3-hexanoyl-NBD Cholesterol

Cayman Chemical Item Number 13221

3-C6-NBD Cholesterol (CAS 201731-19-3)

3-hexanoyl-NBD Cholesterol (CAS 201731-19-3)

See more

Description

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

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).

Synonyms
  • 3-C6-NBD Cholesterol
Formal Name 6-​[(7-​nitro-​2,​1,​3-​benzoxadial-​4-​yl)amino]-​cholest-​5-​en-​3-​ol
CAS Number 201731-19-3
Molecular Formula C39H58N4O5
Formula Weight 662.9
Formulation A crystalline solid
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
[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
Copy InCHI code to clipboard
​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+,
InCHI Key
Copy InCHI key to clipboard
YZAQIPGLFHPDPI-FIWRCADXSA-N

Download free InCHI Key generation software

Size Price Quantity Subtotal
500 µg $68.00 $0.00
1 mg $129.00 $0.00
5 mg $544.00 $0.00
Bulk Contact
Cart Total $0.00

Please Login or Register to use this page.

Pricing updated 2014-04-23. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

25(R)-27-hydroxy Cholesterol
25(S)-27-hydroxy Cholesterol Exclusive
3-dodecanoyl-NBD Cholesterol
7-dehydro Cholesterol
Cholesterol Sulfate (sodium salt)
DISBAC10
Show all 6 Hide all but first 3

Downloads

Batch-specific Information

Get batch-specific data and documents by batch number


Separate multiple batch numbers with commas

Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Join us! · Experimental Biology 2014 · San Diego, California · April 26-30, 2014 · Booth 323 Join us! · ASPET Symposium 2014: Scientists versus Street Chemists: The Toxicity of Designer Marijuana · San Diego, California · April 30, 2014
Other Resources
About Cayman Management Team Company Profile ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map Conference Travel Grants

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2014 Cayman Chemical Company

Manufacturer, supplier, and vendor of biochemical reagents, assay kits, forensic chemistry standards, antibodies, and proteins for scientific research · Buy now! · Analytical testing services and custom synthesis also available

Lost password?