Preservation of ergothioneine

• US 8,933,245 B2
• Filed: 11/08/2012
• Issued: 01/13/2015
• Est. Priority Date: 01/30/2009
• Status: Active Grant

• Current Assignee: ELC Management LLC (The Estee Lauder Companies Inc.)
• Original Assignee: ELC Management LLC (The Estee Lauder Companies Inc.)
• Inventors: Yarosh, Daniel B.
• Primary Examiner(s): Kosack, Joseph
• Assistant Examiner(s): Aguirre, Amanda L
• Application Number:
  US13/671,955
• Publication Number:
  US 20140128615A1
• Time in Patent Office: 796 Days
• Field of Search: 514/398, 514/556, 514/709, 514/580, 548/324.1
• US Class Current: 548/324.1
• CPC Class Codes: A23L 3/3508 containing carboxyl groups
• CPC Class Codes: A23L 33/175 Amino acids
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 2800/52 Stabilizers
• CPC Class Codes: A61K 8/00 Cosmetics or similar toiletry preparations
• CPC Class Codes: A61K 8/19 containing inorganic ingredients
• CPC Class Codes: A61K 8/20 Halogens; Compounds thereof
• CPC Class Codes: A61K 8/23 Sulfur; Selenium; Tellurium; Compounds thereof
• CPC Class Codes: A61K 8/24 Phosphorous; Compounds thereof
• CPC Class Codes: A61K 8/36 Carboxylic acids; Salts or anhydrides thereof
• CPC Class Codes: A61K 8/365 Hydroxycarboxylic acids; Ketocarboxylic acids
• CPC Class Codes: A61K 8/4946 Imidazoles or their condensed derivatives, e.g. benzimidazoles
• CPC Class Codes: A61K 8/676 Ascorbic acid, i.e. vitamin C
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin

Abstract

Compositions comprising ergothioneine and a trimethylamine absorber are provided. Also provided are methods for preventing, reducing or minimizing the fishy, amine odor, due to trimethylamine, that is associated with the processing and/or storage of a preparation containing ergothioneine, by combining with the ergothioneine, during processing or prior to storage, a trimethylamine absorber in an amount sufficient to prevent the detection of any trimethylamine odor by the human nose. A method is further provided for ameliorating the methylamine odor associated with an aqueous ergothioneine-containing preparation after it has developed a fishy trimethylamine odor.

Claims

1. A method for sequestering trimethylamine released from ergothioneine in a topical, aqueous-containing cosmetic or pharmaceutical composition stored at room temperature prior to application of the composition to skin, said composition having a neutral to acidic pH and comprising greater than 20 μ

M (w/v) ergothioneine, said method comprising adding to said composition a trimethylamine absorber comprising a weak organic acid in an amount sufficient to bind the trimethylamine so as to prevent development of a fishy odor when the composition is applied to the skin, wherein the trimethylamine absorber is added to the composition before, during or after the storage.

2. The method of claim 1, wherein the weak organic acid added to said topical, aqueous-containing cosmetic or pharmaceutical composition has an acid dissociation constant (K_a) of between about 1.8×

10<sup>−

16</sup> and 55.5.

3. The method of claim 2, wherein the weak organic acid added to said topical, aqueous-containing cosmetic or pharmaceutical composition is selected from the group consisting of acetic acid, ascorbic acid, citric acid, formic acid, heptanoic acid, hexanoic acid, lactic acid, octanoic acid, oxalic acid, pentanoic acid, propanoic acid, uric acid, and mixtures thereof.

4. The method of claim 3, wherein the weak organic acid added to said topical, aqueous-containing cosmetic or pharmaceutical composition is citric acid.

5. The method of claim 1, wherein the weak organic acid and the ergothioneine are present in the topical, aqueous-containing cosmetic or pharmaceutical composition in a ratio in the range of from about 2:

1 to about 4;

1.

6. The method of claim 1, wherein the topical, aqueous-containing cosmetic or pharmaceutical composition has been stored at room temperature for at least about 60 days.

7. The method of claim 1, wherein the topical, aqueous-containing cosmetic or pharmaceutical composition has been stored at room temperature for about one year.

8. A method for preventing or eliminating development of a fishy odor in a topical, aqueous-containing cosmetic or pharmaceutical product during storage of the product at room temperature, said product having a neutral to acidic pH and comprising greater than 20 μ

M (w/v) ergothioneine, said method comprising introducing the ergothioneine into the product in the form of a composition comprising ergothioneine at a concentration of greater than 20 mM (w/v) and a trimethylamine absorber comprising a weak organic acid before, during or after storing the product, such that the ergothioneine and the weak organic acid are present in the product in amounts sufficient to permit the weak organic acid to bind trimethylamine released from the ergothioneine during storage of the product.

9. The method of claim 8, wherein the weak organic acid is selected from the group consisting of acetic acid, ascorbic acid, citric acid, formic acid, heptanoic acid, hexanoic acid, lactic acid, octanoic acid, oxalic acid, pentanoic acid, propanoic acid, uric acid, and mixtures thereof.

10. The method of claim 9, wherein the weak organic acid comprises citric acid.

11. The method of claim 8, wherein the weak organic acid and the ergothioneine are present in the product in a ratio in the range of from about 2:

1 to about 4;

1.