Filipin III

• CAT Number: I011394
• CAS Number: 480-49-9
• Molecular Formula: C35H58O11
• Molecular Weight: 654.80
• Purity: ≥95%
• Synonyms: (3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,16,27-Octahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• Target: Fungal
• Solubility: Soluble to 5 mM in DMSO
• Storage: Store at -20℃
• IUPAC Name: (3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,16,27-octahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
• InChI: InChI=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-,29+,30+,31-,32+,33+,34-/m1/s1
• InChIKey: IMQSIXYSKPIGPD-YQRUMEKGSA-N
• SMILES: CCCCC[C@H]([C@@H]1[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@H](C[C@@H](/C(=C/C=C/C=C/C=C/C=C/[C@@H]([C@H](OC1=O)C)O)/C)O)O)O)O)O)O)O)O

Filipin III（Cat No.:I011394）is a polyene macrolide antibiotic primarily used in research to study cholesterol and lipid rafts in cellular membranes. It binds specifically to cholesterol, forming a fluorescent complex that can be visualized under a microscope, making it an essential tool for studying membrane structure and function. Due to its ability to disrupt cholesterol-rich membranes, Filipin III is widely used in studies of membrane trafficking, endocytosis, and lipid metabolism. It is also employed in the investigation of various diseases related to lipid dysregulation and cellular cholesterol homeostasis.

Reference

Filipin, an antifungal antibiotic: Isolation and properties. Whitfield G.B. et al. J. Am. Chem. Soc. 1955, 77, 4799.Separation of polyene antifungal antibiotics by high speed liquid chromatography. Mechlinski W. & Schaffner C.P. J. Chromatogr. 1974, 99, 619.Inhibition of fungi by filipin and its antagonism by sterols. Gottlieb D. et al. Phytopathology 1960, 50, 594.