Preservation of Ergothioneine

a technology of ergothioneine and ergothioneine, which is applied in the field of preservation of ergothioneine or ergothioneinecontaining mixtures, can solve the problems of mixed reports of ergothioneine's stability in alkali, fishy, and amine odor associated with ergothioneine is a disadvantage in commercialization, so as to improve the detection of fishy, amine odor, and improve the detection of trimethylamin

Inactive Publication Date: 2015-03-12
ELC MANAGEMENT LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The use of trimethylamine absorbers effectively prevents or minimizes the fishy, amine odor in ergothioneine solutions, ensuring the products remain odorless during storage and application, thus enhancing their commercial viability.

Problems solved by technology

However, the reports of its stability in alkali are mixed in the literature.
However, in the cases of the more dilute solutions, the odor was detected by some individuals and not others.
The fishy, amine odor associated with ergothioneine is a disadvantage in commercialization, particularly in oral pharmaceuticals, injectibles pharmaceuticals, topical pharmaceuticals, cosmetic products, nutritional supplements, nutritional drinks, and other consumer products.
Those skilled in the art have found the removal or prevention of the fishy, amine odor in aqueous solutions to be a particularly difficult problem.
U.S. Pat. No. 4,845,289 describes a method for the removal or reduction of odor by use of methyl chloride at temperatures above 50° C. As disclosed in the patent, “In these products as well as others, there frequently remains upon completion of the reaction excess trimethylamine which is odiferous and has undesirable toxicological problems.
The residual trimethylamine is difficult to remove completely from aqueous system because of its high solubility in water, and extensive purging with an inert gas and / or removal of water is necessary to also remove substantial quantities of amine.
This can be a time-consuming and energy intensive process.”
However, the inventor has now appreciated that the source of the odor associated with the manufacture and storage of ergothioneine is not related to the presence of choline, and that none of the methods of the prior art are useful in preventing the formation of the odor, produced after application to human skin, of a product that contains ergothioneine but that does not contain choline chloride.
However, when the ergothioneine mixture is applied to skin, the aqueous components of the mixture are absorbed and the heat of the skin volatilizes the trimethylamine.

Method used

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  • Preservation of Ergothioneine
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  • Preservation of Ergothioneine

Examples

Experimental program
Comparison scheme
Effect test

example 1

Stability of Ergothioneine with and without Citric Acid

[0070]A sample of ergothioneine was prepared at 2 mM or 0.046% (w / v) in water with or without 0.2% (w / v) citric acid and placed in glass vials of approximately 2 ml volume, purged of air with nitrogen gas and sealed. The samples were stored at 4° C., 25° C. or 40° C. for 30 or 60 days and then analyzed by HPLC. Each vial was used once and then discarded. Each measurement was made in triplicate and the results averaged. A standard curve of ergothioneine concentration was constructed at each time point to quantify the amount of ergothioneine in each vial. Each amount in Table 2 is expressed as percentage of the amount measured in the initial sample at the start of the experiment.

TABLE 2Stability of ergothioneine during storage with and without citricacid as a percent of the starting concentration% EGT without% EGT withTemperatureTimecitric acidcitric acid 4° C.30 days96.1101.6 4° C.60 days106.5105.825° C.30 days84.0101.525° C.60 d...

example 2

Development of Fishy Amine Odor at Room Temperature Storage

[0072]Lotions containing from 20 μM (0.00046%) to 13 mM (0.3%) ergothioneine (w / v) developed a similar fishy, amine odor over time stored at ambient room temperature. These odors were not immediately detected by smelling the container, but were detected after application to the skin and allowing a few seconds before smelling. Another lotion surprisingly did not.

TABLE 3Formula 1: LotionPHASEINGREDIENT% (w / v)1Water61.801Butylene Glycol2.001Phenoxyethanol0.501Disodium EDTA0.101Magnesium Aluminum Silicate10.002Simmondsia Chinensis (Jojoba) Butter4.002Hydrogenated Polyisobutene3.002Neopentyl Glycol Dihptanoate5.002Cetearyl Alcohol / Ceteareth-2001.502Cetyl Alcohol01.752Stearyl Alcohol00.702Tetrahexyldecyl Ascorbate00.502Stearic Acid00.852Glyceryl Stearate / PEG-100 Stearate05.0021,2 Hexanediol / Capryl Glycol01.003Water02.003Ergothioneine00.30Total100.00

[0073]Procedure:

[0074]Combine phase 1 ingredients in main beaker and heat to 78-80°...

example 3

Formation of Fishy Amine Odor by Addition of Sodium Hydroxide

[0078]Four samples of a 5 ml ergothioneine solution at 0.1% (w / v) were prepared in glass test tubes with screw caps. To the first was added 5 ml of water, to the second 5 ml of 0.2% (w / v) sodium metabisulfite, to the third 4 ml of water and 1 ml of 1N sodium hydroxide, and to the fourth 5 ml of 0.2% (w / v) citric acid. The pH of each sample was measured using litmus paper, and they were all pH 5, except for the third sample which had a pH of approximately 10. The samples were boiled for 10 minutes and each one was smelled. The third tube, with sodium hydroxide, had the fishy, amine odor characteristic of ergothioneine solutions after extended storage. None of the other tubes had this odor.

[0079]This experiment replicated the appearance of the fishy amine odor using a simple and fast method of briefly boiling with sodium hydroxide. None of the other components alone produced the fishy amine odor. This allowed the testing of ...

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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.

Description

[0001]The present application is a divisional of U.S. Ser. No. 12 / 362,594, filed Jan. 30, 2009.FIELD OF THE INVENTION[0002]The present invention relates to the preparation of ergothioneine or ergothioneine-containing mixtures that ameliorates changes in the odor of the product during processing and / or storage. In particular, the preparation involves the addition of acids and / or sulfur dioxide donors that reduce or prevent the formation of trace volatile compounds to which the human nose is particularly sensitive. The resulting preparations retain an innocuous odor even after challenge with conditions, such as alkali or storage over time, which would otherwise produce fishy, amine odors in ergothioneine solutions or ergothioneine-containing mixtures. The acids and / or sulfur dioxide donor compounds may also be added to the ergothioneine solutions or ergothioneine-containing mixtures after the detection of the odor to reduce or eliminate the volatile trace compounds to which the human ...

Claims

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Application Information

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Patent Type & AuthorityApplications(United States)
IPC IPC(8): A61K47/12A61K9/00A61K31/417
CPCA61K47/12A61K9/0014A61K31/417A61K8/4946A61K45/06A61Q19/00A61K31/4172A61K8/24A61K8/36A61K8/365A61K8/676A61K8/19A61K8/23A61P17/00A61K2300/00A61K9/08A61K47/02A61K31/4164
InventorYAROSH, DANIEL B.
OwnerELC MANAGEMENT LLC