Application of carnosine, composition containing ergothioneine and application

By adding carnosine and pH adjusting agent to the ergothionine-containing composition, the odor problem of the composition is solved, and the degradation rate and odor of ergothionine are significantly reduced, and its application in the cosmetics field has been expanded.

CN119235688APending Publication Date: 2025-01-03SHENZHEN HUJIA TECH CO LTD
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Patent Information

Application Number
CN202411383135.0
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-09-30
Publication Date
2025-01-03

AI Technical Summary

Technical Problem

The ergothionine-containing compositions produce a strong fishy smell when added to the amount greater than 0.001%, limiting their application in the cosmetics field.

Method used

By adding carnosine to the composition, the pH value is adjusted between 4 and 8.5, and using pH adjusters such as citric acid, sodium citrate and disodium hydrogen phosphate, the ratio of ergothionine to carnosine is controlled to be 1:0.1 to 20 In between, the degradation rate and odor of ergothioneine are reduced.

Benefits of technology

It effectively reduces the odor of ergothionine-containing compositions and expands its application scenarios in cosmetics. Especially in the acid-base environment, it significantly inhibits the degradation rate of ergothionine and avoids yellowing of color.

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Abstract

The embodiment of the invention discloses application of carnosine, the carnosine can be used for relieving the smell of a composition containing ergothioneine, on the basis, the invention further provides the composition containing ergothioneine and application, and the composition containing ergothioneine comprises ergothioneine, carnosine and water.
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Description

Technical Field

[0001] The invention relates to the technical field of ergothioneine, and in particular to uses of carnosine, and compositions containing ergothioneine and uses thereof. Background Art

[0002] Ergothioneine has excellent antioxidant and anti-inflammatory physiological activities and is widely used in the field of cosmetics. However, there are studies (such as the patent document of US8933245B2) recording that in the composition containing ergothioneine, when the addition amount of ergothioneine is greater than 0.001%, a stronger odor (mainly fishy smell) will be produced. Summary of the invention

[0003] One purpose of the embodiments of the present application is to solve at least one problem in the above background and provide corresponding beneficial effects.

[0004] Another object of the present application embodiment is to provide a use of carnosine, which can be used to reduce the odor of a composition containing ergothioneine.

[0005] Another object of the present application embodiment is to provide a composition containing ergothioneine and its use.

[0006] The embodiments of the present application mainly achieve the above objectives through the following technical solutions.

[0007] In a first aspect, the present application embodiment provides a use of carnosine in preparing a composition containing ergothioneine.

[0008] In some technical schemes, the composition containing ergothioneine also includes at least one of ascorbyl glucoside and tranexamic acid.

[0009] In a second aspect, the present application embodiment provides a composition containing ergothioneine, comprising:

[0010] Ergothioneine, carnosine, and water.

[0011] In some technical schemes, the composition containing ergothioneine also includes at least one of ascorbyl glucoside and tranexamic acid.

[0012] In some technical schemes, the pH of the composition containing ergothioneine is greater than or equal to 4.

[0013] In some technical schemes, the pH of the composition containing ergothioneine is greater than or equal to 7.

[0014] In some technical schemes, the pH of the composition containing ergothioneine is between 4 and 8.5.

[0015] In some technical schemes, the pH of the composition containing ergothioneine is between 7 and 8.5.

[0016] In some technical schemes, the composition containing ergothioneine also includes a pH adjuster, and the pH adjuster includes at least one of citric acid, sodium citrate and disodium hydrogen phosphate.

[0017] In some technical schemes, the content ratio of the ergothioneine to the carnosine is between 1:0.1 and 20.

[0018] In a third aspect, an embodiment of the present application provides a use of the composition containing ergothioneine described in the second aspect in preparing cosmetics.

[0019] The beneficial effects of the embodiments of the present invention include:

[0020] 1. In some embodiments, the present application provides a use of carnosine in preparing a composition containing ergothioneine, which can reduce the odor of the composition containing ergothioneine.

[0021] 2. In some embodiments, the embodiments of the present application provide a composition containing ergothioneine, which can reduce the odor of the composition containing ergothioneine.

[0022] 3. In some embodiments, the embodiments of the present application provide a use of a composition containing ergothioneine in the preparation of cosmetics, which can reduce the odor of the cosmetics and expand the application of ergothioneine. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 It is a schematic diagram of the appearance of the composition containing ergothioneine of Examples 16 to 18 and Comparative Examples 7 to 9 in the examples of the present application. DETAILED DESCRIPTION

[0024] The present invention is further described in detail below in conjunction with the accompanying drawings so that those skilled in the art can implement the invention with reference to the description.

[0025] The terms "first", "second", "third", etc. in the embodiments of the present application are used for descriptive purposes only and should not be understood as indicating or implying relative importance or implicitly indicating the number of the indicated technical features. Therefore, the features defined as "first", "second", etc. may explicitly or implicitly include at least one of the features.

[0026] Furthermore, the terms "comprises", "includes", "contains" and any variations thereof are intended to cover non-exclusive inclusions. For example, a process, method, system, product or device comprising a series of steps or units is not limited to the listed steps or units, but may optionally include steps or units not listed, or may optionally include other steps or units inherent to these processes, methods, products or devices.

[0027] In addition to the above, it is still necessary to emphasize that the reference to "embodiment" in this article means that the specific features, structures or characteristics described in conjunction with the embodiment may be included in at least one embodiment of the present application. The appearance of this phrase in various places in the specification does not necessarily refer to the same embodiment, nor is it an independent or alternative embodiment that is mutually exclusive with other embodiments. It is explicitly and implicitly understood by those skilled in the art that the embodiments described herein can be combined with other embodiments.

[0028] In a first aspect, the embodiments of the present application provide a use of carnosine in preparing a composition containing ergothioneine.

[0029] The present application embodiment finds that after adding carnosine, the fishy smell of the composition containing thioneine can be effectively reduced. One of the reasons may be that when thioneine is compounded with carnosine, the stability of thioneine can be enhanced to prevent thioneine from decomposing.

[0030] In addition, it is understood that the reduction of the odor of the composition containing ergothioneine is conducive to the application of ergothioneine in the field of cosmetics.

[0031] In some embodiments, the pH of the composition containing ergothioneine is between 4 and 8.5. Under this pH environment, carnosine can reduce the degradation rate of ergothioneine in the composition containing ergothioneine.

[0032] In some embodiments, the pH of the composition containing ergothioneine is between 5 and 8.5. Under this pH environment, carnosine can reduce the degradation rate of ergothioneine in the composition containing ergothioneine.

[0033] In some embodiments, the pH of the composition containing ergothioneine is between 4 and 7. Under this pH environment, carnosine can reduce the degradation rate of ergothioneine in the composition containing ergothioneine, and can also expand the application scenarios of the composition containing ergothioneine. For example, in some embodiments, when the composition containing ergothioneine contains at least one of ascorbyl glucoside and tranexamic acid, adding carnosine can not only reduce the odor of the composition, but also prevent the color of the composition from turning yellow.

[0034] In some embodiments, the pH of the composition containing ergothioneine is greater than or equal to 7. Under this pH environment, carnosine can reduce the degradation rate of ergothioneine in the composition containing ergothioneine, and can also expand the application scenarios of the composition containing ergothioneine.

[0035] In some embodiments, the pH of the composition containing ergothioneine is between 7 and 8.5. Under this pH environment, carnosine can reduce the degradation rate of ergothioneine in the composition containing ergothioneine.

[0036] In some embodiments, after adding carnosine, the degradation rate of ergothioneine can be controlled to be approximately lower than 22.24% when the pH of the composition containing ergothioneine is within the range of about 4 to 8.5.

[0037] In some embodiments, after adding carnosine, the degradation rate of ergothioneine can be controlled to be approximately less than 10% when the pH of the composition containing ergothioneine is within the range of about 5 to 8.5.

[0038] In some embodiments, after adding carnosine, the degradation rate of ergothioneine can be significantly inhibited in neutral and alkaline environments (the pH of the composition containing ergothioneine is alkaline).

[0039] In some embodiments, the ergothioneine-containing composition comprises ergothioneine, ascorbyl glucoside, and tranexamic acid.

[0040] In a second aspect, the present application embodiment provides a composition containing ergothioneine, comprising:

[0041] Ergothioneine, carnosine, and water.

[0042] Since carnosine is added to the composition containing ergothioneine in the embodiment of the present application, the odor of the composition can be reduced.

[0043] The stink produced by thioneine may be caused by thioneine degradation to a great extent, because thioneine degradation can form trimethylamine molecules, and the human nose is very sensitive to trimethylamine, which limits the application of thioneine in the field of cosmetics. In certain embodiments, the composition containing thioneine of the embodiment of the present application can reduce the degradation rate of thioneine, which is conducive to alleviating the smell of the composition.

[0044] In addition, it can be understood that the reduction of odor is conducive to the application of the composition containing ergothioneine in the field of cosmetics.

[0045] In some embodiments, the pH of the composition containing ergothioneine is greater than or equal to 4. Under this pH environment, the composition containing ergothioneine can reduce the degradation rate of ergothioneine due to the presence of carnosine.

[0046] In some embodiments, the pH of the composition containing ergothioneine is greater than or equal to 7. Under this pH environment, the composition containing ergothioneine can reduce the degradation rate of ergothioneine due to the presence of carnosine.

[0047] In general, the stability of thioneine is greatly affected by the acidity of the environment. When thioneine is in an environment of pH ≥ 7, on the one hand, the electrophilicity of thioneine will be enhanced, and it is easier to react with other substances and cause degradation. On the other hand, the functional group of thioneine is susceptible to alkaline environment, causing the molecular structure of thioneine to change. On the other hand, under alkaline conditions, thioneine is more susceptible to the influence of hydrolysis so that the fracture of molecular structure. Therefore, under pH ≥ 7, especially under alkaline environment, the application of thioneine is very limited, and it is difficult to be used in combination with those compositions (such as ascorbyl glucoside and tranexamic acid) that are stable and bioactive in alkaline environment. And the present application embodiment, owing to the introduction of carnosine in the composition, can be used to overcome the aforementioned defects.

[0048] In some embodiments, the pH of the composition containing thioneine is between 4 and 8.5. Under this pH environment, the composition containing thioneine can reduce the degradation rate of thioneine due to the presence of carnosine. The degradation rate of thioneine can be controlled to be approximately lower than 22.24%.

[0049] In some embodiments, the pH of the composition containing ergothioneine is between 5 and 8.5, and the degradation rate of ergothioneine can be controlled to be approximately lower than 10% due to the presence of carnosine.

[0050] In some embodiments, the pH of the composition containing ergothioneine is between 4 and 7. Under this pH environment, the composition containing ergothioneine can reduce the degradation rate of ergothioneine due to the presence of carnosine.

[0051] In some embodiments, the pH of the composition containing ergothioneine is between 7 and 8.5. Under this pH environment, the composition containing ergothioneine can reduce the degradation rate of ergothioneine due to the presence of carnosine.

[0052] In some embodiments, the composition containing ergothioneine further comprises a pH adjuster for adjusting the pH of the composition.

[0053] Optionally, the pH adjuster includes at least one of citric acid, sodium citrate and disodium hydrogen phosphate.

[0054] In some embodiments, the ergothioneine-containing composition further comprises at least one of ascorbyl glucoside and tranexamic acid.

[0055] Ascorbyl glucoside and tranexamic acid (also known as tranexamic acid, tranexamic acid) are generally suitable for use at a pH of 6-7. If you want to directly use them with thioneine, you will have an obvious fishy smell. Meanwhile, yellowing can also occur. And the present application embodiment, by adding carnosine, can not only alleviate the smell, but also avoid yellowing.

[0056] Therefore, since the composition of the present application contains carnosine, ascorbyl glucoside / tranexamic acid and ergothioneine can be stabilized at the same time without generating odor.

[0057] In some embodiments, in the composition containing thioneine, the mass fraction of thioneine is greater than or equal to 0.001%. The upper limit of thioneine content can be determined according to common knowledge in the art.

[0058] In some embodiments, in the composition containing ergothioneine, the mass fraction of ergothioneine is between 0.001% and 0.2%.

[0059] In some embodiments, in the composition containing ergothioneine, the mass fraction of ergothioneine is between 0.01% and 0.2%.

[0060] In some embodiments, in the ergothioneine-containing composition, the mass fraction of carnosine is between 0.02% and 0.4%.

[0061] In some embodiments, the mass ratio of the ergothioneine to the carnosine is between 1:0.1 and 20.

[0062] In a third aspect, the embodiments of the present application provide a use of a composition containing ergothioneine in preparing cosmetics.

[0063] In certain embodiments, the ergothioneine-containing compositions can be used as cosmetics.

[0064] In certain embodiments, the cosmetics may be external skin care products, such as lotions, essences, emulsions, facial masks, skin care creams, skin care ointments, and the like.

[0065] <Preparation Example and Experimental Test of Composition Containing Ergothioneine>

[0066] The compositions containing ergothioneine of each embodiment and comparative example are experimentally tested below, and the test items at least include an odor evaluation test.

[0067] Preparation of the composition containing thioneine: According to the corresponding formula of each of the following examples and comparative examples, the components in the formula are mixed to form the corresponding composition containing thioneine.

[0068] The odor evaluation test comprises the following steps: taking a composition containing ergothioneine as a test sample, placing it at room temperature and light conditions for 1 month, then taking 0.2 g of the test sample and applying it on the back of the hand, applying it in circles, scoring and evaluating whether the test sample has a fishy smell, and taking the average of the scores of three people.

[0069] Odor level explanation: 1 no fishy smell; 2 slight fishy smell, acceptable; 3 fishy smell, acceptable; 4 obvious fishy smell, unacceptable; 5 too strong fishy smell, unbearable.

[0070] It can be seen from the odor level that when the odor score is between 1 and 5, the larger the odor score, the stronger the odor (ie, fishy smell).

[0071] Examples 1 to 6

[0072] The compositions containing ergothioneine of Examples 1 to 6 were prepared according to the corresponding formulas, and the formulas of Examples 1 to 6 are shown in Table 1.

[0073] Table 1. Formulations of Examples 1 to 6

[0074]

[0075] Comparative Examples 1 to 6

[0076] The compositions containing ergothioneine of Comparative Examples 1 to 6 were prepared according to the corresponding formulas. The formulas of Comparative Examples 1 to 6 are shown in Table 2.

[0077] Table 2, formula of comparative examples 1 to 6

[0078]

[0079]

[0080] <Experimental Example 1>

[0081] Take the compositions containing thioneine of Examples 1 to 6 and Comparative Examples 1 to 6, as samples to be tested, and test smell, pH value and thioneine degradation rate respectively.

[0082] Results of Experimental Example 1:

[0083] The results of Experimental Example 1 are shown in Tables 3 and 4.

[0084] Table 3

[0085] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 pH 3.1 4.1 5.1 6.2 7.3 8.5 Ergothioneine degradation rate (%) 90.63 22.24 3.54 1.84 9.75 5.63 Odor Rating 2 2.3 1 1 2.3 2

[0086] Table 4

[0087] Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 pH 2.9 4.0 4.9 5.9 7.1 8.5 Ergothioneine degradation rate (%) 93.17 29.26 9.98 10.07 26.21 88.79 Odor Rating 3.3 3 2.7 2.3 4 4.3

[0088] Result analysis of Experimental Example 1:

[0089] 1. About the degradation rate of ergothioneine

[0090] In the range of pH being about 4 to 7, for the samples (Comparative Examples 2 to 5) to which carnosine is not added, the degradation rate of thioneine is less than 30%; However, when the pH of the sample (Comparative Example 6) is 8.5, the degradation rate of thioneine reaches about 89%. It can be seen that after pH exceeds 7, the degradation rate of thioneine is greatly improved.

[0091] In the range of pH being about 4 to 8.5, for the samples to which carnosine has been added (embodiments 2 to 5), the degradation rate of thioneine is all less than 10%; and after exceeding pH exceeding 7, the degradation rate of thioneine has produced a significant decline (see the comparison of embodiment 5 and comparative example 5); It is particularly noteworthy that, when the pH of sample (embodiment 6) is 8.5, the degradation rate of thioneine is only 5.63%, which is very significant with the difference of the sample to which carnosine is not added.

[0092] 2. About smell

[0093] For the samples without carnosine, the odor of the samples with pH values ​​of 3 to 4 (Comparative Examples 1 to 2) can be smelled and is acceptable, the odor of the samples with pH values ​​of 4 to 6 (Comparative Examples 3 to 4) is weaker, and the odor of the samples with pH values ​​of 7 to 8.5 (Comparative Examples 5 to 6) is strong and unbearable.

[0094] For the samples to which carnosine was added (Examples 1 to 6), the odor was relatively weak in an environment with a pH value of 3 to 8.5.

[0095] 3. Summary

[0096] From the above results, we can see that after adding carnosine:

[0097] (1) can effectively reduce the fishy smell of the composition containing ergothioneine;

[0098] (2) the degradation rate of ergothioneine can be controlled to be lower than 22.24% within the range of pH 4 to 8.5;

[0099] (2) The degradation rate of ergothioneine can be significantly inhibited in an alkaline environment.

[0100] Embodiments 7 to 12

[0101] The compositions containing thioneine of Examples 7 to 12 were prepared according to corresponding formulas, and the formulas of Examples 7 to 12 are as shown in Table 5.

[0102] Table 5. Formulations of Examples 7 to 12

[0103]

[0104]

[0105] Embodiments 13 to 15

[0106] The compositions containing thioneine of Examples 13 to 15 were prepared according to corresponding formulas, and the formulas of Examples 13 to 15 are as shown in Table 6.

[0107] Table 6. Formulations of Examples 13 to 15

[0108]

[0109] <Experimental Example 2>

[0110] Take the composition containing thioneine of embodiment 7~15, as sample to be tested, test smell, pH value respectively.

[0111] Results of Experiment 2:

[0112] The experimental results are shown in Tables 7 and 8.

[0113] Table 7

[0114] Example 7 Example 8 Example 9 Example 10 Embodiment 11 Example 12 pH 8.5 8.4 8.4 8.4 8.3 8.3 Odor Rating 2 2.3 2.7 1.7 1 3.3

[0115] Table 8

[0116]

[0117]

[0118] Result analysis of Experimental Example 2:

[0119] The above results show that: under alkaline environment (pH greater than 8), when the content ratio of ergothioneine to carnosine is within the range of 1:0.1 to 20, a significant inhibitory effect is produced on the smell of ergothioneine, and the smell of the composition containing ergothioneine is effectively reduced.

[0120] Examples 16 to 18 and Comparative Examples 7 to 9

[0121] The compositions containing ergothioneine of Examples 16 to 18 and Comparative Examples 7 to 9 were prepared according to the corresponding formulas. The formulas of Examples 16 to 18 and Comparative Examples 7 to 9 are shown in Table 9 below.

[0122] Table 9, formulations of Examples 16 to 18 and Comparative Examples 7 to 9

[0123]

[0124] <Experimental Example 3>

[0125] Take the compositions containing thioneine of Examples 16 to 18 and Comparative Examples 7 to 9, as samples to be tested, and test smell, pH value and appearance discoloration respectively.

[0126] Results of Experiment 3:

[0127] The results of Experimental Example 3 are shown in Tables 10 and Figure 1 , Figure 1 It is an appearance comparison diagram of the composition containing ergothioneine of Examples 16 to 18 and Comparative Examples 7 to 9.

[0128] Table 10

[0129]

[0130] Result analysis of Experimental Example 3:

[0131] The above results show:

[0132] According to Comparative Example 7 and Example 16, both compositions do not add ascorbyl glucoside and tranexamic acid, and the component difference of both is mainly whether carnosine is added. In both test results, the comparative example 7 without adding carnosine, smell is larger, color turns yellow, and thioneine degradation rate is also much greater than Example 16.

[0133] According to Comparative Example 8 and Example 17, both compositions are added with ascorbyl glucoside and tranexamic acid, and the component difference of the two is mainly whether carnosine is added. In both test results, the comparative example 8 without adding carnosine, the smell is larger, the color turns yellow, and the degradation rate of ergothioneine and the degradation rate of ascorbyl glucoside are also much greater than Example 17.

[0134] According to Comparative Example 9 and Example 18, both compositions are added with tranexamic acid, and the difference between the two components is mainly whether carnosine is added. In the test results of the two, Comparative Example 9 without carnosine has a stronger odor, a yellower color, and a tranexamic acid degradation rate that is much greater than that of Example 18.

[0135] In summary, when the composition containing ergothioneine contains one or more of tranexamic acid and ascorbyl glucoside, carnosine can not only reduce the smell and color of the composition, reduce the degradation rate of ergothioneine, but also reduce the degradation rate of ascorbyl glucoside and the degradation rate of tranexamic acid.

[0136] <Conclusion>

[0137] From the above results, we can know that:

[0138] 1, in the scope that pH is about 3~8.5, for the sample (comparative example 1~9) that carnosine is not added, the degradation rate of thioneine is larger along with the change of pH, is easily affected by pH, especially when exceeding pH after exceeding 7, the degradation rate of thioneine produces obvious rising, basically more than 25%, up to about 90%.

[0139] However, in the range of pH about 4 to 8.5, when carnosine is added to the composition, the degradation rate of ergothioneine can be effectively controlled to be basically controlled within 25%, and is reduced to less than 10% after the pH exceeds 5, as shown in Examples 2 to 6 and 16 to 18. And the composition containing carnosine can significantly reduce the degradation rate of ergothioneine after the pH exceeds 5 relative to the composition without carnosine, and the reduction trend is more obvious after the pH exceeds 8.

[0140] 2. In the pH range of about 4 to 8, for samples without carnosine (e.g., Comparative Examples 7 to 9), the odor scores were all above 3.7, and the appearance turned yellow; in sharp contrast, for samples with carnosine added (Examples 16 to 18), the odor scores were all lower (below 2.3), and the appearance color did not change, being colorless. This shows that carnosine significantly improves the odor and appearance of the composition.

[0141] 3. If ergothioneine is used together with ascorbyl glucoside and tranexamic acid, the solution will turn yellow obviously and produce an unacceptable fishy smell. When carnosine is added, no yellowing occurs and the release of fishy smell is also suppressed. In this way, the purpose of using ergothioneine and ascorbyl glucoside at the same time in the pH range of 6-8 can be achieved by adding carnosine.

[0142] 4. If ergothioneine and tranexamic acid are used together, the solution will turn yellow significantly and produce an unacceptable fishy smell. When carnosine is added, no yellowing occurs and the release of the fishy smell is also suppressed. In this way, the purpose of using ergothioneine and tranexamic acid simultaneously in the pH range of 6-8 can be achieved by adding carnosine.

[0143] The above specific embodiments have been described in detail for the present invention, but these do not constitute limitations on the present invention. The protection scope of the present invention is not limited to the above embodiments, and any equivalent modifications or changes made by ordinary technicians in the field based on the content disclosed by the present invention should be included in the protection scope recorded in the claims.

Claims

1. Use of carnosine in preparing a composition containing ergothioneine.

2. The use according to claim 1, wherein The ergothioneine-containing composition comprises at least one of ascorbyl glucoside and tranexamic acid.

3. A composition containing ergothioneine, characterized in that, include: Ergothioneine, carnosine, and water.

4. The composition containing ergothioneine according to claim 3, characterized in that, The ergothioneine-containing composition further comprises at least one of ascorbyl glucoside and tranexamic acid.

5. The composition containing ergothioneine according to claim 3, characterized in that, The pH of the composition containing ergothioneine is greater than or equal to 4; The mass fraction of the ergothioneine is greater than or equal to 0.001%.

6. The composition containing ergothioneine according to claim 3, characterized in that, The pH of the composition containing ergothioneine is greater than or equal to 7.

7. The composition containing ergothioneine according to claim 3, characterized in that, The pH of the composition containing ergothioneine is between 4 and 8.5; The mass fraction of the ergothioneine is between 0.001% and 0.2%.

8. The composition containing ergothioneine according to claim 3, characterized in that, The pH of the composition containing ergothioneine is between 7 and 8.5; The mass fraction of the ergothioneine is between 0.01% and 0.2%; The mass fraction of the carnosine is between 0.02% and 0.4%.

9. The composition containing ergothioneine according to claim 3, characterized in that, The composition containing ergothioneine also includes a pH regulator, and the pH regulator includes at least one of citric acid, sodium citrate and disodium hydrogen phosphate; The content ratio of the ergothioneine to the carnosine is between 1:0.1 and 20.

10. Use of the ergothioneine-containing composition according to any one of claims 3 to 9 in the preparation of cosmetics.

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