3-hexanoyl-NBD Cholesterol
Item № 13221
CAS № 201731-19-3
Purity ≥98%
500 µg $68.00 $0.00
1 mg $129.00 $0.00
5 mg $544.00 $0.00

Pricing updated 2016-05-01. Prices are subject to change without notice.

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  • 3-C6-NBD Cholesterol

3-hexanoyl-NBD-Cholesterol is a fluorescently-tagged cholesterol derivative with the hydrophilic NBD fluorophore attached to carbon 3, at the hydrophilic end of cholesterol, separated by a 6-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. Fluorescently-tagged lipids have been used to study their interactions with proteins,1 their utilization by cells2 and liposomes,3 and for the development of assays for lipid metabolism.4,5

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Technical Information
Formal Name 6-[(7-nitro-2,1,3-benzoxadial-4-yl)amino]-cholest-5-en-3-ol
CAS Number 201731-19-3
  • 3-C6-NBD Cholesterol
Molecular Formula C39H58N4O5
Formula Weight 662.9
Purity ≥98%
Formulation A crystalline solid
SMILES [H]N(C1=CC=C([N+]([O-])=O)C2=NON=C12)CCCCCC(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 1S/C39H58N4O5/c1-25(2)10-9-11-26(3)30-15-16-31-29-14-13-27-24-28(19-21-38(27,4)32(29)20-22-39(30,31)5)47-35(44)12-7-6-8-23-40-33-17-18-34(43(45)46)37-36(33)41-48-42-37/h13,17-18,25-26,28-32,40H,6-12,14-16,19-24H2,1-5H3/t26-,28+,29+,30-,31+,32+,

WARNING - This product is not for human or veterinary use.

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Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability As supplied, 1 year from the QC date provided on the Certificate of Analysis, when stored properly
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References & Background Reading
Product Description References

1. Kumagai, K., Yasuda, S., Okemoto, K., et al. CERT mediates intermembrane transfer of various molecular species of ceramides. J Biol Chem 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. Moreno, M.J., Estronca, L.M.B.B., and Vaz, W.L.C. Translocation of phospholipids and dithionite permeability in liquid-ordered and liquid-disordered membranes. Biophys J 91 873-881 (2006).

4. 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 43 815-823 (2002).

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

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