A fluorescently tagged sphingolipid
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C12 NBD Sphingomyelin (d18:1/12:0)

Item No. 24329

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(E)-3-hydroxy-2-(12-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)dodecanamido)octadec-4-en-1-yl (2-(trimethylammonio)ethyl) phosphate
Synonyms
  • NBD SM(d18:1/12:0)
  • NBD Sphingomyelin (d18:1/12:0)
  • N-dodecanoyl-NBD Sphingosylphosphorylcholine
Molecular Formula
C41H73N6O9P
Formula Weight
825.0
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): solubleMethanol: soluble
SMILES
O=C(CCCCCCCCCCCNC1=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/C41H73N6O9P/c1-5-6-7-8-9-10-11-12-13-15-18-21-24-27-38(48)36(34-55-57(52,53)54-33-32-47(2,3)4)43-39(49)28-25-22-19-16-14-17-20-23-26-31-42-35-29-30-37(46(50)51)41-40(35)44-56-45-41/h24,27,29-30,36,38,48H,5-23,25-26,28,31-34H2,1-4H3,(H2-,42,43,45,49,52,53)/b27-24+
InChi Key
FCQMKLRMKNYONQ-SOYKGTTHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    100 µg

    $268

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    1 mg

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    Product Description

    C12 NBD sphingomyelin is a biologically active derivative of sphingomyelin (Item Nos. 22674 | 24345) that is tagged with a fluorescent C12 nitrobenzoxadiazole (C12 NBD) group. C12 NBD sphingomyelin has been used to study the metabolism and transport of sphingomyelins.1,2 It is hydrolyzed by sphingomyelinase to C12 NBD ceramide (Item No. 10007958).1 This product is a mixture of the D-erythro and L-threo isomers of C12 NBD sphingomyelin. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1619]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Loidl, A., Claus, R., Deigner, H.P., et al. High-precision fluorescence assay for sphingomyelinase activity of isolated enzymes and cell lysates. J. Lipid Res. 43(5), 815-823 (2002).

    2. Nakagawa, T., Tani, M., Kita, K., et al. Preparation of fluorescence-labeled GM1 and sphingomyelin by the reverse hydrolysis reaction of sphingolipid ceramide N-deacylase as substrates for assay of sphingolipid-degrading enzymes and for detection of sphingolipid-binding proteins. J. Biochem. 126(3), 601-611 (1999).