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Sphingomyelin

Cat No.:V29092 Purity: ≥98%
Sphingomyelin is a eukaryotic sphingomyelin, one of the major components of cell membranes, and is particularly abundant in the myelin sheath of the membrane of neuronal axons.
Sphingomyelin
Sphingomyelin Chemical Structure CAS No.: 85187-10-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
100mg
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Product Description
Sphingomyelin is a eukaryotic sphingomyelin, one of the major components of cell membranes, and is particularly abundant in the myelin sheath of the membrane of neuronal axons. Sphingomyelin plays important roles in cellular processes, regulation of inflammatory responses, and signal transduction. Sphingomyelin metabolism is associated with a variety of central nervous system diseases as well as Niemann–Pick disease.
Biological Activity I Assay Protocols (From Reference)
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].
References

[1]. Sphingomyelin and its role in cellular signaling. Adv Exp Med Biol. 2013;991:1-14.

[2]. Sphingomyelin in Brain and Cognitive Development: Preliminary Data. eNeuro. 2019 Aug 6;6(4). pii: ENEURO.0421-18.2019.

[3]. Regulation of sphingomyelin metabolism. Pharmacol Rep. 2016 Jun;68(3):570-81.

[4]. Types A and B Niemann-Pick disease. Mol Genet Metab. 2017 Jan - Feb;120(1-2):27-33.

Additional Infomation
N-stearoylsphingosine-1-phosphocholine is a sphingomyelin d18:1 in which the ceramide N-acyl group is specified as stearoyl (octadecanoyl). It has a role as a mouse metabolite. It is a sphingomyelin 36:1 and a sphingomyelin d18:1. It is functionally related to an octadecanoic acid.
N-(octadecanoyl)-sphing-4-enine-1-phosphocholine has been reported in Homo sapiens with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C41H84N2O8P+
Molecular Weight
764.08800
Exact Mass
730.598
CAS #
85187-10-6
PubChem CID
6453725
Appearance
White to off-white solid powder
LogP
9.53
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
38
Heavy Atom Count
50
Complexity
826
Defined Atom Stereocenter Count
2
SMILES
CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP(=O)([O-])OCC[N+](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O
InChi Key
LKQLRGMMMAHREN-YJFXYUILSA-N
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
Chemical Name
[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
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 : ~25 mg/mL
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.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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