Diflucortolone Chemical Properties

Melting point:

240-244°; mp 248-249°

alpha 

D22 +111° (methanol) (Kieslich, 1976)

Boiling point:

534.0±50.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly, Sonicated), DMSO (Slightly)

form 

Off-White to Pale Grey Soild

pka

12.90±0.70(Predicted)

CAS DataBase Reference

2607-06-9(CAS DataBase Reference)

MSDS

• Language:English Provider:6a,9-Difluoro-11b,21-dihydroxy-16a-methylpregna-1,4-diene-3,20-dione

Diflucortolone Usage And Synthesis

Originator

Nerisone,Schering,UK,1976

Uses

Difluocortolone is used as a topical therapy in the treatment of pediatric tinea corporis; a common mycotic infection in children.

Uses

Glucocorticoid. .

Definition

ChEBI: Diflucortolone is a 21-hydroxy steroid.

Manufacturing Process

16α-Methyl-6α,9α-difluoro-δ4-pregnene-11α,21-diol-3,20-dione-21-acetate (MP = 229°/232°-234°C (with decomposition) is dehydrogenated in 1.2- position by means of Bacillus lentus, Mutant MB 284, whereby the 21-acetate group is simultaneously saponified. (It is possible under the same conditions to start with the free 21-hydroxyl compound.)
For this purpose a fermenter made of stainless steel having a 50 liter capacity is charged with 30 liters of a nutrient solution of 0.1% yeast extract, 0.5% cornsteep and 0.2% glucose, heated for one-half hour at 120°C for sterilization purposes, and after cooling, inoculated with a bacterial suspension of Bacillus lentus MB 284.
After 24 hours of growth at 28°C under stirring (220 revolutions per minute) and aeration (1.65 m3/hr), 1.8 liters of the obtained culture is removed under sterile conditions and transferred with 28 liters of the same sterilized nutrient medium into a fermenter of the same size.
Simultaneously, 6 g of 16α-methyl-6α,9α-difluoro-δ4-pregnene-11β,21-diol3,20-dione-21-acetate in 200 cc of dimethylformamide are added and the fermentation is continued for 50 hours under the same conditions.
The course of the fermentation is tested by removal of samples which are extracted with methyl isobutyl ketone. The extracts are analyzed by thin layer chromatography using a system of benzene/ethyl acetate (4:1).
After further working up there is obtained an oily crystalline residue which is subjected to chromatography on silica gel. The 16α-methyl-6α,9α-difluoroδ1,4-pregnadien-11β,21-diol-3,20-dione is eluated with ethyl acetatechloroform (1:2), it is recrystallized from ethyl acetate/ether and then formed to melt at 240°/242°-244°C. The yield is 60% of the theoretical. The product is reacted with valeric acid chloride to give the valerate ester.

Therapeutic Function

Antiinflammatory

Diflucortolone(2607-06-9)Related Product Information

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• Diflucortolone