Ester sustained-release perfume compound based on color quinacridone structure and application thereof

Abstract

This invention discloses an ester compound based on a quinacridone structure or its pharmaceutical salt, with the structure shown in Formula I. The ester compound based on the quinacridone structure in this invention is based on common quinacridones, and only two reaction steps are required to obtain a molecule with both fluorescence and fragrance-releasing functions. The compound prepared by this invention exhibits excellent sustained-release fragrance function and strong fluorescence properties. Furthermore, its preparation method is simple, involves few synthesis steps, uses low-cost and readily available raw materials, is easy to operate, has a short reaction time, high yield, and is easy to purify. This invention can be used in the fields of organic fluorescent materials and fragrances.

Description

Technical Field

[0001] This invention belongs to the field of chemical synthesis technology, specifically, it relates to an ester compound based on the quinacridone structure and its applications. Background Technology

[0002] Quinacridone is a well-known high-performance organic pigment with a rigid planar structure consisting of three alternating benzene rings and two pyridone rings, and a large π-conjugated system in the planar core. Quinacridone typically exhibits good photothermal and electrochemical stability, as well as excellent weather and corrosion resistance, and the molecule is modifiable. The nitrogen atom can be functionalized with alkyl groups, exhibiting high fluorescence quantum yield and improved solubility in organic solvents, further expanding its application range. Currently, quinacridone derivatives are among the most widely used organic fluorescent pigments.

[0003] Fluorescence is a common photoluminescence phenomenon, where a fluorescent compound emits long-wavelength emitted light after being irradiated with short-wavelength incident light of a specific wavelength. For organic fluorescent pigments, high fluorescence quantum yield and stability are important criteria for evaluating their value. Functional pigments have been widely used in coatings, printing, and other fields in recent years, and due to their good biocompatibility and photoelectric properties, they have seen significant development in life sciences, optoelectronic materials, and other fields. With the continuous development of synthesis and application technologies, our understanding of organic fluorescent pigments is deepening, their application scope is continuously expanding, and their development prospects are becoming increasingly broad. Therefore, the research and development of functional organic fluorescent pigments with various practical values ​​has become a topic of great interest to researchers.

[0004] Fragrance molecules release special aromas that bring pleasure and improve the environment, and are therefore widely used in tobacco, food, textiles, papermaking, and various daily chemical products. However, fragrance molecules are often low-molecular-weight and highly volatile substances, and direct addition of fragrances usually fails to achieve a long-lasting fragrance due to rapid evaporation within a short period. Therefore, latent fragrance compounds, which enable the controlled and sustained release of fragrance molecules, are one of the current research hotspots in the fragrance industry. The concept of latent fragrance compounds originated from "prodrugs" in drug delivery, but latent fragrance compounds require highly volatile fragrance molecules to be linked to a parent compound through characteristic chemical bonds, becoming non-volatile or low-volatile latent fragrance compounds. Furthermore, under specific environmental conditions (such as light, hydrolysis, and temperature), these chemical bonds break, releasing fragrance molecules to achieve a controlled fragrance release effect.

[0005] To date, there have been no reports of ester compounds based on the quinacridone structure that possess both fluorescence and aroma-releasing properties. Summary of the Invention

[0006] The first objective of this invention is to provide an ester compound based on a quinacridone structure.

[0007] A second objective of this invention is to provide the application of the ester compounds based on the quinacridone structure in the preparation of organic fluorescent materials or fragrance sustained-release agents.

[0008] To achieve the above objectives, the technical solution adopted by the present invention is as follows:

[0009] The first aspect of this invention provides an ester compound based on a quinacridone structure or a pharmaceutically acceptable salt thereof, with the following structure:

[0010]

[0011] in:

[0012] R is selected from C1-C12 branched or straight-chain alkyl groups.

[0013] R1 is selected from C1-12 branched or straight-chain alkyl groups, halogens (fluorine, chlorine, bromine, iodine), and hydrogen.

[0014] R2 is selected from C1-12 branched or straight-chain alkyl groups, halogens (fluorine, chlorine, bromine, iodine), and hydrogen.

[0015] R3 is selected from C1-12 branched or straight-chain alkyl groups, halogens (fluorine, chlorine, bromine, iodine), and hydrogen.

[0016] R4 is selected from C1-12 branched or straight-chain alkyl groups, halogens (fluorine, chlorine, bromine, iodine), and hydrogen.

[0017] R5 is selected from C1-12 branched or straight-chain alkyl groups, halogens (fluorine, chlorine, bromine, iodine), and hydrogen.

[0018] R6 is selected from halogens (fluorine, chlorine, bromine, iodine), hydrogen, methyl, and ethyl.

[0019] R7 is selected from halogens (fluorine, chlorine, bromine, iodine), hydrogen, methyl, and ethyl.

[0020] Preferably, in the ester compounds based on the quinacridone structure,

[0021] R is selected from methyl, ethyl,

[0022]

[0023] Most preferably, the ester compound based on the quinacridone structure is selected from one of the following structures:

[0024]

[0025] A second aspect of the present invention provides the use of the ester compounds based on the quinacridone structure or pharmaceutical salts thereof in the preparation of organic fluorescent materials or fragrance sustained-release agents.

[0026] A third aspect of the present invention provides the use of the ester compound based on the quinacridone structure or a pharmaceutical salt thereof in the preparation of fragrance latent aroma compounds.

[0027] By adopting the above technical solution, the present invention has the following advantages and beneficial effects:

[0028] Traditional quinacridone derivatives only have pigment and fluorescence functions. This invention introduces latent fragrance molecules into traditional quinacridone pigments to prepare ester compounds based on the quinacridone structure, enabling quinacridone derivatives to have fragrance release functions in addition to pigment and fluorescence functions.

[0029] The ester compounds based on the quinacridone structure in this invention are based on the common trans-linear quinacridone. A two-step reaction is all that is needed to obtain molecules with both fluorescence and fragrance-releasing functions. For example, in Examples 1-4, compared to pure fragrance molecules, the compounds prepared by this invention exhibit excellent sustained-release fragrance function and strong fluorescence properties. Furthermore, the preparation method is simple, involves few synthetic steps, uses low-cost and readily available raw materials, is easy to operate, time-efficient, has high yield, and is easy to purify. This invention can be used in the fields of organic fluorescent materials and fragrances. Attached Figure Description

[0030] Figure 1 The UV-Vis absorption spectra of compounds QA-1, QA-2, QA-3, and QA-4 in the wavelength range of 200-800 nm are shown.

[0031] Figure 2 The fluorescence emission spectra of compounds QA-1, QA-2, QA-3, and QA-4 are shown in the wavelength range of 200-800 nm.

[0032] Figure 3 Thermogravimetric analysis of compounds QA-1, QA-2, QA-3 and QA-4.

[0033] Figure 4 A schematic diagram showing the relationship between the release of flavoring substances from compounds QA-1, QA-2, QA-3, and QA-4 upon heating with water and time. Detailed Implementation

[0034] To more clearly illustrate the present invention, the following description, in conjunction with preferred embodiments, further clarifies the invention. Those skilled in the art should understand that the specific descriptions below are illustrative rather than restrictive, and should not be construed as limiting the scope of protection of the present invention.

[0035] The reagents used in the embodiments of this invention are shown in Table 1:

[0036] Table 1

[0037] name Specification Manufacturer dichloromethane CP Sinopharm Chemical Reagent Co., Ltd. Ethyl acetate CP Shanghai Lingfeng Chemical Reagent Co., Ltd. DMF AR Shanghai Titan Technology Co., Ltd. Tetrahydrofuran AR Shanghai Lingfeng Chemical Reagent Co., Ltd. Quinacridone technical grade Shanghai Titan Technology Co., Ltd. Bromoacetyl bromide AR Shanghai Darui Fine Chemicals Co., Ltd. 1-Phenylephethanol AR Shanghai Darui Fine Chemicals Co., Ltd. L-menthol AR Shanghai Darui Fine Chemicals Co., Ltd. Neroli AR Shanghai Darui Fine Chemicals Co., Ltd. Pyridine AR Shanghai Darui Fine Chemicals Co., Ltd. Sodium hydride AR Shanghai Titan Technology Co., Ltd. Geraniol RG Shanghai Titan Technology Co., Ltd. Tetrabutylammonium bromide RG Shanghai Titan Technology Co., Ltd. Column chromatography silica gel CP Sinopharm Chemical Reagent Co., Ltd.

[0038] Example 1

[0039] The preparation method of compound QA-1 includes the following steps:

[0040] Step 1, Preparation of Intermediate 3-1

[0041]

[0042] In a 100 mL round-bottom flask, compound 1-1α-phenylethanol (3.66 g, 30 mmol), pyridine (2.37 g, 30 mmol), and 15 mL of dichloromethane were added. Compound 2-bromoacetyl bromide (6.03 g, 30 mmol) was added dropwise at 0 °C. After reacting for 1 h, the temperature was gradually raised to room temperature. The reaction was stopped after 2.5 h at room temperature. The white solid was dissolved in water, extracted three times with dichloromethane, and the extracts were combined and concentrated. The solution was purified by column chromatography to give 6.24 g of intermediate 3-1 (eluent: petroleum ether: ethyl acetate = 20:1), with a yield of 86%.

[0043] The second step is the preparation of compound QA-1.

[0044]

[0045] In a 100 mL round-bottom flask, compound 4-quinacridone (0.62 g, 2 mmol), NaH (2.42 g, 10 mmol), tetrabutylammonium bromide (0.032 g, 0.1 mmol), and tetrahydrofuran (30 mL) were added. Under anhydrous and oxygen-free conditions and argon protection, the mixture was heated to 70 °C and reacted for 1 h. Intermediate 3-1 (2.42 g, 10 mmol) was added dropwise. After the addition was complete, the reaction was continued at 70 °C for 24 h. After cooling, the reaction was quenched dropwise with methanol. The mixture was filtered, and the filter cake was washed and dissolved with dichloromethane. The filtrate was concentrated and purified by column chromatography to give 0.80 g of compound QA-1 (eluent: petroleum ether: dichloromethane = 2:1), with a yield of 63%. The NMR and mass spectrometry information of compound QA-1 is as follows: 1 H NMR (400MHz, CDCl3) δ8.59–8.48(m,4H),7.65(t,J=7.6Hz,2H),7.36–7.27(m,12H) ,7.22(d,J=8.7Hz,2H),6.05(q,J=6.4Hz,2H),5.27(s,4H),1.64(d,J=6.6Hz,6H). 13C NMR (151MHz, CDCl3) δ177.90,167.36,142.52,140.48,136.51,134.72,128.57,128.20,127.98 ,126.18,126.10,121.59,121.31,114.12,113.22,77.16,74.73,48.38,22.05.HRMS(ESI):m / z calculated for[C 40 H 33 N2O6] + :637.2339; found:637.2338.

[0046] Example 2

[0047] The preparation method of compound QA-2 includes the following steps:

[0048] Step 1: Preparation of intermediate 3-2

[0049]

[0050] In a 100 mL round-bottom flask, compound 1-2L-menthol (4.68 g, 30 mmol), pyridine (2.37 g, 30 mmol), and 15 mL of dichloromethane were added. Compound 2-bromoacetyl bromide (6.03 g, 30 mmol) was added dropwise at 0 °C. After reacting for 1 h, the temperature was gradually raised to room temperature. The reaction was stopped after 2.5 h at room temperature. The white solid was dissolved in water, extracted three times with dichloromethane, and the extracts were combined and concentrated. The solution was purified by column chromatography to give 8.11 g of intermediate 3-2 (eluent: petroleum ether: ethyl acetate = 20:1), with a yield of 98%.

[0051] The second step is the preparation of compound QA-2.

[0052]

[0053] In a 100 mL round-bottom flask, compound 4-quinacridone (0.62 g, 2 mmol), NaH (2.42 g, 10 mmol), tetrabutylammonium bromide (0.032 g, 0.1 mmol), and tetrahydrofuran (30 mL) were added. Under anhydrous and oxygen-free conditions and argon protection, the mixture was heated to 70 °C and reacted for 1 h. Then, intermediate 3-2 (2.76 g, 10 mmol) was added dropwise. After the addition was complete, the reaction was continued at 70 °C for 24 h. After cooling, the reaction was quenched dropwise with methanol. The mixture was filtered, and the filter cake was washed and dissolved with dichloromethane. The filtrate was concentrated and purified by column chromatography to give 1.13 g of compound QA-2 (eluent: petroleum ether: dichloromethane = 2:1), with a yield of 80%. The NMR and mass spectrometry information of compound QA-2 is as follows: 1H NMR (400MHz, CDCl3) δ8.61–8.50(m,12H),7.70(t,J=7.5Hz,2H),7.32–7.23(m,6H),5.24(d,J=26.7Hz,4H),4.85–4.62(m,2H),2.0 4(d,J=12.6Hz,2H),1.67–1.53(m,6H),1.35–1.19(m,6H),1.05–0.93(m,4H),0.87(d,J=6.4Hz,6H),0.73(dd,J=38.4,6.5Hz,12H). 13 C NMR (151MHz, CDCl3) δ178.13,167.91,142.86,136.84,134.91,128.34,126.49,121.79,121.61,114.26 ,113.47,77.16,76.86,48.60,46.96,40.73,34.15,31.56,23.24,22.07,20.89,16.12.HRMS(ESI):m / z calculated for[C 44 H 53 N2O6] + :705.3904; found:705.3905.

[0054] Example 3

[0055] The preparation method of compound QA-3 includes the following steps:

[0056] Step 1: Preparation of intermediate 3-3

[0057]

[0058] In a 100 mL round-bottom flask, compound 1-3 geraniol (4.62 g, 30 mmol), pyridine (2.37 g, 30 mmol), and 15 mL dichloromethane were added. Compound 2-bromoacetyl bromide (6.03 g, 30 mmol) was added dropwise at 0 °C. After reacting for 1 h, the temperature was gradually raised to room temperature. The reaction was stopped after 2.5 h at room temperature. The white solid was dissolved in water, extracted three times with dichloromethane, and the extracts were combined and concentrated. The solution was purified by column chromatography to give 6.58 g of intermediate 3-3 (eluent: petroleum ether: ethyl acetate = 20:1), with a yield of 80%.

[0059] (2) Preparation of compound QA-3

[0060]

[0061] In a 100 mL round-bottom flask, compound 4-quinacridone (0.62 g, 2 mmol), NaH (2.42 g, 10 mmol), tetrabutylammonium bromide (0.032 g, 0.1 mmol), and tetrahydrofuran (30 mL) were added. Under anhydrous and oxygen-free conditions and argon protection, the mixture was heated to 70 °C and reacted for 1 h. Then, intermediate 3-3 (2.74 g, 10 mmol) was added dropwise. After the addition was complete, the reaction was continued at 70 °C for 24 h. After cooling, the reaction was quenched dropwise with methanol. The mixture was filtered, and the filter cake was washed and dissolved with dichloromethane. The filtrate was concentrated and purified by column chromatography to give 0.95 g of compound QA-3 (eluent: petroleum ether: dichloromethane = 2:1), with a yield of 68%. The NMR and mass spectrometry information of compound QA-3 is as follows: 1 H NMR(400MHz, CDCl3)δ8.45(d,J=12.9Hz,4H),7.64(t,J=7.4Hz,2H),7.24–7.17(m,4H),5.39(t,J=6.5Hz ,2H),5.21(s,2H),5.07(s,2H),4.78(d,J=7.0Hz,4H),2.06(s,8H),1.68(d,J=9.3Hz,12H),1.59(s,6H). 13 C NMR (151MHz, CDCl3) δ177.87,167.98,143.78,142.40,136.34,134.63,131.81,127.88,126.05,123.63,121.46,12 1.16,117.25,114.10,113.17,77.16,62.97,48.11,39.45,26.22,25.62,17.64,16.54.HRMS(ESI):m / zcalculated for[C 44 H 49 N2O6] + :701.3591; found:701.3590.

[0062] Example 4

[0063] The preparation method of compound QA-4 includes the following steps:

[0064] Step 1: Preparation of intermediate 3-4

[0065]

[0066] In a 100 mL round-bottom flask, compound 1-4 nerol (4.62 g, 30 mmol), pyridine (2.37 g, 30 mmol), and 15 mL dichloromethane were added. Compound 2-bromoacetyl bromide (6.03 g, 30 mmol) was added dropwise at 0 °C. After reacting for 1 h, the temperature was gradually raised to room temperature. The reaction was stopped after 2.5 h at room temperature. The white solid was dissolved in water, extracted three times with dichloromethane, and the extracts were combined and concentrated. The solution was purified by column chromatography to give 6.74 g of intermediate 3-4 (eluent: petroleum ether: ethyl acetate = 20:1), with a yield of 82%.

[0067] (2) Preparation of compound QA-4

[0068]

[0069] In a 100 mL round-bottom flask, compound 4-quinacridone (0.62 g, 2 mmol), NaH (2.42 g, 10 mmol), tetrabutylammonium bromide (0.032 g, 0.1 mmol), and tetrahydrofuran (30 mL) were added. Under anhydrous and oxygen-free conditions and argon protection, the mixture was heated to 70 °C and reacted for 1 h. Then, intermediate 3-4 (2.74 g, 10 mmol) was added dropwise. After the addition was complete, the reaction was continued at 70 °C for 24 h. After cooling, the reaction was quenched dropwise with methanol. The mixture was filtered, and the filter cake was washed and dissolved with dichloromethane. The filtrate was concentrated and purified by column chromatography to give 0.98 g of compound QA-4 (eluent: petroleum ether: dichloromethane = 2:1), with a yield of 70%. The NMR and mass spectrometry information of compound QA-4 is as follows: 1 H NMR (400MHz, CDCl3) δ8.46(d,J=10.4Hz,4H),7.65(t,J=7.5Hz,2H),7.22(d,J=7.4Hz,4H),5.39(t,J=6.9Hz,2 H),5.20(s,4H),5.05(s,2H),4.75(d,J=7.0Hz,4H),2.13–2.02(m,8H),1.77(s,6H),1.65(s,6H),1.56(s,6H). 13 C NMR (151MHz, CDCl3) δ178.16,168.16,144.01,142.71,136.69,134.93,132.43,128.19,126.40,123.60,121. 74,121.49,118.43,114.31,113.43,77.16,62.95,48.36,32.37,26.75,25.83,23.69,17.81.HRMS(ESI):m / z calculated for[C 44 H 49N2O6] + :701.3591; found:701.3593.

[0070] UV-Vis absorption spectroscopy of compounds QA-1, QA-2, QA-3 and QA-4

[0071] Compounds QA-1, QA-2, QA-3, and QA-4 were prepared into 5 × 10⁻⁶ solutions using dichloromethane. -5 A mol / L standard solution was prepared. The UV-Vis spectrum of the standard solution in the 200-800 nm range was measured using a UV-Vis spectrometer. The results are shown in the figure. Figure 1 As shown, Figure 1 The UV-Vis absorption spectra of compounds QA-1, QA-2, QA-3, and QA-4 in the wavelength range of 200-800 nm are shown. The results indicate that the maximum absorption wavelength of compounds QA-1, QA-2, QA-3, and QA-4 is around 495 nm.

[0072] Fluorescence emission spectra of compounds QA-1, QA-2, QA-3 and QA-4

[0073] Compounds QA-1, QA-2, QA-3, and QA-4 were prepared into a 10-fold mixture using dichloromethane. -4 ~10 -5 A mol / L standard solution was prepared. The fluorescence emission spectrum of the standard solution in the 200-800 nm range was measured using a fluorescence spectrometer. The results are shown in [Figure number missing]. Figure 2 As shown, Figure 2 The fluorescence emission spectra of compounds QA-1, QA-2, QA-3, and QA-4 in the wavelength range of 200-800 nm are shown. Specifically, A represents the fluorescence emission spectrum of compound QA-1 in the 200-800 nm wavelength range, B represents the fluorescence emission spectrum of compound QA-2 in the 200-800 nm wavelength range, C represents the fluorescence emission spectrum of compound QA-3 in the 200-800 nm wavelength range, and D represents the fluorescence emission spectrum of compound QA-4 in the 200-800 nm wavelength range. The results show that QA-1, QA-2, QA-3, and QA-4 have good solubility in organic solvents and emit orange or yellow fluorescence at low concentrations. The fluorescence intensity gradually increases with increasing concentration. As can be seen from the figures, the fluorescence emission spectral bands are between 490-580 nm, with the main emission peak at approximately 510 nm and a shoulder peak at 540 nm, both exhibiting high fluorescence intensity. This demonstrates that compounds QA-1, QA-2, QA-3, and QA-4 possess good fluorescence properties and can be used as organic fluorescent materials.

[0074] Thermogravimetric analysis of compounds QA-1, QA-2, QA-3 and QA-4

[0075] Thermogravimetric analysis (TGA) was performed on compounds QA-1, QA-2, QA-3, and QA-4. Under programmed temperature control, the relationship between the mass of the test samples and temperature was investigated. Figure 3 As shown. Figure 3 Thermogravimetric analysis (TGA) of compounds QA-1, QA-2, QA-3, and QA-4 is given. Specifically, A represents the TGA of compound QA-1, B represents compound QA-2, C represents compound QA-3, and D represents compound QA-4. As can be seen from the TG and DTG curves of each compound in the figure, compound QA-1 begins to decompose at 269℃, with the TG curve dropping rapidly. At 278℃, the mass changes by 32%, and the DTG curve shows a very significant change within this temperature range. Further decomposition occurs upon continued heating. Compound QA-2 begins to decompose at 327℃, with the TG curve dropping rapidly. At 338℃, the mass changes by 52%, and the DTG curve shows a very significant change within this temperature range. Further decomposition occurs when the temperature rises to 430℃. Compounds QA-3 and QA-4 only begin to decompose between 243-248℃, with mass changes of 36% and 35% respectively between 264-268℃. This is because QA-3 and QA-4 are isomers with similar thermal stability.

[0076] In summary, compounds QA-1, QA-2, QA-3, and QA-4 initially showed almost no change in mass as the temperature increased, only beginning to decompose at high temperatures of 269-338℃, indicating that the synthesized compounds all possess good thermal stability.

[0077] Application Examples 1-4

[0078] The ester-based fragrance substances released by the hydrolysis of compounds QA-1, QA-2, QA-3, and QA-4 were detected and compared with the corresponding pure fragrance molecules.

[0079] The hydrolysis of compounds QA-1, QA-2, QA-3, and QA-4 in alkaline aqueous solution and the volatilization of equimolar amounts of pure fragrance molecules under the same experimental conditions were detected by solid-phase microextraction-gas chromatography. By comparing the data from both methods, it was demonstrated that compounds QA-1, QA-2, QA-3, and QA-4 have the effect of delaying the release of fragrance substances.

[0080] Add 0.05 mmol of compound QA-1, QA-2, QA-3, or QA-4 to a sealed headspace vial, along with 0.5 mL of DMF and 0.5 mL of borax buffer solution. Then place the vial in an oil bath and heat at 40°C. After heating for 10 minutes, insert the extraction fiber into the upper space of the headspace vial for extraction for another 10 minutes. Quickly insert the needle into the GC inlet. At high temperature, the fragrance components adsorbed on the fiber undergo desorption and successfully enter the gas phase for analysis. The desorption time is 10 minutes, and the gas chromatograph is started simultaneously for data acquisition. For reference, pure fragrance molecules should be treated in the same way, and the results are as follows. Figure 4 As shown. Figure 4 This diagram illustrates the relationship between the release of flavoring substances from compounds QA-1, QA-2, QA-3, and QA-4 upon heating with water and time. Specifically, A represents the relationship between the release of flavoring substances from compound QA-1 upon heating with water and time; B represents the relationship between the release of flavoring substances from compound QA-2 upon heating with water and time; C represents the relationship between the release of flavoring substances from compound QA-3 upon heating with water and time; and D represents the relationship between the release of flavoring substances from compound QA-4 upon heating with water and time.

[0081] As can be seen from the figure, the release amount of pure flavor molecules is much greater than that of quinacridone ester compounds QA-1, QA-2, QA-3 and QA-4 released by hydrolysis. Figure 4 Tables A, B, C, and D show the release performance of 0.005 mmol of QA-1, QA-2, QA-3, QA-4, and their equimolar amounts of pure aromatic compounds in headspace vials, respectively. Due to their high volatility, free fragrance alcohols can reach very high concentrations in headspace vials within a short time, resulting in correspondingly large peak areas on the gas chromatograph. However, due to the varying volatility of the fragrance alcohols themselves, the peak areas on the gas chromatographs of the blank control group also show some differences. Furthermore, it can be observed that QA-3 and QA-4 have slightly stronger release effects than QA-1 and QA-2. This is because geraniol and nerol, among these four fragrance alcohols, have straight-chain structures without cyclic or branched structures, resulting in less steric hindrance and thus easier release upon heating. Compared with the blank control group, the prepared quinacridone ester latent fragrance particles had smaller response peak areas in gas chromatography and gradually reached equilibrium after 40 min of release, indicating that the synthesized quinacridone ester latent fragrance particles all have good controllable sustained-release ability.

[0082] As shown in the figure, the release rate of free fragrance alcohols is much higher than that of the modified quinacridone ester latent fragrance compounds, approximately 8-25 times higher. The relatively low concentration of latent fragrance compounds in the headspace vial is mainly due to two factors: firstly, the prepared quinacridone ester latent fragrance compounds require a hydrolysis and bond-breaking process to release fragrance alcohols, and only after the free fragrance alcohols volatilize can they be adsorbed and detected—a relatively slow process; secondly, the fragrance release experiment was conducted in a buffer solution at pH 9.18. Although an appropriate amount of DMF solution was added to the hydrolysis system to improve the solubility of the compound, it could not completely dissolve the test compound, thus still affecting its hydrolysis rate. This also indicates that quinacridone ester latent fragrance compounds have a better and longer-lasting fragrance retention effect.

[0083] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. Although the present invention has been disclosed above with reference to preferred embodiments, it is not intended to limit the present invention. Any person skilled in the art can make some modifications or alterations to the above-described technical content to create equivalent embodiments without departing from the scope of the present invention. Any simple modifications, equivalent changes, and alterations made to the above embodiments based on the technical essence of the present invention without departing from the scope of the present invention shall still fall within the scope of the present invention.

Claims

1. An ester compound based on a quinacridone structure or a pharmaceutically acceptable salt thereof, characterized in that, The ester compounds based on the quinacridone structure are selected from one of the following structures:

2. The use of an ester compound based on the quinacridone structure as described in claim 1, or a pharmaceutical salt thereof, in the preparation of organic fluorescent materials or sustained-release fragrances.

3. The use of an ester compound based on a quinacridone structure as described in claim 1, or a pharmaceutical salt thereof, in the preparation of a fragrance latent body.

Images