Phenol derivatives 4-ethylphenol and 4-acetonyl phenol, and preparation method and application of phenol derivatives 4-ethylphenol and 4-acetonyl phenol

Abstract

The invention provides two phenol derivatives, namely 4-ethyl phenol (1) and 4-acetone phenol (2), and a preparation method and application thereof, and belongs to the technical field of cosmetics and medicines. The 4-ethyl phenol (1) and the 4-acetone phenol (2) are simple in structure, have very remarkable zebra fish melanin formation inhibition activity, have the activity far higher than that of a positive control SymWhite377 (phenethyl resorcinol), have the application value of a whitening effect, and can be applied to preparation of tyrosinase inhibitors and cosmetics.

Description

Technical Field

[0001] The invention belongs to the technical field of cosmetics and medicines, and specifically relates to phenol derivatives 4-ethylphenol and 4-acetonylphenol having zebrafish embryo melanin formation inhibitory activity, and a preparation method thereof, and application of the derivatives in preparing beauty and whitening cosmetics, and in preparing tyrosinase inhibitors. Technical Background

[0002] As people's pursuit of a better life becomes stronger day by day, the demand for beauty and whitening cosmetics has increased significantly. At present, most cosmetics use natural plant functional ingredients as raw materials. Among the natural whitening functional ingredients, kojic acid, niacinamide, arbutin, and vitamin C are all well-known whitening functional ingredients in the cosmetics market. Silver pinesone, a derivative of phenylethyl resorcinol (PR) found in European red pine cones, is a whitening ingredient, but because silver pinesone is extremely unstable, it needs to be chemically derived and modified. Finally, German whitening experts screened out a new and highly effective whitening active ingredient similar to dihydrosilver pinesone - phenylethyl resorcinol (and named it 377), its mechanism of action is believed to be: competitively deceiving and inhibiting the activity of enzymes, reducing the synthesis of melanin. 377) has therefore become a benchmark for tyrosinase inhibition activity and a guide for whitening functional ingredients.

[0003] The applicant discovered from wild Ganoderma lucidum that phenethyl resorcinol ( 377) 2,4-hydroxyacetophenone, which is similar in structure to 2,4-hydroxyacetophenone, showed significant activity in the zebrafish embryo melanin formation inhibition activity experiment: in the same experiment, compared with the positive control The inhibition rates of zebrafish embryo melanin formation of 377 (phenylethyl resorcinol) are 82% (c = 0.0025%) and 15% (c = 0.0005%), respectively. It is a natural product with great whitening function prospects. However, since 2,4-hydroxyacetophenone is a trace substance in Ganoderma lucidum, it is difficult to obtain from natural resources. Therefore, focusing on the analysis of its active functional groups and synthesizing and preparing substances with simpler structures and better activities among these derivatives is a good way.

[0004] So far, there are no reports on the phenol derivatives 4-ethylphenol and 4-acetonylphenol in the prior art, let alone their inhibitory activity on zebrafish embryo melanin formation, nor are there any reports on their preparation methods and their use in the preparation of beauty and whitening cosmetics and their use in the preparation of tyrosinase inhibitors. Summary of the invention

[0005] The purpose of the present invention is to optimize and synthesize a new structure in the structure-activity analysis of 2,4-hydroxyacetophenone in view of the shortcomings of the above-mentioned prior art, and to provide two simple phenol derivatives, 4-ethylphenol (1) and 4-acetonylphenol (2), which are compounds with application value of whitening effect and have very significant zebrafish melanin formation inhibitory activity, and the activity is much stronger than that of the positive control 377 (phenethyl resorcinol); and these two phenol derivatives have simple structures. The present invention also provides a preparation method thereof, which has simple preparation steps, readily available raw materials, and simple operation. In addition, the present invention also provides the use of 4-ethylphenol (1) and 4-acetonylphenol (2) in the preparation of tyrosinase inhibitors and in the preparation of cosmetics.

[0006] In order to achieve the above-mentioned object of the present invention, the present invention provides the following technical solutions:

[0007] The phenol derivatives 4-ethylphenol and 4-acetonylphenol shown in the following structural formula,

[0008]

[0009] The preparation method of 4-ethylphenol and 4-acetonylphenol shown in the structural formula comprises the following steps:

[0010] Synthesis of 4-ethylphenol:

[0011]

[0012] In a container, acetic acid and trifluoromethanesulfonic anhydride are added, mixed and stirred at room temperature for 1 minute, then heated to 60°C, and then phenol is added, magnetically stirred at 60°C for 3 hours and the reaction is detected by TLC, and after the reaction is completed and cooled to room temperature, NaHCO3 is slowly added, and the reaction solution is extracted with ethyl acetate for multiple times, and the ethyl acetate extract is concentrated under reduced pressure. Finally, the product is purified by normal phase silica gel column chromatography with ethyl acetate and petroleum ether to obtain 4-hydroxyacetophenone;

[0013] In a container, 4-hydroxyacetophenone, sodium cyanoborohydride, methyl orange and tetrahydrofuran are added, mixed and stirred at room temperature, and hydrochloric acid is added dropwise to keep the solution in a red state, and then magnetically stirred at room temperature for 12 hours and the reaction is detected by TLC, after the reaction is completed, distilled water is added to dilute the reaction system, and then the reaction solution is extracted with ethyl acetate for multiple times, the ethyl acetate extract is concentrated under reduced pressure, and finally the product is purified by normal phase silica gel column chromatography to obtain 4-ethylphenol;

[0014] Synthesis of 4-acetonylphenol:

[0015]

[0016] In a container, 4-hydroxyphenylacetic acid, sodium acetate and acetic anhydride are added, and the mixture is heated to reflux at 145° C. and magnetically stirred for 6 hours. The reaction is detected by TLC. After the reaction is completed and cooled to room temperature, a NaOH solution is slowly added to neutralize most of the acidic compounds. The reaction solution is then extracted with ethyl acetate for multiple times, and the ethyl acetate extract is concentrated under reduced pressure. NaHCO3 is added to the ethyl acetate concentrate to neutralize the remaining carboxylic acid. The mixture is extracted with ethyl acetate for multiple times, and the ethyl acetate extract is concentrated under reduced pressure. Finally, the product is purified by normal phase silica gel column chromatography using ethyl acetate and petroleum ether to obtain 4-(acetoxyphenyl)-2-propanone;

[0017] In a container, add 4-(acetoxyphenyl)-2-propanone, potassium carbonate and ethanol, heat at 45°C and magnetically stir for 3 hours, and detect the reaction by TLC. After the reaction is completed and cooled to room temperature, filter the reaction solution, add distilled water to the reaction solution after vacuum concentration, and then extract with ethyl acetate for multiple times, and concentrate the ethyl acetate extract under reduced pressure to obtain 4-hydroxyphenyl-2-propanone.

[0018] The application of 4-ethylphenol and / or 4-acetonylphenol shown in the structural formula in the preparation of cosmetics.

[0019] The application of 4-ethylphenol and / or 4-acetonylphenol shown in the structural formula in the preparation of tyrosinase inhibitors.

[0020] A cosmetic containing 4-ethylphenol and / or 4-acetonylphenol shown in the structural formula, wherein the cosmetic is composed of an effective amount of 4-ethylphenol and / or 4-acetonylphenol shown in the structural formula and common cosmetic auxiliary materials.

[0021] A tyrosinase inhibitor containing 4-ethylphenol and / or 4-acetonylphenol shown in the structural formula, wherein the tyrosinase inhibitor contains an effective amount of 4-ethylphenol and / or 4-acetonylphenol shown in the structural formula.

[0022] When the 4-ethylphenol and / or 4-acetonylphenol of the present invention is used to prepare medicines or cosmetics, the content of 4-ethylphenol and / or 4-acetonylphenol accounts for 0.1-99% of the mass of the active ingredients, preferably 0.5-90% of the active ingredients, and the rest are pharmaceutical excipients or carriers that are acceptable in pharmacology and pharmaceutical science and non-toxic to humans and animals.

[0023] The preparations are in various dosage forms that can be used clinically, such as capsules, granules, pills, tablets, injections, ointments, tinctures, oral liquids, etc. The dosage forms of the pharmaceutical composition are lyophilized powders, oral liquids, and capsules, etc. The dosage forms of the cosmetics are creams, facial masks, and hydrogels, etc.

[0024] Compared with the prior art, the present invention has the following advantages:

[0025] The dihydroxyacetophenone compounds with whitening effect were first discovered in Ganoderma lucidum, which may be just one of the more active ingredients in the whitening ingredients of Ganoderma lucidum. Based on the structure of 377 (phenylethyl resorcinol), it was found that there is still a lot of room for the discovery of zebrafish melanin formation inhibitors from phenol derivatives. The key is to compare with benchmark substances 377, whether its activity is significant. In the zebrafish melanin formation inhibition experiment, the two phenol derivatives synthesized and prepared in the present invention: 4-ethylphenol (1) and 4-acetonylphenol (2) have inhibition rates of up to 90% and 78% respectively at a concentration of c = 0.001%, which are significantly different from the positive control benchmark compound. In the same experiment, at the same concentration, The inhibition rate of 377 is only 20%. It shows that the two simple compounds, 4-ethylphenol (1) and 4-acetonylphenol (2), have great application value. The preparation method of the present invention is simple and easy to operate, with readily available raw materials, simple steps and easy operation. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 Schematic diagram of the structures of 4-ethylphenol (1) and 4-acetonylphenol (2). DETAILED DESCRIPTION

[0027] Synthesis of 4-ethylphenol (1):

[0028] 1) In a 25 mL round-bottom flask, acetic acid (10 mmol, 570 μL) and trifluoromethanesulfonic anhydride (11 mmol, 1.8 mL) were added, mixed and stirred at room temperature for 1 minute, then heated to 60°C, and then phenol (10 mmol, 940 mg) was added, magnetically stirred at 60°C for 3 hours and the reaction was detected by TLC. After the reaction was completed and cooled to room temperature, 8 mL of 10% NaHCO3 was slowly added, and the reaction solution was extracted with ethyl acetate for multiple times. The ethyl acetate extract was concentrated under reduced pressure, and finally the product was purified by normal phase silica gel column chromatography using ethyl acetate and petroleum ether to obtain 4-hydroxyacetophenone.

[0029] 2) In a 25 mL round-bottom flask, 4-hydroxyacetophenone (2 mmol, 272.3 mg), sodium cyanoborohydride (6 mmol, 377.04 mg), about 1 mg of methyl orange and 5 mL of tetrahydrofuran were added, mixed and stirred at room temperature, and 2 mol / L hydrochloric acid was added dropwise to keep the solution in a red state (pH ≤ 3), and then magnetically stirred at room temperature for 12 hours and the reaction was detected by TLC. After the reaction was completed, 10 mL of distilled water was added to dilute the reaction system, and the reaction solution was extracted with ethyl acetate for multiple times, and the ethyl acetate extract was concentrated under reduced pressure. Finally, the product was purified by normal phase silica gel column chromatography to obtain 4-ethylphenol, with a reaction yield of 90.9% and a purity of 99%.

[0030]

[0031] Structural Characterization of 4-Ethylphenol (1)

[0032]

[0033] Molecular formula: C8H 10 O; molecular weight: 122.1670

[0034] HR-EIS:121.0660([MH] - )(Calculated value: 121.0659)

[0035] 1 H NMR (600MHz, DMSO-d6) δ (ppm): 9.15 (1H, s, -OH), 6.96 (2H, d, J = 8.5Hz, 3, 5-2xH), 6.64 (2H,d,J=8.5Hz,2,6-2xH),2.45(2H,q,J=7.6Hz,-CH2-),1.10(3H,t,J=7.6Hz,-CH3).

[0036] 13 C NMR (150MHz, DMSO-d6) δ (ppm): 155.26 (1-C-OH), 134.02 (4-C), 128.66 (3,5-2xCH), 115.15 (2,6-2xCH), 27.44 (-CH2-), 16.15 (-CH3).

[0037] Synthesis of 4-acetonylphenol (2):

[0038] 1) In a 10 mL round-bottom flask, 4-hydroxyphenylacetic acid (10 mmol, 1.5215 g), sodium acetate (11 mmol, 902.33 mg) and 5 mL of acetic anhydride were added, heated to reflux at 145° C. and magnetically stirred for 6 hours, and the reaction was detected by TLC. After the reaction was completed and cooled to room temperature, 3 mL of 30% NaOH solution was slowly added to neutralize most of the acidic compounds, and then the reaction solution was extracted with ethyl acetate for multiple times, and the ethyl acetate extract was concentrated under reduced pressure. 5 mL of 10% NaHCO3 was added to the ethyl acetate concentrate to neutralize the remaining carboxylic acid, and ethyl acetate was extracted for multiple times, and the ethyl acetate extract was concentrated under reduced pressure. Finally, the product was purified by normal phase silica gel column chromatography using ethyl acetate and petroleum ether to obtain 4-(acetoxyphenyl)-2-propanone.

[0039] 2) In a 10 mL round-bottom flask, add 4-(acetoxyphenyl)-2-propanone (1 mmol, 192.21 mg), potassium carbonate (0.2 mmol, 27.642 mg) and 1 mL of ethanol, heat at 45 ° C and stir magnetically for 3 hours, and detect the reaction by TLC. After the reaction is completed and cooled to room temperature, filter the reaction solution, add 2 mL of distilled water to the reaction solution after vacuum concentration, and then extract with ethyl acetate for multiple times. Concentrate the ethyl acetate extract under reduced pressure to obtain 4-hydroxyphenyl-2-propanone, reaction yield: 98%; purity: 99%.

[0040]

[0041] Structural Characterization of 4-Acetonylphenol (2)

[0042]

[0043] Molecular formula: C9H 10 O2; molecular weight: 150.1770

[0044] HR-EIS: 149.0613([MH] - )(Calculated value: 149.0608)

[0045] 1 H NMR (600MHz, DMSO-d6) δ (ppm): 9.34 (1H, s, -OH), 6.95 (2H, d, J = 8.5Hz, 3, 5-2xH ),6.68(2H,d,J=8.4Hz,2,6-2xH),3.58(2H,s,-CH2CO-),2.05(3H,s,-COCH3).

[0046] 13C NMR (150MHz, DMSO-d6) δ (ppm): 206.95 (O=CCH3), 156.12 (1-C-OH), 130.61 (3,5-2x CH),125.14(4-C),115.30(2,6-2xCH),49.06(-CH2CO-),29.26(-COCH3).

[0047] Example 2

[0048] Experiment on the inhibitory activity of 4-ethylphenol (1) and 4-acetonylphenol (2) on zebrafish melanin formation.

[0049] 1) Experimental principle

[0050] The main pathway for small molecule compounds to exert their whitening effect is to inhibit the activity of tyrosinase, thereby reducing the production of melanin. Zebrafish are transparent throughout their bodies in the early stages of development, and melanin begins to grow from the retinal epithelium at 24 hours of embryonic development. Pigment cells originate from a group of cells differentiated from the dorsal ectoderm - neural crest cells, which then proliferate, migrate, and differentiate into pigment stem cells. The melanin regulation mechanism in zebrafish skin is highly conserved with that in humans, and the melanin production rate is fast, which can be clearly observed by the naked eye under a microscope. The melanin can be quantified through image processing technology, thereby achieving the evaluation of whitening effect.

[0051] 2) Experimental conditions

[0052] i) Experimental system: wild-type AB strain zebrafish.

[0053] ii) Zebrafish age: 6 hours post fertilization (6 hpf).

[0054] iii) Sample size for each experimental group: 6 (N=3).

[0055] iv) Adult fish rearing and breeding methods: The methods are in accordance with the standard rearing and breeding methods for zebrafish experiments, which meet the requirements of the international AAALAC certification (certification number: 001458).

[0056] v) Experimental system: Wild-type AB strain zebrafish.

[0057] vi) Zebrafish age: 6 hours post fertilization (6 hpf).

[0058] vii) Sample size for each experimental group: 6 (N=3).

[0059] viii) Adult fish rearing and breeding methods: The methods are in accordance with the standard rearing and breeding methods for zebrafish experiments, which meet the requirements of the international AAALAC certification (certification number: 001458).

[0060] 3) Experimental steps i) Zebrafish embryos 6 hours after fertilization were randomly selected and placed in a 12-well plate, with 6 embryos per well.

[0061] ii) Set up a normal control group and a sample intervention group. The normal control group is not treated, and the sample intervention group is cultured with the sample solution. Each well has 1 mL of culture solution.

[0062] iii) Incubate at 28°C in the dark for 45 h.

[0063] iv) After the incubation, three zebrafish were randomly selected from each experimental group and photographed under a dissecting microscope. The data were analyzed and collected using advanced image processing software. The melanin signal intensity (S) of the zebrafish head was analyzed and the formula was used to calculate and determine whether the sample had a whitening effect. The calculation formula is as follows:

[0064]

[0065] 4) Experimental results of the inhibitory activity of 4-ethylphenol (1) and 4-acetonylphenol (2) on zebrafish melanin formation (Table 1).

[0066] Table 1 Inhibition rate of zebrafish melanin formation by 4-ethylphenol (1) and 4-acetonylphenol (2)

[0067]

[0068] The above zebrafish melanin formation inhibition activity experimental results show that the two phenol derivatives synthesized and prepared by the present invention: 4-ethylphenol (1) and 4-acetonylphenol (2) have inhibition rates of up to 90% and 78% respectively at a concentration of c = 0.001% in the zebrafish melanin formation inhibition experiment; while in the same experiment at the same concentration, The inhibition rate of 377 is only 20%. These two phenol derivatives have simple structures, significant zebrafish melanin formation inhibition activity, and are compounds with whitening application value.

[0069] Since the applicant discovered that Ganoderma lucidum has the active substance 2,4-dihydroxyacetophenone that inhibits the formation of zebrafish melanin, the yield of 2,4-dihydroxyacetophenone (6) in Ganoderma lucidum is only 0.000082% (8.2x10 -5%), it is extremely difficult to obtain from natural resources, so efforts have been made to synthesize and prepare such derivatives. The two simple phenol derivatives of the present invention are structures optimized in structure-activity analysis. 4-ethylphenol (1) and 4-acetonylphenol (2) have such significant zebrafish melanin formation inhibitory activity, indicating that the zebrafish melanin formation inhibitory mechanism is very complex and worthy of in-depth study; it can not only explain the stage details of the tyrosinase mechanism of melanin production, but also play a very positive role in the development of efficient and harmless whitening functional molecules. The phenol compounds with simple and easy preparation methods, stable structures and obvious whitening effects are applied in beauty functional ingredients, which is of great significance.

[0070] Example 3

[0071] 4-Ethylphenol (1) and 4-acetonylphenol (2) facial mask.

[0072] 1. Materials

[0073] 4-Ethylphenol (Compound 1) and 4-acetonylphenol (Compound 2) were obtained in the same manner as in Example 1, and other materials were cosmetic grade or food grade raw materials.

[0074] 2. Formulation

[0075] 4-ethylphenol and / or 4-acetonylphenol 12g, xanthan gum 3.5g, hydrolyzed hyaluronic acid 2.0g, sodium hyaluronate 2.0g, propylene glycol 0.3g, carbomer 0.5g, paraben 0.1, PPG-10 methyl glucose ether 0.25g, glyceryl glucoside 1.0g, deionized water 45g.

[0076] 3. Mask preparation process

[0077] Step 1: Add deionized water, xanthan gum, hydrolyzed hyaluronic acid, sodium hyaluronate, propylene glycol, carbomer and paraben into an emulsifier and heat to 75°C while stirring. After reaching the temperature, keep warm and continue stirring until the solution is transparent and uniform. Then keep warm for 20 minutes and then cool down to 42°C.

[0078] Step 2: Adjust pH = 7.6 ± 0.2.

[0079] Step 3: Continue to cool to 35°C, add PPG-10 methyl glucose ether, 4-ethylphenol and / or 4-acetonylphenol, glycerol glucoside, continue to stir evenly, and discharge after passing the inspection. Coating is performed on a non-woven fabric substrate with a coating amount of 2.1 g per square centimeter.

[0080] Example 4

[0081] 4-Ethylphenol (1) and 4-acetonylphenol (2) facial cleanser.

[0082] 1. Materials

[0083] 4-Ethylphenol (Compound 1) and 4-acetonylphenol (Compound 2) are obtained in the same manner as in Example 1, using cosmetic grade or food grade raw materials.

[0084] 2. Formulation

[0085] 4-ethylphenol and / or 4-acetonylphenol 7g, glycerol 2.0g, butylene glycol 4.0g, propylene glycol 0.5g, sodium EDTA 0.1g, guar gum 0.3g, zinc dioxide 2.0g, C12-15 alcohol benzoate 4.0g, C12-20 alkyl glucoside 3.0g, C14-22 alcohol 0.5g, cetearyl alcohol 1.2g, paraben 0.2g, sodium stearate 0.3g, polydimethylsiloxane alcohol 0.5g, polysorbate 0.2g, deionized water 55g.

[0086] 3. Preparation process

[0087] Weigh the prescribed amount of 4-ethylphenol and / or 4-acetonylphenol, add purified water to completely dissolve; take glycerol, butylene glycol, propylene glycol, sodium EDTA, guar gum, zinc dioxide, sodium stearate, C12-15 alcohol benzoate, C12-20 alkyl glucoside, C14-22 alcohol, cetearyl alcohol, add purified water to completely dissolve; take paraben, polydimethylsiloxane alcohol, polysorbate, add purified water to completely dissolve. Mix the above-prepared solutions, stir well, filter with a 0.22μm microporous membrane, can the filtrate in 30mL per bottle, seal and sterilize to obtain the product.

[0088] Example 5

[0089] 4-Ethylphenol (1) and 4-acetonylphenol (2) capsules.

[0090] 1. Materials

[0091] 4-Ethylphenol and / or 4-acetonylphenol, and food or pharmaceutical grade starch are obtained in the same manner as in Example 1.

[0092] 2. Prescription

[0093]

[0094] 3. Preparation process

[0095] Weigh the prescribed amount of 4-ethylphenol and / or 4-acetonylphenol and starch, stir to mix thoroughly, add appropriate amount of talcum powder, wet granulate with ethanol, sieve and dry, and then put into No. 2 capsule shells, with each capsule body filled with 60 mg of 4-ethylphenol and / or 4-acetonylphenol, to prepare capsules.

[0096] Example 6

[0097] 4-Ethylphenol (1) and / or 4-acetonylphenol (2) oral solution.

[0098] 1. Materials

[0099] The 4-ethylphenol and / or 4-acetonylphenol obtained by the method of Example 1, and the food or pharmaceutical grade flavoring agent are and caramel flavor.

[0100] 2. Prescription

[0101]

[0102] 3. Preparation process

[0103] Weigh the prescribed amount of 4-ethylphenol and / or 4-acetonylphenol, sucrose and caramel essence, add purified water to completely dissolve them, filter through a 0.22 μm microporous filter membrane, and fill 2 mL of the filtrate into an oral liquid filling machine per bottle. The bottle is sealed and sterilized to obtain the product.

[0104] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0105] The above-mentioned embodiments only express several implementation methods of the present invention, and the description is relatively specific and detailed, but it cannot be understood as limiting the scope of the invention patent. It should be pointed out that for ordinary technicians in this field, several modifications and improvements can be made without departing from the concept of the present invention, which all belong to the protection scope of the present invention.

Claims

1. Phenol derivatives 4-ethylphenol and 4-acetonylphenol as shown in the following structural formula, 2. The method for preparing 4-ethylphenol and 4-acetonylphenol shown in the structural formula of claim 1, characterized in that: The method comprises the following steps: Synthesis of 4-ethylphenol: In a container, acetic acid and trifluoromethanesulfonic anhydride are added, mixed and stirred at room temperature for 1 minute, then heated to 60°C, and then phenol is added, magnetically stirred at 60°C for 3 hours and the reaction is detected by TLC, and after the reaction is completed and cooled to room temperature, NaHCO3 is slowly added, and the reaction solution is extracted with ethyl acetate for multiple times, and the ethyl acetate extract is concentrated under reduced pressure. Finally, the product is purified by normal phase silica gel column chromatography with ethyl acetate and petroleum ether to obtain 4-hydroxyacetophenone; In a container, 4-hydroxyacetophenone, sodium cyanoborohydride, methyl orange and tetrahydrofuran are added, mixed and stirred at room temperature, and hydrochloric acid is added dropwise to keep the solution in a red state, and then magnetically stirred at room temperature for 12 hours and the reaction is detected by TLC, after the reaction is completed, distilled water is added to dilute the reaction system, and then the reaction solution is extracted with ethyl acetate for multiple times, the ethyl acetate extract is concentrated under reduced pressure, and finally the product is purified by normal phase silica gel column chromatography to obtain 4-ethylphenol; Synthesis of 4-acetonylphenol: In a container, 4-hydroxyphenylacetic acid, sodium acetate and acetic anhydride are added, and the mixture is heated to reflux at 145° C. and magnetically stirred for 6 hours. The reaction is detected by TLC. After the reaction is completed and cooled to room temperature, a NaOH solution is slowly added to neutralize most of the acidic compounds. The reaction solution is then extracted with ethyl acetate for multiple times, and the ethyl acetate extract is concentrated under reduced pressure. NaHCO3 is added to the ethyl acetate concentrate to neutralize the remaining carboxylic acid. The mixture is extracted with ethyl acetate for multiple times, and the ethyl acetate extract is concentrated under reduced pressure. Finally, the product is purified by normal phase silica gel column chromatography using ethyl acetate and petroleum ether to obtain 4-(acetoxyphenyl)-2-propanone; In a container, add 4-(acetoxyphenyl)-2-propanone, potassium carbonate and ethanol, heat at 45°C and magnetically stir for 3 hours, and detect the reaction by TLC. After the reaction is completed and cooled to room temperature, filter the reaction solution, add distilled water to the reaction solution after vacuum concentration, and then extract with ethyl acetate for multiple times, and concentrate the ethyl acetate extract under reduced pressure to obtain 4-hydroxyphenyl-2-propanone.

3. Use of 4-ethylphenol and / or 4-acetonylphenol shown in the structural formula of claim 1 in the preparation of cosmetics.

4. Use of 4-ethylphenol and / or 4-acetonylphenol represented by the structural formula according to claim 1 in the preparation of tyrosinase inhibitors.

5. A cosmetic containing 4-ethylphenol and / or 4-acetonylphenol of the structural formula according to claim 1, characterized in that: The cosmetics are composed of an effective amount of 4-ethylphenol and / or 4-acetonylphenol and common cosmetic auxiliary materials.

6. A tyrosinase inhibitor containing 4-ethylphenol and / or 4-acetonylphenol represented by the structural formula according to claim 1, characterized in that: The tyrosinase inhibitor contains an effective amount of 4-ethylphenol and / or 4-acetonylphenol.

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