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FILIPIN III

CAS No.
480-49-9
Chemical Name:
FILIPIN III
Synonyms
u-5956;nsc3364;Nsc38092;27-lactone;FILIPIN III;filimarisin;15-Deoxylagosin;1'-epi-Filipin IV;1'-Hydroxyfilipin II;FILIPIN III USP/EP/BP
CBNumber:
CB0276061
Molecular Formula:
C35H58O11
Molecular Weight:
654.83
MDL Number:
MFCD30742956
MOL File:
480-49-9.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

FILIPIN III Properties

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.
FDA UNII 87Z59R7D14

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  RN9800000
HS Code  2932990090
NFPA 704
0
2 0

FILIPIN III price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich F4767 Filipin III from Streptomyces filipinensis ≥85% (HPLC) 480-49-9 1mg $198 2024-03-01 Buy
Sigma-Aldrich F4767 Filipin III from Streptomyces filipinensis ≥85% (HPLC) 480-49-9 5mg $785 2024-03-01 Buy
Cayman Chemical 70440 Filipin III ≥90% 480-49-9 500μg $110 2024-03-01 Buy
Cayman Chemical 70440 Filipin III ≥90% 480-49-9 1mg $152 2024-03-01 Buy
Cayman Chemical 70440 Filipin III ≥90% 480-49-9 5mg $602 2024-03-01 Buy
Product number Packaging Price Buy
F4767 1mg $198 Buy
F4767 5mg $785 Buy
70440 500μg $110 Buy
70440 1mg $152 Buy
70440 5mg $602 Buy

FILIPIN III Chemical Properties,Uses,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

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

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

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.

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

Global( 69)Suppliers
Supplier Tel Email Country ProdList Advantage
career henan chemical co
+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-89586680 +86-18192503167 1026@dideu.com China 9320 58
BOC Sciences
+16314854226 inquiry@bocsci.com United States 19743 58
Shanghai Acmec Biochemical Technology Co., Ltd.
+undefined18621343501 product@acmec-e.com China 33349 58
Aladdin Scientific
+1-833-552-7181 sales@aladdinsci.com United States 57511 58
Sinopharm Chemical Reagent Co,Ltd. 86-21-63210123 sj_scrc@sinopharm.com China 9823 79
Guangzhou Isun Pharmaceutical Co., Ltd 020-39119399 18927568969 isunpharm@qq.com China 4428 55
ShangHai Caerulum Pharma Discovery Co., Ltd. 18149758185 sales-cpd@caerulumpharma.com China 3420 58
Sigma-Aldrich 021-61415566 800-8193336 orderCN@merckgroup.com China 51471 80

View Lastest Price from FILIPIN III manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
FILIPIN III pictures 2019-12-26 FILIPIN III
480-49-9
US $1.00 / g 1g ≥98% g/kg/Ton Career Henan Chemical Co
  • FILIPIN III pictures
  • FILIPIN III
    480-49-9
  • US $1.00 / g
  • ≥98%
  • Career Henan Chemical Co

FILIPIN III Spectrum

filimarisin 28-dimethyl--3-(1-hydroxyhexyl)-1 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 FILIPIN III USP/EP/BP 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)- (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 27-nonahydroxy-2-(1-hydroxyhexyl)-16-methyl- 27-lactone 24-Octacosapentenoic acid (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 480-49-9 C35H58O11 Enzymes, Inhibitors, and Substrates Enzyme Inhibitors by Type Enzyme Inhibitors BioChemical Biochemicals and Reagents Substrate Analogs Enzyme Inhibitors Enzyme Inhibitors by Type Substrate Analogs