A fluorescently tagged C12 sphingomyelin
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Unlabeled Version(s)
46184C12 Sphingomyelin (d18:1/12:0)
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BODIPY-C12 Sphingomyelin

Item No. 45795

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(T-4)-[(7S)-20-[5-[(3,5-dimethyl-2H-pyrrol-2-ylidene-κN)methyl]-1H-pyrrol-2-yl-κN]-4-hydroxy-7-[(1R,2E)-1-hydroxy-2-hexadecen-1-yl]-N,N,N-trimethyl-9-oxo-3,5-dioxa-8-aza-4-phosphaeicosan-1-aminium 4-oxidato(2-)]difluoro-boron
CAS Number
956294-43-2
Synonyms
  • BODIPY-N-Dodecanoyl-D-erythro-Sphingosylphosphorylcholine
  • BODIPY-Lauroyl Sphingomyelin
  • BODIPY-SM(d18:1/12:0)
  • BODIPY-Sphingomyelin (d18:1/12:0)
  • B12SPM
Molecular Formula
C46H80BF2N4O6P
Formula Weight
864.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): Soluble
SMILES
O[C@H](/C=C/CCCCCCCCCCCCC)[C@H](COP(OCC[N+](C)(C)C)([O-])=O)NC(CCCCCCCCCCCC1=CC=C2[N]1[B-]([F])([N+]3=C(C=C(C3=C2)C)C)[F])=O
InChi Code
InChI=1S/C46H80BF2N4O6P/c1-7-8-9-10-11-12-13-14-15-18-21-24-27-30-45(54)43(38-59-60(56,57)58-35-34-53(4,5)6)50-46(55)31-28-25-22-19-16-17-20-23-26-29-41-32-33-42-37-44-39(2)36-40(3)51(44)47(48,49)52(41)42/h27,30,32-33,36-37,43,45,54H,7-26,28-29,31,34-35,38H2,1-6H3,(H-,50,55,56,57)/b30-27+/t43-,45+/m0/s1
InChi Key
PYNXQOJZZCZSSS-BDMUPLOZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $208

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    1 mg

    $395

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    Product Description

    BODIPY-C12 Sphingomyelin is a fluorescently tagged form of C12 sphingomyelin (Item No. 46184). Upon hydrolysis by acid sphingomyelinase, BODIPY-C12 ceramide (B12Cer; Item No. 25997) is released and its fluorescence can be used to quantify acid sphingomyelinase activity.1 BODIPY-C12 Sphingomyelin has been used to quantify acid sphingomyelinase activity in plasma from patients with Niemann-Pick disease and in the cerebrospinal fluid (CSF) of mice and humans.1,2 It can also be used for studying sphingomyelin cellular transport and signaling pathways.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. He, X., Chen, F., Dagan, A., et al. A fluorescence-based, high-performance liquid chromatographic assay to determine acid sphingomyelinase activity and diagnose types A and B Niemann-Pick disease. Anal. Biochem. 314(1), 116-120 (2003).

    2. Mühle, C., Huttner, H.B., Walter, S., et al. Characterization of acid sphingomyelinase activity in human cerebrospinal fluid. PLos One 8(5), e62912 (2013).