A fluorescently tagged cholesterol
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3-dodecanoyl-NBD Cholesterol

Item No. 13220

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-(3S,10R,13R)-3-methoxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-tetradecahydro-1H-cyclopenta[α]phenanthrene
CAS Number
1246303-05-8
Synonyms
  • 3-C12-NBD Cholesterol
Molecular Formula
C45H70N4O5
Formula Weight
747.1
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 0.25 mg/mlEthanol: 1 mg/ml
λmax
229, 335, 465 nm
SMILES
[H]N(C1=CC=C([N+]([O-])=O)C2=NON=C12)CCCCCCCCCCCCC(O[C@H](C3)CC[C@@]4(C)C3=CC[C@]5([H])[C@]4([H])CC[C@@]6(C)[C@@]5([H])CC[C@]6([H])[C@@](C)([H])CCCC(C)C)=O
InChi Code
InChI=1S/C45H70N4O5/c1-31(2)16-15-17-32(3)36-21-22-37-35-20-19-33-30-34(25-27-44(33,4)38(35)26-28-45(36,37)5)53-41(50)18-13-11-9-7-6-8-10-12-14-29-46-39-23-24-40(49(51)52)43-42(39)47-54-48-43/h19,23-24,31-32,34-38,46H,6-18,20-22,25-30H2,1-5H3/t32-,34
InChi Key
TXCIESALPKGCNM-QNKNOTAZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    5 mg

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    Product Description

    C-12 NBD cholesterol is a fluorescently tagged cholesterol with the hydrophilic NBD fluorophore attached to the hydrophilic end of cholesterol, separated by a 12-carbon spacer. This design allows the cholesterol to properly orient in membrane bilayers while the fluorescent tag is presented outside of the bilayer. This should model the behavior of cholesterol in membranes better than the previously used 25-NBD cholesterol, which positions NBD directly on the 25th carbon of cholesterol at the hydrophobic terminus. NBD has excitation/emission maxima of 465/535 nm, respectively. Fluorescently tagged lipids have been used to study their interactions with proteins, their utilization by cells and liposomes, and for the development of assays for lipid metabolism.1,2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kumagai, K., Yasuda, S., Okemoto, K., et al. CERT mediates intermembrane transfer of various molecular species of ceramides. The Journal of Biological Chemisty 280(8), 6488-6495 (2005).

    2. Luo, M., Jones, S.M., Peters-Golden, M., et al. Nuclear localization of 5-lipoxygenase as a determinant of leukotriene B4 synthetic capacity. Proc. Natl. Acad. Sci. USA 100(21), 12165-12170 (2003).

    3. Tani, M., Okino, N., Mitsutake, S., et al. Specific and sensitive assay for alkaline and neutral ceramidases involving C12-NBD-ceramide. J. Biochem. 125(4), 746-749 (1999).