Phenylethyl resorcinol diglucoside compound as well as preparation process and application thereof

Abstract

The invention discloses a phenylethyl resorcinol diglucoside compound as well as a preparation process and application thereof, belongs to the technical field of cosmetics, and relates to application of the phenylethyl resorcinol diglucoside compound in preparation of cosmetics. The phenethyl resorcinol diglucoside compound disclosed by the invention has the beneficial effects that the phenethyl resorcinol diglucoside compound has the effects of resisting wrinkles, tightening, relieving and whitening.

Description

Technical Field

[0001] This invention belongs to the field of cosmetic technology, and more specifically relates to a phenylethyl resorcinol diglucoside compound, its preparation process, and its application. Background Technology

[0002] Phenylethyl resorcinol is an ingredient widely used in skin whitening products. It is a whitening ingredient developed by the German raw material supplier Symrise. In 2013, my country's CFDA also included it in the list of qualified cosmetic ingredients, allowing its use in the production of daily chemical products.

[0003] Phenethyl resorcinol is extracted from plants, primarily from an extract of a pine tree called pine resin, so it is relatively safe. However, if the concentration is too high, it may cause contact dermatitis, resulting in skin redness, swelling, itching, and pain. There are certain limitations to the use of phenylethyl resorcinol in formulations, especially since it is prone to discoloration after exposure to light. It should be protected from light and chelating agents and other antioxidants should be added. Summary of the Invention

[0004] To address the aforementioned problems and overcome the shortcomings of existing technologies, this invention provides a phenylethyl resorcinol diglucoside compound, its preparation process, and its applications.

[0005] The specific technical solution of this invention to solve the above-mentioned technical problems is as follows: The structural formula of the phenylethyl resorcinol diglucoside compound is as follows: .

[0006] This invention also provides a process for synthesizing a phenylethyl resorcinol diglucoside compound, which includes the following steps: Step (1): Add phenylethyl resorcinol, β-D-glucose pentaacetate, and toluene to the reaction flask. Add boron trifluoride diethyl ether dropwise to the system at 27°C and keep the system at this temperature for reaction. Quench the reaction solution with water at 0°C. Add saturated sodium bicarbonate solution to the toluene phase and concentrate under reduced pressure to obtain the crude product. Step (2): Add methanol and crude product from step (1) to the reaction flask, cool to 0°C in an ice bath, add 3M sodium methoxide methanol solution dropwise, heat to 25±5°C and keep the reaction at that temperature after the addition is complete, add water to the reaction solution, and concentrate the system under reduced pressure at 45°C after the system is cleared to obtain phenylethyl resorcinol diglucoside compound. Further, in step (1), the molar ratio of phenylethyl resorcinol to β-D-glucose pentaacetate is 1:(4-8); wherein the mass-volume ratio of phenylethyl resorcinol to toluene is 1:(20-35). Further, in step (2), the mass ratio of phenylethyl resorcinol diglucose pentaethyl ester to methanol is 1:(4-8). On the other hand, the present invention provides the use of the phenylethyl resorcinol diglucoside compound as described above in the preparation of cosmetics; Furthermore, the dosage forms of the cosmetics include ointments, creams, emulsions, liquids, oils, gels, powders, tablets, muds, patches, films, aerosols, sprays, lyophilized preparations, or nano-preparations; Furthermore, the cosmetic product has anti-wrinkle and firming effects; Furthermore, the cosmetic product has a soothing effect; Furthermore, the cosmetic product has a whitening effect; The beneficial effects of this invention are: This invention creatively proposes a phenylethyl resorcinol diglucoside compound, which, compared to phenylethyl resorcinol, has anti-wrinkle and firming effects, is less irritating to the skin and has a soothing effect, and can be used in cosmetics. Attached Figure Description

[0007] Appendix Figure 1 This is the 1H NMR spectrum of the phenylethyl resorcinol diglucoside compound of this invention; Appendix Figure 2 This is the mass spectrometry of the phenylethyl resorcinol diglucoside compound of the present invention; Appendix Figure 3 It is a cell viability graph used in a cytotoxicity test; Appendix Figure 4 This is a summary chart of Collagen I immunofluorescence staining results; Appendix Figure 5 This is a summary chart of Collagen III immunofluorescence staining results; Detailed Implementation Specific embodiments of the present invention: To better understand the present invention, specific embodiments are described. It is worth emphasizing that the effects of these embodiments are not substantially different from those of various embodiments within the scope of protection of the present invention, including their respective reagents and reagent content ratios. All of them can achieve the effects described in the present invention and solve the above-mentioned problems. Other combinations are not described here. Example 1: Step 1: Synthesis of phenylethyl resorcinol diglucose pentaethyl ester Add 3g of phenylethyl resorcinol, 27.3g of β-D-glucose pentaacetate, and 90mL of toluene to a reaction flask. The system is initially white and turbid. Add 10.1g of boron trifluoride ether dropwise to the system at 27°C. The system gradually turns yellow and turbid. Insulate the system for 12 hours. Quench the reaction solution with 100mL of water at 0°C. Wash the toluene phase twice with 100mL of saturated sodium bicarbonate solution each time. Concentrate the toluene phase under reduced pressure at 50°C in a water bath until no fraction flows out, yielding a brownish-red oily crude product for the next step. Step 2: Synthesis of phenylethyl resorcinol diglucoside compound Add 60g methanol and 12g crude oily product from the previous step to the reaction flask, cool to 0℃ in an ice bath, and add 1.48g of 3M sodium methoxide methanol solution dropwise. The system first turns black and then gradually precipitates solids, turning the system into an earthy-colored turbidity. After the addition is complete, heat to 25±5℃ and maintain the temperature for 2 hours. Add 50g water to the reaction solution. After the system is dissolved, concentrate it under reduced pressure at 45℃ to remove methanol. A small amount of solid precipitates from the system. After filtration, the solid is discarded. The mother liquor is separated by acetonitrile:water = 1:4 to obtain phenylethyl resorcinol diglucoside compound, with a yield of 80.4%. Characterization data of phenylethyl resorcinol diglucoside:

[0008] C 26 H 34 O 12 [M+Na]+=561.3.

[0009] Example 2: Preparation of phenylethyl resorcinol diglucoside compound The difference between this embodiment and Embodiment 1 is that: Step 1: The molar ratio of phenylethyl resorcinol to β-D-glucose pentaacetate is 1:4; wherein the mass-to-volume ratio of phenylethyl resorcinol to toluene is 1:20; The mass ratio of phenylethyl resorcinol diglucose pentaethyl ester to methanol in step 2 was 1:4; the yield was 75.3%.

[0010] Example 3: Preparation of phenylethyl resorcinol diglucoside compound The difference between this embodiment and Embodiment 1 is that: Step 1: The molar ratio of phenylethyl resorcinol to β-D-glucose pentaacetate is 1:8; wherein the mass-to-volume ratio of phenylethyl resorcinol to toluene is 1:35; Step 2: The mass ratio of phenylethyl resorcinol disaccharide pentaethyl ester to methanol is 1:8; the yield is 76.2%.

[0011] Comparative Example 1: Preparation of phenylethyl resorcinol diglucoside compound. The difference between Comparative Example 1 and Example 1 is as follows: Step 1: The molar ratio of phenylethyl resorcinol to β-D-glucose pentaacetate is 1:2; wherein the mass-to-volume ratio of phenylethyl resorcinol to toluene is 1:15; The mass ratio of phenylethyl resorcinol diglucose pentaethyl ester to methanol in step 2 was 1:3; the yield was 45.3%.

[0012] Comparative Example 2: Preparation of phenylethyl resorcinol diglucoside compound. The difference between Comparative Example 2 and Example 1 is as follows: Step 1: The molar ratio of phenylethyl resorcinol to β-D-glucose pentaacetate is 1:10; wherein the mass-to-volume ratio of phenylethyl resorcinol to toluene is 1:40; Step 2: The mass ratio of phenylethyl resorcinol disaccharide pentaethyl ester to methanol is 1:10; yield is 56.7%.

[0013] Table 1: Effect of different component ratios on the yield of phenethylresorcinol diglucoside

[0014] Analysis of the data in Table 1 shows that: Compared to Comparative Examples 1-2, there is a close correlation between the amounts of each additive in Comparative Examples 1-2 and Comparative Examples 1-3 of the present invention. In Comparative Examples 1-2, the addition ratios of β-D-glucose pentaacetate, toluene, and methanol were not within the scope of protection of this invention. As can be seen from the data, the yield decreased drastically, from 80.4% in this invention to 45.3%, a decrease of 46.65%. Therefore, it can be inferred that the addition ratios of phenylethyl resorcinol, β-D-glucose pentaacetate, toluene, and methanol have a significant impact on the yield of phenylethyl resorcinol diglucoside compound.

[0015] The test sample information for the efficacy verification experiment is as follows: Experimental Group 1: JT-070115 is a phenylethyl resorcinol diglucoside compound prepared according to the embodiments of the present invention. As a preferred scheme, it was prepared by the specific technical solution of Example 1 and has no significant difference from other embodiments. Experimental Group 2: Phenethyl resorcinol was purchased; Experimental Group 3: Glycyrrhizin diglucoside was prepared by dissolving glycyrrhizin in methanol and adding sodium methoxide methanol solution dropwise to the system. Experimental Group 4: Glycyrrhiza glabra was determined to be obtained through procurement; (1) Whitening effect of phenylethyl resorcinol diglucoside compound 1. Experimental Objective Skin color is determined by various pigments and chromophores, with melanin playing a dominant role. Melanin is a double-edged sword; it absorbs ultraviolet rays and protects epidermal and dermal cells from sun damage, but excessive melanin production and deposition can lead to skin darkening. Increased local melanin synthesis and deposition can cause age spots. Melanin is produced by melanocytes located in the basal layer of the epidermis, which account for about 10% of basal cells. After melanin production, melanocytes transport melanin granules to basal and spinous cells via dendritic processes. Tyrosinase is a key enzyme in the biosynthesis of melanin in the skin, catalyzing the conversion of dopa to dopaquinone. Dopaquinone then undergoes a series of reactions to form melanin. Dopaquinone has a characteristic absorption peak at 475 nm on a spectrophotometer. Samples with tyrosinase activity inhibition can reduce the conversion of dopa to dopaquinone, thereby lowering the absorbance. Therefore, inhibiting tyrosinase activity and melanin synthesis are common methods for skin whitening.

[0016] Based on this mechanism, this test uses A875 human melanoma cells as an evaluation model. By testing the inhibitory effect of the sample on tyrosinase activity and the inhibitory effect on melanin synthesis, the whitening efficacy of the sample is comprehensively evaluated. 2 Test Items Whitening efficacy test - A875 melanocyte tyrosinase activity inhibition test; A875 cell melanin synthesis inhibition test; 3 Test Materials 3.1 Test System A875 human melanoma cells; 3.2 Main Reagents High glucose DMEM culture medium (Gibco), fetal bovine serum (Gibco), PBS (VivaCell), MTT (Sigma), DMSO (Sinopharm), trypsin (Gibco), NaOH (Sigma), levodopa (Sinopharm); 3.3 Main Equipment CO2 incubator (Thermo, 160i), biosafety cabinet (Sujing Antai, BSC-1604ⅡA2), microplate reader (Tecan, Spark). 4.1 Cytotoxicity test 1) Cell seeding: at 1×10 4 Seed cells at a density of cells / well into 96-well plates and incubate overnight in an incubator (37°C, 5% CO2); 2) Experimental Groups: The experiment included a zeroing group, a control group, a positive control group, and a sample group; within the sample group, each sample was configured with 8 concentration gradients. Three replicate wells were set up for each concentration gradient; 3) Solution preparation: Using the phenylethyl resorcinol diglucoside compound prepared in this invention, sample batch number JT-070115 (product of Example 1): prepare sample working solutions of different concentrations according to the test concentration setting table. Table 2: Concentration settings for working solutions of different concentrations

[0017] 4) Sample loading: Load samples when the cell seeding rate in the 96-well plate reaches 40%~60%; add 200μL of culture medium containing 10% PBS to each well of the control group; add 200μL of culture medium containing 10% DMSO to each well of the positive control group; add 200μL of culture medium containing the corresponding concentration of the sample to each well of the sample group; no cell seeding is done in the zeroing group, only 200μL of cell culture medium is added; after sample loading, place the 96-well plate in an incubator (37℃, 5% CO2) for incubation. 5) Detection: After culturing cells for 24 hours, discard the supernatant, add MTT working solution (0.5 mg / mL), and incubate at 37°C in the dark for 4 hours. After incubation, discard the supernatant, add 100 µL LDMSO to each well, and read the OD value at 490 nm. 6) Cell viability calculation: Calculated according to the formula: ; 7) Cytotoxicity test results: Eight sample concentrations were set, and cytotoxicity assays were performed. The MTT assay results are as follows; Table 3: MTT assay results for cytotoxicity detection

[0018] A cell viability graph was plotted using the eight selected concentrations of JT-070115 as the x-axis and cell viability values ​​as the y-axis, as shown below. Figure 3 ; Therefore, based on the MTT results, sample JT-070115 did not exhibit A875 melanocyte cytotoxicity; 4.2 Cellular Tyrosinase Activity Inhibition Test 1) Collect cells in the logarithmic growth phase, at a cell density of 1×10⁻⁶. 5 Cells / well were seeded into 24-well plates; after culturing in an incubator (37℃, 5% CO2) for 24 h, the test samples were added according to Table 3 based on the cytotoxicity results. Kojic acid (3 mg / mL) was used as a positive control, and untreated cells were used as a blank control. The sample volume was 1 mL, and 3 replicates were set up for each group. 2) After adding the samples, continue culturing in an incubator (37℃, 5% CO2) for 24 h. Discard the culture medium, wash twice with PBS, add 100 μL of lysis buffer to each well, and lyse on ice for 5 minutes. Remove the 24-well plate, aspirate 50 μL of the supernatant and add it to a new 96-well plate. Add 50 μL of 1 mg / mL levodopa to each well, incubate at 37℃ for 1 h, read the absorbance at 475 nm and calculate the inhibition rate of cellular tyrosinase activity. ; Table 4: Experimental Design and Results of Tyrosinase Activity Inhibition Test

[0019] Analysis of the data in Table 4 shows that: In experimental group 1, melanocytes treated with 0.0100% phenylethyl resorcinol diglucoside showed a significantly increased tyrosinase activity inhibition rate, which was statistically different from the blank control (p<0.05), but lower than the positive control and experimental group 2. 4.3 Cellular melanin synthesis inhibition test 1) Collect cells in the logarithmic growth phase, at a cell density of 3 × 10⁻⁶. 4 Cells / well were seeded into 12-well plates; after culturing in an incubator (37℃, 5% CO2) for 24 h, the test samples were added according to Table 4 based on the cytotoxicity results, with untreated cells as a blank control. The sample volume was 1 mL, and 3 replicates were set up for each group. 2) After adding the sample, continue culturing in an incubator (37℃, 5% CO2) for 24 hours; 3) Melanin content determination: Discard the supernatant, add 0.5 mL of 1M NaOH containing 10% DMSO, incubate in an 80℃ constant temperature oven for 1 h, and after returning to room temperature, transfer 200 μL to each well of a 96-well plate. Use 1M NaOH containing 10% DMSO as a blank well, read the absorbance value at 405 nm and calculate the relative inhibition rate of melanin in cells.

[0020] Table 5: Experimental Design and Results of Cellular Melanin Synthesis Inhibition Assay

[0021] Analysis of the data in Table 5 shows that: The melanocytes treated with sample JT-070115 in experimental group 1 showed a significantly increased melanin synthesis inhibition rate, which was statistically different from the blank control (p<0.05), but lower than the positive control and experimental group 2. Therefore, based on the above mechanism, this test uses A875 human melanoma cells as an evaluation model. By testing the inhibitory effect of the sample on tyrosinase activity and the inhibitory effect on melanin synthesis, the sample JT-070115 is comprehensively evaluated to have a certain whitening effect compared with the blank group. 4.4 Solubility Test Table 6 Solubility Test Results

[0022] As shown in Table 6, the solubility of sample JT-070115 is better than that of phenylethyl resorcinol.

[0023] 4.5 Soothing Efficacy Test 4.5.1 Test Objective Skin irritation mainly involves the physiological processes of skin barrier-neurovascular-immune inflammation. Soothing the skin inflammatory response can improve skin irritation. When cells are stimulated, they secrete factors such as tumor necrosis factor α (TNF-α), prostaglandin E2 (PGE2), interleukin-1α (IL-1α), interleukin-1β (IL-1β), interleukin-8 (IL-8), and interleukin-6 (IL-6), which can cause skin irritation. This experiment was based on the LPS-stimulated RAW264.7 macrophage model. The soothing efficacy of the test samples was evaluated by detecting changes in the levels of inflammatory factors (TNF-α, IL-6, IL-1β) secreted by the cells. 4.5.2 Test Items Soothing efficacy test - detection of LPS-stimulated RAW264.7 macrophage inflammatory factor (TNF-α, IL-6, IL-1β) content; 4.5.3 Test Materials 4.5.3.1 Test System Macrophages RAW264.7; 4.5.3.2 Main Reagents High glucose DMEM culture medium (Gibco), fetal bovine serum (Gibco), PBS (VivaCell), MTT (Sigma), DMSO; (Sinopharm), trypsin (Gibco), LPS (Sigma), dexamethasone (Sigma), Mouse TNF-α ELISA kit; (Boster), MouseIL-6 ELISA kit (Shanghai Enzyme-Linked Biotechnology), MouseIL-1β ELISA kit (Shanghai Enzyme-Linked Biotechnology); 4.5.3.3 Main Equipment CO2 incubator (Thermo, 160i), biosafety cabinet (Sujing Antai, BSC-1604ⅡA2), microplate reader (Tecan, Spark). 4.5.3.4 Sample Information Phenylacetyl resorcinol diglucoside, phenylacetyl resorcinol, glycyrrhizin diglucoside, and glycyrrhizin; 4.5.4 Test Method 1) Cell seeding: at 1×10 5 Seed cells at a density of cells / well into 24-well plates and incubate overnight in an incubator (37°C, 5% CO2); 2) Solution preparation: Prepare working solutions of the test substance at different concentrations according to the experimental design table; 3) Induction and sample loading: When the cell deposition rate in the 24-well plate reaches 40-60%, add 100 μL of 10×LPS working solution to each well according to the experimental design. Shake the plate left and right to mix the drug. Add the sample at the same time. The final LPS concentration is 1 μg / mL. Each group has 3 replicates; after loading the sample, place it in an incubator (37℃, 5% CO2) and continue to incubate for 24 hours; 4) Sample collection: After incubation, collect the cell culture supernatant into EP tubes. After collection, freeze the samples at -80℃. 5) TNF-α level detection: Detection was performed according to the instructions for the Mouse TNF-α ELISA kit; IL-6 level detection: Perform the detection according to the instructions of the MouseIL-6ELISA kit; IL-1β level detection: The detection was performed according to the instructions of the Mouse IL-1β ELISA kit; Table 7: Experimental Design for Soothing Efficacy Testing

[0024] Table 8: Results of the soothing efficacy test

[0025] Analysis of the data in Table 8 shows that: (1) The sample JT-070115 of the present invention can promote a high inhibition rate of the content of inflammatory factors (TNF-α, IL-6, IL-1β) secreted by cells, and is higher than that of phenylethyl resorcinol in test group 2, glycyrrhizin diglucoside in test group 3 and glycyrrhizin in test group 4. (2) Compared with glycyrrhizin in experimental group 4, glycyrrhizin diglucoside in experimental group 3 did not achieve the technical effect of significantly improving the inhibition rate of cell secretion of inflammatory factors (TNF-α, IL-6, IL-1β) as the present invention. Overall, the difference in the enhancement effect was not significant. In particular, the inhibition rate of cell secretion of inflammatory factor IL-6 by glycyrrhizin diglucoside was only 32.31%, even lower than that of glycyrrhizin at 34.26%. Therefore, the phenylethyl resorcinol diglucoside prepared in this invention has a relatively significant soothing effect; 4.6 Anti-wrinkle and firming effects 1. Test Objective This test uses human fibroblasts as the test system and uses immunofluorescence technology to detect changes in the expression levels of type I collagen (Collagen I) and type III collagen (Collagen III) in human fibroblasts to evaluate whether the test sample has anti-wrinkle and firming effects. 2. Test Items: Anti-wrinkle and firming efficacy test - UVA-stimulated immunofluorescence detection of type I and type III collagen in human fibroblasts; 3 Test Materials 3.1 Test system: human fibroblasts; 3.2 Main reagents: low glucose DMEM culture medium (Pronosai), fetal bovine serum (Gibco), PBS (VivaCell), MTT (Sigma), DMSO (Sinopharm), trypsin (Gibco), primary antibody (Abcam), secondary antibody (Abcam), BSA (Sigma); 3.3 Main equipment: CO2 incubator (Thermo, 160i), biosafety cabinet (Sujing Antai, BSC-1604ⅡA2), inverted fluorescence microscope (Keyence BZ-X1000), microplate reader (Tecan, Spark), ultraviolet phototherapy device (SIGMA, SS-03). 3.4 Sample Information Phenylacetyl resorcinol diglucoside, phenylacetyl resorcinol, glycyrrhizin diglucoside, and glycyrrhizin; 4. Collagen I and Collagen III content testing 1) Cell seeding: Seed at an appropriate seeding density (8 × 10⁻⁶). 4 Cells were seeded into 24-well plates and incubated overnight in an incubator (37°C, 5% CO2). 2) Experimental grouping: The experiment included a blank control group, a negative control group, a positive control group, and an experimental group; 3) Solution preparation: Prepare working solutions of different concentrations of the test substance according to the test concentration setting table in Table 9; 4) Irradiation: Irradiation was carried out when the cell deposition rate in the 24-well plates reached 40-60%. The negative control group, positive control group, and experimental group received a dose of 9 J / cm². 2 The control group was placed under UVA radiation, while the blank control group was placed in the same environment (UVA radiation dose of 0 J / cm²). 2 ); 5) Sample loading: After irradiation, sample loading is performed. 1 mL of cell culture medium is added to each well of the blank control group and negative control group; 1 mL of culture medium containing 100 μg / mL VC and 7 μg / mL VE is added to each well of the positive control group; 1 mL of culture medium containing the corresponding concentration of the test substance is added to each well of the experimental group. 6) Immunofluorescence assay for Collagen I and Collagen III expression: Cell collection: After sample loading, discard the supernatant and wash the cells 3 times with PBS; Immunofluorescence staining: Perform routine immunofluorescence staining; The main steps are: fixation, blocking, adding primary antibody, adding secondary antibody, DAPI counterstaining, and then taking pictures using a fluorescence microscope; 7) Results analysis: The fluorescence intensity and expression levels of Collagen I and Collagen III were quantitatively analyzed using ImageProPlus software; Table 9: Experimental Design and Results of Anti-wrinkle and Firming Efficacy Tests

[0026] Analysis of the data in Table 9 shows that, based on the UVA-stimulated human fibroblast model, (1) The sample JT-070115 of the present invention can significantly enhance the expression levels of Collagen I and Collagen III in human fibroblasts, and is much higher than the expression levels of Collagen I and Collagen III in human fibroblasts by phenylethyl resorcinol in experimental group 2. (2) The glycyrrhizin diglucoside in experimental group 3 and the glycyrrhizin in experimental group 4 did not promote the expression of Collagen I and Collagen III in human fibroblasts; Therefore, the phenylethyl resorcinol diglucoside prepared in this invention significantly enhances the expression levels of Collagen I and Collagen III in human fibroblasts, and has anti-wrinkle and firming effects.

[0027] In summary: (1) The phenylethyl resorcinol diglucoside prepared in this invention did not show A875 melanocyte toxicity, had a certain whitening effect, and had better solubility than phenylethyl resorcinol. (2) The phenylethyl resorcinol diglucoside prepared in this invention has a relatively significant soothing effect; (3) The phenylethyl resorcinol diglucoside prepared in this invention has a significant effect on increasing the expression of Collagen I and Collagen III in human fibroblasts, and has anti-wrinkle and firming effects.

Claims

1. A phenylethyl resorcinol bisglucoside compound characterized in that The compound has the structure as shown in the following formula: 。 2. The phenylethyl resorcinol bis-glucoside compound according to claim 1, characterized by The phenylethyl resorcinol bis-glucoside compound has anti-wrinkle and firming effects.

3. The phenylethyl resorcinol bis-glucoside compound according to claim 1, characterized by The phenylethyl resorcinol bis-glucoside compound has soothing effects.

4. The phenylethyl resorcinol bis-glucoside compound according to claim 1, characterized by The phenylethyl resorcinol bis-glucoside compound has whitening effects.

5. A process for preparing phenylethyl resorcinol bis glucoside compound, which produces the phenylethyl resorcinol bis glucoside compound according to claim 1, characterized by The preparation process of the phenylethyl resorcinol bis-glucoside compound comprises the following steps: Step (1): adding phenylethyl resorcinol, β-D-glucose pentaacetate and toluene into a reaction bottle, adding dropwise boron trifluoride ether into the system, and reacting after heat preservation; adding water into the above reaction solution at 0°C to quench, adding saturated sodium bicarbonate solution into the toluene phase, and concentrating under reduced pressure to obtain a crude product; Step (2): adding methanol and the crude product of step (1) into a reaction bottle, cooling to 0°C in an ice bath, adding dropwise sodium methoxide methanol solution, heating to 25±5°C after dropwise addition, adding water into the reaction solution, and concentrating under reduced pressure after the system is dissolved to obtain the phenylethyl resorcinol bis-glucoside compound.

6. The process for the preparation of phenylethyl resorcinol bis glucoside compound as claimed in claim 5, wherein In step (1), the molar ratio of phenylethyl resorcinol to β-D-glucose pentaacetate is 1: (4-8), and the mass-volume ratio of phenylethyl resorcinol to toluene is 1: (20-35).

7. The process for the preparation of phenylethyl resorcinol bis glucoside compound as claimed in claim 5, wherein In step (2), the mass ratio of phenylethyl resorcinol bis-glucose pentaacetate to methanol is 1: (4-8).

8. The phenylethyl resorcinol bis-glucoside compound according to any one of claims 1 to 4, wherein The phenylethyl resorcinol bis-glucoside compound is used for preparing cosmetics, and the dosage forms of the cosmetics include ointments, creams, emulsions, aqueous preparations, oil preparations, gels, powders, tablets, mud preparations, patches, film preparations, aerosol preparations, spray preparations, freeze-dried preparations or nano preparations.

9. The process for the preparation of phenylethyl resorcinol bis glucoside compound as claimed in any one of claims 5-7, wherein the process comprises The phenylethyl resorcinol bis-glucoside compound is used for preparing cosmetics, and the dosage forms of the cosmetics include ointments, creams, emulsions, aqueous preparations, oil preparations, gels, powders, tablets, mud preparations, patches, film preparations, aerosol preparations, spray preparations, freeze-dried preparations or nano preparations.

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