Method of manufacturing 3-(4-hydroxyphenyl)propanoic acid amide, its application in the manufacture of anti-aging compositions and anti-aging composition
AssigneeInstytut Chemii Bioorganicznej Pan
InventorsJan Barciszewski, Leszek Rychlewski, Lech Celewicz, Krzysztof Ciszewski, Eliza Wyszko, Katarzyna Rolle
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Abstract
The subjects of the present invention are a method of manufacturing 3-(4-hydroxyphenyl)propanoic acid amide, its application in the manufacture of anti-aging compositions and an anti-aging composition. As phloretamide possesses a series of biological properties it might be use as a composition for skin having excellent anti-aging effect to prevent the sagging of skin and loss of luster.
Claims12
A method of manufacturing 3-(4-hydroxyphenyl) propanoic acid amide using an active 4-nitrophenyl ester comprising:
- (a) reacting a mixture of 3-(4-hydroxyphenyl) propanoic acid with 4-nitrophenol in ethyl acetate supplemented with N,N′-dicyclohexylcarbodiimide;
- (b) stirring and reacting said reaction mixture in (a) to form a precipitate of N,N′-dicyclohexylurea;
- (c) filtering said precipitate;
- (d) drying said precipitate under vacuum;
- (e) adding anhydrous methanol saturated with ammonia to said dried precipitate;
- (f) stirring said precipitate mixed with anhydrous methanol saturated with ammonia;
- (g) evaporating said precipitate mixed with anhydrous methanol saturated with ammonia until dry to create a dried product;
- (h) loading said dried product onto a chromatography column packed with silica gel and washing with a chloroform-methanol mixture to create a chromatographically clean product;
- (i) crystallizing said chromatographically clean product from methanol;
- and
- (j) drying said chromatographically clean product in a vacuum dessicator to yield 3-(4-hydroxyphenyl) propanoic acid amide.
A method of manufacturing 3-(4-hydroxyphenyl) propanoic acid amide using an active 4-nitrophenyl ester comprising:
- (a) reacting a mixture of 3-(4-hydroxyphenyl) propanoic acid with 4-nitrophenol in ethyl oxide supplemented with N,N′-dicyclohexylcarbodiimide, wherein from 5 to 15 times excess of N,N′-dicyclohexylcarbodiimide in relation to 4-nitrophenol is used;
- (b) stirring and reacting said reaction mixture for from 10 to 50 minutes at a temperature of from 0° C. to 10° C. followed by stifling and reacting said reaction mixture for from 1.5 to 3.0 hours at room temperatures, to form a precipitate of N,N′-dicyclohexylurea;
- (c) filtering said precipitate;
- (d) washing said precipitate in ethyl acetate;
- (e) drying said precipitate under vacuum;
- (f) adding anhydrous methanol saturated with ammonia to said dried precipitate;
- (g) stirring said precipitate mixed with anhydrous methanol saturated with ammonia;
- (h) evaporating said precipitate mixed with anhydrous methanol saturated with ammonia until dry to create a dried product;
- (i) loading said dried product onto a chromatography column packed with silica gel and washing with a chloroform-methanol mixture to create a chromatographically clean product;
- (j) crystallizing said chromatographically clean product from methanol;
- and
- (k) drying said chromatographically clean product in a vacuum dessicator to yield 3-(4-hydroxyphenyl) propanoic acid amide.
A cosmetic or pharmaceutical composition comprising 3-(4-hydroxyphenyl) propanoic acid amide.
Dependencies are inferred from the claim text.