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FILIPIN III Basic information

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Product Name:

FILIPIN III

Synonyms:

nsc3364;oxacyclooctacosa-17,19,21,23,25-pentaen-2-one,4,6,8,10,12,14,16,27-octahydroxy;u-5956;4S,6S,8S,10R,12R,14R,16S,27S-OCTAHYDROXY-3R-(1R-HYDROXY-HEXYL)17,28R-DIMETHYL-OXACYCLOOCTACOSA-17E,19E,21E,23E,25E-PENTAEN-2-ONE;FILIPIN III;filipin iii from streptomyces*filipinensis;4,6,8,10,12,14,16,27-Octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyloxacyclooctacosa-17,19,21,23,25-pentaen-2-one;16,18,20,22,24-Octacosapentenoic acid, 3,5,7,9,11,13,15,26,27-nonahydroxy-2-(1-hydroxyhexyl)-16-methyl-, 27-lactone

CAS:

480-49-9

MF:

C35H58O11

MW:

654.83

EINECS:

Product Categories:

Enzyme Inhibitors;Enzyme Inhibitors by Type;Substrate Analogs

Mol File:

480-49-9.mol

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FILIPIN III Chemical Properties

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Melting point

163-180° (Bergy, Eble)

alpha

D25 -245° (c = 0.8 in DMF)

Boiling point

913.9±65.0 °C(Predicted)

density

1.161±0.06 g/cm3(Predicted)

storage temp.

−20°C

pka

12.77±0.70(Predicted)

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Safety Information

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Hazard Codes

Risk Statements

36/37/38

Safety Statements

26-36

WGK Germany

RTECS

RN9800000

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MSDS Information

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Provider

Language

SigmaAldrich

English

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FILIPIN III Usage And Synthesis

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Uses

Filipin III is the major component of the filipin complex, a family of pentaene antifungal metabolites first isolated from Streptomyces filipinensis and reported by researchers at Upjohn in 1955. Filipin III is a potent broad spectrum antifungal agent that also exhibits antitumor and antiviral activities. Filipin III acts by binding cell membrane sterols, disrupting membrane integrity. This sterol selectivity has led to the use of filipin III as a routine diagnostic probe for quantifying cholesterol in mammalian cells.

Uses

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. The binding of cholesterol also decreases the intrinsic fluorescence of Filipin, and this property has also been used to detect cholesterol in membrane fractions.[Cayman Chemical]

Uses

Produces arthritis rapidly in rabbits: Pras, Weissman, Drug Trade News, July 4, 1966, p 40; as a sterol probe in freeze-fracture cytochemistry.

Definition

ChEBI: A macrolide that is the major component of a mixture of four isomeric polyene macrolides isolated from Streptomyces filipinensis.

Product Name	FILIPIN III
CAS No	480-49-9
EC-No
Min. Order	1g
Purity	≥98%
Supply Ability	g/kg/Ton
Release date	2019/12/26

FILIPIN III

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