IP Library Granted Patent US 8,115,033
Granted Patent B2
US 8,115,033 · App. 12/670,509 · Granted Feb 14, 2012

3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone and use thereof as an antimicrobial active ingredient

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Quick Facts
Patent No.
US 8,115,033
App. No.
12/670,509
Granted
Feb 14, 2012
Kind
B2
Abstract

Antimicrobially active 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-1-propanone of the following formula 1 is described, as is a method for producing this compound and the use thereof as an antimicrobial active ingredient.

Claims (32)

1. A compound of the formula

2. A method for killing bacteria in perspiration comprising contacting the bacteria with the compound of claim 1 .

3. A method for producing the compound of claim 1 , comprising reducing 3-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one to afford the compound of claim 1 .

4. A method for making an antimicrobially active cosmetic formulation, an antimicrobially active medical device, or an antimicrobially active pharmaceutical formulation comprising adding an antimicrobially active amount of a compound of claim 1 to a cosmetic formulation, a medical device, or a pharmaceutical formulation.

5. A method for the cosmetic and/or therapeutic treatment of body odor comprising the topical administration of an antimicrobially active amount of the compound according to claim 1 onto a human or animal body.

6. A composition comprising:

(a) an antimicrobially active amount of a compound of the formula

and

(b) a carrier substance compatible with component (a).

7. The composition as claimed in claim 6 , wherein the composition is a cosmetic formulation, a medical device, or a pharmaceutical formulation.

8. A fragrance composition comprising:

(a) an organoleptically active amount of a fragrance;

(b) an antimicrobially active amount of the compound according to claim 1 ; and

(c) optionally one or more carriers and/or additives.

9. The method of claim 5 , wherein the body odor is underarm odor.

10. The method of claim 5 , wherein the body odor is foot odor.

11. The method of claim 3 , wherein the reduction is a hydrogenation.

12. A method for producing the compound as claimed in claim 1 , comprising:

(a) reacting by aldol condensation p-hydroxyacetophenone with vanillin; and

(b) reducing the reaction product obtained in step (a) to afford the compound of claim 1 .

13. The method of claim 12 , wherein the reduction is a hydrogenation.

14. The composition of claim 6 comprising from 0.001 to 10 wt % of the compound of component (a).

15. The composition of claim 6 comprising from 0.005 to 5 wt % of the compound of component (a).

16. The composition of claim 6 comprising from 0.01 to 1.0 wt % of the compound of component (a).

17. The method according to claim 2 , wherein the bacteria is at least one of: Corynebacterium xerosis, Staphylococcus epidermidis , or Brevibacterium epidermidis.

18. The fragrance composition according to claim 8 , wherein the fragrance composition comprises approximately 5-50 wt. % of the compound of Formula (I).

19. The composition according to claim 6 , wherein the composition is in the form of a solution, cream, lotion, gel, spray, tablet, capsule, powder, or drop.

20. The composition according to claim 6 , further comprising at least one of:

(a) a substance which is primarily used to inhibit growth of undesired microorganisms on or in animal organisms;

(b) an antiperspirant active ingredient;

(c) an odor absorber; or

(d) a preservative.

Assignments (2)
MERGER Recorded Apr 22, 2011
From: SYMRISE GMBH & CO. KG
To: SYMRISE AG
Reel/Frame 026171/0582 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2010
From: KOCH, OSKAR; SCHMAUS, GERHARD
To: SYMRISE GMBH & CO. KG
Reel/Frame 024544/0081 →