyms |
N-neuroacyl-D-erythrosylphosphocholine
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.2297 mL | 6.1484 mL | 12.2968 mL | |
| 5 mM | 0.2459 mL | 1.2297 mL | 2.4594 mL | |
| 10 mM | 0.1230 mL | 0.6148 mL | 1.2297 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.
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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