A sphingolipid
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Sphingomyelin (bovine buttermilk)

Item No. 31559

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(9Z,11E)-octadeca-9,11-dienoate
CAS Number
475662-40-9
Synonyms
  • SMs (buttermilk)
Molecular Formula
C46H93N2O6P (for tricosanoyl)
Formula Weight
801.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleChloroform: solubleEthanol: Soluble
SMILES
[R]C(N[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)[C@H](O)/C=C/CCCCCCCCCCCCC)=O
InChi Code
InChI=1S/C46H93N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-28-30-32-34-36-38-40-46(50)47-44(43-54-55(51,52)53-42-41-48(3,4)5)45(49)39-37-35-33-31-29-27-19-17-15-13-11-9-7-2/h37,39,44-45,49H,6-36,38,40-43H2,1-5H3,(H-,47,50,51,52)/b39-37+/t44-,45+/m0/s1
InChi Key
SXZWBNWTCVLZJN-NMIJJABPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    Product Description

    Sphingomyelins (SMs) are bioactive sphingolipids found in mammalian cell membranes.1 SMs make up 2-15% of the total organ phospholipid population but are found at higher concentrations in the brain and myelin sheaths surrounding peripheral nerves. They interact with cholesterol to control its distribution within cellular membranes and maintain cholesterol homeostasis in cells. SMs undergo hydrolysis by sphingomyelinase to form ceramides, which are sphingolipid mediators of intracellular signaling.2 This product contains SM molecular species with primarily C22:0, C23:0, and C24:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1329]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Slotte, J.P., and Ramstedt, B. The functional role of sphingomyelin in cell membranes. Eur. J. Lipid Sci. Technol. 109(10), 977-981 (2007).

    2. Shayman, J.A. Sphingolipids. Kidney Int. 58(1), 11-26 (2000).