Filipin III
Item № 70440
CAS № 480-49-9
Purity ≥85%
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500 µg $89.00 $0.00
1 mg $124.00 $0.00
5 mg $496.00 $0.00

Pricing updated 2015-10-05. Prices are subject to change without notice.

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Cholesterol is both an important structural component of cell membranes and an early intermediate in hormone and bile acid biosynthesis. The localization and measurement of cholesterol in cells is therefore of great interest. Filipin is the collective name given to four isomeric polyene macrolides isolated from cultures of S. filipinensis; Filipin III is the predominant isomer and the one used in most studies. Filipin binds to cholesterol in membranes, forming ultrastructural aggregates and complexes which can be visualized by freeze-fracture electron microscopy.1,2 The binding of cholesterol also decreases the intrinsic fluorescence of Filipin, and this property has also been used to detect cholesterol in membrane fractions.3

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Technical Information
Formal Name 4S,6S,8S,10R,12R,14R,16S,27S-octahydroxy-3R-(1R-hydroxy-hexyl)17,28R-dimethyl-oxacyclooctacosa-17E,19E,21E,21E,23E,25E-pentaen-2-one
CAS Number 480-49-9
Molecular Formula C35H58O11
Formula Weight 654.8
Purity ≥85%
Formulation A crystalline solid
λmax 323, 339, 357 nm
SMILES O[C@@H]1/C(C)=C/C=C/C=C/C=C/C=C/[C@H](O)[C@@H](C)OC([C@@]([C@H](O)CCCCC)([H])[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C1)=O
InChI Code 1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+/t24-,25+,26-,27+,28-

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

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability 1 year
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References & Background Reading
Product Description References

1. Castanho, M.A.R.B., Coutinho, A., and Prieto, M.J.E. Absorption and fluorescence spectra of polyene antibiotics in the presence of cholesterol. J Biol Chem 267 204-209 (1992).

2. Miller, R.G. Mini Review. The use and abuse of filipin to localize cholesterol in membranes. Cell Biol Int Rep 8(7) 519-535 (1984).

3. Severs, N.J., and Robenek, H. Detection of microdomains in biomembranes. An appraisal of recent developments in freeze-fracture cytochemistry. Biochim Biophys Acta 737 373-408 (1983).

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