A sphingolipid
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Labeled Version(s)
9003460C26 Sphingomyelin-d4 (d18:1/26:0-d4)
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C26 Sphingomyelin (d18:1/26:0)

Item No. 9003457

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7S)-4-hydroxy-7-[(1R,2E)-1-hydroxy-2-hexadecen-1-yl]-N,N,N-trimethyl-9-oxo-3,5-dioxa-8-aza-4-phosphatetratriacontan-1-aminium, 4-oxide, inner salt
CAS Number
221097-57-0
Synonyms
  • Cerotyl Sphingomyelin
  • N-Hexacosanoyl-D-erythro-Sphingophosphorylcholine
  • SM(d18:1/26:0)
  • Sphingomyelin (d18:1/26:0)
Molecular Formula
C49H99N2O6P
Formula Weight
843.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): soluble
SMILES
O=C(CCCCCCCCCCCCCCCCCCCCCCCCC)N[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)[C@H](O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C49H99N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-29-31-33-35-37-39-41-43-49(53)50-47(46-57-58(54,55)56-45-44-51(3,4)5)48(52)42-40-38-36-34-32-30-19-17-15-13-11-9-7-2/h40,42,47-48,52H,6-39,41,43-46H2,1-5H3,(H-,50,53,54,55)/b42-40+/t47-,48+/m0/s1
InChi Key
VRAWSAPVSSLIRI-MVUJCARGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    C26 Sphingomyelin is a sphingolipid that has been found in serum and cell or brain extracts.1,2,3 C26 sphingomyelin levels are increased in the serum of patients with hemophagocytic lymphohistiocytosis, an inflammatory condition characterized by excessive immune activation.3 C26 sphingomyelin has been used a component of monolayers to study the influence of sphingomyelin acyl chain length on sphingomyelin-sterol interactions.4 [Matreya, LLC. Catalog No. 2137]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, J.-R., Zhang, H., Yau, L.D., et al. Improved sphingolipidomic approach based on ultra-high performance liquid chromatography and multiple mass spectrometries with application to cellular neurotoxicity. Anal. Chem. 86(12), 5688-5696 (2014).

    2. Willmann, J., Mahlstedt, K., Leibfritz, D., et al. Characterization of sphingomyelins in lipid extracts using a HPLC-MS-offline-NMR method. Anal. Chem. 79(11), 4188-4191 (2007).

    3. Jenkins, R.W., Clarke, C.J., Lucas, J.T., Jr., et al. Evaluation of the role of secretory sphingomyelinase and bioactive sphingolipids as biomarkers in hemophagocytic lymphohistiocytosis. Am. J. Hematol. 88(11), E265-E272 (2013).

    4. Li, X.M., Momsen, M.M., Brockman, H.L., et al. Sterol structure and sphingomyelin acyl chain length modulate lateral packing elasticity and detergent solubility in model membranes. Biophys. J. 85(6), 3788-3801 (2003).