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FILIPIN III

Product Name
FILIPIN III
CAS No.
480-49-9
Chemical Name
FILIPIN III
Synonyms
u-5956;nsc3364;Nsc38092;27-lactone;filimarisin;FILIPIN III;15-Deoxylagosin;1'-epi-Filipin IV;1'-Hydroxyfilipin II;FILIPIN III USP/EP/BP
CBNumber
CB0276061
Molecular Formula
C35H58O11
Formula Weight
654.83
MOL File
480-49-9.mol
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FILIPIN III Property

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
solubility 
Soluble in Methanol (up to 10 mg/ml)
form 
solid
pka
12.77±0.70(Predicted)
color 
White or light yellow
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in methanol may be stored under inert gas at -20°C for up to 2 months.
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
RN9800000
HS Code 
2932990090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
F4767
Product name
Filipin III from Streptomyces filipinensis
Purity
≥85% (HPLC)
Packaging
1mg
Price
$198
Updated
2024/03/01
Sigma-Aldrich
Product number
F4767
Product name
Filipin III from Streptomyces filipinensis
Purity
≥85% (HPLC)
Packaging
5mg
Price
$785
Updated
2024/03/01
Cayman Chemical
Product number
70440
Product name
Filipin III
Purity
≥90%
Packaging
500μg
Price
$110
Updated
2024/03/01
Cayman Chemical
Product number
70440
Product name
Filipin III
Purity
≥90%
Packaging
1mg
Price
$152
Updated
2024/03/01
Cayman Chemical
Product number
70440
Product name
Filipin III
Purity
≥90%
Packaging
5mg
Price
$602
Updated
2024/03/01
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FILIPIN III Chemical Properties,Usage,Production

Description

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.

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.

Biochem/physiol Actions

Filipin is a polyene macrolide antibiotic and antifungal. The antifungal mechanism of action may be due to altering membrane permeability and associated functions by binding to membrane sterols. Filipin inhibits prion protein (PrP) endocytosis and causes the release of PrP from the plasma membrane.

storage

Store at -20°C

References

1) Smejkal and Hof (1994),?Cholesterol-specific probe for lipoproteins immobilized on nitrocellulose membranes; Biotechniques,?16?68 2) Bornig and Geyer ?(1974),?Staining of cholesterol with the fluorescent antibiotic “filipin”; Acta Histochemica,?50?110 3) Huo?et al. (2003),?Lipid rafts/caveolae are essential for insulin-like growth factor-1 receptor signaling during 3T3-L1 preadipocyte differentiation induction; J. Biol. Chem.,?278?11561 4) Marella?et al. (2002),?Filipin prevents pathological prion protein accumulation by reducing endocytosis and inducing cellular PrP release; J. Biol. Chem.,?277?25457

FILIPIN III Preparation Products And Raw materials

Raw materials

Preparation Products

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FILIPIN III Suppliers

Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
Advantage
55
ShangHai Caerulum Pharma Discovery Co., Ltd.
Tel
18149758185 18149758185
Email
sales-cpd@caerulumpharma.com
Country
China
ProdList
3466
Advantage
58
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51456
Advantage
80
Beijing Jin Ming Biotechnology Co., Ltd.
Tel
010-60605840 18892239720
Fax
010-60605840
Email
psaitong@jm-bio.com
Country
China
ProdList
12306
Advantage
58
Lynnchem
Tel
86-(0)29-85992781 17792393971
Email
info@lynnchem.com
Country
China
ProdList
4587
Advantage
58
Novachemistry
Tel
44-20819178-90 02081917890
Fax
(0)2080432064
Email
info@novachemistry.com
Country
United Kingdom
ProdList
4381
Advantage
58
Aikon International Limited
Tel
025-66113011 13155353615
Fax
(7)02557626880
Email
qzhang@aikonchem.com
Country
China
ProdList
15394
Advantage
58
Shanghai Hongye Biotechnology Co. Ltd
Tel
400-9205774
Email
sales@glpbio.cn
Country
China
ProdList
6777
Advantage
58
Shenzhen Polymeri Biochemical Technology Co., Ltd.
Tel
+86-400-002-6226 +86-13028896684;
Email
sales@rrkchem.com
Country
China
ProdList
57401
Advantage
58
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View Lastest Price from FILIPIN III manufacturers

Career Henan Chemical Co
Product
FILIPIN III 480-49-9
Price
US $1.00/g
Min. Order
1g
Purity
≥98%
Supply Ability
g/kg/Ton
Release date
2019-12-25

480-49-9, FILIPIN IIIRelated Search:


  • filimarisin
  • 28-dimethyl--3-(1-hydroxyhexyl)-1
  • (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
  • 16;20;22;24-OCTACOSAPENTENOIC ACID; 3;5;7;9;11;13;15;26;27-NONAHYDROXY-2-(1-HYDROXYHEXYL)-16-METHYL-; 27-LACTONE
  • 24-Octacosapentenoic acid
  • 27-lactone
  • 27-nonahydroxy-2-(1-hydroxyhexyl)-16-methyl-
  • (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
  • 1',26-Dihydroxyfilipin I
  • 15-Deoxylagosin
  • 1'-epi-Filipin IV
  • 1'-Hydroxyfilipin II
  • 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
  • Nsc38092
  • Oxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,16,27-octahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-
  • 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
  • nsc3364
  • oxacyclooctacosa-17,19,21,23,25-pentaen-2-one,4,6,8,10,12,14,16,27-octahydroxy
  • u-5956
  • Oxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,16,27-octahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-, (3R,4S,6S,8S,10R,12R,14R,16S,17E,19E,21E,23E,25E,27S,28R)-
  • FILIPIN III USP/EP/BP
  • 480-49-9
  • C35H58O11
  • Enzymes, Inhibitors, and Substrates
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