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Merck
CN

700002P

Avanti

F7-Cholesterol

Avanti Research™ - A Croda Brand

Synonym(s):

25,26,26,26,27,27,27-heptafluorocholesterol

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About This Item

Empirical Formula (Hill Notation):
C27H39OF7
CAS Number:
153463-21-9
Molecular Weight:
512.59
MDL number:
MFCD28143665
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

F7-Cholesterol, Avanti Research™ - A Croda Brand

form

powder

SMILES string

FC(F)(F)C(F)(C(F)(F)F)CCC[C@H]([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@]4(CC[C@@H](CC4=CC3)O)C)CC2)CC1)C)C

InChI

1S/C27H39F7O/c1-16(5-4-12-25(28,26(29,30)31)27(32,33)34)20-8-9-21-19-7-6-17-15-18(35)10-13-23(17,2)22(19)11-14-24(20,21)3/h6,16,18-22,35H,4-5,7-15H2,1-3H3/t16-,18+,19+,20-,21+,22+,23+,24-/m1/s1

InChI key

DUAIJEYNEJQOCE-OLSVQSNTSA-N

assay

>99% (TLC)

packaging

pkg of 1 × 5 mg (700002P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

shipped in

dry ice

storage temp.

−20°C

Application

F7-Cholesterol has been used:
  • in the preparation of liposomes for DNA delivery studies
  • to investigate its rescue functionality in hedgehog signaling in sterol-depleted cells
  • in preparation of monolayers for pressure and area isotherms studies

Biochem/physiol Actions

F7-Cholesterol has potential biological applications. It has a negative dipole moment. F7-Cholesterol rescues hedgehog signaling in sterol-depleted cells. The molecular orientation and phospholipid interaction of F7-cholesterol is similar to hydrogenated cholesterol.

General description

F7-Cholesterol is a fluorinated derivative of cholesterol. It is a cholesterol analog. F7-Cholesterol is useful as helper lipid in conjunction with vectors for DNA transfection.

Packaging

5 mL Amber Glass Screw Cap Vial (700002P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

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Fluorocholesterols, in contrast to hydroxycholesterols, exhibit interfacial properties similar to cholesterol
Kauffman JM, et al.
Journal of Lipid Research, 41(6), 991-1003 (2000)
The effect of a fluorinated cholesterol derivative on the stability and physical properties of cationic DNA vectors
Paiva D, et al.
Soft Matter, 9(2), 401-409 (2013)
Langmuir monolayers of monocationic lipid mixed with cholesterol or fluorocholesterol: DNA adsorption studies
Paiva D, et al.
Langmuir, 29(6), 1920-1925 (2013)
Synthesis of deuterium-and tritium-labeled 25, 26, 26, 26, 27, 27, 27-heptafluorocholesterol
Su X, et al.
Journal of Labelled Compounds, 42(6), 509-518 (1999)
Cellular cholesterol directly activates smoothened in hedgehog signaling
Huang P, et al.
Cell, 166(5), 1176-1187 (2016)
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