An internal standard for the quantification of C16 sphingomyelin
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C16 Sphingomyelin-d9 (d18:1/16:0-d9)

Item No. 27551

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7S)-4-hydroxy-7-[(1R,2E)-1-hydroxy-2-hexadecenyl]-N,N,N-trimethyl-9-oxo-3,5-dioxa-8-aza-4-phosphatetracosan-21,21,22,22,23,23,24,24,24-d9-1-aminium, 4-oxide, inner salt
CAS Number
2415226-88-7
Synonyms
  • Palmitoyl Sphingomyelin-d9
  • N-Palmitoyl-D-erythro-Sphingosylphosphorylcholine-d9
  • SM(d18:1/16:0-d9)
  • Sphingomyelin (d18:1/16:0-d9)
Molecular Formula
C39H70D9N2O6P
Formula Weight
712.1
Purity
≥99% deuterated forms (d1-d9)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Ethanol: 10 mg/ml
SMILES
O=C(CCCCCCCCCCCC([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])N[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)[C@H](O)/C=C/CCCCCCCCCCCCC
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/i2D3,7D2,9D2,11D2
InChi Key
RWKUXQNLWDTSLO-YWFJKMPESA-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

    C16 Sphingomyelin-d9 is intended for use as an internal standard for the quantification of C16 sphingomyelin (Item No. 10007946) by GC- or LC-MS. 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 As this product is derived from a natural source, there may be variations in the sphingoid backbone.

    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).