A fluorescently tagged sphingolipid
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C6 NBD Sphingomyelin (d18:1/6:0)

Item No. 24328

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-14-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-9-oxo-3,5-dioxa-8-aza-4-phosphatetradecan-1-aminium, 4-oxide inner salt
Synonyms
  • N-hexanoyl-NBD Sphingosylphosphorylcholine
  • NBD SM(d18:1/6:0)
  • NBD Sphingomyelin (d18:1/6:0)
Molecular Formula
C35H61N6O9P
Formula Weight
740.9
Purity
≥98% (mixture of isomers)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C(CCCCCNC1=CC=C([N+]([O-])=O)C2=NON=C12)NC(COP(OCC[N+](C)(C)C)([O-])=O)C(O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C35H61N6O9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-18-21-32(42)30(28-49-51(46,47)48-27-26-41(2,3)4)37-33(43)22-19-17-20-25-36-29-23-24-31(40(44)45)35-34(29)38-50-39-35/h18,21,23-24,30,32,42H,5-17,19-20,22,25-28H2,1-4H3,(H2-,36,37,39,43,46,47)/b21-18+
InChi Key
YDBDYTGWMRUUSN-DYTRJAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

    $215

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    1 mg

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    Product Description

    C6 NBD sphingomyelin is a biologically active derivative of sphingomyelin (Item Nos. 22674 | 24345) that is tagged with a fluorescent C6 nitrobenzoxadiazole (C6 NBD; Item No. 18871) group. C6 NBD sphingomyelin has been used to study the metabolism and transport of sphingomyelins.1,2 It is degraded in the plasma membrane to C6 NBD ceramide (Item No. 62527) by neutral sphingomyelinase, an enzyme with three-fold higher activity in undifferentiated HT29 cells than in differentiated cells.1 Unlike endogenous long-chain sphingomyelin and C6 sphingomyelin, C6 NBD sphingomyelin can be transported to the cell surface even in the presence of the vesicular transport inhibitor brefeldin A (Item No. 11861), but this transport can be blocked by multidrug resistance protein inhibitors in CHO cells.2 This product is a mixture of the D-erythro and L-threo isomers of sphingomyelin. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1912]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kok, J.W., Babia, T., Klappe, K., et al. Fluorescent, short-chain C6-NBD-sphingomyelin, but not C6-NBD-glucosylceramide, is subject to extensive degradation in the plasma membrane: Implications for signal transduction related to cell differentiation. Biochem. J. 309(Pt 3), 905-912 (1995).

    2. van Helvoort, A., Giudici, M.L., Thielemans, M., et al. Transport of sphingomyelin to the cell surface is inhibited by brefeldin A and in mitosis, where C6-NBD-sphingomyelin is translocated across the plasma membrane by a multidrug transporter activity. J. Cell Sci. 110(Pt 1), 75-83 (1997).