Ferulic acid-Ectoin supramolecular eutectic as well as preparation method and application of ferulic acid-Ectoin supramolecular eutectic

Abstract

The invention discloses a ferulic acid-ectoine supramolecular eutectic as well as a preparation method and application thereof, and relates to the technical field of supramolecular eutectic preparation. The ferulic acid-ectoine supramolecular eutectic comprises ferulic acid and ectoine, and the molar ratio of the ferulic acid to the ectoine is 1: (1-3). The invention provides a ferulic acid-Ectoine supramolecular eutectic as well as a preparation method and application thereof, the ferulic acid-Ectoine supramolecular eutectic is prepared by adopting a mechanical grinding method or a solvent method, and the prepared ferulic acid-Ectoine supramolecular eutectic can improve the solubility of ferulic acid by 3.8 times or more, and can obtain excellent synergistic antioxidant and soothing effects.

Description

Technical Field

[0001] The present invention relates to the technical field of supramolecular eutectic preparation, and in particular to a ferulic acid-ectoine supramolecular eutectic and a preparation method and application thereof. Background Art

[0002] Ferulic acid is chemically known as 3-methoxy-4-hydroxycinnamic acid, which is a derivative of cinnamic acid and is found in Chinese medicinal materials such as Chuanxiong, Angelica sinensis, and zucchini. Ferulic acid is an all-round functional raw material with significant effects in multiple dimensions such as anti-oxidation, anti-photoaging, whitening, anti-aging, soothing and anti-inflammatory.

[0003] The INCI name of Ectoin is tetrahydromethylpyrimidine carboxylic acid. The main effects of Ectoin are moisturizing, repairing skin barrier, anti-photoaging, improving skin immunity, and anti-inflammatory.

[0004] Ferulic acid has poor solubility in aqueous solution. At 72°C, the solubility in 100g of hot water is 0.43mg; at 10.3°C, the solubility in 100g of cold water is 0.006mg. According to literature and manufacturer information, the amount of ferulic acid used in the formula (by weight) needs to be more than 0.5% to have a good effect. At present, the use of ferulic acid in products is generally neutralized with alkali, and a large amount of polyols are required for solubilization. L'Oreal's research shows that the use of a large amount of dipropylene glycol or butylene glycol can dissolve ferulic acid, and the stability is good, but due to the problem of impurity residues in the synthesis process of dipropylene glycol, if the amount used in the formula is too high, it will have a noticeable sour taste, which will bring unpleasant experience to consumers. Secondly, the excessive amount of polyols in the formula may cause some consumers with sensitive skin to feel hot.

[0005] Chinese patent CN114652654A discloses a mild, non-irritating, hydrating, moisturizing and whitening composition and a preparation method thereof, which achieves the effects of whitening and moisturizing by compounding ascorbic acid, ferulic acid, tranexamic acid, ectoine, undecylenoyl phenylalanine, etc. However, the composition does not solve the problem of the difficulty in dissolving ferulic acid, and still uses a large amount of polyols to dissolve ferulic acid.

[0006] Supramolecular eutectics refer to two or more active ingredients that are combined in a specific ratio by hydrogen bonding, van der Waals forces, and π-π stacking to form a complex, organized aggregate, and maintain a certain integrity so that it has a clear microstructure and macroscopic properties. Supramolecular eutectics will not destroy the efficacy of the active ingredient itself, but can change some of its physical and chemical properties, such as solubility, melting point, bioavailability, etc. The application of supramolecular eutectic technology in cosmetic products has been a hot topic in recent years.

[0007] Chinese patent CN115417811A discloses a eutectic compound of niacinamide and ferulic acid and a method for preparing the same, which not only solves the problem that the effect of niacinamide is not significantly improved by simply mixing niacinamide and ferulic acid, but also improves the stability of ferulic acid in water. Chinese patent CN117720412A discloses a eutectic compound of ferulic acid and tranexamic acid and a method for preparing the same, which greatly improves the solubility of ferulic acid in water, and also improves the pH stability and appearance color stability of ferulic acid in the formula. However, the above-mentioned disclosed technical solutions basically only focus on the whitening effect of ferulic acid, and do not focus on the antioxidant, soothing, and anti-inflammatory effects of ferulic acid, nor do they study whether the soothing and anti-inflammatory effects can be improved after ferulic acid forms a eutectic compound. Summary of the invention

[0008] In order to solve the above technical problems, the present invention provides a ferulic acid-ectoine supramolecular co-crystal and a preparation method and application thereof.

[0009] The specific technical solutions include the following:

[0010] In a first aspect, a ferulic acid-ectoine supramolecular co-crystal is provided, comprising ferulic acid and ectoine, wherein the molar ratio of ferulic acid to ectoine is 1:(1-3).

[0011] Furthermore, the molar ratio of ferulic acid to ectoine is 1:(1-2).

[0012] Furthermore, the molar ratio of ferulic acid to ectoine is 1:1.

[0013] Furthermore, the molar ratio of ferulic acid to ectoine is 1:2.

[0014] In the second aspect, a method for preparing the ferulic acid-ectoine supramolecular eutectic as described in the first aspect is provided, wherein the method for preparing the ferulic acid-ectoine supramolecular eutectic is a mechanical grinding method or a solvent method.

[0015] Furthermore, the preparation method of the ferulic acid-ectoine supramolecular eutectic is a mechanical grinding method, which includes the following steps: weighing ferulic acid and ectoine into a vortex mixer to mix the solids evenly, then transferring the evenly mixed solids to a mortar, and directly mechanically grinding for 30-60 minutes to obtain ferulic acid-ectoine supramolecular eutectic.

[0016] Furthermore, the preparation method of the ferulic acid-ectoine supramolecular eutectic is a solvent method, comprising the following steps: dissolving ferulic acid in anhydrous ethanol and dissolving ectoine in water of the same mass, mixing the two evenly, and then performing reduced pressure distillation at 40-50°C to remove ethanol and water, and then drying at 40-50°C to obtain ferulic acid-ectoine supramolecular eutectic.

[0017] In a third aspect, there is provided the use of the ferulic acid-ectoine supramolecular co-crystal as described in the first aspect in the preparation of cosmetics or skin care products.

[0018] In a fourth aspect, a cosmetic is provided, comprising the ferulic acid-ectoine supramolecular eutectic described in the first aspect, and also comprising an emollient, an emulsifier, a moisturizer, a skin conditioner, a preservative, and a thickener.

[0019] In the fifth aspect, a washing and care product is provided, comprising the ferulic acid-ectoine supramolecular eutectic as described in the first aspect of claim, and also comprising an emollient, an emulsifier, a moisturizer, a skin conditioner, a preservative, and a thickener.

[0020] Among them, the cosmetics and cleaning products all have anti-oxidation, whitening, soothing and anti-inflammatory effects.

[0021] Preferably, the emollient is one or more of cetearyl alcohol, dimethicone, caprylic / capric triglyceride, avocado tree (BUTYROSPERMUM PARKII) fruit butter, isononyl isononanoate, jojoba (SIMMONDSIA CHINENSIS) seed oil, phytosterol / octyldodecanol lauroyl glutamate, macadamia (MACADAMIATERNIFOLIA) seed oil, squalane, diisostearyl malate, and phytosteryl macadamia oleate.

[0022] Preferably, the emulsifier is one or more of glyceryl stearate, PEG-100 stearate, cetearyl glucoside, cocoyl glucoside, hydrogenated lecithin, behenyl alcohol, polyglyceryl-10 stearate, potassium cetyl phosphate, sodium stearoyl glutamate, polyglyceryl-4 diisostearate / polyhydroxystearate / sebacate, and batyl alcohol.

[0023] Preferably, the moisturizing agent is glycerin, butylene glycol, 1,3-propylene glycol, 1,2-hexanediol, caprylyl glycol, panthenol, ethylhexylglycerin, pentylene glycol, glyceryl polyether-26, dipropylene glycol, polyethylene glycol-32, polyethylene glycol-8, PPG-10 methyl glucose ether, etc.

[0024] Preferably, the skin conditioning agent is one or more of p-hydroxyacetophenone, sodium hyaluronate, acetylated sodium hyaluronate, polyglutamic acid, inositol, tremella polysaccharide, dipotassium glycyrrhizinate, allantoin, niacinamide, tranexamic acid, carnosine, decarboxylated carnosine hydrochloride, trehalose, mannitol, bisabolol, ascorbyl glucoside, ubiquinone, tocopheryl acetate, glyceryl glucoside, xylitol glucoside, and xylitol.

[0025] Preferably, the preservative is one or more of phenoxyethanol, methylparaben, and o-cymene-5-ol.

[0026] Preferably, the thickener is one or more of hydroxyethyl cellulose, cellulose, carbomer, xanthan gum, gum arabic, acrylic acid (esters) / C10-30 alkyl acrylate crosspolymer, polyacrylate crosspolymer-6, sodium acrylate / sodium acryloyldimethyl taurate copolymer, ammonium acryloyldimethyl taurate / VP copolymer, and hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer.

[0027] The beneficial effects of the present invention are:

[0028] The present invention provides a ferulic acid-ectoine supramolecular eutectic and a preparation method and application thereof. The ferulic acid-ectoine supramolecular eutectic is prepared by a mechanical grinding method or a solvent method. The prepared ferulic acid-ectoine supramolecular eutectic can increase the solubility of ferulic acid by more than 3.8 times, and can obtain excellent synergistic antioxidant and soothing effects. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the accompanying drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are some embodiments of the present invention. For ordinary technicians in this field, other accompanying drawings can be obtained based on these accompanying drawings without paying any creative work.

[0030] Figure 1 X-ray diffraction patterns of ferulic acid-ectoine supramolecular co-crystal, ectoine and ferulic acid according to Example 2 of the present invention;

[0031] Figure 2 The infrared spectra of the ferulic acid-ectoine supramolecular co-crystal, ferulic acid and ectoine of Example 2 of the present invention;

[0032] Figure 3 The test results of the free radical scavenging rate of ABTs by the ferulic acid-ectoine supramolecular co-crystal, ferulic acid and ectoine of Example 2 of the present invention;

[0033] Figure 4These are the test results of the inhibition rate of cellular NO by the ferulic acid-ectoine supramolecular co-crystal, ferulic acid and ectoine of Example 2 of the present invention. DETAILED DESCRIPTION

[0034] The technical solutions in the embodiments of the present invention are described clearly and completely below. Obviously, the described embodiments are only 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.

[0035] It should be understood that when used in this specification and the appended claims, the terms "include" and "comprises" indicate the presence of described features, integers, steps, operations, elements and / or components, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components and / or combinations thereof.

[0036] It should also be understood that the terms used in this specification of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. As used in the specification of the present invention and the appended claims, unless the context clearly indicates otherwise, the singular forms "a", "an" and "the" are intended to include plural forms.

[0037] It should be further understood that the term "and / or" used in the present description and the appended claims refers to any and all possible combinations of one or more of the associated listed items, and includes these combinations.

[0038] In order to more fully understand the technical content of the present invention, the technical solution of the present invention is further introduced and illustrated in conjunction with specific embodiments below.

[0039] Example 1

[0040] A ferulic acid-ectoine supramolecular eutectic crystal consists of ferulic acid and ectoine, wherein the molar ratio of the ferulic acid to the ectoine is 1:1.

[0041] Example 1 The preparation method of ferulic acid-ectoine supramolecular co-crystals is a mechanical grinding method, which includes the following steps: weighing ferulic acid and ectoine into a vortex mixer to mix the solids evenly, then transferring the evenly mixed solids to a mortar, and directly mechanically grinding for 45 minutes to obtain ferulic acid-ectoine supramolecular co-crystals.

[0042] Example 2

[0043] A ferulic acid-ectoine supramolecular eutectic crystal consists of ferulic acid and ectoine, wherein the molar ratio of ferulic acid to ectoine is 1:2.

[0044] The preparation method of the ferulic acid-ectoine supramolecular co-crystal in Example 2 is the same as that in Example 1.

[0045] Example 3

[0046] A ferulic acid-ectoine supramolecular eutectic crystal consists of ferulic acid and ectoine, wherein the molar ratio of ferulic acid to ectoine is 1:3.

[0047] The preparation method of the ferulic acid-ectoine supramolecular eutectic in Example 3 is a solvent method, comprising the following steps: dissolving ferulic acid in anhydrous ethanol and dissolving ectoine in water of the same mass, mixing the two evenly, and then distilling under reduced pressure at 45°C to remove ethanol and water, and then drying at 45°C to obtain ferulic acid-ectoine supramolecular eutectic.

[0048] Comparative Example 1

[0049] Comparative Example 1 is ferulic acid of the same mass as that of Example 1.

[0050] Comparative Example 2

[0051] A ferulic acid-ectoine supramolecular eutectic is composed of ferulic acid and ectoine. The difference between comparative example 2 and example 1 is that the molar ratio of ferulic acid to ectoine in comparative example 2 is 1:0.5, and other conditions are the same.

[0052] Comparative Example 3

[0053] Comparative Example 3 is a mixture of ferulic acid and butanediol of the same mass as that of Example 1. The preparation process is to add butanediol with a mass concentration of 10% during the dissolution of ferulic acid. The specific preparation conditions are the same as those of Example 1.

[0054] Comparative Example 4

[0055] Comparative Example 4 is a mixture of ferulic acid and glycerol of the same mass as that of Example 1. The preparation process is to add glycerol with a mass concentration of 10% during the dissolution of ferulic acid. The specific preparation conditions are the same as those of Example 1.

[0056] Comparative Example 5

[0057] Comparative Example 5 is a mixture of ferulic acid and 1,3-propylene glycol of the same mass as that of Example 1. The preparation process is to add 1,3-propylene glycol with a mass concentration of 10% during the dissolution of ferulic acid. The specific preparation conditions are the same as those of Example 1.

[0058] Comparative Example 6

[0059] Comparative Example 6 is a mixture of ferulic acid and propylene glycol of the same mass as that of Example 1. The preparation process is to add propylene glycol with a mass concentration of 10% during the dissolution of ferulic acid. The specific preparation conditions are the same as those of Example 1.

[0060] Comparative Example 7

[0061] Comparative Example 7 is a mixture of ferulic acid and dipropylene glycol of the same mass as that of Example 1. The preparation process is to add dipropylene glycol with a mass concentration of 10% during the dissolution of ferulic acid. The specific preparation conditions are the same as those of Example 1.

[0062] Performance Testing

[0063] 1. Solubility test

[0064] Test steps:

[0065] Weigh the mass of the dry filter paper (record the data as m0).

[0066] At room temperature (25°C), the prepared ferulic acid-ectoine supramolecular eutectics of Examples 1-3 and Comparative Examples 2-3 and the ferulic acid of Comparative Example 1 were placed in a 250 mL beaker, (100.00 ± 0.05) g of water was added, a stirrer was added, and stirring was stopped after 3 hours on a stirrer. The solid was allowed to settle to the bottom of the beaker, and the supernatant was slowly dumped and discarded. The insoluble matter was transferred to a glass funnel together with a small amount of liquid for filtration, the beaker was washed with cold water 2-3 times, the washing liquid was transferred to a funnel, and the insoluble matter was washed with water 2-3 times.

[0067] Transfer the filter paper and the insoluble matter to a 45°C oven and dry overnight (more than 8 hours). After cooling, weigh the total mass of the filter paper and the insoluble matter (record the data as m1). Repeat each experiment 3 times and take the average value.

[0068] Solubility calculation:

[0069] The solubility of ferulic acid-ectoine supramolecular cocrystal is represented by X, and the value is expressed in %, and is calculated according to formula (1):

[0070] X=m1-m0……………………(1)

[0071] Where:

[0072] m0——mass of dry filter paper, g;

[0073] m1——total mass of dry filter paper and filter residue, g.

[0074] The solubility of ferulic acid in the ferulic acid-ectoine supramolecular cocrystal is represented by Y and calculated according to formula (2):

[0075]

[0076] The solubility test was performed on Examples 1-3 and Comparative Examples 1-7. The test results are shown in Table 1 below:

[0077] Table 1 Solubility test results of Examples 1-3 and Comparative Examples 1-7

[0078]

[0079] It can be seen from the test results in Table 1 that the solubility of Examples 1-3 of the present invention is significantly improved by forming a co-crystal with ferulic acid and ectoine. When the molar ratio of the two is 1: (1-3), the solubility can reach more than 0.5%. The test results of the ferulic acid-ectoine supramolecular co-crystals of Comparative Examples 1-2 show that when ferulic acid is used alone or when the molar ratio of ferulic acid to ectoine is not within the scope defined by the present invention, its solubility is poor and cannot reach the conventional use concentration of more than 0.5%. The test results of Comparative Examples 3-7 show that when ferulic acid is dissolved using a common polyol in the formula, its solubility is poor and cannot reach the solubility level of the ferulic acid-ectoine supramolecular co-crystal in the embodiment. Therefore, preferably, the molar ratio of ferulic acid to ectoine is 1: (1-3).

[0080] 2. Structural characterization test of co-crystal

[0081] Powder X-ray Diffraction (XRD) Analysis:

[0082] X-ray diffraction is the most direct and accurate characterization method to determine the crystal structure. XRD analysis was performed on individual ferulic acid, ectoine and the ferulic acid-ectoine supramolecular eutectic samples prepared in Example 2. When the sample forms a eutectic, the eutectic structure will produce a new diffraction peak, indicating that a new crystal structure has been generated. At the same time, the original diffraction peak of the single sample will be weakened or disappear to a certain extent, which can be used to determine that the eutectic structure has been formed.

[0083] Infrared spectroscopy analysis:

[0084] Infrared spectrometry (IR) is an absorption spectrum obtained by using the transition of vibration and rotation energy levels of molecules produced by the interaction of molecules with infrared radiation. It belongs to the category of molecular spectroscopy and vibrational spectroscopy. Specific functional groups of different molecules will absorb electromagnetic radiation of specific wavelengths in the infrared light region, producing infrared absorption spectra corresponding to the structure of the material.

[0085] Hydrogen bonds are usually formed between the hydrogen of an electron-donating group XH, such as (-OH, -NH2), and an electron-withdrawing group Y, where Y is usually a group with strong electronegativity, such as O, N, and halogen. The main effect of hydrogen bonds on infrared spectra is to shift the peaks and cause the group frequencies to shift. Hydrogen bonds can change the force constants of the two groups. The XH stretching frequency is reduced by hydrogen bonds, and the XH deformation vibration frequency is increased by hydrogen bonds, but not as significantly as the frequency changes caused by stretching vibrations.

[0086] When the sample components form a eutectic through intermolecular forces such as hydrogen bonds, under the action of infrared light, its hydrogen bonds and other chemical bonds are excited to produce corresponding vibration rotation energy levels. According to its characteristic frequency, it can be judged that its chemical bond absorption peak has shifted. By comparing the spectrum of the eutectic components, it can be judged whether a eutectic is formed. The stronger the hydrogen bond formed, the wider the shift span. Therefore, the strength of the hydrogen bond formed can be qualitatively judged by infrared spectroscopy.

[0087] The structural characterization test of the ferulic acid-ectoine supramolecular co-crystal of Example 2 and the same mass of ectoine and ferulic acid (Comparative Example 1) were performed on the co-crystal.

[0088] Figure 1 The X-ray diffraction diagram of ferulic acid-ectoine supramolecular co-crystal, ectoine and ferulic acid in Example 2 of the present invention. Figure 1 It can be seen that the characteristic peaks of ferulic acid are 9.78°, 10.50°, 12.76°, 15.64°, 17.33°, 18.14°, 21.59°, 24.65°, 26.47°, 29.48° and 31.56°. The characteristic peaks of ectoine are 11.55°, 18.65°, 20.58°, 22.67°, 24.11°, 25.88°, 27.58°, 28.47° and 29.32°. After the ferulic acid and ectoine were prepared by mechanical grinding, the XRD spectrum of the ferulic acid-ectoine supramolecular eutectic changed, and the 2θ angle characteristic peaks of the raw materials ferulic acid and ectoine from 10° to 30° all weakened or disappeared to a certain extent.

[0089] In addition, from Figure 1 It can also be seen that new characteristic peaks appeared at 2θ angles of 10.90°, 14.69°, and 32.05° in the XRD spectrum of the eutectic, indicating that ferulic acid and ectoine produced substances with new crystalline structures through grinding.

[0090] Figure 2 The infrared spectra of ferulic acid-ectoine supramolecular co-crystal, ferulic acid and ectoine of Example 2 of the present invention are shown in FIG. Figure 2 It can be seen that the absorption peak of the hydroxyl group OH on the carboxyl group of ferulic acid is at 3437 cm -1 The stretching vibration absorption peak of the carbonyl C=O bond on the carboxyl group is around 1666cm-1 The CH stretching vibration absorption peak of the benzene ring is around 2900-3100cm -1 The absorption peak of the secondary amine group (-NH-) of Ecdoin is at 3501cm -1 The stretching vibration absorption peak of CN is around 1445cm -1 The stretching vibration absorption peak of the carbonyl C=O on the carboxyl group is at 1633cm -1 The stretching vibration absorption peak of the hydroxyl group -OH on the carboxyl group is around 3200cm- 1 The absorption peak of the pyrimidine ring is between 2800 and 3200 cm -1 about.

[0091] In the infrared spectrum of the ferulic acid-ectoine supramolecular co-crystal of Example 2, the secondary amine group (-NH-) of ectoine ranges from 3501 cm -1 Shifted to the broad absorption peak of hydroxyl (OH) (3450-3000cm -1 ), the absorption peak of the carbonyl C=O on the carboxyl group of ferulic acid is from 1666cm -1 Blue shift to 1599cm -1 The absorption peak of carbonyl C=O on the carboxyl group of Ecdoin changes from 1633cm -1 Red shifted to 1659 cm -1 The characteristic peaks of the co-crystal shifted, indicating that there was no proton transfer between ferulic acid and ectoine in the ferulic acid-ectoine supramolecular co-crystal sample of Example 2, and the co-crystal was formed through hydrogen bonding.

[0092] 3. In vitro efficacy test - scavenging rate of ABTs free radicals

[0093] Experimental principle:

[0094] 2,2-Azo-bis(3-ethyl-benzothiazole-6-sulfonic acid) diammonium salt (ABTs for short) reacts with potassium persulfate to generate green ABTs free radicals. The free radical has a maximum absorption at 734nm, and its concentration can be determined by detecting the absorbance at 734nm. After a substance is added to the ABTS free radical solution, if the absorbance at 734nm decreases, it means that the substance has free radical scavenging activity and antioxidant ability. This method is called the ABTS free radical scavenging method.

[0095] Test method:

[0096] Sample treatment: Add 50 μL of standard / sample solution to a 96-well plate. For negative control, add 50 μL of sample solvent, and then add 100 μL of DDPPH solution.

[0097] Background control: add 50 μL of standard / sample solution to the 96-well plate, and for negative control, add 50 μL of sample solvent and then add 100 μL of 95% ethanol (i.e., DPPH is replaced by the same volume of 95% ethanol). Perform 3 replicates for each sample.

[0098] The ferulic acid-ectoine supramolecular co-crystal of Example 2 and the same mass of ferulic acid and ectoine were subjected to an in vitro efficacy test - the scavenging rate of ABTs free radicals. Figure 3 The results of the test on the free radical scavenging rate of ABTs by ferulic acid-ectoine supramolecular co-crystal, ferulic acid and ectoine in Example 2 of the present invention. Figure 3 It can be seen that the ferulic acid-ectoine supramolecular co-crystal of Example 2 of the present invention has a good effect of scavenging ABTs free radicals, which is better than the effect of using ferulic acid or ectoine alone.

[0099] IV. In vitro efficacy test - soothing efficacy test

[0100] Experimental principles and methods:

[0101] The LPS inflammation model was established using macrophage RAW264.7 cells, and the inhibition rate of cellular NO under the inflammation model conditions was detected.

[0102] First, the sample toxicity test was performed, and 50 μL of the toxicity test supernatant was taken for cell inflammatory factor detection. When the cell survival rate was ≥90%, the sample inhibited the production of NO, and the data analysis showed significant differences, indicating that the sample had a soothing effect.

[0103] The ferulic acid-ectoine supramolecular co-crystal of Example 2 and the same mass of ferulic acid and ectoine were subjected to an in vitro efficacy test - a soothing efficacy test.

[0104] Figure 4 These are the test results of the inhibition rate of cellular NO by the ferulic acid-ectoine supramolecular co-crystal, ferulic acid and ectoine of Example 2 of the present invention.

[0105] from Figure 4 It can be seen that the ferulic acid-ectoine supramolecular co-crystal of the embodiment of the present invention has a good inhibitory effect on cellular NO production, which is better than using ferulic acid or ectoine alone.

[0106] The above is only a specific embodiment of the present invention, but the protection scope of the present invention is not limited thereto. Any technician familiar with the technical field can easily think of various equivalent modifications or replacements within the technical scope disclosed by the present invention, and these modifications or replacements should be included in the protection scope of the present invention. Therefore, the protection scope of the present invention shall be based on the protection scope of the claims.

Claims

1. A ferulic acid-ectoine supramolecular eutectic, characterized in that: The invention comprises ferulic acid and ectoine, wherein the molar ratio of the ferulic acid to ectoine is 1:(1-3).

2. The ferulic acid-ectoine supramolecular eutectic as claimed in claim 1, characterized in that: The molar ratio of ferulic acid to ectoine is 1:(1-2).

3. The ferulic acid-ectoine supramolecular eutectic as claimed in claim 1, characterized in that: The molar ratio of ferulic acid to ectoine is 1:

1.

4. The ferulic acid-ectoine supramolecular eutectic as claimed in claim 1, characterized in that: The molar ratio of ferulic acid to ectoine is 1:

2.

5. The method for preparing the ferulic acid-ectoine supramolecular co-crystal according to any one of claims 1 to 4, characterized in that: The preparation method of the ferulic acid-ectoine supramolecular eutectic is a mechanical grinding method or a solvent method.

6. The method for preparing the ferulic acid-ectoine supramolecular eutectic as claimed in claim 5, characterized in that: The preparation method of the ferulic acid-ectoine supramolecular eutectic is a mechanical grinding method, which includes the following steps: weighing ferulic acid and ectoine into a vortex mixer to mix the solids evenly, then transferring the evenly mixed solids into a mortar, and directly mechanically grinding for 30-60 minutes to obtain ferulic acid-ectoine supramolecular eutectic.

7. The method for preparing the ferulic acid-ectoine supramolecular eutectic as claimed in claim 5, characterized in that: The preparation method of the ferulic acid-ectoine supramolecular eutectic is a solvent method, comprising the following steps: dissolving ferulic acid in anhydrous ethanol and dissolving ectoine in water of the same mass, mixing the two evenly, performing reduced pressure distillation at 40-50° C. to remove ethanol and water, and then drying at 40-50° C. to obtain the ferulic acid-ectoine supramolecular eutectic.

8. Use of the ferulic acid-ectoine supramolecular co-crystal as described in any one of claims 1 to 4 in the preparation of cosmetics or skin care products.

9. A cosmetic, characterized in that: The invention comprises the ferulic acid-ectoine supramolecular eutectic as described in any one of claims 1 to 4, and also comprises an emollient, an emulsifier, a moisturizer, a skin conditioner, a preservative and a thickener.

10. A cleaning product, characterized in that: The invention comprises the ferulic acid-ectoine supramolecular eutectic as described in any one of claims 1 to 4, and also comprises an emollient, an emulsifier, a moisturizer, a skin conditioner, a preservative and a thickener.

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