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860063 | Milk SM

Sphingomyelin (Milk, Bovine)

Milk SM

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Size SKU Packaging Price
200mg 860063P-200mg 860063P-200mg 1 x 200mg $352.00
25mg 860063P-25mg 860063P-25mg 1 x 25mg $175.75
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Chloroform

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25mg 860063C-25mg 860063C-25mg 1 x 25mg 10mg/mL 2.5mL $175.75 175.75
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Info

Milk SM

Sphingomyelin (Milk, Bovine)

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]
Data
Hygroscopic
No
Light Sensitive
No
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
475662-40-9
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
785.034
Synonyms
23:0 SMN-(tricosanoyl)-sphing-4-enine-1-phosphocholine
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References

Fitzgerald BL, Molins CR, Islam MN, Graham B, Hove PR, Wormser GP, Hu L, Ashton LV, Belisle JT. Host Metabolic Response in Early Lyme Disease. J Proteome Res. 2020 Jan 9;10.1021/acs.jproteome.9b00470. doi: 10.1021/acs.jproteome.9b00470. [Epub ahead of print]. PMID: 31821002.

 PubMed ID: 31821002

Et-Thakafy O, Guyomarc'h F, Lopez C. Young modulus of supported lipid membranes containing milk sphingomyelin in the gel, fluid or liquid-ordered phase, determined using AFM force spectroscopy. Biochim Biophys Acta Biomembr. 2019 Sep 1;1861(9):1523-1532. doi: 10.1016/j.bbamem.2019.07.005. Epub 2019 Jul 8.

 PubMed ID: 31295476

Milard M, Penhoat A, Durand A, Buisson C, Loizon E, Meugnier E, Bertrand K, Joffre F, Cheillan D, Garnier L, Viel S, Laugerette F, Michalski MC. Acute effects of milk polar lipids on intestinal tight junction expression: towards an impact of sphingomyelin through the regulation of IL-8 secretion? J Nutr Biochem. 2019 Mar;65:128-138. doi: 10.1016/j.jnutbio.2018.12.007. Epub 2018 Dec 21.

 PubMed ID: 30685581

Hauser J, Sultan S, Rytz A, Steiner P, Schneider N. A blend containing docosahexaenoic acid, arachidonic acid, vitamin B12, vitamin B9, iron and sphingomyelin promotes myelination in an in vitro model. Nutr Neurosci. 2019 Feb 26:1-15. doi: 10.1080/1028415X.2019.1580918. [Epub ahead of print]

 PubMed ID: 30806182

Milard M, Penhoat A, Durand A, Buisson C, Loizon E, Meugnier E, Bertrand K, Joffre F, Cheillan D, Garnier L, Viel S, Laugerette F, Michalski MC. Acute effects of milk polar lipids on intestinal tight junction expression: towards an impact of sphingomyelin through the regulation of IL-8 secretion?. J Nutr Biochem. 2018 Dec 21;65:128-138. doi: 10.1016/j.jnutbio.2018.12.007. [Epub ahead of print]

 PubMed ID: 30685581

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

Acyl Chain Length and Saturation Modulate Interleaflet Coupling in Asymmetric Bilayers: Effects on Dynamics and Structural Order. Salvatore Chiantia and Erwin London, Biophysical Journal, Volume 103, Issue 11, 2311-2319, 5 December 2012. [Abstract]

 PubMed ID: 23283230

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
Fatty Acid Distribution

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.

860063FattyAcidDistribution.gif
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