860061 | Egg SM

Sphingomyelin (Egg, Chicken)


Chloroform

Size SKU Packaging Price
25mg 860061C-25mg 860061C-25mg 1 x 25mg 10mg/mL 2.5mL $121.00
200mg 860061C-200mg 860061C-200mg 2 x 100mg 25mg/mL 4mL $242.00
1g 860061C-1g 860061C-1g 2 x 500mg 25mg/mL 20mL $590.00

Powder

Size SKU Packaging Price
25mg 860061P-25mg 860061P-25mg 1 x 25mg $121.00
200mg 860061P-200mg 860061P-200mg 1 x 200mg $242.00
1g 860061P-1g 860061P-1g 1 x 1g $590.00
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Egg SM

Egg SM

Sphingomyelin (Egg, Chicken)

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 Years
Storage Temperature
-20°C
CAS Number
383907-87-7
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
710.965
Exact Mass
0.000
Synonyms
<p>16:0 SMHexadecanoyl SphingomyelinN-hexadecanoyl-D-erythro-sphingosylphosphorylcholineN-(hexadecanoyl)-sphing-4-enine-1-phosphocholine</p>

Shell Ip, Christina MacLaughlin, Michelle Joseph, Nisa Mullauthilaga, Guisheng Yang, Chen Wang, and Gilbert C Walker.Dual-mode dark field and surface enhanced Raman scattering liposomes for lymphoma and leukemia cell imaging. Langmuir, Just Accepted Manuscript. DOI: 10.1021/acs.langmuir.8b02313. Publication Date (Web): October 11, 2018


Wang Q, London E. Lipid Structure and Composition Control Consequences of Interleaflet Coupling in Asymmetric Vesicles. Biophys J. 2018 Jul 19. pii: S0006-3495(18)30814-2. doi: 10.1016/j.bpj.2018.07.011. [Epub ahead of print]

PubMed ID: 30082033

Parkkila P, Elderdfi M, Bunker A, Viitala T. Biophysical Characterization of Supported Lipid Bilayers Using Parallel Dual-Wavelength Surface Plasmon Resonance and Quartz Crystal Microbalance Measurements. Langmuir. 2018 Jun 25. doi: 10.1021/acs.langmuir.8b01259. [Epub ahead of print]

PubMed ID: 29894192

Parkkila P, Elderdfi M, Bunker A, Viitala T. Biophysical Characterization of Supported Lipid Bilayers Using Parallel Dual-Wavelength Surface Plasmon Resonance and Quartz Crystal Microbalance Measurements. Langmuir. 2018 Jun 25. doi: 10.1021/acs.langmuir.8b01259. [Epub ahead of print]

PubMed ID: 29894192

Parkkila P, Elderdfi M, Bunker A, Viitala T. Biophysical characterization of supported lipid bilayers using parallel dual-wavelength surface plasmon resonance and quartz crystal microbalance measurements. Langmuir. 2018 Jun 12. doi: 10.1021/acs.langmuir.8b01259. [Epub ahead of print]

PubMed ID: 29894192

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 ID: 23356741

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 ID: 28272888

Matsufuji T, Kinoshita M, Möuts A, Slotte JP, Matsumori N Preparation and Membrane Properties of Oxidized Ceramide Derivatives. Langmuir. 2017 Dec 27. doi: 10.1021/acs.langmuir.7b02654.

PubMed ID: 29231736

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

Peñalva DA, Antollini S, Ambroggio E, Aveldaño MI, Fanani ML. MEMBRANE RESTRUCTURING EVENTS DURING THE ENZYMATIC GENERATION OF CERAMIDES WITH VERY LONG-CHAIN POLYUNSATURATED FATTY ACIDS. Langmuir. 2018 Mar 15. doi: 10.1021/acs.langmuir.7b04374. [Epub ahead of print]

PubMed ID: 29540057

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.
860061FattyAcidDistribution.gif