Alkane chain-modified formononetin, preparation method and application thereof

Abstract

The present invention provides an alkane chain-modified formononetin and a preparation method and application thereof, belonging to the technical field of pharmaceutical chemistry. The present invention provides an alkane chain-modified formononetin, having a structure shown in formula I, wherein R in the formula I is C3-C 12 n-alkyl, X is a halogen. The alkane chain-modified formononetin provided by the present invention has low toxicity and a high safe dose in cosmetics. Moreover, the alkane chain-modified formononetin provided by the present invention has excellent whitening, spot-lightening and anti-inflammatory effects, and a low dose can achieve good whitening, spot-lightening and anti-inflammatory effects, and has a good application prospect in cosmetics. The present invention provides a method for preparing the alkane chain-modified formononetin derivatives described in the above technical scheme. The preparation method provided by the present invention is simple and quick to operate, has low production cost, has a wide source of raw materials and low cost, and is suitable for industrial production.

Description

Technical Field

[0001] The invention relates to the technical field of pharmaceutical chemistry, and in particular to an alkane chain-modified formononetin and a preparation method and application thereof. Background Art

[0002] Formononetin (structural formula as shown in Formula II), also known as formononetin and formononetin, belongs to the isoflavone compounds and is widely found in plants such as Astragalus, Licorice, Pueraria, Trichosanthes, Millettia reticulata, etc. It is a representative component of the isoflavone compounds in Astragalus. It has good anti-inflammatory, antioxidant, antibacterial, anti-tumor, and estrogen-like effects. It is used in cosmetics to relieve skin damage and the decline of skin protection function caused by stress or anxiety, and treat and delay skin aging and the formation of wrinkles.

[0003] However, formononetin is highly toxic, resulting in a lower safe dose in cosmetics.

[0004] Summary of the invention

[0005] In view of this, the object of the present invention is to provide an alkane chain-modified formononetin and a preparation method and application thereof. The alkane chain-modified formononetin provided by the present invention has low toxicity and a high safe dosage in cosmetics.

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

[0007] The present invention provides an alkane chain-modified formononetin having a structure shown in Formula I:

[0008]

[0009] In the formula I, R is C3 to C 12 n-alkyl, X is halogen.

[0010] Preferably, the R includes -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, -(CH2)9-, -(CH2) 10 -or-(CH2) 12 -.

[0011] Preferably, X is chlorine or bromine.

[0012] Preferably, the alkane chain-modified formononetin has any one of the structures shown in Formulas I-1 to I-8:

[0013]

[0014] The present invention provides a method for preparing the alkane chain-modified formononetin described in the above technical solution, comprising the following steps:

[0015] Mixing formononetin, carbonate and ketone solvent to carry out a first substitution reaction to obtain a first substitution reaction solution;

[0016] The first substitution reaction reaction liquid and the compound XRX are mixed to carry out a second substitution reaction to obtain the alkane chain-modified formononetin;

[0017] In the compound XRX, X is a halogen, and R is C3-C 12 Normal alkyl.

[0018] Preferably, the molar ratio of formononetin to anhydrous carbonate is 1:(9-37).

[0019] Preferably, the temperature of the first substitution reaction is 50-60° C., and the time is 30-60 min.

[0020] Preferably, the molar ratio of formononetin to compound XRX is 1:(1-10).

[0021] Preferably, the temperature of the second substitution reaction is 50-60° C. and the time is 24-48 hours.

[0022] The present invention provides the use of the alkane chain-modified formononetin described in the above technical scheme or the alkane chain-modified formononetin prepared by the preparation method described in the above technical scheme in cosmetics.

[0023] The present invention provides an alkane chain-modified formononetin having a structure shown in Formula I, wherein R in Formula I is C3 to C 12 n-alkyl, X is halogen. The alkane chain modified formononetin provided by the present invention is substituted and protected by the active group hydroxyl of formononetin, and the alkane chain is removed during the action, which not only protects the active group, but also reduces irritation, has low toxicity, and has a high safe dose in cosmetics. Moreover, as the number of carbon atoms increases, according to the principle of like dissolves like, the fat solubility of the alkane chain modified formononetin provided by the present invention is further enhanced, the transmembrane ability is improved, and the absorption capacity is further improved, so that the efficacy can be exerted at a low dose, and the problem of low absorption and bioavailability of the parent structure is solved, and the toxicity is reduced while protecting the active group, and the formononetin has excellent whitening, spot-lightening and anti-inflammatory effects, and a low dose can achieve good whitening, spot-lightening and anti-inflammatory effects, and has a good application prospect in cosmetics.

[0024] The present invention provides a method for preparing the alkane chain-modified formononetin derivatives described in the above technical solution. The preparation method provided by the present invention is simple and fast to operate, has low production cost, has a wide source of raw materials and low cost, and is suitable for industrial production. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 is the mass spectrum of FMN-PROBr prepared in Example 1;

[0026] Figure 2 The mass spectrum of FMN-BUTBr prepared in Example 2;

[0027] Figure 3 The mass spectrum of FMN-PENBr prepared in Example 3;

[0028] Figure 4 The mass spectrum of FMN-HEXBr prepared in Example 4;

[0029] Figure 5 is the mass spectrum of FMN-OCTBr prepared in Example 5;

[0030] Figure 6 The mass spectrum of FMN-DECBr prepared in Example 6;

[0031] Figure 7 The mass spectrum of FMN-NONBr prepared in Example 7;

[0032] Figure 8 is the mass spectrum of FMN-DODBr prepared in Example 8;

[0033] Fig. 9 This is a graph showing the accumulation of inflammatory cells in the wound of the zebrafish tail fin after the sample was treated in Test Example 2;

[0034] Fig.10 This is the result of the anti-inflammatory experiment of the sample in Test Example 2;

[0035] Fig.11 This is a qualitative result diagram of the whitening experiment of the alkane chain-modified formononetin derivative in Test Example 3;

[0036] Fig.12 This is a graph showing the experimental results of the inhibition of melanin production by the alkane chain-modified formononetin derivatives in Test Example 3;

[0037] Fig.13 This is a graph showing the experimental results of the inhibition of tyrosinase activity by the alkane chain-modified formononetin derivatives in Test Example 3;

[0038] Fig.14It is the effect of the spot-lightening experiment of alkane chain modification in Test Example 4, wherein a is the observation diagram of the qualitative results of the zebrafish spot-lightening experiment, b is the quantitative analysis bar graph of the melanin inhibition rate, and c is the quantitative analysis bar graph of the tyrosinase activity inhibition rate. DETAILED DESCRIPTION

[0039] The present invention provides an alkane chain-modified formononetin having a structure shown in Formula I:

[0040]

[0041] In the formula I, R is C3 to C 12 n-alkyl, X is halogen.

[0042] In the present invention, the R preferably includes -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)6-, -(CH2)8-, -(CH2)9-, -(CH2) 10 -or-(CH2) 12 In the present invention, X is preferably chlorine or bromine, more preferably bromine.

[0043] In the present invention, the alkane chain-modified formononetin preferably has any one of the structures shown in Formulas I-1 to I-8:

[0044]

[0045]

[0046] The present invention provides a method for preparing the alkane chain-modified formononetin described in the above technical solution, comprising the following steps:

[0047] Mixing formononetin, carbonate and ketone solvent to carry out a first substitution reaction to obtain a first substitution reaction solution;

[0048] The first substitution reaction reaction liquid and the compound XRX are mixed to carry out a second substitution reaction to obtain the alkane chain-modified formononetin;

[0049] In the compound XRX, X is a halogen, and R is C3-C 12 Normal alkyl.

[0050] In the present invention, unless otherwise specified, all raw material components are commercially available products well known to those skilled in the art.

[0051] The present invention mixes formononetin, carbonate and ketone solvent, performs a first substitution reaction, and obtains a first substitution liquid. In the present invention, the carbonate is preferably anhydrous carbonate; the carbonate preferably includes potassium carbonate. In the present invention, the molar ratio of formononetin to anhydrous carbonate is preferably 1:9. In the present invention, the ketone solvent preferably includes acetone. The present invention does not specifically limit the amount of the ketone solvent, as long as the first substitution reaction can proceed smoothly. In the present invention, the temperature of the first substitution reaction is preferably 50 to 60°C, more preferably 55°C, and the time of the first substitution reaction is preferably 30 to 60 minutes, more preferably 30 to 40 minutes.

[0052] After obtaining the first substitution reaction solution, the present invention mixes the first substitution reaction solution and the compound XRX to perform a second substitution reaction to obtain the alkane chain-modified formononetin; wherein X in the compound XRX is a halogen, and R is C3-C 12 n-alkyl. In the present invention, the molar ratio of the formononetin to the compound XRX is preferably 1:(1-10), more preferably 1:(2-5). In the present invention, the temperature of the second substitution reaction is preferably 50-60°C, more preferably 55°C, and the time of the second substitution reaction is preferably 24-48h, more preferably 30-40h; in a specific embodiment of the present invention, the second substitution reaction is preferably monitored by TLC until the formononetin raw material disappears, and then the second substitution reaction is stopped.

[0053] After completing the second substitution reaction, the present invention preferably further comprises subjecting the second substitution reaction liquid to a first solid-liquid separation, concentrating the obtained liquid component, mixing the obtained concentrate with water, and subjecting the obtained solid product to water washing, drying and silica gel column chromatography separation in sequence to obtain the alkane chain modified chrysanthemum yellow. The present invention has no special restrictions on the first solid-liquid separation and the second solid-liquid separation, and a solid-liquid separation method well known to those skilled in the art can be used, such as suction filtration; the first solid-liquid separation method is to remove carbonates; the second solid-liquid separation method is to remove water-soluble impurities. In the present invention, the present invention has no special restrictions on the concentration method, and a concentration method well known to those skilled in the art can be used, such as reduced pressure concentration. In the present invention, the drying temperature is preferably 25 to 50°C, more preferably 40 to 45°C; the present invention has no special restrictions on the drying time, and drying to constant weight is sufficient. In the present invention, the eluent used for the silica gel column chromatography separation preferably includes dichloromethane.

[0054] The present invention also provides the use of the alkane chain modified formononetin described in the above technical solution or the alkane chain modified formononetin prepared by the preparation method described in the above technical solution in cosmetics. The alkane chain modified formononetin provided by the present invention has whitening, spot lightening and anti-inflammatory effects, and has a good application prospect in cosmetics.

[0055] The technical solutions in the present invention will be described clearly and completely below in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0056] Example 1

[0057] In a 50 mL single-mouth bottle, formononetin (0.8 mmol), anhydrous potassium carbonate (1 g) and 15 mL of acetone were added, and the first substitution reaction was carried out at 55° C. for 30 min. 1,3-dibromopropane (8 mmol) was added to the reaction solution of the first substitution reaction, and the second substitution reaction was carried out under heating reflux until the TLC monitoring reaction disappeared. The second substitution reaction was stopped, and the potassium carbonate was removed by filtration. The obtained liquid component was concentrated under reduced pressure, and water was added to the obtained concentrate, stirred and mixed evenly, and filtered. The obtained solid product was washed with water, dried at 40° C. to constant weight, and separated on a silica gel column (the eluent was dichloromethane) to obtain alkane chain-modified formononetin having the structure shown in Formula I-1 (abbreviated as FMN-PROBr, 230 mg, yield 47.4%).

[0058] The mass spectrum of FMN-PROBr is shown in Figure 1 As shown, ESI-MS: found 389.0381, cal.389.03.([M+H] + ).

[0059] Example 2

[0060] The product was prepared according to the method of Example 1, the only difference from Example 1 being that 1,3-dibromopropane was replaced with 1,4-dibromobutane to obtain alkane chain-modified formononetin having the structure shown in Formula I-2 (abbreviated as FMN-BUTBr, 252 mg, yield of 50.1%).

[0061] The mass spectrum of FMN-BUTBr is shown in Figure 2 As shown, ESI-MS: found 403.0543, cal.403.05.([M+H] + ); found 425.0358, cal.425.04.([M+Na]+ ).

[0062] Example 3

[0063] The product was prepared according to the method of Example 1, the only difference from Example 1 being that 1,3-dibromopropane was replaced with 1,5-dibromopentane to obtain alkane chain-modified formononetin having the structure shown in Formula I-3 (abbreviated as FMN-PENBr, 268 mg, yield of 51.5%).

[0064] The mass spectrum of FMN-PENBr is shown in Figure 3 As shown, ESI-MS: found 417.0699, cal.417.06.([M+H] + ); found 439.0517, cal.439.05.([M+Na] + ).

[0065] Example 4

[0066] The product was prepared according to the method of Example 1, the only difference from Example 1 being that 1,3-dibromopropane was replaced with 1,6-dibromohexane to obtain alkane chain-modified formononetin having the structure shown in Formula I-4 (abbreviated as FMN-HEXBr, 284 mg, yield of 52.8%).

[0067] The mass spectrum of FMN-HEXBrr is shown in Figure 4 As shown, ESI-MS: found 431.0847, cal.431.08.([M+H] + ).

[0068] Example 5

[0069] The product was prepared according to the method of Example 1, the only difference from Example 1 being that 1,3-dibromopropane was replaced with 1,8-dibromooctane to obtain alkane chain-modified formononetin having the structure shown in Formula I-5 (abbreviated as FMN-OCTBr, 244 mg, yield 42.6%).

[0070] The mass spectrum of FMN-OCTBr is shown in Figure 5 As shown, ESI-MS: found 459.1154, cal.459.11.([M+H] + ); found 481.0971, cal.481.10.([M+Na] + ).

[0071] Example 6

[0072] Prepared according to the method of Example 1, the only difference from Example 1 is that 1,3-dibromopropane is replaced by 1,9-dibromononane to obtain alkane chain modified formononetin having the structure shown in Formula I-6 (abbreviated as FMN-DECBr, 310 mg, yield 52.5%).

[0073] The mass spectrum of FMN-DECBr is shown in Figure 6 As shown, ESI-MS: found 473.1311, cal.473.12.([M+H] + ); found495.1128, cal.495.11.([M+Na] + ).

[0074] Example 7

[0075] Prepared according to the method of Example 1, the only difference from Example 1 is that 1,3-dibromopropane is replaced by 1,10-dibromodecane to obtain alkane chain modified formononetin having the structure shown in Formula I-7 (abbreviated as FMN-NONBr, 279 mg, yield 45.9%).

[0076] The mass spectrum of FMN-NONBr is as follows Figure 7 As shown, ESI-MS: found 487.1465, cal.487.14.([M+H] + ); found 509.1284, cal.509.13.([M+Na ]+ ).

[0077] Example 8

[0078] The product was prepared according to the method of Example 1, the only difference from Example 1 being that 1,3-dibromopropane was replaced with 1,12-dibromododecane to obtain alkane chain-modified formononetin having the structure shown in Formula I-2 (abbreviated as FMN-DODBr, 340 mg, yield of 52.9%).

[0079] The mass spectrum of FMN-DODBr is shown in Figure 8 As shown, referring to Example 1, 1,3-dibromopropane is replaced with 1,12-dibromododecane to obtain the target product as shown in Formula I-8, recorded as FMN-DODBr. In this example, the molar ratio of formononetin to 1,12-dibromododecane is 1:10.

[0080] ESI-MS: found 514.1779, cal.514.17.([M+H] + ); found 537.1597, cal.537.16.([M+Na] + ).

[0081] Test Example 1

[0082] Maximum safe concentration test of alkane chain modified formononetin derivatives prepared in Examples 1 to 8 and formononetin (i.e. formononetin)

[0083] The alkane chain-modified formononetin derivative (sample) was diluted to multiple concentrations in multiple ratios with standard dilution water to obtain sample solutions of different concentrations (concentrations were 100, 50, 25, 12.5, 6.25 and 3.125 μM, respectively). Each concentration of sample solution was tested with 10 zebrafish larvae (24-well cell culture plate, 1.0 mL sample solution). The survival of larvae at 24 hpf (hpf is the abbreviation of hours post-fertilization, 24 hpf means 24 hours after fertilization), 48 hpf and 72 hpf was observed and recorded under a stereo microscope (objective lens 2-3 times), and the cumulative mortality rate and deformity rate were calculated. The approximate concentration range of sample dilution corresponding to the estimated cumulative mortality rate and deformity rate of larvae from 0 to 100% is shown in Table 1:

[0084] Table 1 Statistical table of safe concentrations of alkane chain modified formononetin derivatives

[0085]

[0086]

[0087] As shown in Table 1, compared with the parent structure, formononetin, the safe concentration of the derivatives modified with alkane chains is significantly increased, the toxicity is reduced, and the application concentration range is significantly broadened.

[0088] Test Example 2

[0089] Anti-inflammatory evaluation experiment of alkane chain-modified formononetin derivatives prepared in Examples 1 to 8

[0090] Sample group: Normally developed 72hpf Tg (corola: EGFP) zebrafish embryos were selected and placed in a 6-well plate, with 14 embryos in each group. After pretreatment with 5.0mL of drug solution (10μM) for 1h, the tail fin was cut off and 5.0mL of drug solution was added again. After incubation at 28°C for 6h, the FITC channel was selected under a fluorescence microscope to observe the aggregation of inflammatory cells in the zebrafish tail fin wound and count the number of inflammatory cells. The only difference between the blank control group and the experimental group was that the alkane chain-modified formononetin derivative was not added; the only difference between the control group and the experimental group was the addition of formononetin. The aggregation of inflammatory cells in the zebrafish tail fin wound of the sample treatment group and the blank control group and the results of the anti-inflammatory experiment are shown in the figure. Figures 9-10 As shown in Table 2, Fig. 9This is a picture showing the accumulation of inflammatory cells in the wound of the zebrafish tail fin after sample treatment. Fig.10 This is the result of anti-inflammatory experiment.

[0091] Table 2 The number of inflammatory cells after treatment with formononetin and alkane chain-modified formononetin derivatives

[0092]

[0093] In Table 2, compared with the blank control group: *P<0.05; **P<0.01; ***P<0.001.

[0094] Depend on Figures 9-10 As shown in Table 2, the alkane chain-modified formononetin derivatives have an inhibitory effect on the aggregation of neutrophils and macrophages in the damaged caudal fin of zebrafish larvae, and the results are significantly different, indicating that they have potential anti-inflammatory activity.

[0095] Test Example 3

[0096] Whitening evaluation experiment of alkane chain modified formononetin derivatives

[0097] (1) Melanin production inhibition

[0098] Experimental group: 9hpf healthy AB zebrafish embryos were randomly placed in a 6-well cell culture plate, 30 embryos / well, and 5mL sample solutions with concentrations of 50μM and 75μM were added to each well. A positive control group (the compound was replaced with arbutin) and a blank control group (the compound was replaced with standard dilution water) were also set up in the experiment. Three replicate wells were set up in each group and incubated in a curve-controlled biochemical incubator.

[0099] After incubation for 72 hours, the lysate solution was added and ultrasonically prepared into a homogenate. The precipitate was taken and vibrated to fully dissolve the melanin in the centrifuge tube. 100 μL of the solution was placed in a 96-well plate and the absorbance was measured at a wavelength of 405 nm using an ELISA reader. The inhibition rate of the sample on melanin synthesis was calculated according to formula (1):

[0100]

[0101] The experimental data are expressed as mean ± SEM data. Figures 11-12 As shown in Table 3, Fig.11 This is the qualitative result of the whitening experiment of alkane chain modified formononetin derivatives. Fig.12 This is a diagram showing the experimental results of alkane chain-modified formononetin derivatives inhibiting melanin production.

[0102] Table 3 Melanin production inhibition rate of formononetin and alkane chain modified formononetin derivatives

[0103]

[0104] (2) Tyrosinase activity inhibition

[0105] After selecting fertilized eggs, 9hpf healthy AB zebrafish embryos were randomly placed in a 6-well cell culture plate, 30 pieces / well, and 5mL of sample solutions with concentrations of 50μM and 75μM were added to each well. A blank control group (zebrafish breeding water) was also set up in the experiment. A positive control group (the compound was replaced with arbutin) and a blank control group (the compound was replaced with standard dilution water) were also set up in the experiment. Each group was set up with 3 replicates, and the solution of the corresponding well was replaced every 24h, and incubated in a curve-controlled biochemical incubator.

[0106] When the incubation reaches 72 hours, the lysate solution is added, and the homogenate is prepared by ultrasound, centrifuged, and the supernatant is placed in a 96-well plate, and the levodopa solution is added at the same time, and incubated for 1 hour. The absorbance value (OD475nm value) of each experimental group is detected by an ELISA instrument, and the tyrosinase activity inhibition rate is calculated according to formula (2):

[0107]

[0108] The experimental data are expressed as mean ± SEM data. The test results are shown in Table 4 and Fig.13 As shown, Fig.13 This is a graph showing the experimental results of alkane chain-modified formononetin derivatives inhibiting tyrosinase activity.

[0109] Table 4 Tyrosinase inhibition rate of formononetin and alkane chain modified formononetin derivatives

[0110]

[0111] Depend on Figures 11 to 13 As shown in Tables 3 and 4, the alkane chain-modified formononetin derivatives all showed a certain whitening effect, among which FMN-NONBr and FMN-DODBr had the most significant effects, and the effect of FMN-DODBr was better than that of FMN-NONBr.

[0112] Test Example 4

[0113] Spot lightening evaluation experiment of alkane chain-modified formononetin derivative FMN-DODBr

[0114] (1) Melanin production inhibition

[0115] Experimental group: 72hpf healthy AB zebrafish embryos were randomly placed in a 6-well cell culture plate, 30 per well, and 5 mL of 50μM and 75μM FMN-DODBr solutions were added to each well. A blank control group (standard dilution water) was also set up. Three replicates were set up in each group. The cells were placed in a curve-controlled biochemical incubator for incubation.

[0116] After 72 hours of treatment, the lysate solution was added and ultrasonically prepared into a homogenate, centrifuged, the precipitate was taken, and the melanin in the centrifuge tube was fully dissolved by shaking. 100 μL of the solution was placed in a 96-well plate, and the absorbance was measured at a wavelength of 405 nm using an ELISA reader. The inhibition rate of the sample on melanin synthesis was calculated according to the formula (1), and the experimental data were expressed as mean ± SEM data.

[0117] (2) Tyrosinase activity inhibition

[0118] After selecting fertilized eggs, 72 hpf healthy AB zebrafish embryos were randomly placed in a 6-well cell culture plate, 30 per well, and 5 mL of FMN-DODBr at concentrations of 50 μM and 75 μM was added to each well. A control group (zebrafish culture water) and a blank control group were set up in the experiment. Each group had 3 replicates. The solution in the corresponding well was replaced every 24 hours and incubated in a curve-controlled biochemical incubator.

[0119] After 72 hours of treatment, the lysate solution was added and ultrasonically prepared into a homogenate, centrifuged, and the supernatant was placed in a 96-well plate. L-DOPA solution was added and incubated for 1 hour. The absorbance value (OD475nm value) of each experimental group was detected using an ELISA instrument. The tyrosinase activity inhibition rate was calculated according to formula (2), and the experimental data were expressed as mean ± SEM data.

[0120] The effect of FMN-DODBr on lightening of spots is as follows Fig.14 As shown, a is the observation diagram of the qualitative results of the zebrafish spot lightening experiment, b is the quantitative analysis bar graph of the melanin inhibition rate, and c is the quantitative analysis bar graph of the tyrosinase activity inhibition rate. Fig.14It can be seen that compared with the blank group, the zebrafish black spots were reduced after being treated with FMN-DODBr solutions at concentrations of 50μM and 75μM for 72h, and the reduction of black spots was more obvious after treatment with FMN-DODBr solution at concentration of 75μM. The melanin inhibition rates of zebrafish treated with FMN-DODBr solutions at concentrations of 50μM and 75μM for 72h were 7.41±0.67% and 10.72±1.81%, respectively, and the tyrosinase activity inhibition rates were 40.43±6.82% and 34.20±8.76%, respectively. This shows that zebrafish treated with FMN-DODBr solutions at concentrations of 50μM and 75μM for 72h had a certain lightening effect, and the lightening effect of 75μM FMN-DODBr solution was better than that of 50μM FMN-DODBr solution.

[0121] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the scope of protection of the present invention.

Claims

1. Application of alkane chain-modified formononetin as an active ingredient in the preparation of whitening and spot-lightening cosmetics, wherein the alkane chain-modified formononetin has a structure shown in Formula I-7 and / or Formula I-8:

2. The use according to claim 1, characterized in that: The alkane chain-modified formononetin has a structure shown in Formula I-7:

3. The use according to claim 1, characterized in that: The alkane chain-modified formononetin has a structure shown in Formula I-8:

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