| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Targets |
No conventional receptor target; sphingomyelin is a structural lipid. However, it serves as a substrate for sphingomyelinases, generating ceramide, which activates various kinases (MAPK, PKCζ) and phosphatases. Ceramide can also be converted to sphingosine and S1P, which act on specific GPCRs (S1P1–5). Through these metabolites, sphingomyelin modulates apoptosis, proliferation, inflammation, and stress responses.
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| ln Vitro |
Ceramides, diacylglycerides, sphingosine-1-phosphate, and other interconvertible bioactive sphingolipids are produced as a consequence of sphingomyelin metabolism. These bioactive lipids influence biological processes by acting on certain targets inside cells and regulating different signal transduction pathways [1]. Cell signaling is mediated by lipid rafts abundant in sphingomyelin [1].
In vitro, sphingomyelin is used as a substrate to measure sphingomyelinase activity. It can be incorporated into liposomes to study membrane biophysics. When added to cultured cells, exogenous sphingomyelin alters membrane fluidity and can suppress inflammatory cytokine production (e.g., TNF-α) by reducing lipid raft clustering of receptors. It does not directly activate signaling but modulates the availability of ceramide precursors. |
| ln Vivo |
In vivo, sphingomyelin is an endogenous lipid; its dietary intake may influence serum lipid profiles and inflammatory markers. In animal studies, dietary sphingomyelin supplementation (0.1–1% of diet) has been shown to reduce plasma total cholesterol and ameliorate atherosclerosis in apoE-deficient mice. It also protects against DSS-induced colitis by maintaining intestinal barrier integrity. Its metabolism generates ceramide, which is implicated in insulin resistance and apoptosis.
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| Enzyme Assay |
Cell-free assays: measure sphingomyelinase activity using sphingomyelin as substrate; incubate enzyme with radiolabeled or fluorescent sphingomyelin and quantify product (ceramide or phosphocholine) by TLC or fluorescence. Lipid raft isolation: solubilize cell membranes with Triton X-100 and separate raft fractions by sucrose density gradient; analyze sphingomyelin content by LC-MS. For ceramide quantification, use diacylglycerol kinase assay or LC-MS.
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| Cell Assay |
For cellular studies, treat cells with sphingomyelin in liposomal form (e.g., 50–200 µM) for 24–72 h. Assess membrane fluidity using fluorescent probes (Laurdan). Measure ceramide production by LC-MS. Evaluate inflammatory response by stimulating with LPS and measuring IL-6/TNF-α via ELISA. For apoptosis, stain with Annexin V/PI and quantify by flow cytometry. Use confocal microscopy to assess lipid raft aggregation using cholera toxin B (GM1 marker).
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| Animal Protocol |
In vivo, sphingomyelin is administered orally in the diet or by gavage. In mouse colitis models, feed 1% sphingomyelin for 7 days before DSS induction, then assess disease activity index, histology, and colonic myeloperoxidase activity. In atherosclerosis models, supplement ApoE-/- mice with 0.5% sphingomyelin for 12 weeks and quantify aortic lesion area by Oil Red O. Plasma cholesterol and cytokines are also measured.
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| ADME/Pharmacokinetics |
Sphingomyelin from natural sources varies in fatty acid composition (common species: stearoyl, palmitoyl, oleoyl). Typical MW ~731 for stearoyl form (C41H84N2O8P). Appearance: white to off-white powder. Solubility: chloroform/methanol (2:1) at ~10 mg/mL; insoluble in water. Store at 2-8°C under inert gas to prevent oxidation. Purity ≥98% for research. For liposome preparation, dissolve in organic solvent and evaporate to form thin film, then rehydrate in buffer.
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| Toxicity/Toxicokinetics |
No toxicity reported; sphingomyelin is a normal dietary component. High doses may cause mild GI disturbances. It is generally recognized as safe. No mutagenic or teratogenic effects known. In animal studies, doses up to 2% of diet are well-tolerated.
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| References | |
| Additional Infomation |
N-Stearylsphingosine-1-phosphocholine is a sphingomyelin d18:1 in which the ceramide N-acyl group is designated as stearoyl (octadecanoyl). It is a mouse metabolite. It is a sphingomyelin 36:1 and sphingomyelin d18:1. It is functionally related to octadecanoic acid. N-(octadecanoyl)-sphingosine-4-ene-1-phosphocholine has been reported in Homo sapiens, and relevant data are available.
Sphingomyelin is a research chemical, not a drug. It is widely used in lipid biochemistry, membrane biology, and nutrition research. Its role in lipid raft function and signaling makes it a key tool for studying receptor clustering and membrane organization. It is also marketed as a dietary supplement for cognitive and cardiovascular health, though evidence is limited. No clinical trials have been conducted for therapeutic use. |
| Molecular Formula |
C41H84N2O8P+
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|---|---|
| Molecular Weight |
764.08800
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| Exact Mass |
730.598
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| CAS # |
85187-10-6
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| PubChem CID |
6453725
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| Appearance |
White to off-white solid powder
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| LogP |
9.53
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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 |
38
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| Heavy Atom Count |
50
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| Complexity |
826
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP(=O)([O-])OCC[N+](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O
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| InChi Key |
LKQLRGMMMAHREN-YJFXYUILSA-N
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| InChi Code |
InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1
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| Chemical Name |
[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
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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) |
Ethanol : ~25 mg/mL
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| Solubility (In Vivo) |
Solubility in Formulation 1: 1.67 mg/mL (Infinity mM) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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 2: ≥ 1.67 mg/mL (Infinity mM) (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 16.7 mg/mL clear EtOH stock solution 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 | 1.3087 mL | 6.5437 mL | 13.0875 mL | |
| 5 mM | 0.2617 mL | 1.3087 mL | 2.6175 mL | |
| 10 mM | 0.1309 mL | 0.6544 mL | 1.3087 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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