A composition of ellagic acid and its use

Abstract

This invention provides an ellagic acid composition and its applications. The ellagic acid composition of this invention comprises the following components in weight percentages: 0.5%–1% ellagic acid, 25%–40% polyol, 5%–10% hydroxypropyl cyclodextrin, and the balance being water, and is prepared through a specific process. The ellagic acid composition of this invention significantly improves the water solubility and stability of ellagic acid, and also possesses excellent antioxidant and whitening activities, greatly expanding the application of ellagic acid in the cosmetics field.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of cosmetics. More particularly, it relates to a gallic acid composition and its application. BACKGROUND

[0002] Gallic acid is a natural polyphenol dione widely present in pomegranate, raspberry, blueberry, walnut and other plants. It not only can effectively scavenge free radicals, has antioxidant capacity far exceeding that of vitamin C and vitamin E, but also can block melanin production by inhibiting tyrosinase activity, achieve strong whitening effect, and can absorb ultraviolet rays and neutralize free radicals, reduce the damage of ultraviolet rays to the skin. Therefore, gallic acid is highly valued in the field of cosmetics. However, the synergistic effect of multiple phenolic hydroxyl groups and lactone rings in its molecule, as well as the formation of intramolecular hydrogen bonds, jointly limit its interaction with water molecules, resulting in poor water solubility, which seriously limits its application in cosmetics.

[0003] The current methods commonly used to improve the water solubility of gallic acid are: (1) wrapping with cyclodextrin, but this method has limited effect on improving water solubility, and particles will precipitate after a long time; (2) solubilization with alkaline organic solvents such as N-methyl pyrrolidone and pyridine, but the use of such organic solvents in cosmetics is strictly limited, and the alkaline group will form an ionic salt with the weakly acidic phenolic hydroxyl group of gallic acid, which will significantly reduce the antioxidant properties and stability.

[0004] Therefore, it is crucial to find a method that can significantly improve the water solubility and stability of gallic acid while ensuring its antioxidant ability, for the wide application of gallic acid in the field of cosmetics. SUMMARY

[0005] The present application aims to provide a gallic acid composition that can significantly improve the water solubility and stability of gallic acid, while ensuring its excellent antioxidant ability, greatly expanding the application of gallic acid in the field of cosmetics.

[0006] The first object of the present application is to provide a gallic acid composition.

[0007] The second object of the present application is to provide the application of the above-mentioned gallic acid composition in the preparation of cosmetics.

[0008] The third object of the present application is to provide the application of the above-mentioned gallic acid composition in the preparation of antioxidant products.

[0009] The fourth object of the present application is to provide the application of the above-mentioned gallic acid composition in the preparation of whitening products.

[0010] The fifth object of the present application is to provide a cosmetic.

[0011] The sixth objective of this invention is to provide an antioxidant product.

[0012] The seventh objective of this invention is to provide a skin whitening product.

[0013] The above-mentioned objective of this invention is achieved through the following technical solution:

[0014] The present invention provides an ellagic acid composition comprising the following components in weight percentage: 0.5%–1% ellagic acid, 25%–40% polyol, 5%–10% hydroxypropyl cyclodextrin, and the balance being water;

[0015] The polyol is one or both of glycerol and 1,2-pentanediol;

[0016] The preparation process of the ellagic acid composition is as follows: ellagic acid is dispersed in a polyol, heated to 50-60 °C, water is added, the pH is adjusted to 7-8 with arginine, hydroxypropyl cyclodextrin is added and mixed well, and the solid-liquid separation is performed to obtain the final product.

[0017] Preferably, the ellagic acid composition comprises the following components in the indicated weight percentages: 0.5%–0.7% ellagic acid, 30%–35% polyol, 6%–8% hydroxypropyl cyclodextrin, and the balance being water.

[0018] Most preferably, the ellagic acid composition comprises the following components in the following weight percentages: 0.5% ellagic acid, 34% polyol, 7% hydroxypropyl cyclodextrin, and the balance being water.

[0019] Preferably, the mass ratio of glycerol to 1,2-pentanediol is 2-3:2-3, and most preferably 1:1.

[0020] Preferably, the heating is performed at 52–58 °C, and most preferably at 55 °C.

[0021] Preferably, the heating is performed at 400–600 rpm, and most preferably at 500 rpm.

[0022] Preferably, the pH is 7.2 to 7.8, and most preferably 7.5.

[0023] Preferably, the mixing speed is 400-600 rpm, and most preferably 500 rpm.

[0024] Preferably, the solid-liquid separation is filtration.

[0025] More preferably, the filter membrane used for filtration has a specification of 0.2 to 0.4 μm.

[0026] The above-mentioned ellagic acid composition is clear and transparent, can maintain the stability of high ellagic acid content, and has excellent antioxidant and whitening activities, which greatly broadens the application of ellagic acid in cosmetics, antioxidant products, whitening products and other fields. Therefore, the application of the above-mentioned ellagic acid composition in the preparation of cosmetics, antioxidant products and whitening products, as well as cosmetics, antioxidant products and whitening products containing the above-mentioned ellagic acid composition, should all be within the protection scope of this invention.

[0027] The present invention has the following beneficial effects:

[0028] The ellagic acid composition of the present invention is prepared through specific components and processes, which can significantly improve the water solubility and stability of ellagic acid, and also has excellent antioxidant and whitening activities, greatly expanding the application of ellagic acid in the cosmetic field. Attached Figure Description

[0029] Figure 1 These are photographs of the products obtained in Examples 1-5 after standing at 25°C for 60 days.

[0030] Figure 2 This is a photograph of the products obtained in Comparative Examples 1 to 10 after standing at 25°C for 60 days. Detailed Implementation

[0031] The present invention will be further described below with reference to the accompanying drawings and specific embodiments, but the embodiments do not limit the present invention in any way. Unless otherwise specified, the reagents, methods and equipment used in the present invention are conventional reagents, methods and equipment in this technical field.

[0032] Unless otherwise specified, all reagents and materials used in the following examples are commercially available.

[0033] Ellagic acid, 98% purity, purchased from Shaanxi Jinkangtai Biotechnology Co., Ltd.

[0034] Example 1: An Ellagic Acid Composition

[0035] I. Each component contains the following percentages by mass.

[0036] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0037] II. Preparation Method

[0038] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, water was added, the pH was adjusted to 7.5 with arginine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 500 rpm. The mixture was then filtered through a 0.2 μm filter membrane to obtain the final product.

[0039] Example 2: An Ellagic Acid Composition

[0040] I. Each component contains the following percentages by mass.

[0041] Ellagic acid 0.5%, glycerol 12%, 1,2-pentanediol 18%, hydroxypropyl cyclodextrin 6%, balance water.

[0042] II. Preparation Method

[0043] Ellagic acid was dispersed in a polyol, heated to 52 °C at 600 rpm, water was added, the pH was adjusted to 7.8 with arginine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 600 rpm and filtered through a 0.2 μm filter membrane to obtain the final product.

[0044] Example 3: An Ellagic Acid Composition

[0045] I. Each component contains the following percentages by mass.

[0046] Ellagic acid 0.7%, glycerol 21%, 1,2-pentanediol 14%, hydroxypropyl cyclodextrin 8%, balance water.

[0047] II. Preparation Method

[0048] Ellagic acid was dispersed in a polyol, heated to 58 °C at 400 rpm, water was added, the pH was adjusted to 7.2 with arginine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 400 rpm. The mixture was then filtered through a 0.4 μm filter membrane to obtain the final product.

[0049] Example 4: An Ellagic Acid Composition

[0050] I. Each component contains the following percentages by mass.

[0051] Ellagic acid 1%, glycerol 16%, 1,2-pentanediol 24%, hydroxypropyl cyclodextrin 10%, balance water.

[0052] II. Preparation Method

[0053] Ellagic acid was dispersed in a polyol, heated to 60 °C at 400 rpm, water was added, the pH was adjusted to 7 with arginine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 400 rpm and filtered through a 0.2 μm filter membrane to obtain the final product.

[0054] Example 5: An ellagic acid composition

[0055] I. Each component contains the following percentages by mass.

[0056] Ellagic acid 0.5%, glycerol 15%, 1,2-pentanediol 10%, hydroxypropyl cyclodextrin 5%, balance water.

[0057] II. Preparation Method

[0058] Ellagic acid was dispersed in a polyol, heated to 50 °C at 600 rpm, water was added, the pH was adjusted to 8 with arginine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 600 rpm and filtered through a 0.4 μm filter membrane to obtain the final product.

[0059] Comparative Example 1

[0060] I. Each component contains the following percentages by mass.

[0061] Ellagic acid 0.5%, glycerol 17%, butylene glycol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0062] II. Preparation Method

[0063] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, water was added, the pH was adjusted to 7.5 with arginine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 500 rpm. The mixture was then filtered through a 0.2 μm filter membrane to obtain the final product.

[0064] Comparative Example 2

[0065] I. Each component contains the following percentages by mass.

[0066] Ellagic acid 0.5%, glycerol 17%, 1,3-propanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0067] II. Preparation Method

[0068] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, water was added, the pH was adjusted to 7.5 with arginine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 500 rpm. The mixture was then filtered through a 0.2 μm filter membrane to obtain the final product.

[0069] Comparative Example 3

[0070] I. Each component contains the following percentages by mass.

[0071] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0072] II. Preparation Method

[0073] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, water was added, the pH was adjusted to 7.5 with sodium hydroxide, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 500 rpm. The mixture was then filtered through a 0.2 μm filter membrane to obtain the final product.

[0074] Comparative Example 4

[0075] I. Each component contains the following percentages by mass.

[0076] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0077] II. Preparation Method

[0078] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, water was added, the pH was adjusted to 7.5 with triethanolamine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 500 rpm and filtered through a 0.2 μm filter membrane to obtain the final product.

[0079] Comparative Example 5

[0080] I. Each component contains the following percentages by mass.

[0081] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0082] II. Preparation Method

[0083] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, water was added, the pH was adjusted to 7.5 with lysine, hydroxypropyl cyclodextrin was added, and the mixture was stirred at 500 rpm and filtered through a 0.2 μm filter membrane to obtain the final product.

[0084] Comparative Example 6

[0085] I. Each component contains the following percentages by mass.

[0086] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, cyclodextrin 7%, balance water.

[0087] II. Preparation Method

[0088] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, water was added, the pH was adjusted to 7.5 with arginine, cyclodextrin was added, and the mixture was stirred at 500 rpm. The mixture was then filtered through a 0.2 μm filter membrane to obtain the final product.

[0089] Comparative Example 7

[0090] I. Each component contains the following percentages by mass.

[0091] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0092] II. Preparation Method

[0093] Same as Example 1, except that heating is not performed, as detailed below:

[0094] Ellagic acid was dispersed in a polyol, water was added, the pH was adjusted to 7.5 with arginine, hydroxypropyl cyclodextrin was added, and the mixture was mixed at 500 rpm and filtered through a 0.2 μm filter membrane to obtain the final product.

[0095] Comparative Example 8

[0096] I. Each component contains the following percentages by mass.

[0097] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0098] II. Preparation Method

[0099] Same as Example 1, except that arginine is not added, i.e., the pH is not adjusted, as follows:

[0100] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, water was added, and then hydroxypropyl cyclodextrin was added. The mixture was stirred at 500 rpm and filtered through a 0.2 μm filter membrane to obtain the final product.

[0101] Comparative Example 9

[0102] I. Each component contains the following percentages by mass.

[0103] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0104] II. Preparation Method

[0105] Same as Example 1, except that the addition point of hydroxypropyl cyclodextrin is changed, as follows:

[0106] Ellagic acid was dispersed in a polyol, heated to 55 °C at 500 rpm, hydroxypropyl cyclodextrin and water were added, and the mixture was stirred at 500 rpm. The pH was adjusted to 7.5 with arginine, and the mixture was filtered through a 0.2 μm filter membrane to obtain the final product.

[0107] Comparative Example 10

[0108] I. Each component contains the following percentages by mass.

[0109] Ellagic acid 0.5%, glycerol 17%, 1,2-pentanediol 17%, hydroxypropyl cyclodextrin 7%, balance water.

[0110] II. Preparation Method

[0111] Same as Example 1, except that the addition point of the polyol is changed, as follows:

[0112] Ellagic acid was dispersed in water and heated to 55 °C at 500 rpm. The pH was adjusted to 7.5 with arginine, polyol was added and mixed well, then hydroxypropyl cyclodextrin was added and mixed well at 500 rpm. The mixture was then filtered through a 0.2 μm filter membrane to obtain the final product.

[0113] Test Example 1: Stability and Solubility Test

[0114] The products obtained in Examples 1-5 and Comparative Examples 1-10 were placed at 5 °C, 25 °C, and -18 °C for 60 days, respectively. The presence of instability phenomena such as precipitation on the 60th day was recorded, and a photograph of the product after 60 days of standing at 25 °C was taken. Furthermore, the products obtained in Examples 1-5 and Comparative Examples 1-10 were added to water to a concentration of 10 wt%, and their complete dissolution was observed.

[0115] The results are shown in Table 1 and... Figures 1-2 As shown. Among them, Figure 1 These are photographs of the products obtained in Examples 1-5 after standing at 25°C for 60 days. Figure 2 This is a photograph of the products obtained in Comparative Examples 1 to 10 after standing at 25°C for 60 days.

[0116] Table 1

[0117]

[0118] Note: The order of particles from fewest to most in Table 1 is: few particles < particles.

[0119] Depend on Figures 1-2 It can be seen that the products obtained in Examples 1-5 remained clear after standing at 25 °C for 60 days, while the products obtained in Comparative Examples 1-10 all showed obvious particle precipitation at the bottom of the bottle. This indicates that the stability of the products obtained in Examples 1-5 was significantly higher than that of the products obtained in Comparative Examples 1-10, demonstrating that the ellagic acid composition prepared by the specific components and process of this invention can significantly improve the stability of ellagic acid.

[0120] As shown in Table 1, the stability and water solubility of the products obtained in Examples 1-5 are significantly higher than those obtained in Comparative Examples 1-10, indicating that the ellagic acid composition prepared by the present invention using specific components and processes can significantly improve the water solubility and stability of ellagic acid.

[0121] Test Example 2: Antioxidant Activity Test

[0122] DPPH, also known as 1,1-diphenyl-2-trinitrophenylhydrazine, is a very stable nitrogen-centered free radical. Its ethanol solution is purple and exhibits strong absorption at a wavelength of 517 nm. In the presence of a free radical scavenger, the light absorption of the DPPH ethanol solution decreases due to electron pairing. The degree of fading of the DPPH ethanol solution is linearly related to the number of electrons it accepts, thus allowing evaluation of the test sample's ability to scavenge free radicals, i.e., its antioxidant activity. Referring to patent application CN114632040A, the free radical scavenging abilities of the products obtained in Examples 1-5 and Comparative Examples 1-10 were tested to evaluate their antioxidant activity. The results are shown in Table 2.

[0123] Table 2

[0124]

[0125] As can be seen, the DPPH scavenging ability of the products obtained in Examples 1 to 5 is significantly stronger than that of the products obtained in Comparative Examples 1 to 10, indicating that the ellagic acid composition prepared by the present invention using specific components and processes has excellent antioxidant activity.

[0126] Test Example 3: Whitening Activity Test

[0127] Drug administration well: Collect B16 cells in logarithmic growth phase, at 8 × 10⁻⁶ 5 Cells were seeded at a density of 1 cell / flask into T25 cell culture flasks containing DMEM medium and then cultured in an incubator (37 °C, 5% CO2) for 24 h. The products obtained in Examples 1-5 were then added to bring the final concentration in the medium to 0.1%. v / v The cells were cultured for 48 hours in an incubator (37 °C, 5% CO2), then digested with 0.25% trypsin, collected and counted, and a cell suspension containing an equal number of cells was centrifuged. The supernatant was discarded, and 0.5 mL of 1 M NaOH solution containing 10 wt% DMSO was added. The cells were then incubated in a water bath at 80 °C for 30 min. After centrifugation, the supernatant was added to a 96-well plate, and the absorbance was read at 475 nm.

[0128] Negative control wells: Collect B16 cells in logarithmic growth phase, at 8 × 10⁻⁶ cells / well. 5 Cells were seeded at a density of 1 cell per flask into T25 cell culture flasks containing DMEM medium and cultured in an incubator (37 ℃, 5% CO2) for 72 h. After digestion with 0.25% trypsin, the cells were collected and counted. An equal number of cell suspensions were centrifuged, the supernatant was discarded, and 0.5 mL of 1 M NaOH solution containing 10 wt% DMSO was added. The mixture was then incubated in a water bath at 80 ℃ for 30 min. After centrifugation, the supernatant was added to a 96-well plate, and the absorbance was read at 475 nm.

[0129] Blank wells: Add 0.5 mL of 1 M NaOH solution containing 10 wt% DMSO to a 96-well plate and read the absorbance value at 475 nm.

[0130] The cell melanin synthesis inhibition rate was calculated according to the formula: "Cellular melanin synthesis inhibition rate (%) = [1 - (OD of drug administration well - OD of blank well) / (OD of negative control well - OD of blank well) × 100%]". Three parallel samples were set up for each group, and the average value of the results was taken. The results are shown in Table 3.

[0131] Table 3

[0132]

[0133] As can be seen, the products obtained in Examples 1 to 5 can effectively inhibit the synthesis of melanin in cells, indicating that the ellagic acid composition of the present invention has excellent whitening activity.

[0134] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. A ellagic acid composition, characterized in that, It contains the following components by weight percentage: ellagic acid 0.5%–1%, polyol 25%–40%, hydroxypropyl cyclodextrin 5%–10%, and the balance being water; The polyol is glycerol and 1,2-pentanediol in a mass ratio of 2-3:2-3; The preparation process of the ellagic acid composition is as follows: ellagic acid is dispersed in a polyol, heated to 50-60 °C, water is added, the pH is adjusted to 7-8 with arginine, hydroxypropyl cyclodextrin is added and mixed well, and then filtered through a 0.2-0.4 μm filter membrane to obtain the final product.

2. The ellagic acid composition according to claim 1, characterized in that, It contains the following components in the indicated weight percentages: ellagic acid 0.3%–0.7%, polyol 30%–35%, hydroxypropyl cyclodextrin 6%–8%, and the balance being water.

3. The use of the ellagic acid composition according to any one of claims 1 to 2 in the preparation of cosmetics.

4. The use of the ellagic acid composition according to any one of claims 1 to 2 in the preparation of antioxidant cosmetics.

5. The use of the ellagic acid composition according to any one of claims 1 to 2 in the preparation of whitening cosmetics.

6. A cosmetic product, characterized in that, A composition containing ellagic acid as described in any one of claims 1 to 2.

7. An antioxidant cosmetic, characterized in that, A composition containing ellagic acid as described in any one of claims 1 to 2.

8. A whitening cosmetic product, characterized in that, A composition containing ellagic acid as described in any one of claims 1 to 2.

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