Products

Egg SM | 860061

Sphingomyelin (Egg, Chicken)

860061P

Powder

860061P-
25 mg
$121.00
860061P-
200 mg
$242.00
860061P-
500 mg
$375.00
860061P-
1 g
$590.00

860061C

Chloroform

860061C-
25 mg
$121.00
860061C-
200 mg
$242.00
860061C-
500 mg
$375.00
860061C-
1 g
$590.00

All Prices in US Dollars
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  • Product
  • Data
  • Downloads
  • Reference
  • Fatty Acid Distribution
As a major constituent of cell membranes, sphingomyelin is found at particularly high concentrations in the membranes of nerve cells (in the myelin sheaths) and red blood cells. It was previously thought to have a purely structural role, similar to the function of phosphatidylcholine, through intermolecular interactions mediated by the 2-amide group, the 3-hydroxy group and the 4,5-trans double bond of the sphingoid base1. However, it is now appreciated that sphingomyelin has a high affinity for cholesterol and that these two lipids pack tightly into liquid-ordered domains among a liquid-disordered phase to form lipid rafts1,2. These membrane microdomains are thought to function as signaling platforms that regulate the localization and interactions of proteins. But sphingomyelin does not just influence signaling as a component of lipid rafts — it is also a precursor to ceramides and other sphingolipid metabolites that comprise the sphingomyelin cycle or sphingolipid network1,2.
1. Christie, W.W. Sphingomyelin and related lipids. The AOCS Lipid Library.
2. Milhas, D., Clarke, C.J. & Hannun, Y.A. Sphingomyelin metabolism at the plasma membrane: implications for bioactive sphingolipids. FEBS Lett. 584, 1887-1894 (2010). [PubMed]
Purity
>99%
Stability
1 Years
Storage
-20°C
CAS Number
383907-87-7
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
710.965 (average based on fatty acid distribution in product)
Synonyms
16:0 SM
Hexadecanoyl Sphingomyelin
N-hexadecanoyl-D-erythro-sphingosylphosphorylcholine
N-(hexadecanoyl)-sphing-4-enine-1-phosphocholine
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Notes
GIF Graphics File. 
GIF Graphics File. 
MDL Molfile. 
CDX File. 
Lonnfors, M., O. Langvik, A. Bjorkbom, and J.P. Slotte. (2013). Cholesteryl Phosphocholine - A Study on Its Interactions with Ceramides and Other Membrane Lipids. Langmuir [PubMed]Preferential Adsorption of l-Histidine onto DOPC/Sphingomyelin/3β-[N-(N′,N′-dimethylaminoethane)carbamoyl]cholesterol Liposomes in the Presence of Chiral Organic Acids Keishi Suga, Atsushi Tauchi, Takaaki Ishigami, Yukihiro Okamoto, and Hiroshi Umakoshi* Langmuir, Article ASAP [PubMed]
This Natural Lipid is a mixture and the structure shown above is only representative of one possible structure present in the product. Refer to chart for average fatty acid distribution.