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Diflorasone diacetate

Diflorasone diacetate Structure
Diflorasone diacetate
  • CAS No.33564-31-7
  • Chemical Name:Diflorasone diacetate
  • CBNumber:CB5754117
  • Molecular Formula:C26H32F2O7
  • Formula Weight:494.52
  • MOL File:33564-31-7.mol
Diflorasone diacetate Property
  • Melting point 221-223° (dec)
  • alpha D +61° (chloroform)
  • Boiling point 235°C (rough estimate)
  • Density 1.2001 (estimate)
  • storage temp. Refrigerator
  • solubility Chloroform (Slightly), Methanol (Slightly)
  • pka 12.63±0.70(Predicted)
  • form Solid
  • color White to Off-White
  • Water Solubility 6.5mg/L(22 ºC)
  • CAS DataBase Reference 33564-31-7(CAS DataBase Reference)
  • FDA UNII 7W2J09SCWX
Safety
  • Hazard Codes  :Xn
  • Risk Statements  :20/21/22-40
  • Safety Statements  :22-36
  • WGK Germany  :3
  • RTECS  :TU3722000
  • HS Code  :2937220000
  • NFPA 704:
    0
    3 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H312+H332-H351
  • Precautionary statements P202-P261-P280-P302+P352+P312-P304+P340+P312-P308+P313

Diflorasone diacetate Chemical Properties,Usage,Production

  • Chemical Properties White Solid
  • Originator Florone,Upjohn,US,1978
  • Uses Anti-inflammatory (topical)
  • Uses An anti-inflammatory and anti-itching corticosteroid usually present in topical creams.
  • Definition ChEBI: The 17,21-diacetate derivative of diflorasone. It is used topically for its anti-inflammatory and antipruritic properties in the treatment of various skin disorders.
  • Manufacturing Process 6α-Fluoro-9β-epoxy-17α,21-dihydroxy-16α-methyl-1,4-pregnadiene-3,20- dione-21-acetate:To a solution of 6.78 g of 6α-fluoro-9α-bromo-11β,17α,21- trihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione-21-acetate in 175 ml of acetone was added 6.78 g of potassium acetate and the resulting suspension was heated under reflux for a period of 17 hours. The mixture was then concentrated to approximately 60 ml volume at reduced pressure on the steam bath, diluted with water and extracted with methylene chloride. The methylene chloride extracts were combined, washed with water, dried over anhydrous sodium sulfate and evaporated. The residue was redissolved in methylene chloride and chromatographed over 500 g of Florisil anhydrous magnesium silicate. The column was eluted with 1 liter portions of hexanes (Skellysolve B) containing increasing proportions of acetone. There was so eluted 6α-fluoro-9β,11β-epoxy-16α-methyl-17α,21-dihydroxy-1,4- pregnadiene-3,20-dione-21-acetate which was freed of solvent by evaporation of the eluates.
    6α,9α-Difluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,20- dione-2-1-acetate: To approximately 1.3 g of hydrogen fluoride contained in a polyethylene bottle and maintained at -60C was added 2.3 ml of tetrahydrofuran and then a solution of 500 mg (0,0012 mol) of 6α-fluoro9β,11β-epoxy-16α-methyl-17α,21-dihydroxy-1,4-pregnadiene-3,20-dione-21- acetate in two ml of methylene chloride. The steroid solution was rinsed in with an additional 1 ml of methylene chloride. The light red colored solution was then kept at approximately -30°C for 1 hour and at -10°C for 2 hours. At the end of this period it was mixed cautiously with an excess of cold sodium bicarbonate solution and the organic material extracted with the aid of additional methylene chloride.
    The combined extracts were washed with water, dried over anhydrous sodium sulfate and concentrated to approximately 35 ml. The solution was chromatographed over 130 g of Florisil anhydrous magnesium silicate. The column was developed with 260 ml portions of hexanes (Skellysolve B) containing increasing proportions of acetone. There was thus eluted 6α,9αdifluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione-21- acetate which was freed of solvent by evaporation of the eluate fractions.
    6α,9α-Difluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,20- dione: 3.25 g of 6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methyl-1,4- pregnadiene-3,20-dione-21-acetate was dissolved in 325 ml of methanol, previously purged of air-oxygen by passing nitrogen through it for 10 minutes and thereto was added a solution of 1.63 g of potassium bicarbonate in 30 ml of water, similarly purged of oxygen. The mixture was allowed to stand at room temperature for a period of 5 hours in a nitrogen atmosphere, thereupon neutralized with 2.14 ml of acetic acid in 40 ml of water. The mixture was concentrated to approximately one-third volume at reduced pressure on a 60°C water bath. Thereupon 250 ml of water was added and the mixture chilled. The crystalline product was collected on a filter, washed with water and dried to give 6α,9α-difluoro-11β,17α,21-trihydroxy-16αmethyl-1,4-pregnadiene-3,20-dione.
    The diflorasone is reacted with orthoacetic acid trimethyl ester in the presence of toluenesulfonic acid to give diflorasone diacetate.
  • brand name Florone (Pharmacia & Upjohn); Psorcon (Pharmacia & Upjohn); Psorcon (Sanofi Aventis).
  • Therapeutic Function Antiinflammatory
Diflorasone diacetate Preparation Products And Raw materials
Raw materials
Preparation Products
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Diflorasone diacetate Spectrum
33564-31-7, Diflorasone diacetateRelated Search:
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  • Analytical Chromatography Product Catalog
  • DID - DIN
  • 49452
  • C26H32F2O7
  • 1-13-8
  • 乙腈中二氟拉松双醋酸酯
  • 甲醇中二氟拉松双醋酸酯(醋酸双氟拉松)溶液标准物质
  • 甲醇中二氟拉松双醋酸酯
  • 双氟拉松杂质3
  • 二氟拉松二醋酸酯
  • 二氟拉松二乙酯
  • 双醋酸双氟拉松
  • 二氟拉松杂质3
  • 乙腈中二氟拉松双醋酸酯溶液,100ΜG/ML
  • DIFLORASONE DIACETATE标准品
  • 醋酸双氟拉松 USP标准品
  • 醋酸双氟拉松 标准品
  • 醋酸双氟拉松
  • 二乙酸二氟拉松酯
  • 二乙酸二氟拉松溶液,100PPM
  • 二氟拉松双醋酸酯溶液,100PPM
  • 二氟拉松双醋酸酯溶液,1000PPM
  • 双氟拉松双醋酸脂
  • 双氟拉松乙酸酯
  • 6Α,9-二氟-11Β,17,21-三羟基-16Β-甲基孕甾-1,4-二烯-3,20-二酮 17,21-二乙酸酯
  • 双醋二氟拉松
  • 双氟拉松双醋酸酯
  • 二氟拉松双醋酸酯
  • 33564-31-7
  • C12626500 DiflorasonEDiacetate
  • Diflorasone Diacetate (1197302)
  • Diflorasone Diacetate RS
  • Diflorasone diacetate Solution in Acetonitrile, 100μg/mL
  • iflorasonediacetate
  • Diflorasone Impurity 3
  • DIFLORASONEDIACETATE,USP
  • 6α,9-difluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-diacetate
  • (6α,11β,16β)-17,21-Bis(acetyloxy)-6,9-difluoro-11-hydroxy-16-Methyl-pregna-1,4-diene-3,20-dione
  • Diflorasone Diacetate (200 mg)
  • Diflorasone diacetate,6α,9-Difluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-diacetate
  • acetic acid [(6S,8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-acetoxyacetyl)-6,9-difluoro-11-hydroxy-3-keto-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] ester
  • [(6S,8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-acetyloxyethanoyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] ethanoate
  • [(6S,8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] acetate
  • 6alpha,9-Difluoro-11beta,1
  • U-34865

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