Molecular structure of Sphingomyelin, CAS Number: 85187-10-6
Sphingomyelin (CAS 85187-10-6)
See product citations (3)
Alternate Names:
N-Acyl-4-sphingenyl-1-O-phosphorylcholine;N-Acyl-D-sphingosine-1-phosphocholine
Application:
Sphingomyelin is a sphingosine bonded to a fatty acid
CAS Number:
85187-10-6
Purity:
≥98%
Molecular Weight:
731.1 (stearoyl form)
Molecular Formula:
C41H83N2O6P
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Sphingomyelin contains primarily stearic and nervonic acids. Structurally Sphingomyelin has a ceramide core and a sphingosine bonded to a fatty acid via an amide linkage. The compound is synthesized in the cis/medial-Golgi and is a precursor to ceramide second messengers via the action of sphingomyelinase. This is found to have a function in signal transduction. The plasma membrane of cells is highly enriched in sphingomyelin (SPH) and is considered largely to be found in the exoplasmic leaflet of the cell membrane. Transport of sphingomyelin to the cell surface has been demonstrated to occur independent of protein secretion in rat hepatocytes. It has been observed that sphyngomyelin is a key molecule for ganglioside-bound amyloid beta-protein generation on the surface of PC12 cells.
Sphingomyelin (CAS 85187-10-6) References
- Sphingomyelin in the suppression of colon tumors: prevention versus intervention. | Lemonnier, LA., et al. 2003. Arch Biochem Biophys. 419: 129-38. PMID: 14592456
- Inhibition of sphingomyelin synthesis reduces atherogenesis in apolipoprotein E-knockout mice. | Park, TS., et al. 2004. Circulation. 110: 3465-71. PMID: 15545514
- Sphingomyelin accumulation provides a favorable milieu for GM1 ganglioside-induced assembly of amyloid beta-protein. | Yuyama, K. and Yanagisawa, K. 2010. Neurosci Lett. 481: 168-72. PMID: 20599476
- Interaction of cholesterol with various glycerophospholipids and sphingomyelin. | Sankaram, MB. and Thompson, TE. 1990. Biochemistry. 29: 10670-5. PMID: 2176878
- Reducing plasma membrane sphingomyelin increases insulin sensitivity. | Li, Z., et al. 2011. Mol Cell Biol. 31: 4205-18. PMID: 21844222
- An update of the enzymology and regulation of sphingomyelin metabolism. | Merrill, AH. and Jones, DD. 1990. Biochim Biophys Acta. 1044: 1-12. PMID: 2187537
- Pharmacological reversion of sphingomyelin-induced dendritic spine anomalies in a Niemann Pick disease type A mouse model. | Arroyo, AI., et al. 2014. EMBO Mol Med. 6: 398-413. PMID: 24448491
- Free sphingosine formation from endogenous substrates by a liver plasma membrane system with a divalent cation dependence and a neutral pH optimum. | Slife, CW., et al. 1989. J Biol Chem. 264: 10371-7. PMID: 2499578
- Evidence for a new biosynthetic pathway of sphingomyelin in SV 40 transformed mouse cells. | Diringer, H., et al. 1972. Biochem Biophys Res Commun. 47: 1345-52. PMID: 4339164
- The enzymatic formation of sphingomyelin from ceramide and lecithin in mouse liver. | Ullman, MD. and Radin, NS. 1974. J Biol Chem. 249: 1506-12. PMID: 4817756
- The formation of sphingomyelin from phosphatidylcholine in plasma membrane preparations from mouse fibroblasts. | Marggraf, WD., et al. 1981. Biochim Biophys Acta. 664: 61-73. PMID: 6263341
- Sphingomyelin transport to the cell surface occurs independently of protein secretion in rat hepatocytes. | Shiao, YJ. and Vance, JE. 1993. J Biol Chem. 268: 26085-92. PMID: 8253724
- Increased sphingomyelin content of plasma lipoproteins in apolipoprotein E knockout mice reflects combined production and catabolic defects and enhances reactivity with mammalian sphingomyelinase. | Jeong, Ts., et al. 1998. J Clin Invest. 101: 905-12. PMID: 9466986
Inhibitor of:
CD1B, Ceramide Synthase (CERS; LASS), and LASS3.Activator of:
β-1,4-GalNAc-T2, ACBD5, ASAH2B, ASAH3, C1s, CD60b, EG629667, epsin2, Gα 12, Ganglioside GD3, GD3 Synthase, HPS-3, KRTAP5-4, LASS6, Measles H, MFSD2B, ORMDL3, ORP-1, Peroxin 19, Raftlin, RPE, saposin, SMAP1L, SMPD5, SMPDL3B, StARD7, Synaptotagmin VIII, and ZDHHC25.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Sphingomyelin, 100 mg | sc-201381 | 100 mg | $180.00 | |||
Sphingomyelin, 500 mg | sc-201381A | 500 mg | $560.00 |