Filipina

Base Information

• Chemical Name: Filipina
• CAS No.: 480-49-9
• Molecular Formula: C35H58O11
• Molecular Weight: 654.839
• Hs Code.: 2932990090
• European Community (EC) Number: 637-175-3
• NSC Number: 760132
• Wikipedia: Filipin
• NCI Thesaurus Code: C80959
• ChEMBL ID: CHEMBL154669
• Mol file: 480-49-9.mol

Synonyms:Desoxylagosin;Filimarisin;Filipin;Filipin I;Filipin II;Filipin III;Filipin IV;NSC 3364;NSC-3364;NSC3364;U 5956;U-5956;U5956

Chemical Property of Filipina

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 163-180° (Bergy, Eble)
• Refractive Index: 1.535
• Boiling Point: 913.9 °C at 760 mmHg
• PKA: 12.77±0.70(Predicted)
• Flash Point: 279.3 °C
• PSA: 208.37000
• Density: 1.161 g/cm³
• LogP: 1.88800
• Storage Temp.: −20°C
• Solubility.: Soluble in Methanol (up to 10 mg/ml)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 654.39791266
• Heavy Atom Count: 46
• Complexity: 991

Purity/Quality:

98%,99%, ^*data from raw suppliers

Filipin III ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C1C(CC(CC(CC(CC(CC(CC(C(=CC=CC=CC=CC=CC(C(OC1=O)C)O)C)O)O)O)O)O)O)O)O
• Isomeric SMILES: CCCCCC(C1C(CC(CC(CC(CC(CC(CC(/C(=C/C=C/C=C/C=C/C=C/C(C(OC1=O)C)O)/C)O)O)O)O)O)O)O)O
• 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. 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] Produces arthritis rapidly in rabbits: Pras, Weissman, Drug Trade News, July 4, 1966, p 40; as a sterol probe in freeze-fracture cytochemistry.

Technology Process of Filipina

There total 30 articles about Filipina which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 39.0%

1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III (198955-38-3) → 15-Deoxylagosin (480-49-9)

Guidance literature:

1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III; With pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; ethylene glycol; at 20 - 60 ℃; for 3h;

With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 0 - 20 ℃; for 12h;

DOI:10.1016/S0040-4020(99)00457-3

Reference yield:

(10S,11R)-11-hydroxy-10-(1,1-dimethylethyl)dimethylsiloxy-2,4,6,8-dodecatetraenal (245681-49-6) → 15-Deoxylagosin (480-49-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 16 h

1.2: 70 percent / DMAP / toluene / 2 h

2.1: 49 percent / K₂CO₃; 18-crown-6 / toluene / 20 h / 60 °C

3.1: 70 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.33 h / -78 °C

4.1: 72 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

5.1: PPTS / methanol; ethane-1,2-diol; tetrahydrofuran / 3 h / 20 - 60 °C

5.2: 39 percent / HF*pyridine / pyridine; tetrahydrofuran / 12 h / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; ethylene glycol; toluene; 1.1: Esterification / 1.2: Esterification / 2.1: Cyclization / 3.1: Reduction / 4.1: Substitution / 5.1: Reduction / 5.2: Substitution;

DOI:10.1016/S0040-4020(99)00457-3

Reference yield:

(4E,6E,8E,10E)-(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-12,12-dimethoxy-dodeca-4,6,8,10-tetraen-2-ol → 15-Deoxylagosin (480-49-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 52 mg / Amberlyst-15; H₂O / tetrahydrofuran / 2 h

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 16 h

2.2: 70 percent / DMAP / toluene / 2 h

3.1: 49 percent / K₂CO₃; 18-crown-6 / toluene / 20 h / 60 °C

4.1: 70 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.33 h / -78 °C

5.1: 72 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

6.1: PPTS / methanol; ethane-1,2-diol; tetrahydrofuran / 3 h / 20 - 60 °C

6.2: 39 percent / HF*pyridine / pyridine; tetrahydrofuran / 12 h / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; amberlyst-15; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; water; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; ethylene glycol; toluene; 1.1: Hydrolysis / 2.1: Esterification / 2.2: Esterification / 3.1: Cyclization / 4.1: Reduction / 5.1: Substitution / 6.1: Reduction / 6.2: Substitution;

DOI:10.1016/S0040-4020(99)00457-3

upstream raw materials:

1',26-bis-O-(1,1-dimethylethyl)dimethylsilyl-3,5:7,9:11,13-tris-O-(1-methylethylidine)-15-O-triisopropylsiloxy-filipin III

(10S,11R)-11-hydroxy-10-(1,1-dimethylethyl)dimethylsiloxy-2,4,6,8-dodecatetraenal

(6S,7R)-7-benzoyloxy-6-(1,1-dimethylethyl)dimethylsiloxy-2,4-octadienal

(10S,11R)-11-benzoyloxy-10-(1,1-dimethylethyl)dimethylsiloxy-2,4,6,8-dodecatetraenal

Downstream raw materials:

1',3:5,7:9,11:13,15-tetrakis-O-(1-methylethylidene)filipin III

Refernces

• 1、 Richardson, Timothy I.,Rychnovsky, Scott D.. "Total Synthesis of Filipin III". . p. 12360 - 12361. Retrieved 2007/10/03.