A sphingolipid
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C16 Sphingomyelin (d18:1/16:0)

Item No. 10007946

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxy-7S-[(1R,2E)-1-hydroxy-2-hexadecen-1-yl]-N,N,N-trimethyl-9-oxo-3,5-dioxa-8-aza-4-phosphatetracosan-1-aminium, 4-oxide, inner salt
CAS Number
6254-89-3
Synonyms
  • Palmitoyl Sphingomyelin
  • N-Palmitoyl-D-erythro-Sphingosylphosphorylcholine
  • SM(d18:1/16:0)
  • Sphingomyelin (d18:1/16:0)
Molecular Formula
C39H79N2O6P
Formula Weight
703.0
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Ethanol: 10 mg/ml
SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N([H])C(CCCCCCCCCCCCCCC)=O)COP(OCC[N+](C)(C)C)([O-])=O
InChi Code
InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1
InChi Key
RWKUXQNLWDTSLO-GWQJGLRPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    C16 Sphingomyelin is a naturally occurring sphingolipid.1,2,3 Levels of C16 sphingomyelin are elevated in the prefrontal cortex and cerebellum in a rat model of diabetes induced by streptozotocin (STZ; Item No. 13104), as well as in the liver in mouse models of Niemann-Pick type C1 disease.1,2 Plasma levels of C16 sphingomyelin are decreased in patients with prostate cancer.3 Model membranes containing C16 sphingomyelin, 1-palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC; Item No. 15102), and cholesterol (Item No. 9003100) have been used in the study of lipid raft dynamics and membrane organization.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fiedorowicz, A., Prokopiuk, S., Zendzian-Piotrowska, M., et al. Sphingolipid profiles are altered in prefrontal cortex of rats under acute hyperglycemia. Neuroscience 256, 282-291 (2014).

    2. Praggastis, M., Tortelli, B., Zhang, J., et al. A murine Niemann-Pick C1 I1061T knock-in model recapitulates the pathological features of the most prevalent human disease allele. J. Neurosci. 35(21), 8091-8106 (2015).

    3. Awwad, H.M., Ohlmann, C.H., Stoeckle, M., et al. Choline-phospholipids inter-conversion is altered in elderly patients with prostate cancer. Biochimie 126, 108-114 (2016).

    4. de Almeida, R.F.M., Loura, L.M.S., Fedorov, A., et al. Lipid rafts have different sizes depending on membrane composition: A time-resolved fluorescence resonance energy transfer study. J. Mol. Biol. 346(4), 1109-1120 (2005).

    5. Halling, K.K., Ramstedt, B., Nyström, J.H., et al. Cholesterol interactions with fluid-phase phospholipids: Effect on the lateral organization of the bilayer. Biophys. J. 95(8), 3861-3871 (2008).

    Product Citations

    Nobumoto, W., Naganuma, T., Nozaka, N., et al. Acid ceramidase ASAH1 is a key regulator of epidermal ceramide levels and composition. The Journal of Biological Chemisty 302(3), 111178 (2026).