Supramolecular avobenzone as well as preparation method and application thereof
By forming supramolecular structures with ligands such as avobenzone, ferulic acid, ergothioneine, and nicotinamide, the problem of poor stability of avobenzone is solved, resulting in better sun protection and biocompatibility.
Patent Information
- Application Number
- CN202510996397.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-07-18
- Publication Date
- 2025-11-14
AI Technical Summary
Avobenzone sunscreens, whether single or physically mixed, have poor stability because they cannot form supramolecular structures through intermolecular forces.
Supramolecular avobenzone is prepared by forming supramolecular compounds with ligands such as ferulic acid, ergothioneine, nicotinamide, or tranexamic acid, and then connecting them using intermolecular forces such as hydrogen bonds, van der Waals forces, hydrophobic forces, and π-π stacking interactions.
It improves the stability and sun protection effect of avobenzone while maintaining its biocompatibility and bioactivity, thus enhancing the performance of sunscreen products.
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Figure CN120944124A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of supramolecular technology, and in particular to a supramolecular avobenzone, its preparation method, and its application. Background Technology
[0002] Avobenzone is a widely used chemical sunscreen agent, primarily used to absorb the UVA band (320-400nm) of ultraviolet light, reducing UV damage to the skin by converting light energy into heat. It is one of the mainstream ingredients in sunscreens for UVA protection, but its stability needs improvement. For single, physically mixed, or compounded avobenzone sunscreens, their stability is relatively poor because they cannot form supramolecular structures through intermolecular forces.
[0003] Therefore, existing technologies still need to be improved and developed. Summary of the Invention
[0004] In view of the shortcomings of the prior art, the present invention provides a supramolecular avobenzone, its preparation method and application, aiming to solve the problem that avobenzone sunscreens, whether single, physically mixed or compounded, cannot form supramolecular structures through intermolecular forces, resulting in poor stability.
[0005] The technical solution adopted by the present invention to solve the above-mentioned technical problems is as follows:
[0006] In a first aspect, the present invention provides a supramolecular avobenzone, wherein the supramolecular avobenzone comprises two main bodies, an avobenzone-like substance and a ligand, and each pair of main bodies is connected by intermolecular forces; wherein the ligand is at least one of ferulic acid, ergothioneine, nicotinamide and tranexamic acid.
[0007] Preferably, the mass ratio of the avobenzone to the ligand is (1-10):(1-10).
[0008] Preferably, the mass ratio of the avobenzone to the ligand is 1:2.
[0009] Preferably, the avobenzone is selected from one or more of avobenzone and avobenzone derivatives;
[0010] The intermolecular forces include one or more of the following: hydrogen bonds, van der Waals forces, hydrophobic interactions, electrostatic interactions, and π-π stacking interactions.
[0011] A second aspect of the present invention provides a method for preparing the above-described supramolecular avobenzone, the method comprising the following steps:
[0012] Avobenzone-like substances and ligands are dispersed in a solvent and subjected to ionization to form salts. After evaporation and drying, the supramolecular avobenzone is obtained.
[0013] Preferably, the ionization salt formation reaction takes 1-24 hours.
[0014] Preferably, the evaporation treatment is carried out at a temperature of 30℃-100℃ for 1h-4h.
[0015] Preferably, the drying process is carried out at a temperature of 30℃-100℃ for 4h-48h.
[0016] Preferably, the solvent is selected from one or more of ethanol, water, methanol, isopropanol, acetone, propylene glycol, butanediol, and pentanediol.
[0017] In a third aspect of the present invention, the above-mentioned supramolecular avobenzone is used to prepare sunscreen skin care products with anti-photoaging, anti-oxidation, and anti-aging properties, or to prepare a carrier for drug delivery.
[0018] Beneficial effects:
[0019] This invention discloses a supramolecular avobenzone, its preparation method, and its application. The supramolecular avobenzone comprises two main components: an avobenzone-like substance and a ligand. Each pair of main components is connected by intermolecular forces. It has good biocompatibility and mildness, which improves the stability and sun protection effect of avobenzone. Moreover, the supramolecular avobenzone completely retains the supramolecular molecular framework, thereby enhancing the bioactivity and efficacy of the supramolecular avobenzone.
[0020] Furthermore, the preparation method of the present invention has mild reaction conditions, simple synthesis steps, convenient post-processing, and the obtained product has high purity and high yield, which can meet general research requirements. Attached Figure Description
[0021] Figure 1 The image shows the hydrogen NMR spectrum of the supramolecular avobenzone-ferulic acid prepared in Example 1 of this invention.
[0022] Figure 2 The image shows the hydrogen NMR spectrum of the supramolecular avobenzone-ferulic acid-ergothione prepared in Example 2 of this invention.
[0023] Figure 3 This is a two-dimensional hydrogen NMR spectrum of the supramolecular avobenzone-ferulic acid prepared in Example 1 of the present invention.
[0024] Figure 4 The image shows the two-dimensional hydrogen NMR spectrum of the supramolecular avobenzone-ferulic acid-ergothione prepared in Example 2 of this invention.
[0025] Figure 5Transmission electron microscopy and particle size distribution of the supramolecular avobenzone-ferulic acid prepared in Example 1 and the supramolecular avobenzone-ferulic acid-ergothione prepared in Example 2 of this invention.
[0026] Figure 6 Transdermal efficiency diagrams of supramolecular avobenzone-ferulic acid prepared in Example 1 and supramolecular avobenzone-ferulic acid-ergothionein prepared in Example 2 of this invention.
[0027] Figure 7 The image shows the keratinocyte viability of the supramolecular avobenzone-ferulic acid prepared in Example 1 and the supramolecular avobenzone-ferulic acid-ergothionein prepared in Example 2 of this invention.
[0028] Figure 8 The diagram shows the DPPH radical scavenging rates of the supramolecular avobenzone-ferulic acid prepared in Example 1 and the supramolecular avobenzone-ferulic acid-ergothionein prepared in Example 2 of this invention.
[0029] Figure 9 The ultraviolet absorption spectra of the supramolecular avobenzone-ferulic acid prepared in Example 1 and the supramolecular avobenzone-ferulic acid-ergothionein prepared in Example 2 are shown. Detailed Implementation
[0030] This invention provides a supramolecular avobenzone, its preparation method, and its applications. To make the objectives, technical solutions, and effects of this invention clearer and more explicit, the invention is further described in detail below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
[0031] This invention provides a supramolecular avobenzone, which comprises two main components: an avobenzone-like substance and a ligand. Each pair of main components is connected by intermolecular forces (such as hydrogen bonds, van der Waals forces, hydrophobic interactions, electrostatic interactions, π-π stacking interactions, or one or more of these). The ligand is at least one of ferulic acid, ergothioneine, nicotinamide, and tranexamic acid.
[0032] The supramolecular avobenzone provided in this invention has good stability because supramolecular technology enables intermolecular forces to form between avobenzone and its ligands. The presence of these forces can improve the stability of avobenzone and thus enhance its sun protection effect.
[0033] In this embodiment of the invention, the ligand is at least one of ferulic acid, ergothioneine, niacinamide, and tranexamic acid. Ferulic acid has three main functions in skincare products: anti-oxidation, anti-inflammation, and sun protection. Its antioxidant capacity protects the skin from free radical damage and prevents skin aging; its anti-inflammatory effect helps reduce skin inflammation and has a good improvement effect on skin problems such as red acne marks; at the same time, ferulic acid also has a certain sun protection ability, protecting the skin from ultraviolet radiation damage. Ergothioneine is a natural antioxidant that is not easily oxidized. When added to cosmetics at a concentration of 0.01% to 0.03%, it can effectively inhibit melanin formation and brighten skin tone. Niacinamide can inhibit melanin deposition, prevent it from reaching the stratum corneum, and promote the shedding of melanin-containing keratinocytes, thereby reducing skin dullness and brightening skin tone. Tranexamic acid can block the specificity of melanocytes, completely preventing the formation and deposition of melanin formed by ultraviolet radiation, and has whitening and spot-removing effects.
[0034] Furthermore, all of the aforementioned ligands can form intermolecular forces with avobenzone compounds. Utilizing intermolecular forces can improve the solubility and stability of avobenzone compounds. These ligands can form supramolecular structures with avobenzone compounds through intermolecular forces. This is because avobenzone compounds (carbonyl group, benzene ring) interact with ferulic acid (phenolic hydroxyl group, benzene ring) via hydrogen bonding and π-π stacking; avobenzone compounds (carbonyl group, benzene ring) interact with ergothioneine (amino group, imidazole ring) via hydrogen bonding and π-π stacking; avobenzone compounds (carbonyl group, benzene ring) interact with nicotinamide (amide group, pyridine ring) via hydrogen bonding and π-π stacking; and avobenzone compounds (carbonyl group, benzene ring) interact with tranexamic acid (amino or carboxyl group, cyclohexane ring) via hydrogen bonding and π-π stacking.
[0035] Avobenzone compounds cannot form supramolecular structures with certain polymers (such as polydimethylsiloxane), inorganic sunscreens (such as titanium dioxide and zinc oxide), nonpolar oily raw materials (such as liquid paraffin and petrolatum), and ethylhexyl methoxycinnamate. This is because the surfaces of these ligands lack functional groups that can form intermolecular forces with avobenzone compounds. Specifically, some polymers, such as common cosmetic polymers like polydimethylsiloxane, lack functional groups on their molecular chains that can generate strong non-covalent interactions with avobenzone compounds, thus preventing the formation of supramolecular structures. Inorganic sunscreens such as titanium dioxide and zinc oxide typically exist in crystalline form, have significantly different surface properties from avobenzone compounds, and lack active sites for forming non-covalent bonds with avobenzone compounds, making supramolecular formation difficult. Nonpolar oily raw materials lack groups capable of forming non-covalent interactions such as hydrogen bonds or π-π stacking with avobenzone compounds. They have a uniform charge distribution and primarily interact with other substances through van der Waals forces, failing to form supramolecular structures with avobenzone compounds. Ethylhexyl methoxycinnamate (OMC) increases the photostability of avobenzone compounds; the mixture of the two leads to photodecomposition of avobenzone compounds, rather than supramolecular formation.
[0036] In some embodiments, the mass ratio of the avobenzone to the ligand is (1-10):(1-10). For example, the mass ratio of the avobenzone to the ligand can be 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, and other specific values within the above range can be selected, and will not be listed here. This is mainly because the avobenzone at this mass ratio not only maintains its good activity, but also synergistically increases its stability and bioavailability.
[0037] In some preferred embodiments, the mass ratio of the avobenzone to the ligand is 1:2. At this mass ratio, the avobenzone not only maintains its optimal activity but also synergistically increases its stability and bioavailability.
[0038] In some embodiments, the avobenzone is selected from one or more of avobenzone and avobenzone derivatives.
[0039] This invention provides a method for preparing the above-mentioned supramolecular avobenzone, the preparation method comprising the following steps:
[0040] Avobenzone-like substances and ligands are dispersed in a solvent and subjected to ionization to form salts. After evaporation and drying, the supramolecular avobenzone is obtained.
[0041] This invention uses avobenzone-like substances as cationic precursors and ligands such as ferulic acid, ergothioneine, nicotinamide, and tranexamic acid as anionic precursors to synthesize supramolecular avobenzone solutions (also known as supramolecular avobenzone ionic salt solutions) through an ionization salt formation reaction. After the reaction, the solutions are separated and purified by concentration and crystallization to obtain supramolecular avobenzone (also known as supramolecular avobenzone ionic salts). Compared with avobenzone alone, supramolecular avobenzone ionic salts exhibit improved stability and enhanced bioactivity of avobenzone.
[0042] In some embodiments, the method for preparing the supramolecular avobenzone includes the following steps:
[0043] Avobenzone compounds and ligands are dispersed in a solvent and subjected to ionization and salt formation reactions to obtain supramolecular avobenzone solutions (also known as avobenzone ion salt solutions).
[0044] The solvent in the supramolecular avobenzone solution was removed by rotary evaporation to obtain crude supramolecular avobenzone product;
[0045] The crude supramolecular avobenzone product was subjected to recrystallization, filtration, and vacuum drying to obtain supramolecular avobenzone with high purity.
[0046] In some embodiments, the supramolecular avobenzone solution is concentrated to 1 / 5 to 1 / 10 of its volume under vacuum conditions using a rotary evaporator, then recrystallized by vacuum distillation, and finally filtered and vacuum dried to obtain pure supramolecular avobenzone.
[0047] In some embodiments, the drying temperature is 30°C-100°C and the drying time is 4h-48h to completely remove residual water or solvents such as ethanol.
[0048] In some embodiments, the ionization salt formation reaction time is 1-24 hours. The ionization salt formation reaction time can be 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 13 hours, 14 hours, 15 hours, 16 hours, 17 hours, 18 hours, 19 hours, 20 hours, 21 hours, 22 hours, 23 hours, or 24 hours. Other specific values within the above range are also acceptable and will not be listed here. This is mainly because a reaction time that is too short will lead to incomplete reaction, while a reaction time that is too long will cause avobenzone-like substances to oxidize and lose their activity.
[0049] In some preferred embodiments, the ionization salt formation reaction takes 24 hours.
[0050] In some embodiments, the evaporation treatment temperature is 30℃-100℃ and the time is 1-4h. For example, the evaporation treatment temperature can be 30℃-40℃, 40℃-50℃, 50℃-60℃, 60℃-70℃, 70℃-80℃, 80℃-90℃, 90℃-100℃, and the time can be 1h, 2h, 3h, 4h. Other specific values within the above range can be selected, and will not be listed here.
[0051] In some preferred embodiments, the evaporation treatment is carried out at a temperature of 50°C for 1 hour.
[0052] In some embodiments, the drying process is carried out at a temperature of 30℃-100℃ for a duration of 4h-48h. The drying temperature can be 30℃-40℃, 40℃-50℃, 50℃-60℃, 60℃-70℃, 70℃-80℃, 80℃-90℃, or 90℃-100℃, and the drying time can be 4h-8h, 8h-16h, 16h-20h, 20h-24h, 24h-28h, 28h-32h, 32h-36h, 36h-40h, 40h-44h, or 44h-48h.
[0053] In some embodiments, the solvent is selected from one or more of ethanol, water, methanol, isopropanol, acetone, propylene glycol, butanediol, and pentanediol. This can improve the recrystallization separation results of the final supramolecular avobenzone.
[0054] This invention provides an application of supramolecular avobenzone, which is used to prepare sunscreen skincare products with anti-photoaging and anti-oxidation properties, or to prepare drug delivery carriers.
[0055] This invention also provides an application of supramolecular avobenzone, wherein the supramolecular avobenzone described in this invention is used as a formulation ingredient in cosmetics, pharmaceuticals, and life sciences; or, the supramolecular avobenzone described in this invention is used as a pharmaceutical ingredient in drugs such as those delivered transdermally. In other words, the supramolecular avobenzone described in this embodiment can be used as a formulation ingredient in pharmaceuticals and cosmetics, as well as as a raw material for drugs such as drug delivery carriers.
[0056] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are merely some embodiments of the present invention, not all embodiments, and are intended only to illustrate the present invention and not to limit it. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.
[0057] Example 1
[0058] The preparation of a supramolecular avobenzone-ferulic acid includes the following steps:
[0059] Under a nitrogen atmosphere, 1 g of avobenzone was dissolved in 50 mL of ethanol in a reactor, and 1 g of ferulic acid was dissolved in 50 mL of ethanol. The solutions were then added dropwise to the reactor containing the dissolved avobenzone. The reactor was heated to 40 °C and subjected to an ionization salt formation reaction for 24 hours to obtain a supramolecular avobenzone-ferulic acid solution.
[0060] After the reaction was complete, supramolecular avobenzone-ferulic acid was obtained by evaporation under vacuum conditions. After drying for 48 hours, supramolecular avobenzone-ferulic acid with a purity of over 99% was obtained, with a yield of 96.59%.
[0061] The supramolecular avobenzone-ferulic acid prepared in this embodiment has a melting point of 173°C.
[0062] Example 2
[0063] The preparation of a supramolecular avobenzone-ferulic acid-ergothioneine includes the following steps:
[0064] Under a nitrogen atmosphere, 1 g of avobenzone and 1 g of ferulic acid were dissolved in 50 mL of ethanol in a reactor. Then, an aqueous solution containing 1 g of ergothioneine was added dropwise. The mixture was heated to 40 °C and subjected to an ionization salt formation reaction for 24 hours to obtain a supramolecular avobenzone-ferulic acid-ergothioneine solution.
[0065] After the reaction was complete, the supramolecular avobenzone-ferulic acid-ergothioneine was obtained by evaporation under vacuum conditions. After drying for 48 hours, supramolecular avobenzone-ferulic acid-ergothioneine with a purity of over 95% was obtained, with a yield of 94.32%.
[0066] The supramolecular avobenzone-ferulic acid-ergothioneine prepared in this embodiment has a melting point of 253°C.
[0067] Test results:
[0068] When verifying supramolecular structures using nuclear magnetic resonance spectroscopy, the sample was first dissolved in deuterated DMSO solvent. The instrument used for nuclear magnetic resonance spectroscopy was a Bruker nuclear magnetic resonance spectrometer with the nuclear magnetic intensity set to 400 MHz and 1024 scans performed. Liquid nitrogen was used to control the ambient temperature.
[0069] The results are as follows Figure 1 As shown, the proton NMR spectrum data of the supramolecular avobenzone-ferulic acid prepared in Example 1 of this invention are as follows: 1H NMR(400MHz,DMSO)δ12.15(s,1H),9.57(s,1H),8.16(s,1H),8.09(m,2H),7.95(m,1H),7.90(m,1H),7.55(m,1H),7.25(m,1H),7.1 0(m,1H),6.88(s,2H),6.42(dd,1H),4.74(dd,1H),4.42(dd,1H),3.44(t,2H),3.34(m,3H),1.39(s,2H);1.05(d,4H);1.04(s,4H).
[0070] The carbon NMR data are as follows: 13 C NMR(400MHz,DMSO)δ189.07(s),176.71(s),168.48(s),167.10(s),165.91(s),156.81(s) ),153.67(s),151.23(s),149.51(s),148.36(s),144.96(s),139.35(s),137.14(s),136. 38(s),135.26(s),133.76(s),131.43(s),126.07(s),123.97(s),116.00(s),111.80(s) ,132.68(s),129.44(s),113.14(s),92.29(s),55.45(s),48.28(s),35.45(s),31.28(s).
[0071] like Figure 2 As shown, the 1H NMR data of the supramolecular avobenzone-ferulic acid-ergothioneine prepared in Example 2 of this invention are as follows: 1 H NMR(400MHz,DMSO)δ11.97(s,1H),11.75(s,1H),9.61(s,1H),8.16(s,1H),8.07(s, 1H),7.95(s,1H),7.90(s,1H),7.55(s,1H),7.52(s,1H),7.46(s,1H),7.29(s,1H),7 .22(s,2H),7.10(s,2H),6.80(s,2H),6.41(s,2H),6.39(d,2H),4.74(m,2H),4.37(m ,6H),3.82(d,1H),3.86(s,1H),3.42(m,6H),3.36(m,4H),1.06(s,4H),1.01(s,5H).
[0072] The carbon NMR data are as follows: 13C NMR (400MHz, DMSO) δ186.05(s),184.05(s),168.48(s),163.65(s),156.32(s),149.09(s),148.37(s),144.98(s),132.41(s),129. 54(s),127.64(s),125.45(s),123.29(s),116.02(s),114.57(s),111.56(s),92.63(s),56.08(s),51.59(s),35.29(s),31.28(s).
[0073] Depend on Figure 3 It can be seen that there is an interaction force between avobenzone and ferulic acid, indicating that a supramolecular structure is formed between avobenzone and ferulic acid.
[0074] Depend on Figure 4 It is known that there are interaction forces between avobenzone, ferulic acid and ergothioneine, indicating that a supramolecular structure is formed between avobenzone, ferulic acid and ergothioneine.
[0075] When verifying supramolecular particle size using a Zetasizer Nano series potentiometer, the sample is first diluted with water to prepare a 1 mg / mL solution, and then directly tested using the instrument. Results are obtained from... Figure 5 As shown in (a)-(d), the supramolecular avobenzone-ferulic acid has a particle size of approximately 531 nm and is uniformly dispersed; the supramolecular avobenzone-ferulic acid-ergothioneine has a particle size of approximately 712 nm and is also uniformly dispersed. This indicates that supramolecular avobenzone-ferulic acid and supramolecular avobenzone-ferulic acid-ergothioneine possess good safety and low permeability.
[0076] When verifying supramolecular permeation using the Franz diffusion cell, the sample was first prepared as a 1 mg / mL solution, and then 0.5 mL of this solution was added to the diffusion cell. After setting the temperature and sampling time, the permeation experiment could begin. Results were obtained from... Figure 6 It was found that the permeability of supramolecular avobenzone-ferulic acid was 3.02 times lower than that of avobenzone alone; the permeability of supramolecular avobenzone-ferulic acid-ergothioneine was 6.48 times lower than that of avobenzone alone. This indicates that supramolecular avobenzone-ferulic acid and supramolecular avobenzone-ferulic acid-ergothioneine possess good low permeability and safety.
[0077] When validating supramolecular toxicity using keratinocytes, a 1 mg / mL sample solution was first added to a 96-well plate and co-incubated with cells. Then, a CCK-8 assay kit was added, and co-incubation continued for 4 hours before analysis. Results were obtained from... Figure 7It was found that when the concentration of supramolecular avobenzone-ferulic acid and supramolecular avobenzone-ferulic acid-ergothioneine was 1 mg / mL, the cell viability of both supramolecular avobenzone-ferulic acid and supramolecular avobenzone-ferulic acid-ergothioneine was higher than 90%, indicating that supramolecular avobenzone-ferulic acid and supramolecular avobenzone-ferulic acid-ergothioneine have good safety and biocompatibility at this concentration.
[0078] To verify the supramolecular antioxidant activity using DDPH, DPPH was first weighed and dissolved in anhydrous ethanol to prepare a DPPH storage solution. Then, the DPPH solution and sample solution were added to a 96-well plate. After reacting at room temperature in the dark for 30 minutes, the UV absorbance was measured using a microplate reader. The results were obtained from... Figure 8 It can be seen that when the concentration of supramolecular avobenzone-ferulic acid is 1 mg / mL, the scavenging rate of supramolecular avobenzone-ferulic acid on DPPH free radicals is 90.54%; the scavenging rate of supramolecular avobenzone-ferulic acid-ergothioneine on DPPH free radicals is 98.07%, while the scavenging rate of avobenzone alone on DPPH free radicals is 85.68%.
[0079] When verifying the sun protection effect of supramolecular SPF, a PMMA plate was fixed onto a sample plate. First, the background curve of the blank plate was measured. Then, the sample was evenly applied to the PMMA plate using a spotter, and spread with a finger wearing a latex finger cot at a concentration of 2 mg / cm³. 2 Apply the sample gently and evenly to a 25cm area. 2 The sample was applied to a PMMA plate of a specific area. The plate was then placed in a dark environment at (25±5)℃ and (50±10)% relative humidity to air dry for 20 minutes. Finally, six points on the PMMA plate were tested using an SPF-290AS analyzer, and the analysis was performed using the instrument's software. Table 1 below shows that the concentration of supramolecular avobenzone-ferulic acid was 2 mg / cm³. 2 At a concentration of 2 mg / cm³, supramolecular avobenzone-ferulic acid has an SPF of 14.33 and exhibits ++ sun protection against UVA (UVA PFA of 4–8), which is superior to physically mixed avobenzone-ferulic acid (SPF of 8.46); 2 At that time, the supramolecular avobenzone-ferulic acid-ergothioneine had an SPF of 28.52 and a ++++ sun protection effect against UVA (UVA PFA ≥15), which was superior to the physically mixed avobenzone-ferulic acid-ergothioneine (SPF value 12.52).
[0080] Table 1. Sunscreen efficacy data of supramolecular avobenzone-ferulic acid prepared in Example 1 and supramolecular avobenzone-ferulic acid-ergothioneine prepared in Example 2.
[0081] name SPF value UVA PFA value Avobenzan 1.79 1.54 Supramolecular avobenzone-ferulic acid 14.33 7.81 Physical mixture of avobenzone-ferulic acid 8.46 4.28 Supramolecular avobenzone-ferulic acid-ergothionein 28.52 15.01 Physical mixture of avobenzone-ferulic acid-ergothioneine 12.52 6.83
[0082] The ultraviolet absorption effect of supramolecular molecules was verified using a UV-Vis spectrophotometer. First, the sample was prepared into a solution of a specific concentration, and then directly tested using the spectrophotometer. The results were obtained from… Figure 9 It can be seen that the ultraviolet absorption intensity of supramolecular avobenzone-ferulic acid and supramolecular avobenzone-ferulic acid-ergothionein in UVA and UVB is stronger than that of avobenzone alone, indicating that supramolecular avobenzone-ferulic acid and supramolecular avobenzone-ferulic acid-ergothionein have better ultraviolet absorption effects.
[0083] Therefore, all of the above results indicate that supramolecular avobenzone-ferulic acid and supramolecular avobenzone-ferulic acid-ergothioneine have good biocompatibility and high bioavailability, which improve the stability and sun protection effect of avobenzone.
[0084] In summary, this invention provides a supramolecular avobenzone, its preparation method, and its applications. This invention uses avobenzone-like substances as cationic precursors and ligands such as ferulic acid, ergothioneine, nicotinamide, and tranexamic acid as anionic precursors. A supramolecular avobenzone ionic salt solution is synthesized through an ionization salt formation reaction. After the reaction, concentration and crystallization are used to separate and purify the solution, yielding the supramolecular avobenzone ionic salt. Compared to single avobenzone, the supramolecular avobenzone ionic salt exhibits improved stability and enhanced bioactivity of avobenzone.
[0085] It should be understood that the application of the present invention is not limited to the examples above. Those skilled in the art can make improvements or modifications based on the above description, and all such improvements and modifications should fall within the protection scope of the appended claims.
Claims
1. A supramolecular avobenzone, characterized in that, The supramolecular avobenzone comprises two main components: an avobenzone-like substance and a ligand, with each pair of main components connected by intermolecular forces; wherein the ligand is at least one of ferulic acid, ergothioneine, nicotinamide, and tranexamic acid.
2. The supramolecular avobenzone according to claim 1, characterized in that, The mass ratio of the avobenzone to the ligand is (1-10):(1-10).
3. The supramolecular avobenzone according to claim 2, characterized in that, The mass ratio of the avobenzone to the ligand is 1:
2.
4. The supramolecular avobenzone according to claim 1, characterized in that, The avobenzone-like substances are selected from one or more of avobenzone and avobenzone derivatives; The intermolecular forces include one or more of the following: hydrogen bonds, van der Waals forces, hydrophobic interactions, electrostatic interactions, and π-π stacking interactions.
5. A method for preparing supramolecular avobenzone according to any one of claims 1-4, characterized in that, The preparation method includes the following steps: Avobenzone-like substances and ligands are dispersed in a solvent and subjected to ionization to form salts. After evaporation and drying, the supramolecular avobenzone is obtained.
6. The method for preparing supramolecular avobenzone according to claim 5, characterized in that, The ionization salt formation reaction takes 1-24 hours.
7. The method for preparing supramolecular avobenzone according to claim 5, characterized in that, The evaporation process is carried out at a temperature of 30℃-100℃ for 1h-4h.
8. The method for preparing supramolecular avobenzone according to claim 5, characterized in that, The drying process is carried out at a temperature of 30℃-100℃ for 4h-48h.
9. The method for preparing supramolecular avobenzone according to claim 5, characterized in that, The solvent is selected from one or more of ethanol, water, methanol, isopropanol, acetone, propylene glycol, butanediol, and pentanediol.
10. A supramolecular avobenzone according to any one of claims 1-4 for use in the preparation of sunscreen skin care products or for the preparation of a carrier for drug delivery.