Phenylethyl resorcinol-containing dual synergistic whitening composition and application thereof

Abstract

The invention belongs to the technical field of cosmetics, and discloses a dual synergistic whitening composition containing phenylethyl resorcinol and application thereof. The composition disclosed by the invention is prepared from phenylethyl resorcinol and benzylidene dimethoxy dimethyl indanone. The composition efficiently inhibits the generation of melanin and the activity of tyrosinase through the synergistic interaction of the phenylethyl resorcinol and the benzylidene dimethoxy dimethyl indanone, the inhibition effect is obviously superior to that of a single component, and the composition shows a good whitening effect at a lower concentration, and is free of toxic and side effects. The side effect caused by high-concentration use of a single chemical component is reduced, and the safety is higher.

Description

Technical Field

[0001] This invention belongs to the field of cosmetic technology, and specifically relates to a composition containing phenylethyl resorcinol for dual synergistic whitening and its application. Background Technology

[0002] With the rise of efficacy-based skincare concepts, people's demands for skin whitening have become more professional and diverse, directly driving the continuous expansion of the skin whitening industry's market share. Against this backdrop, various whitening ingredients have emerged, but the market situation is uneven. Some ingredients are double-edged swords, possessing both efficacy and irritation, while others have shown less than ideal clinical results. Therefore, developing highly effective and safe whitening ingredients while minimizing irritation risks has become a core technical challenge that urgently needs to be addressed by those skilled in the art.

[0003] Currently, various whitening and melanin-inhibiting ingredients exist on the market. Some ingredients, due to their single-pathway whitening effect, are difficult to achieve high-efficiency whitening. Others exhibit poor transdermal absorption due to bioavailability issues, thus limiting their whitening efficacy. Still others are limited in application due to cost, mildness, or safety concerns. Phenylethyl resorcinol, as a registered whitening agent in China, still requires further research into its synergistic or antagonistic effects with different active ingredients. Discovering complementary ingredients that can significantly enhance its whitening efficacy has become a key research direction—this strategy can enhance efficacy while reducing the amount of phenylethyl resorcinol added, avoiding skin irritation and burden caused by high concentrations, and effectively controlling formulation costs. This synergistic-based formulation optimization is not only crucial for whitening products to gain consumer recognition and solidify market competitiveness, but also brings significant economic benefits to businesses, possessing clear application value and industrial significance. Summary of the Invention

[0004] The present invention aims to at least solve one of the technical problems existing in the prior art. Therefore, the object of the present invention is to provide a composition containing phenylethyl resorcinol for dual synergistic whitening and its application; the composition of the present invention, through the synergistic effect of phenylethyl resorcinol and benzyl dimethoxydimethyl indanone, effectively inhibits the production of melanin and the activity of tyrosinase, with a significantly better inhibitory effect than a single component, and exhibits good whitening effect at lower concentrations, reducing the side effects caused by high concentrations of single chemical components and improving safety.

[0005] In a first aspect, the present invention provides a composition comprising phenylethyl resorcinol and benzenemethylenedimethoxydimethylindanone.

[0006] Specifically, benzenemethylenedimethoxydimethylindanone (CAS: 924626-15-3), as an antagonist of aromatic hydrocarbon receptors, is currently commonly used in anti-inflammatory applications. This invention unexpectedly reveals for the first time that combining it with phenylethyl resorcinol exhibits a significant synergistic effect in whitening efficacy, with results significantly superior to single components. Furthermore, it demonstrates good whitening effects at lower concentrations, reducing the side effects associated with high concentrations of single chemical components and improving safety.

[0007] In some embodiments of the present invention, the molar ratio of phenylethyl resorcinol to benzyl dimethoxydimethyl indanone is (0.01-1):(0.01-10).

[0008] In some embodiments of the present invention, the molar ratio of phenylethyl resorcinol to benzenemethylenedimethoxydimethylindanone is 0.01:(0.01-10). This molar ratio can be any point value or any two points within the range of 0.01:(0.01-10), such as 0.01:0.01, 0.01:0.1, 0.01:1, 0.01:3, 0.01:5, 0.01:7, 0.01:10, etc.; preferably 0.01:(5-10).

[0009] In some embodiments of the present invention, the molar ratio of phenylethyl resorcinol to benzenemethylenedimethoxydimethylindanone is 1:(0.01-10). This molar ratio can be any point value or any two points within the range of 1:(0.01-10), such as 1:0.01, 1:0.1, 1:1, 1:3, 1:5, 1:7, 1:10, etc.; preferably 1:(5-10).

[0010] A second aspect of the present invention provides the use of the composition described in the first aspect of the present invention in the preparation of cosmetics having whitening effects.

[0011] In some embodiments of the present invention, in the application, both phenylethyl resorcinol and benzyl dimethoxydimethyl indanone in the composition are used as whitening active ingredients.

[0012] In some embodiments of the present invention, in the application, both phenylethyl resorcinol and benzyl dimethoxydimethyl indanone in the composition are the sole whitening active ingredients.

[0013] In some embodiments of the present invention, in the application, the amount of the composition added to the cosmetic is ≤10wt%, preferably ≤5wt%, more preferably ≤1wt%, and even more preferably 0.1-0.5wt%.

[0014] A third aspect of the present invention provides a cosmetic product comprising the composition described in the first aspect of the present invention.

[0015] In some embodiments of the present invention, in the cosmetic, both phenylethyl resorcinol and benzyl dimethoxydimethyl indanone in the composition are used as whitening active ingredients.

[0016] In some embodiments of the present invention, in the cosmetic, phenylethyl resorcinol and benzenemethylene dimethoxydimethyl indanone in the composition are both used as the sole whitening active ingredients.

[0017] In some embodiments of the present invention, the content of the composition in the cosmetic is ≤10wt%, preferably ≤5wt%, more preferably ≤1wt%, and even more preferably 0.1-0.5wt%.

[0018] In some embodiments of the present invention, the dosage form of the cosmetic is selected from creams, lotions, serums, waters, oils, gels, or masks.

[0019] Compared with the prior art, the beneficial effects of the present invention are as follows: (1) The composition provided by the present invention, by combining benzenemethylenedimethoxydimethylindanone and phenylethyl resorcinol, has a significant synergistic effect in inhibiting melanin content and tyrosinase activity, and its whitening effect is significantly better than that of each single component.

[0020] (2) The composition provided by the present invention can exhibit significant inhibitory effects on melanin and tyrosinase at low concentrations (micromolar level). While ensuring the whitening effect, it significantly reduces the probability of adverse reactions caused by the use of high concentrations of single chemical components, and is safer. Detailed Implementation

[0021] To enable those skilled in the art to more clearly understand the technical solutions described in this invention, the following embodiments are provided for illustration. It should be noted that the following embodiments do not constitute a limitation on the scope of protection claimed by this invention.

[0022] Unless otherwise specified, the raw materials, reagents, and apparatus used in the following examples can be obtained from conventional commercial sources or by existing known methods.

[0023] Example 1 This embodiment provides a composition consisting of phenylethyl resorcinol and benzenemethylenedimethoxydimethylindanone.

[0024] Comparative Example 1 This comparative example provides a single component, namely phenylethyl resorcinol.

[0025] Comparative Example 2 This comparative example provides a single component, namely benzenemethylenedimethoxydimethylindanone.

[0026] Comparative Example 3 This comparative example provides a composition comprising phenylethyl resorcinol and glucosyl rutin.

[0027] Comparative Example 4 This comparative example provides a composition comprising phenylethyl resorcinol and glucosyl hesperidin.

[0028] Comparative Example 5 This comparative example provides a composition consisting of hydroquinone and benzenemethylenedimethoxydimethylindanone.

[0029] Comparative Example 6 This comparative example provides a composition comprising 4-butylresorcinol and benzenemethylenedimethoxydimethylindanone.

[0030] Experiment 1: Inhibition of Melanin Synthesis and Tyrosinase Activity 1.1 Preparation of sample solution Using DMSO as a solvent, sample solutions containing different molar concentrations of components from Example 1 (phenylethyl resorcinol and benzyl dimethoxydimethyl indanone) were prepared, including 1 / 0.01 μM phenylethyl resorcinol mixed with 10 / 5 / 1 / 0.1 / 0.01 μM benzyl dimethoxydimethyl indanone, and the results were tested.

[0031] Using DMSO as a solvent, Comparative Example 1 (phenylethyl resorcinol) was prepared into sample solutions with molar concentrations of 1 μM and 0.01 μM for testing.

[0032] Using DMSO as a solvent, Comparative Example 2 (benzyl dimethoxydimethyl indanone) was prepared into sample solutions with molar concentrations of 1 μM, 0.1 μM, and 0.01 μM for testing.

[0033] Using DMSO as a solvent, Comparative Example 3 (phenylethyl resorcinol and glucosyl rutin) was prepared into sample solutions containing components of different molar concentrations, including 1 μM phenylethyl resorcinol mixed with 10 / 5 μM glucosyl rutin, and 0.01 μM phenylethyl resorcinol mixed with 10 / 5 / 1 / 0.1 μM glucosyl rutin, and the experiments were conducted.

[0034] Using DMSO as a solvent, Comparative Example 4 (phenylethyl resorcinol and glucosyl hesperidin) was prepared into sample solutions containing components of different molar concentrations, including 1 μM phenylethyl resorcinol mixed with 10 / 5 μM glucosyl hesperidin, and 0.01 μM phenylethyl resorcinol mixed with 5 / 1 / 0.1 μM glucosyl hesperidin, and the experiments were conducted.

[0035] Using DMSO as a solvent, Comparative Example 5 (hydroquinone and benzenemethylenedimethoxydimethylindanone) was prepared into sample solutions containing components of different molar concentrations, including 1 μM hydroquinone mixed with 10 / 5 μM benzenemethylenedimethoxydimethylindanone, and 0.01 μM hydroquinone mixed with 10 / 5 / 1 / 0.1 μM benzenemethylenedimethoxydimethylindanone, and the results were tested.

[0036] Using DMSO as a solvent, Comparative Example 6 (4-butylresorcinol and benzenemethylenedimethoxydimethylindanone) was prepared into sample solutions containing components of different molar concentrations, including 1 μM 4-butylresorcinol mixed with 10 / 5 μM benzenemethylenedimethoxydimethylindanone, and 0.01 μM 4-butylresorcinol mixed with 10 / 5 / 1 / 0.1 μM benzenemethylenedimethoxydimethylindanone, and the results were tested.

[0037] 1.2 Experimental Principle Melanin is a biological pigment synthesized and secreted by melanocytes. Within melanocytes, tyrosine is catalyzed by tyrosinase and undergoes a series of reactions to ultimately produce melanin.

[0038] B16-F10 mouse melanoma cells are widely used as test cells for assessing the efficacy of skin-whitening chemicals. α-MSH, an α-melanocyte-stimulating agent, can promote melanin secretion from B16-F10 cells and increase intracellular tyrosinase activity. By inducing B16-F10 cells with α-MSH, the inhibitory effects of test substances on melanin synthesis and tyrosinase activity can be measured.

[0039] 1.3 Experimental Methods (1) Cell culture and treatment B16-F10 cells were cultured in 1640 complete medium (1640 medium + 10% FBS + antibiotics) in a carbon dioxide incubator at 37°C and 5% CO2, and passaged every 2-3 days.

[0040] (2) Determination of intracellular melanin content B16-F10 cells in logarithmic growth phase were selected, digested with 0.25% trypsin, and seeded into 6-well plates with 2 mL of culture medium per well. The plates were incubated at 37°C in a 5% CO2 incubator. The day after seeding, culture medium containing different concentrations of the test substance and 1 μM α-MSH was added, and a control group (containing only 1 μM α-MSH) was set up with 2 mL per well. Each concentration was replicated in triplicate. After incubation at 37°C in a 5% CO2 incubator for 48 h, the supernatant was discarded, and 0.5 mL of 0.25% trypsin digestion solution was added to each well. Digestion was carried out at room temperature for 1 min. Digestion was stopped by adding 1 mL of culture medium, and the cells were pipetted into a single-cell suspension. Take 20 μL for cell counting, take 0.7 mL of cell suspension, centrifuge at 2000 r / min for 5 min, discard the supernatant, add 1 mL of 1 mol / L NaOH solution (containing 10% DMSO by mass), and incubate in an 80℃ water bath for 30 min. Then measure the absorbance at 490 nm using an ELISA reader.

[0041] (3) Determination of intracellular tyrosinase activity After the cells were treated with the above sample solution, they were digested and counted with trypsin (specific steps are the same as 1.3-(2)). 0.7 mL of the cell suspension was centrifuged at 2000 r / min for 5 min, the supernatant was discarded, and 1 mL of 0.5% sodium deoxycholate solution was added. The cells were incubated on ice for 15 min to lyse them and prepare an extract containing tyrosinase. After preheating at 37℃, 0.5 mL of 0.3% dopa solution was added, and the reaction was carried out at 37℃ for 10 min. The absorbance was then measured at 475 nm using an ELISA reader.

[0042] (4) Results statistics The OD value is calibrated by the number of cells.

[0043] Melanin production inhibition rate (%) = [1 - (As / Ds) / (Ac / Dc)] × 100; Tyrosinase activity inhibition rate (%) = [1 - (As / Ds) / (Ac / Dc)] × 100; In the formula: As is the absorbance of the sample group, Ac is the absorbance of the control group, Ds is the cell concentration of the sample group, and Dc is the cell concentration of the control group.

[0044] 1.4 Experimental Results The results are shown in Table 1-2.

[0045] Table 1

[0046] Table 2

[0047] It is understandable that melanin is mainly produced and secreted by melanocytes in the basal layer of the skin. The level of melanin directly affects skin color, and dullness, age spots, and pigmentation are all related to abnormal melanin production and metabolism. Tyrosinase, as the rate-limiting enzyme regulating melanin production, directly affects melanin synthesis. Therefore, cellular methods are commonly used to detect the effects of cosmetic ingredients on melanin content and tyrosinase activity, thereby assessing their whitening effects.

[0048] Hydroquinone and 4-butylresorcinol are both known cosmetic ingredients with phenolic structures and good whitening effects. Glucosylrutin is an antioxidant with excellent UV absorption and free radical scavenging capabilities, effectively improving photoaging of the skin. Glucosylhesperidin has anti-inflammatory and antioxidant effects, improving skin damage caused by UV radiation. Therefore, glucosylrutin and glucosylhesperidin are also used in sunscreen products. In this invention, glucosylrutin and glucosylhesperidin were used to replace benzenemethylenedimethoxydimethylindanone in Example 1 to form Comparative Examples 3 and 4, respectively; and hydroquinone and 4-butylresorcinol were used to replace phenylethylresorcinol in Example 1 to form Comparative Examples 5 and 6, respectively.

[0049] As shown in Tables 1 and 2, Example 1 (phenylethyl resorcinol + benzyl dimethoxydimethyl indanone) exhibits strong inhibitory effects on tyrosinase activity and melanin production at low concentrations (micromolar levels). The inhibitory effects of different concentration combinations are significantly better than those of their individual components (Comparative Example 1 and Comparative Example 2). In Example 1, phenylethyl resorcinol and benzyl dimethoxydimethyl indanone both showed strong inhibitory effects on tyrosinase activity and a certain degree of synergy within a molar ratio of (0.01-1):(0.01-10), and within this molar ratio range, they also showed strong inhibitory effects on melanin production and a certain degree of synergy. However, when the components in Example 1 were replaced to form Comparative Examples 3-6, the results showed that Comparative Examples 3 and 4 had poor inhibitory effects on tyrosinase activity, and were even worse than phenylethyl resorcinol (Comparative Example 1) at the same concentration. Furthermore, Example 1, at the same addition amount, showed significantly better effects than Comparative Examples 3 and 4. Comparative Examples 5 and 6 showed some inhibitory effect on tyrosinase activity only when 5-10 μM of benzyldimethoxydimethylindanone was added, but the effect was significantly weaker than that of Example 1 with the same amount of benzyldimethoxydimethylindanone. Regarding melanin production, Comparative Examples 3, 4, and 5 showed poor overall performance, significantly weaker than Example 1. Comparative Example 6 showed some inhibitory effect on melanin production (inhibition rate >10%) when 10 μM of benzyldimethoxydimethylindanone was added, but the overall effect was weaker than that of Example 1.

[0050] In summary, Example 1 demonstrates a significant and synergistic effect in inhibiting melanin synthesis and tyrosinase activity. This is an efficacy characteristic not found in other types of compositions, resulting in a stronger whitening effect while reducing the amount of any single ingredient required, minimizing irritation, and lowering costs.

[0051] Application Example 1 An emulsion containing the composition of the present invention, the specific formulation of which is shown in Table 3.

[0052] Table 3

[0053] The above emulsion is prepared by the following method: S1. Heat and stir the aqueous raw material to 80°C to ensure uniform dispersion; S2. Add the oil phase raw materials into the oil phase preparation pot, heat and stir to 80°C until completely melted and homogeneous; S3. Slowly pour the oil phase into the aqueous phase while homogenizing at high speed (3000 rpm) for 5 minutes to form a fine emulsion, and keep warm for 15 minutes. S4. Cool down to 40°C, add the composition of the present invention, stir for 10 minutes, and then filter and discharge.

[0054] Application Example 2 A face cream containing the composition of the present invention, the specific formula of which is shown in Table 4.

[0055] Table 4

[0056] The preparation method of the above face cream is as follows: S1. Heat and stir the aqueous raw material to 80°C to ensure uniform dispersion; S2. Add the oil phase raw materials into the oil phase preparation pot, heat and stir to 80°C until completely melted and homogeneous; S3. Slowly pour the oil phase into the water phase while homogenizing at high speed (3500 rpm) for 8 minutes to fully emulsify, and keep warm for 15 minutes. S4. Cool down to 45°C, add the composition of the present invention, stir for 15 minutes, and then filter and discharge.

[0057] Application Example 3 An essence containing the composition of the present invention, the specific formulation of which is shown in Table 5.

[0058] Table 5

[0059] The above-mentioned essence is prepared by the following method: S1. Heat and stir the aqueous raw material to 75°C until it is uniformly stirred. S2. Cool to 40°C, slowly add the composition of the present invention, and stir for 10 minutes; S3. Continue cooling to 35℃, add Centella Asiatica extract, stir for 5 minutes until the system is homogeneous, then filter and discharge.

[0060] It is easy to imagine that the cosmetics prepared by the present invention in Examples 1-3, since they contain the compositions of the present invention, have good whitening effects.

[0061] The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the embodiments described. Those skilled in the art can make various equivalent modifications or substitutions without departing from the spirit of the present invention, and these equivalent modifications or substitutions are all included within the scope defined by the claims of this application.

Claims

1. A composition, characterized in that, The composition consists of phenylethyl resorcinol and benzenemethylenedimethoxydimethylindanone.

2. The composition according to claim 1, characterized in that, The molar ratio of phenylethyl resorcinol to benzyl dimethoxydimethyl indanone is (0.01-1):(0.01-10).

3. The composition according to claim 2, characterized in that, The molar ratio of phenylethyl resorcinol to benzyl dimethoxydimethyl indanone is 0.01:(0.01-10).

4. The composition according to claim 2, characterized in that, The molar ratio of phenylethyl resorcinol to benzene methylene dimethoxydimethyl indanone is 1:(0.01-10).

5. The use of the composition according to any one of claims 1-3 in the preparation of a cosmetic having whitening effects.

6. The application according to claim 5, characterized in that, Both phenylethyl resorcinol and benzyl dimethoxydimethyl indanone in the composition are whitening active ingredients.

7. The application according to claim 5, characterized in that, The amount of the composition added to the cosmetic is ≤10wt%.

8. A cosmetic product, characterized in that, The cosmetic product includes the composition according to any one of claims 1-3.

9. The cosmetic product according to claim 8, characterized in that, Both phenylethyl resorcinol and benzyl dimethoxydimethyl indanone in the composition are whitening active ingredients.

10. The cosmetic product according to claim 8, characterized in that, The content of the composition in cosmetics is ≤10wt%.

Images