860062 | Brain SM

Sphingomyelin (Brain, Porcine)


Chloroform

Size SKU Packaging Price
25mg 860062C-25mg 860062C-25mg 1 x 25mg 10mg/mL 2.5mL $121.00
200mg 860062C-200mg 860062C-200mg 2 x 100mg 25mg/mL 4mL $242.00

Powder

Size SKU Packaging Price
25mg 860062P-25mg 860062P-25mg 1 x 25mg $121.00
200mg 860062P-200mg 860062P-200mg 1 x 200mg $242.00
500mg 860062P-500mg 860062P-500mg 1 x 500mg $375.00
1g 860062P-1g 860062P-1g 1 x 1g $590.00
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Brain SM

Brain SM

Sphingomyelin (Brain, Porcine)

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]
Hygroscopic
No
Light Sensitive
No
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
383907-91-3
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
760.223
Exact Mass
0.000
Synonyms

18:0 SMOctadecanoyl SphingomyelinN-octadecanoyl-D-erythro-sphingosylphosphorylcholineN-(octadecanoyl)-sphing-4-enine-1-phosphocholine

Ausili A, Martinez Valera P, Torrecillas A, Gómez-Murcia V, deGodos AM, Corbalan-Garcia S, Teruel JA, Gomez-Fernandez JC. The anticancer agent edelfosine exhibits a high affinity for cholesterol and disorganizes liquid ordered membrane structures. Langmuir. 2018 Jun 20. doi: 10.1021/acs.langmuir.8b01539. [Epub ahead of print]

PubMed ID: 29924618

Widder K, Träger J, Kerth A, Harauz G, Hinderberger D. Interaction of myelin basic protein with myelin-like lipid monolayers at the air-water interface. Langmuir. 2018 May 3. doi: 10.1021/acs.langmuir.8b00321.

PubMed ID: 29722987

James Kurniawan, João Ventrici, Gregory Kittleson and Tonya L. Kuhl Interaction Forces between Lipid Rafts. Langmuir. Publication Date (Web): December 21, 2016 DOI: 10.1021/acs.langmuir.6b03717 Metabolomics and lipidomics using traveling-wave ion mobility mass spectrometry, Giuseppe Paglia & Giuseppe Astarita Nature Protocols 12, 797-813 (2017) doi:10. 1038/nprot.2017.013 [PubMed]

PubMed ID: 28301461

Li G, Kim J, Huang Z, St Clair JR, Brown DA, London E. Efficient replacement of plasma membrane outer leaflet phospholipids and sphingolipids in cells with exogenous lipids. Proc Natl Acad Sci U S A. 2016 Dec 6;113(49):14025-14030. Epub 2016 Nov 21.

PubMed ID: 27872310

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.
860062FattyAcidDistribution.gif