A damascenone-based hybrid flavor molecule device, and a preparation method and application thereof

Abstract

The application provides a damascone-based hybrid flavor molecular device and a preparation method and application thereof, and belongs to the technical field of natural plant oil detection. The damascone-based hybrid flavor molecular device provided by the application contains a freely rotatable carbon-carbon double bond large conjugated hybrid structure, can freely mechanically rotate in low-viscosity rice oil, and efficiently dissipates excited state energy through mechanical movement, and the released light signal intensity is weak; in high-viscosity rice oil, the free mechanical rotation of the molecular device is significantly limited, the excited state energy is dissipated in the form of radiation transition, the released light signal intensity is synchronously enhanced, the 'turn-on' visual imaging effect is realized, and the higher the consistency, the stronger the light signal. Based on this, the molecular device can be used as a molecular-level tool for controlling the dilution and thickening process of rice oil, and helps to accurately regulate the viscosity of rice oil.

Description

Technical Field

[0001] This invention relates to the field of natural plant oil detection technology, and in particular to a damascene ketone-based hybrid fragrance molecular device, its preparation method, and its application. Background Technology

[0002] Natural rice bran oil is a type of green functional oil that combines edible value with industrial application potential, made from rice bran, a byproduct of rice processing, through refining and extraction. Its micro-viscosity, a key indicator determining product quality and application suitability, is crucial. Compared to traditional chemically synthesized oils, natural rice bran oil inherently possesses excellent environmentally friendly properties and is rich in natural active components such as oryzanol and phytosterols. Differences in the types and amounts of these components impart different micro-viscosity characteristics to rice bran oil, ultimately affecting its performance in various application scenarios. For example, when the content of active components such as oryzanol in rice bran oil is low, the intermolecular forces are weak, resulting in better fluidity, making it suitable for food frying and as a base oil in industrial cold rolling solutions. Conversely, when the content of active components is high, the molecular association effect is enhanced, resulting in superior stability and film-forming properties, making it suitable for food coating and as a base oil in cosmetics.

[0003] Precisely controlling the micro-viscosity of rice bran oil can significantly enhance its application specificity and meet the differentiated needs of various fields such as food and chemical industry. However, currently there are few functionalized molecular tools based on natural product reconstruction that can perform in-situ detection of the micro-viscosity of the physical microenvironment of rice bran oil. Therefore, there is an urgent need to develop a natural product-based molecular-level tool adapted to the complex system of natural rice bran oil to achieve precise, in-situ monitoring of micro-viscosity changes. Summary of the Invention

[0004] The purpose of this invention is to provide a damascon ketone-based hybrid fragrance molecular device, its preparation method, and its application. The damascon ketone-based hybrid fragrance molecular device can be used as a molecular-level tool for controlling the viscosity of rice bran oil, enabling precise measurement of the micro-region viscosity of rice bran oil.

[0005] To achieve the above-mentioned objectives, the present invention provides the following technical solution: This invention provides a damascene ketone hybrid fragrance molecule device having the structure shown in Formula I: Formula I.

[0006] This invention provides a method for preparing the above-mentioned damascene ketone hybrid fragrance molecule device, comprising the following steps: Damascone is dissolved in the first solvent to obtain a damascone solution; Dissolve trans-2-hexene-4-oxo-aldehyde in a second solvent to obtain a trans-2-hexene-4-oxo-aldehyde solution; A metal inorganic salt is dissolved in a third solvent to obtain a metal inorganic salt solution; an organic base is dissolved in a fourth solvent to obtain an organic base solution; the metal inorganic salt solution and the organic base solution are mixed to obtain a composite base solution. The damascone solution, the trans-2-hexene-4-oxo-aldehyde solution, and the composite alkaline solution are mixed and subjected to a dehydration condensation reaction to obtain a damascone-based hybrid fragrance molecule device with the structure shown in Formula I.

[0007] Preferably, the inorganic metal salt includes one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, potassium hydroxide, and calcium hydroxide. The organic base includes one or more of trimethylamine, N,N-diisopropylethylamine, pyridine, imidazole, 4-dimethylaminopyridine, N,N,N',N'-tetramethylethylenediamine, and triethylamine.

[0008] Preferably, the molar ratio of damascone, trans-2-hexene-4-oxo-aldehyde, metal inorganic salt and organic base is 1~3:1~5:1~6:1~5.

[0009] Preferably, the first solvent is an alcohol-polar solvent, wherein the volume ratio of alcohol solvent to polar solvent in the alcohol-polar solvent is 1~6:1, the alcohol solvent includes anhydrous ethanol, and the polar solvent includes N,N-dimethylformamide; the concentration of the damascone solution is 1~3 mol / L; The second solvent is a tetrahydrofuran-alcohol mixture, wherein the volume ratio of tetrahydrofuran to alcohol solvent in the tetrahydrofuran-alcohol mixture is 1:1 to 6, and the alcohol solvent includes one or more of methanol, anhydrous ethanol, propanol, ethylene glycol, and 1,2-propanediol; the concentration of the trans-2-hexene-4-oxo-aldehyde solution is 1 to 6 mol / L. The third solvent is a mixture of alcohol and water, with a volume ratio of alcohol to water of 1 to 6:1. The alcohol includes one or more of methanol, anhydrous ethanol, propanol, ethylene glycol, and 1,2-propanediol. The concentration of the metal inorganic salt solution is 1 to 3 mol / L. The fourth solvent includes one or more of N,N-dimethylformamide, anhydrous ethanol, dimethyl sulfoxide, and methanol; the concentration of the organic base solution is 1~5 mol / L.

[0010] Preferably, the dehydration condensation reaction is carried out at a temperature of 80~120℃ for 2~4 hours.

[0011] This invention provides the application of the above-mentioned damascone-based hybrid fragrance molecular device or the damascone-based hybrid fragrance molecular device prepared by the above preparation method in measuring the micro-region viscosity of rice bran oil. The method of application includes the following steps: Damask ketone-based hybrid fragrance molecular devices are mixed with organic solvents to obtain a damask ketone-based hybrid fragrance molecular device solution. The solution of the damascene-based hybrid fragrance molecule device was mixed with natural rice bran oil. The resulting test solution was subjected to optical signal intensity measurement. The micro-area viscosity of the rice bran oil was obtained based on the correspondence between optical signal intensity and rice bran oil viscosity value.

[0012] Preferably, the organic solvent includes oleic acid, linoleic acid, palmitic acid, stearic acid, or linolenic acid.

[0013] Preferably, the volume ratio of the damascene ketone hybrid fragrance molecule device solution to natural rice bran oil is 1:99; The concentration of the damascene-based hybrid fragrance molecule device in the test solution is 10 μmol / L.

[0014] Preferably, the excitation wavelength for the optical signal intensity measurement is 275~320 nm, and the emission wavelength is 350~600 nm.

[0015] The beneficial effects of this invention are: The damascene-based hybrid fragrance molecular device of this invention contains a freely rotatable carbon-carbon double bond large conjugated hybrid structure. This type of conjugated structure can achieve free mechanical rotation in low-viscosity rice bran oil, where excited-state energy is efficiently dissipated through mechanical motion, resulting in a relatively weak emitted light signal intensity. This indicates that the rice bran oil has good fluidity and is suitable for applications requiring high fluidity, such as textile auxiliaries. As the viscosity of the rice bran oil gradually increases, the free mechanical rotation of the molecular device is significantly restricted, and the excited-state energy is dissipated through radiative transitions, resulting in a synchronous increase in the emitted light signal intensity, achieving a "turbo" effect. The device exhibits a "n-on" visualization effect, with a stronger light signal at higher viscosity. Based on this, the molecular device can serve as a molecular-level tool for controlling the viscosity of rice bran oil, enabling precise modulation of its viscosity. This method is highly beneficial for controlling the edible and cooking compatibility and industrial lubrication properties of rice bran oil. Rice bran oil with higher viscosity (>80 cP at room temperature) is more suitable for industrial applications such as specialty lubricants and soap production, while rice bran oil with lower viscosity is more suitable for everyday cooking and food processing. This provides effective support for the multi-scenario development and targeted design of rice bran oil for specific users and applications.

[0016] The damascene-based hybrid fragrance molecule device of the present invention can emit strong fluorescence at 350-600 nm under external excitation light irradiation at 275-320 nm, which can accurately measure the micro-region viscosity of rice bran oil and thus determine its viscosity. This provides real-time data reference for the refining, modification and process modulation of rice bran oil, and more efficiently controls the product viscosity parameters.

[0017] The damasone-based hybrid fragrance molecular device provided by this invention is a pale yellow powder, easily soluble in fat-soluble solvents such as oleic acid and rice bran oil. It is prepared using damasone (a natural fragrance precursor) and trans-2-hexene-4-oxo-aldehyde as core raw materials through a green modification and synergistic catalytic dehydration coupling process. The raw materials are environmentally friendly, the steps are simple, and it aligns with the low-carbon development concept, making it suitable for large-scale chemical production. This hybrid fragrance molecular device exhibits excellent aroma and light stability, stable chemical structure, low hygroscopicity, and is not easily deliquescent or deteriorated, making it suitable for long-term storage. It is also less susceptible to damage from triglycerides, oryzanol, and phytosterols within rice bran oil. Despite the influence of natural components such as alcohols and a small amount of processing aids, the intensity of the released light signal conforms to the Förster-Hoffmann relationship with the logarithmic function of rice bran oil viscosity, with a viscosity sensitivity coefficient of 0.69, indicating high sensitivity to rice bran oil viscosity. This molecular device is very suitable for in-situ, non-destructive detection of micro-region viscosity of rice bran oil. In photostability testing, it maintains a stable signal release intensity in both high- and low-viscosity rice bran oils. Furthermore, the absorbance of the molecular device is largely unaffected in lipid-soluble systems of different polarities, with the absorption spectrum peak concentrated around 410 nm, indicating stable performance in complex rice bran oil systems. In addition, its detection limit is as low as 1.022 cP, enabling it to capture subtle changes in rice bran oil viscosity and effectively avoid the shear thinning effect caused by rotational shearing of pseudoplastic components (such as phospholipids and polymers) in industrial operations such as stirring and pumping, thus accurately capturing the intrinsic viscosity state of rice bran oil. This molecular device provides an efficient and accurate viscosity detection solution for the rice bran oil industry, enabling in-situ, real-time, and visualized precise monitoring of the viscosity of rice bran oil in micro-regions. It significantly improves the controllability of rice bran oil production processes, makes outstanding contributions to optimizing the cooking experience of edible rice bran oil and the functional adaptability of industrial rice bran oil, and promotes the high-value application of rice bran oil in the food, chemical and other fields. Attached Figure Description

[0018] Figure 1 A schematic diagram illustrating the mechanism of viscosity detection in the physical microenvironment of rice bran oil using a damascena ketone-based hybrid fragrance molecular device; Figure 2 The carbon NMR spectrum of the BDCHD prepared in Example 1; Figure 3 High-resolution mass spectrum of BDCHD prepared in Example 1; Figure 4 Emission spectra of BDCHD prepared in Example 1 in mixed solutions of glycerol / water with volume fractions of 0%, 10%, 30%, 50%, 70% and 99%; Figure 5 The graph shows the logarithmic function of fluorescence intensity versus viscosity for the BDCHD prepared in Example 1. Figure 6The photostability test results of BDCHD prepared in Example 1 in a purified water system with low micro-viscosity and a glycerol solution system with high micro-viscosity are shown. Figure 7 Stokes displacement test image of BDCHD prepared in Example 1; Figure 8 Linear fitting plot of the detection limit of BDCHD prepared in Example 1; Figure 9 The emission spectra of BDCHD prepared in Example 1 in different commercially available edible natural rice bran oils are shown.

[0019] Figure 10 The emission spectra of BDCHD prepared in Example 1 in different commercially available industrial rice bran oils are shown. Detailed Implementation

[0020] This invention provides a damascene ketone hybrid fragrance molecule device having the structure shown in Formula I: Formula I.

[0021] This invention provides a method for preparing the above-mentioned damascene ketone hybrid fragrance molecule device, comprising the following steps: Damascone is dissolved in the first solvent to obtain a damascone solution; Dissolve trans-2-hexene-4-oxo-aldehyde in a second solvent to obtain a trans-2-hexene-4-oxo-aldehyde solution; A metal inorganic salt is dissolved in a third solvent to obtain a metal inorganic salt solution; an organic base is dissolved in a fourth solvent to obtain an organic base solution; the metal inorganic salt solution and the organic base solution are mixed to obtain a composite base solution. The damascone solution, the trans-2-hexene-4-oxo-aldehyde solution, and the composite alkaline solution are mixed and subjected to a dehydration condensation reaction to obtain a damascone-based hybrid fragrance molecule device with the structure shown in Formula I.

[0022] In this invention, unless otherwise specified, all raw materials required for preparation are commercially available products well known to those skilled in the art.

[0023] In this invention, damascone is preferably dissolved in a first solvent at room temperature, sonicated at 25°C using an ultrasonic-assisted machine, and then transferred to a constant-temperature shaker for further mixing for 1-3 hours to obtain a damascone solution.

[0024] In this invention, the first solvent is preferably an alcohol-polar solvent, and the volume ratio of the alcohol solvent to the polar solvent in the alcohol-polar solvent is preferably 1 to 6:1, more preferably 3.5:1; the alcohol solvent preferably includes anhydrous ethanol, and the polar solvent preferably includes N,N-dimethylformamide.

[0025] In this invention, the power of the ultrasound is preferably 10~40 kHz, more preferably 25 kHz, the rotation speed is preferably 600~1200 rpm, more preferably 800 rpm, and the time is preferably 0.5~1.5 h, more preferably 1 h.

[0026] In this invention, the concentration of the damascone solution is preferably 1-3 mol / L, and more preferably 2 mol / L.

[0027] In this invention, trans-2-hexene-4-oxo-aldehyde is dissolved in a second solvent at 30-50°C, and the mixture is continuously mechanically stirred during the mixing process to obtain a trans-2-hexene-4-oxo-aldehyde solution.

[0028] In this invention, the second solvent is preferably a tetrahydrofuran-alcohol mixed solvent, wherein the volume ratio of tetrahydrofuran to alcohol solvent in the tetrahydrofuran-alcohol mixed solvent is preferably 1:1 to 6, more preferably 1:3.5, and the alcohol solvent preferably includes one or more of methanol, anhydrous ethanol, propanol, ethylene glycol and 1,2-propanediol, more preferably anhydrous ethanol.

[0029] In this invention, the stirring rate of the mechanical stirring is preferably 1000~2000 rpm, more preferably 1500 rpm, and the stirring time is preferably 0.5~2 h, more preferably 1.25 h.

[0030] In this invention, the concentration of the trans-2-hexene-4-oxo-aldehyde solution is preferably 1 to 6 mol / L, and more preferably 3 mol / L.

[0031] In this invention, the metal inorganic salt solid powder is added to a third solvent at room temperature, preferably with continuous stirring at a rate of 1000-2000 rpm until the addition is complete. After the addition is complete, stirring is continued for 0.5-1 h to obtain a metal inorganic salt solution. At room temperature, an organic base is dissolved in a fourth solvent and stirred at a rate of 500-1500 rpm to obtain an organic base solution. The above metal inorganic salt solution and the above organic base solution are mixed by uniform addition at a rate of 1-3 drops / s until the addition is complete, and stirring is continued for 0.1-0.5 h to obtain a composite base solution.

[0032] In this invention, the rate at which the metal inorganic salt solid powder is added to the third solvent is preferably 1-3 g / 30 s, more preferably 2 g / 30 s; the metal inorganic salt preferably includes one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, potassium hydroxide, and calcium hydroxide, more preferably sodium carbonate; the third solvent is preferably a mixture of alcohol and water, the preferred volume ratio of alcohol to water is 1-6:1, more preferably 3.5:1, the alcohol preferably includes one or more of methanol, anhydrous ethanol, propanol, ethylene glycol, and 1,2-propanediol, more preferably anhydrous ethanol.

[0033] In this invention, the concentration of the metal inorganic salt solution is preferably 1~3 mol / L, and more preferably 2 mol / L.

[0034] In this invention, the organic base preferably includes one or more of trimethylamine, N,N-diisopropylethylamine, pyridine, 4-(2-aminoethyl)pyridine, imidazole, 4-dimethylaminopyridine, N,N,N',N'-tetramethylethylenediamine, and triethylamine, more preferably triethylamine; the fourth solvent preferably includes one or more of N,N-dimethylformamide, anhydrous ethanol, dimethyl sulfoxide, and methanol, more preferably anhydrous ethanol.

[0035] In this invention, the concentration of the organic base solution is preferably 1-5 mol / L, and more preferably 3 mol / L.

[0036] In this invention, the molar ratio of damasone, trans-2-hexene-4-oxo-aldehyde, metal inorganic salt and organic base is preferably 1~3:1~5:1~6:1~5, and more preferably 1~2:1~3:1~3.5:1~3.

[0037] In this invention, the above-mentioned composite alkaline solution is slowly added to the damascone solution, and then the trans-2-hexene-4-oxo-aldehyde solution is added by spraying. After the spraying is completed, stirring is continued for 0.1 to 0.3 h, and then the temperature is raised to carry out a dehydration condensation reaction to obtain a damascone-based hybrid fragrance molecule device with the structure shown in Formula I.

[0038] In this invention, the composite alkaline solution is slowly added to the damascone solution by direct mixing at room temperature, accompanied by continuous nitrogen blowing. The stirring rate during mixing is preferably 500-1500 rpm, more preferably 1000 rpm, and the time is preferably 0.2-1 h, more preferably 0.6 h. The nitrogen blowing rate during nitrogen blowing is preferably 1-5 L / min, more preferably 3 L / min.

[0039] In this invention, the spray rate is preferably 5-10 mL / min, more preferably 7.5 mL / min, and the stirring rate is preferably 1500-2500 rpm, more preferably 2000 rpm.

[0040] In this invention, the temperature of the dehydration condensation reaction is preferably 80~120℃, more preferably 100℃, and the time is preferably 2~4 h, more preferably 3 h.

[0041] The present invention preferably involves reducing the pressure to atmospheric pressure and cooling to room temperature after the dehydration condensation reaction is completed, followed by purification; the purification includes sequential nitrogen blowing filtration, chromatography separation, directional crystallization and vacuum drying.

[0042] In this invention, the nitrogen blowing filtration preferably involves taking the supernatant of the solution after the reaction and transferring it to a nitrogen blowing concentrator. The nitrogen flow rate is set to 0.3~0.8 m / s, the concentration temperature to 30~50℃, and the reduced pressure to -0.09~-0.07MPa. The solution is concentrated to 1 / 5~1 / 3 of its original volume. Then, it is diluted in a mixture of ethanol and purified water with a volume ratio of 1:1~5, and the dilution ratio is controlled to be 1:1~5. The solution is then filtered 1~3 times through 1~3 layers of neutral filter paper to obtain the filtered liquid.

[0043] In this invention, the chromatographic separation is preferably performed by packing a chromatographic column with 200-600 mesh neutral silica gel powder, using a mixed solution of dichloromethane and methanol with a volume ratio of 1-12:1 as the eluent, controlling the elution flow rate at 1-2 mL / min, collecting the corresponding eluent, and then performing vacuum distillation in a rotary evaporator. The vacuum pressure is preferably -0.07 to -0.09 MPa, the rotation speed is preferably 100-300 rpm, and the mixture is heated to 30-50°C to obtain a high-purity chromatographic separation product.

[0044] In this invention, the directional crystallization preferably involves dispersing the chromatographically separated product in anhydrous ethanol, stirring until homogeneous, cooling to 0-5°C at a rate of 0.5-1°C / h, and allowing it to stand at a constant temperature for 8-12 h. The crude product solution is then subjected to standing and filtration sequentially to induce directional crystallization and avoid the formation of amorphous products. Subsequently, the product is vacuum filtered under a pressure of -0.09 to -0.07 MPa to collect the crystallized product. The product is then washed 2-3 times with anhydrous ethanol pre-cooled to 0-5°C to obtain the directionally crystallized product.

[0045] In this invention, the vacuum drying preferably involves dispersing the directional crystallization product in purified water at a solid-liquid mass-to-volume ratio of 10-30 mg:1 mL, transferring it to a freeze dryer, freezing it at -40 to -30°C for 2-4 hours to completely freeze the material, then reducing the pressure to 1-5 Pa, gradually raising the temperature to 0-10°C, maintaining sublimation drying for 12-24 hours, raising the temperature to 20-25°C, and continuing desorption drying for 4-6 hours to finally obtain a light yellow, loose powder product, namely, a damastone-based hybrid fragrance molecular device.

[0046] This invention provides the application of the above-mentioned damascin-based hybrid fragrance molecular device or the damascin-based hybrid fragrance molecular device prepared by the above-mentioned preparation method in measuring the micro-region viscosity of rice bran oil. The application method includes the following steps: mixing the damascin-based hybrid fragrance molecular device with an organic solvent to obtain a damascin-based hybrid fragrance molecular device solution; mixing the damascin-based hybrid fragrance molecular device solution with natural rice bran oil; measuring the light signal intensity of the resulting test solution; and obtaining the micro-region viscosity of rice bran oil based on the correspondence between the light signal intensity and the viscosity value of rice bran oil. The detection mechanism of this invention for measuring the micro-region viscosity of rice bran oil using the damascin-based hybrid fragrance molecular device is as follows: as the viscosity of the rice bran oil system increases, the light signal intensity released by the damascin-based hybrid fragrance molecular device gradually increases, achieving a "turn-on" visual monitoring effect. Specifically, the damascin-based hybrid fragrance molecular device contains a freely rotatable carbon-carbon double bond large conjugated hybrid structure, which can exhibit differentiated mechanical rotational behavior in micro-region atmospheres of different viscosities of rice bran oil. Figure 1 As shown, in low-viscosity rice bran oil, molecules can rotate freely mechanically, and the excited-state energy is efficiently dissipated through non-radiative transitions, resulting in a weak light signal intensity. However, as the viscosity of rice bran oil increases, molecular rotation is significantly restricted in high-viscosity rice bran oil, and the excited-state energy is released through radiative transitions, leading to a significant difference in light signal intensity. This phenomenon is a typical example of the change in photoluminescence mode regulated by the micro-mechanical forces (viscosity correlation) of rice bran oil, and its essence lies in the precise adaptation of the molecular device structure to the physical microenvironment of rice bran oil.

[0047] In this invention, the organic solvent preferably includes oleic acid, linoleic acid, palmitic acid, stearic acid, or linolenic acid; the volume ratio of the damascone-based hybrid fragrance molecule to natural rice bran oil is preferably 1:99; and the concentration of the damascone-based hybrid fragrance molecule in the test solution is preferably 10 μmol / L.

[0048] In this invention, the excitation wavelength for measuring the optical signal intensity is preferably 275~320 nm, more preferably 290 nm, and the emission wavelength is preferably 350~600 nm, more preferably 410 nm.

[0049] The technical solutions provided by the present invention will be described in detail below with reference to the embodiments, but they should not be construed as limiting the scope of protection of the present invention.

[0050] Example 1

[0051] 761.2 g of damascone was dissolved in a solvent of anhydrous ethanol and N,N-dimethylformamide in a volume ratio of 3.5:1. The mixture was stirred continuously at 25 °C at 25 kHz and 800 rpm for 1 h with the aid of an ultrasonic assisted machine. The mixture was then transferred to a constant temperature shaker and mixed for 2 h to obtain a damascone solution with a concentration of 2 mol / L. 336.4 g of trans-2-hexene-4-oxo-aldehyde was dissolved in a solvent of anhydrous ethanol and tetrahydrofuran in a volume ratio of 3.5:1, and stirred at 1500 rpm for 1.25 h at 40 °C to obtain a trans-2-hexene-4-oxo-aldehyde solution with a concentration of 3 mol / L. 371 g of inorganic sodium carbonate was added to anhydrous ethanol and water in a volume ratio of 3.5:1 at a rate of 2 g / 30 s. The mixture was stirred at 1500 rpm at room temperature, and stirring continued for 0.75 h after the addition was complete, resulting in a sodium carbonate solution with a concentration of 2 mol / L. 303.6 g of triethylamine organic base was dissolved in 1 L of anhydrous ethanol and stirred at 1000 rpm at room temperature, resulting in an organic base solution with a concentration of 3 mol / L. The organic base solution was then added dropwise to the sodium carbonate solution at a rate of 2 drops / s. After the addition was complete, stirring continued for 0.3 h, resulting in a composite base solution. The compound alkaline solution was slowly added to the damascone solution, and mechanically stirred at 1000 rpm for 0.6 h at room temperature. The trans-2-hexene-4-oxo-aldehyde solution was then added by spraying at a rate of 7.5 mL / min and a stirring rate of 2000 rpm, accompanied by continuous nitrogen blowing at a rate of 3 L / min. After spraying, stirring continued for 0.2 h, followed by a dehydration condensation reaction at 100℃ and 2000 rpm for 3 h. After the condensation reaction, the pressure was reduced to atmospheric pressure and cooled to room temperature. Then, nitrogen blowing filtration, chromatographic separation, directional crystallization, and vacuum drying were performed sequentially. For nitrogen blowing filtration, the supernatant of the solution after the reaction was collected and transferred to a nitrogen blowing concentrator. The nitrogen flow rate was set at 0.55 m / s, the concentration temperature at 40℃, and the reduced pressure at -0.08 MPa, concentrating to 1 / 4 of the original volume. The solution was then diluted in a 1:3 mixture of ethanol and purified water (1:3 volume ratio). The solution was filtered twice through two layers of neutral filter paper, and the filtrate was collected. For chromatographic separation, a 400-mesh neutral silica gel column was packed with a 6:1 mixture of dichloromethane and methanol as the eluent, with an elution flow rate of 1.5 mL / min. The eluent was collected and then evaporated in a rotary evaporator at -0.08 MPa. High-purity chromatographically separated products were obtained by vacuum distillation at MPa, 200 rpm, and 40℃. Directional crystallization involved dispersing the chromatographically separated products in anhydrous ethanol, stirring until homogeneous, and then gradually cooling to 2.5℃ at a rate of 0.75℃ / h. The mixture was then allowed to stand at this temperature for 10 h. The crude product solution was sequentially allowed to stand and filtered to induce directional crystallization. Vacuum filtration was then performed at -0.08 MPa, and the crystallized product was collected and washed twice with anhydrous ethanol pre-cooled to 2.5℃ to obtain the directionally crystallized product. Vacuum drying involved dispersing the directionally crystallized product in purified water at a mass-to-volume ratio of 20 mg:1 mL and transferring it to a freeze dryer. The product was first pre-frozen at -35℃ for 3 h, then the pressure was reduced to 3 Pa, and the temperature was gradually increased to 5℃, maintaining sublimation drying for 18 h. Finally, the temperature was increased to 22.5℃ for further desorption drying for 5 h, ultimately yielding 529.8 g of a light yellow, loose powder with a yield of 92.5%, which is the damascon ketone-based hybrid fragrance molecular device, denoted as BDCHD.

[0052] Example 2

[0053] 190.28 g of damascone was dissolved in a solvent of anhydrous ethanol and N,N-dimethylformamide in a volume ratio of 1:1. The mixture was stirred continuously at 10 kHz and 600 rpm for 0.5 h with ultrasonic assistance at 25 °C. The mixture was then transferred to a constant temperature shaker and mixed for 1 h to obtain a damascone solution with a concentration of 1 mol / L. 112.13 g of trans-2-hexene-4-oxo-aldehyde was dissolved in a solvent of tetrahydrofuran and anhydrous ethanol in a volume ratio of 1:1, and stirred at 1000 rpm for 2 h at 30 °C to obtain a trans-2-hexene-4-oxo-aldehyde solution with a concentration of 1 mol / L. 105.99 g of inorganic sodium carbonate was added to a solvent of anhydrous ethanol and purified water in a volume ratio of 1:1 at a rate of 1 g / 30 s. The mixture was stirred at 1000 rpm at room temperature, and stirring was continued for 0.5 h after the addition was complete to prepare a sodium carbonate solution with a concentration of 1 mol / L. 101.19 g of triethylamine organic base was dissolved in 1 L of anhydrous ethanol and mechanically stirred at 500 rpm at room temperature to obtain an organic base solution with a concentration of 1 mol / L. The organic base solution was added dropwise to the sodium carbonate solution at a rate of 1 drop / s. After the addition was complete, stirring was continued for 0.1 h to obtain a composite base solution. The compound alkaline solution was slowly added to the damascone solution, and mechanically stirred at 500 rpm for 0.2 h at room temperature. Then, the trans-2-hexene-4-oxo-aldehyde solution was added via a spray method at a spray rate of 5 mL / min and a stirring rate of 1500 rpm, accompanied by continuous nitrogen blowing at 1 L / min. After spraying, stirring continued for 0.1 h, followed by a dehydration condensation reaction at 80℃ and 1500 rpm for 4 h. After the condensation reaction, the pressure was reduced to atmospheric pressure and cooled to room temperature. Then, nitrogen blowing filtration, chromatographic separation, directional crystallization, and vacuum drying were performed sequentially. For nitrogen blowing filtration, the supernatant was collected and transferred to a nitrogen blowing concentrator, with the nitrogen flow rate set at 0.3 m / s, the concentration temperature at 30℃, and the reduced pressure at -0.09. The solution was concentrated to 1 / 5 of its original volume at MPa, then diluted in a 1:1 ethanol-purified water mixture (1:1 volume ratio). The solution was filtered once through a layer of neutral filter paper, and the filtrate was collected. Chromatographic separation was performed using a 200-mesh neutral silica gel column packed with a 1:1 dichloromethane-methanol mixture as the eluent at a flow rate of 1 mL / min. The eluent was collected and then subjected to vacuum distillation at -0.09 MPa, 100 rpm, and 30°C in a rotary evaporator to obtain a high-purity chromatographic product. Directional crystallization involved dispersing the chromatographic product in anhydrous ethanol, stirring thoroughly, and then gradually cooling to 0°C at a rate of 0.5°C / h. The mixture was then allowed to stand at this temperature for 12 h. The crude product solution was sequentially subjected to standing and filtration to induce directional crystallization, followed by further crystallization at -0.09 MPa. Vacuum filtration was performed under MPa pressure to collect the crystalline product. The product was washed twice with anhydrous ethanol pre-cooled to 0℃ to obtain the oriented crystalline product. Vacuum drying was performed by dispersing the oriented crystalline product in purified water at a mass-volume ratio of 10 mg: 1 mL and transferring it to a freeze dryer. The product was first pre-frozen at -40℃ for 4 h, then the pressure was reduced to 1 Pa, and the temperature was gradually increased to 0℃ and maintained for sublimation drying for 24 h. Finally, the temperature was increased to 20℃ and desorption drying was continued for 6 h, finally yielding 258.1 g of light yellow loose powder with a yield of 90.1%, which is the damascon ketone hybrid fragrance molecular device, denoted as BDCHD.

[0054] The mass spectrometry results of the damascene-based hybrid fragrance molecule device obtained in this embodiment are the same as those obtained in Example 1.

[0055] Example 3

[0056] 190.28 g of damascone was dissolved in a solvent of anhydrous ethanol and N,N-dimethylformamide in a volume ratio of 6:1. The mixture was stirred continuously at 25°C at 40 kHz and 1200 rpm for 1.5 h with the aid of an ultrasonic assisted mixer. The mixture was then transferred to a constant temperature shaker and mixed for 3 h to obtain a damascone solution with a concentration of 3 mol / L. 560.65 g of trans-2-hexene-4-oxo-aldehyde was dissolved in a solvent of tetrahydrofuran and anhydrous ethanol in a volume ratio of 6:1, and stirred at 2000 rpm for 0.5 h at 50 °C to obtain a trans-2-hexene-4-oxo-aldehyde solution with a concentration of 6 mol / L. 635.94 g of inorganic sodium carbonate was added to a solvent of anhydrous ethanol and water in a volume ratio of 6:1 at a rate of 3 g / 30 s. The mixture was stirred at 2000 rpm at room temperature, and stirring was continued for 1 h after the addition was complete to obtain a sodium carbonate solution with a concentration of 3 mol / L. 506.0 g of triethylamine organic base was dissolved in 1 L of anhydrous ethanol and stirred at 1500 rpm at room temperature to obtain an organic base solution with a concentration of 5 mol / L. The organic base solution was added dropwise to the sodium carbonate solution at a rate of 3 drops / s. After the addition was complete, stirring was continued for 0.5 h to obtain a composite base solution. The compound alkaline solution was slowly added to the damascone solution, and mechanically stirred at 1500 rpm for 1 h at room temperature. Then, the trans-2-hexene-4-oxo-aldehyde solution was added via spraying at a rate of 10 mL / min, with stirring at 2500 rpm and continuous nitrogen blowing at 5 L / min. After spraying, stirring continued for 0.3 h, followed by a dehydration condensation reaction at 120℃ and 2500 rpm for 2 h. After the condensation reaction, the pressure was reduced to atmospheric pressure and cooled to room temperature. Then, nitrogen blowing filtration, chromatography, directional crystallization, and vacuum drying were performed sequentially. For nitrogen blowing filtration, the supernatant was collected and transferred to a nitrogen blowing concentrator, with the nitrogen flow rate set at 0.8 m / s, the concentration temperature at 50℃, and the reduced pressure at -0.07 m / s. The solution was concentrated to 1 / 3 of its original volume at MPa, then diluted in a 1:5 mixture of ethanol and purified water (1:5 volume ratio). The solution was filtered three times through three layers of neutral filter paper, and the filtrate was collected. Chromatographic separation was performed using a 600-mesh neutral silica gel column packed with a 12:1 dichloromethane and methanol mixture as the eluent, controlled at a flow rate of 2 mL / min. The eluent was collected and then subjected to vacuum distillation at -0.07 MPa, 300 rpm, and 50°C in a rotary evaporator to obtain a high-purity chromatographic product. Directional crystallization involved dispersing the chromatographic product in anhydrous ethanol, stirring thoroughly, and then gradually cooling to 5°C at a rate of 1°C / h. The mixture was then allowed to stand at this temperature for 8 h. The crude product solution was sequentially subjected to standing and filtration to induce directional crystallization, followed by further crystallization at -0.07 MPa. Vacuum filtration was performed under MPa pressure to collect the crystalline product. The product was washed three times with anhydrous ethanol pre-cooled to 5°C to obtain the oriented crystalline product. Vacuum drying was performed by dispersing the oriented crystalline product in purified water at a mass-volume ratio of 30 mg: 1 mL, transferring it to a freeze dryer, pre-freezing at -30°C for 2 h, then reducing the pressure to 5 Pa, gradually increasing the temperature to 10°C, maintaining sublimation drying for 12 h, and finally increasing the temperature to 25°C for further desorption drying for 4 h, finally obtaining 262.4 g of light yellow loose powder with a yield of 91.6%, which is the damascon ketone hybrid fragrance molecular device, denoted as BDCHD.

[0057] The mass spectrometry results of the damascene-based hybrid fragrance molecule device obtained in this embodiment are the same as those obtained in Example 1.

[0058] Characterization and performance testing

[0059] 1. (1) The carbon NMR spectrum of the damascene-based hybrid fragrance molecule device prepared in Example 1 was analyzed, and the results are shown in the figure. Figure 2 ; like Figure 2 As shown, the NMR results are 13C NMR (101 MHz, DMSO-d6) δ 200.2, 152.4, 145.1, 142.2, 135.5, 134.7, 130.8, 130.1, 125.6, 37.8, 34.6, 32.1, 30.5, 29.7, 19.6, 8.8. The NMR spectra confirmed that the target product was a damastanone-based hybrid fragrance molecular device.

[0060] (2) The damascene-based hybrid fragrance molecular device prepared in Example 1 was subjected to high-resolution mass spectrometry detection. The results are shown in the figure. Figure 3 ; like Figure 3 As shown, the relative molecular mass of the damasone-based hybrid fragrance molecule device reconstructed from natural products prepared in this embodiment is 286.41720 [M]. + Its theoretical relative molecular mass estimate is 286.41500. It can be confirmed that the obtained product has the same relative molecular mass as the damascena ketone-based hybrid fragrance molecule 7-(2-(but-2-enoyl)-3,3-dimethylcyclohex-1-en-1-yl)hept-4,6-dien-3-one (BDCHD), with the molecular formula C. 19 H 26 O2.

[0061] 2. The performance of the damasone-based hybrid fragrance molecule device prepared in Example 1 was tested.

[0062] (1) Response test to viscosity of rice bran oil in physical microenvironment

[0063] Rice bran oil was simulated using a mixture of glycerol and water, with glycerol volume fractions of 0%, 10%, 30%, 50%, 70%, and 99% (corresponding to viscosities of 1.0 cP, 1.74 cP, 3.72 cP, 10.72 cP, 58.89 cP, and 956.0 cP). The damastone-based hybrid fragrance molecular device (BDCHD) prepared in Example 1 was added to the mixture. The external excitation wavelength was controlled at 290 nm, and the concentration of BDCHD in the system was 10 μM. The test was performed in real-time at room temperature, and the results are as follows: Figure 4 As shown; from Figure 4 It can be seen that the molecular device has an instant response to changes in the viscosity of rice bran oil, and can quickly capture viscosity fluctuations in the physical microenvironment. As the viscosity of rice bran oil gradually increases, the intensity of the released light signal increases synchronously. When the volume concentration of glycerol reaches more than 50%, the increase in light signal intensity is particularly significant. When the volume concentration of glycerol reaches 99%, the increase is up to about 104 times, which fully demonstrates its precise adaptability to the viscosity of rice bran oil in different application scenarios.

[0064] Furthermore, the logarithmic function of the optical signal intensity of this molecular device and the viscosity of rice bran oil can be well fitted to a straight line (e.g. Figure 5 As shown in the figure, its response law is in high agreement with the Förster-Hoffmann relation, with a viscosity sensitivity coefficient of 0.69 and a fitting determination coefficient (R²). 2 The value was 0.97. The test results show that the damascene ketone hybrid flavoring molecule device has excellent detection sensitivity to the micro-region viscosity of the physical microenvironment of rice bran oil, and the monitoring process does not require complex pretreatment. It has both real-time performance and accuracy, and can effectively avoid interference caused by pseudoplastic components in rice bran oil. It can provide real-time data support for viscosity adjustment processes in rice bran oil refining, modification and industrial mass production. It has great potential application value in large-scale production scenarios such as rice bran oil food processing and industrial additive preparation.

[0065] (2) Photostability test of Damask ketone hybrid fragrance molecular device (BDCHD)

[0066] 1.43 mg of the damastone-based hybrid flavor molecular device (BDCHD) prepared in Example 1 was added to a mixture of glycerol and anhydrous ethanol (v / v = 1:1) to prepare a 5 mmol / L stock solution. During testing, this stock solution was diluted to 10 μmol / L and then added to purified water (low micro-region viscosity) and glycerol solution (high micro-region viscosity), respectively. The signal retention of BDCHD in edible and industrial-grade rice bran oil under different micro-region viscosities was simulated and measured. The device was continuously excited for 60 min under an external excitation light source at 290 nm, and the change in light signal intensity was monitored in real time. The test results are as follows: Figure 6 As shown; Depend on Figure 6 The obtained data shows that the BDCHD of Example 1 exhibits outstanding photostability. Under continuous excitation for up to 60 minutes, the light signal intensity remained stable without significant attenuation or fluctuation. This excellent photostability makes it suitable for the long-term in-situ monitoring requirements in rice bran oil industrial production, avoiding detection deviations caused by light signal drift, ensuring continuous and accurate capture of viscosity changes in the physical microenvironment of rice bran oil. It fully meets the application scenarios of continuous monitoring in rice bran oil refining, modification, and mass production, providing stable and reliable data support for industrial production, highlighting its core advantages and huge potential in the large-scale application of rice bran oil in the industry.

[0067] (3) Stokes displacement test of Damask ketone hybrid fragrance molecular device (BDCHD)

[0068] 1.72 mg of the damastone-based hybrid fragrance molecular device (BDCHD) prepared in Example 1 was added to a 6 mmol / L stock solution in a mixture of glycerol and anhydrous ethanol (v / v = 1:1). For testing, this stock solution was diluted to 10 μmol / L and then added to a simulated complex rice bran oil system (containing triglycerides, oryzanol, and other natural components). The absorption and emission spectra were measured at room temperature, and the Stokes shift was further determined. The results are as follows: Figure 7 As shown; Depend on Figure 7 The results show that the Stokes shift of BDCHD is as high as 122.2 nm. This significant large shift characteristic allows it to effectively avoid interference from background fluorescence and excitation light scattering of rice bran oil components, greatly improving the detection signal-to-noise ratio. This advantage enables the molecular device to accurately capture viscosity-related optical signal changes in the complex physical microenvironment of rice bran oil, unaffected by spectral interference from lipid-soluble components in the system. It is fully adaptable to the monitoring needs of complex systems in rice bran oil industrial production, providing accurate and reliable viscosity data for refining, modification, and other processes. It has strong application adaptability and great potential value in in-situ monitoring scenarios for large-scale rice bran oil production.

[0069] (4) Detection limit test of Damask ketone hybrid fragrance molecular device (BDCHD)

[0070] 2.00 mg of the damastone-based hybrid fragrance molecular device (BDCHD) prepared in Example 1 was added to a mixture of glycerol and anhydrous ethanol to prepare a 7 mmol / L stock solution. For testing, this stock solution was diluted to 10 μmol / L using this mixture. The molecular device was then added to a simulated extremely low viscosity system of rice bran oil (a mixture of low-viscosity rice bran oil and glycerol, simulating the low viscosity state during the initial refining stage of rice bran oil). The viscosity detection sensitivity was tested at room temperature, and a linear fitting plot of the detection limit of the BDCHD obtained in Example 1 was obtained. The results are shown in [Figure number missing]. Figure 8 (I max (The optical signal intensity value corresponding to the peak wavelength); Depend on Figure 8 It can be seen that in the simulated rice bran oil system with extremely low viscosity, the viscosity value of BDCHD shows a good linear relationship with the logarithm of the light signal emission intensity, and the coefficient of determination (R0) is well-fitted. 2The viscosity coefficient (CLC) reaches 0.96, and the detection limit is calculated to be as low as 1.022 cP. This extremely low detection limit allows it to accurately capture subtle viscosity fluctuations in the physical microenvironment of rice bran oil. It can respond quickly even when the viscosity changes slightly during the refining and modification of rice bran oil. It is perfectly suited to the monitoring needs of the entire viscosity range (0~100 cP) of edible and industrial grade rice bran oil, providing reliable data support for the refined control of rice bran oil production processes. It has strong adaptability and broad application prospects in in-situ viscosity monitoring of large-scale industrial production of rice bran oil.

[0071] 3. (1) Dissolve 2.29 mg of the BDCHD prepared in Example 1 in oleic acid to prepare an 8 mmol / L stock solution. Dilute it to 10 μmol / L with oleic acid during testing. Select three common food-grade rice bran oils on the market as test objects: Jinlongyu Guweiduo Light Rice Bran Oil, Changshouhua High Guwei Rice Bran Oil, and Fulinmen Nutritional Rice Bran Oil. Add the above BDCHD solution to the three rice bran oils at a volume ratio of 1:99. Conduct the test at room temperature, control the wavelength of the external excitation light source to 290 nm, and see the test results. Figure 9 , Figure 9 Edible rice bran oil 1 is Jinlongyu Valley Vitamin Light Rice Bran Oil, Edible rice bran oil 2 is Changshouhua High Valley Vitamin Rice Bran Oil, Edible rice bran oil 3 is Fulinmen Nutritional Rice Bran Oil. Depend on Figure 9It can be seen that there are significant differences in the light signal release intensity of the three types of food-grade rice bran oil, indicating that the viscosity of their physical microenvironment has obvious gradient differences. This difference is directly related to the refining process of rice bran oil and the retention of natural active components: Jinlongyu Guweiduo Light Refined Rice Bran Oil has a high degree of refining, with lower retention of components such as oryzanol and phytosterols, and a lower system viscosity; Changshouhua High Oryzanol Rice Bran Oil adopts a medium refining process, with a moderate retention of active components (about 1.8%) and a medium viscosity; Fulinmen Nutritional Rice Bran Oil focuses on the enrichment of active ingredients, with a total content of oryzanol and phytosterols reaching 2.5%, stronger intermolecular forces, and a higher system viscosity. Different viscosities of rice bran oil are suited to different food processing scenarios: low-viscosity rice bran oil has excellent fluidity, spreading evenly and producing less smoke in high-temperature cooking scenarios such as frying and deep-frying, making it more suitable for quick home cooking; medium-viscosity rice bran oil combines fluidity and stability, making it suitable as a dressing oil and seasoning base oil, fully penetrating the surface of ingredients and improving flavor adhesion; high-viscosity rice bran oil is suitable for coating and shaping processes in food processing, such as water-retaining coatings on pastries and oil carriers in meal replacement foods, enhancing the shape stability and shelf life of food. From the final test results, Jinlongyu Valley Vitamin Light Reduced Viscosity Rice Bran Oil had the weakest light signal intensity, a typical characteristic of low-viscosity systems; Changshouhua High Vitamin B1 Rice Bran Oil had a moderate light signal intensity, matching the response characteristics of medium-viscosity systems; Fulinmen Rice Bran Oil had the strongest light signal intensity, perfectly matching the detection patterns of high-viscosity systems. The test results show that the Damask ketone hybrid flavoring molecular device (BDCHD) of the present invention can accurately sense the micro-region viscosity changes of different food-grade rice bran oils and convert them into visual light signal differences. This is of great significance for guiding the process optimization and product development of rice bran oil, and can help develop special rice bran oil products that better meet the needs of different food processing, thereby enhancing the high-value application potential of rice bran oil in the food industry.

[0072] (2) 2.58 mg of the BDCHD prepared in Example 1 was dissolved in propylene glycol to prepare a 9 mmol / L stock solution, which was diluted to 10 μmol / L with oleic acid for testing. Three commercially available industrial rice bran oils were selected as test objects: DK-803 industrial rice bran oil (62 cP at room temperature), Teco industrial rice bran oil (75 cP at room temperature), and Yihai Kerry refined industrial rice bran oil (88 cP at room temperature). The above BDCHD solution was added to the three industrial rice bran oils at a volume ratio of 1:99. The test was conducted at room temperature, with the wavelength of the external excitation light source controlled at 290 nm. The test results are shown in […]. Figure 10 , Figure 10Industrial rice bran oil 1 is Delekang industrial grade rice bran oil DK-803, industrial rice bran oil 2 is Teco industrial rice bran oil Teco-RBO-68, and industrial rice bran oil 3 is Yihai Kerry industrial refined rice bran oil YK-RBO-32. Depend on Figure 10 It can be seen that the light signal release intensity of the three types of industrial rice bran oils showed a significant gradient difference, indicating that there were obvious differences in the viscosity of their physical microenvironment. This difference is directly related to the refining process and the retention of natural components in the rice bran oil: DK-803 of 62 cP is a semi-refined process, with low retention of pseudoplastic components such as oryzanol and phospholipids, and good system fluidity; Teco-RBO-68 of 75 cP is a crude refining process, retaining an appropriate amount of wax and unsaponifiable matter, and moderate intermolecular forces; Yihai Kerry YK-RBO-32 of 88 cP is a deep retention process, with a high content of natural active components, significant molecular association effect, and higher system viscosity. Different viscosities of industrial rice bran oil are suited to different application scenarios: 62 cP low-viscosity rice bran oil has excellent fluidity and is suitable as a base oil for textile fiber softeners and metalworking cold rolling fluids, effectively reducing the shear resistance of auxiliary systems and improving processing efficiency; 75 cP medium-viscosity rice bran oil combines fluidity and film-forming properties, making it suitable as a release agent for rubber products and a raw material for soap grease, forming a uniform film during demolding to ensure the integrity of the product's shape; 88 cP high-viscosity rice bran oil has high consistency and strong adhesion, making it suitable as a base oil for cosmetic makeup removers and a carrier for industrial lubricants, enhancing the stability and efficacy of the formulation system. From the final test results, 62 cP of Delekang rice bran oil corresponds to the weakest light signal intensity, perfectly matching the response characteristics of low-viscosity systems; 75 cP of Tyco rice bran oil has a moderate light signal intensity, consistent with the limited molecular rotation in medium-viscosity systems; 88 cP of Yihai Kerry rice bran oil has the strongest light signal intensity, consistent with the increased efficiency of excited-state energy radiative transitions in molecular devices under high-viscosity systems. The test results show that the Damask ketone hybrid fragrance molecular device (BDCHD) of the present invention can accurately sense the micro-region viscosity changes of different industrial rice bran oils and convert them into visual light signal differences. It can also effectively avoid the shear thinning effect caused by pseudoplastic components. It is of great significance for guiding the optimization of refining process, category classification and application scenario expansion of industrial rice bran oil, and can help develop more special rice bran oil products that meet the needs of different industrial fields.

[0073] As can be seen from the above embodiments, the damascene-based hybrid flavoring molecular device provided by the present invention has a unique flexible conjugated hybrid structure, which can exhibit differentiated molecular rotation states according to the micro-region viscosity differences in the physical microenvironment of rice bran oil. It can accurately convert viscosity changes into visualized light signals, achieving efficient detection of the key physical indicator of rice bran oil viscosity from a molecular perspective. Various test results show that the molecular device has excellent photostability, maintaining a stable light signal intensity even under long-term excitation light source irradiation; its emission wavelength is around 410 nm, which can effectively avoid background fluorescence interference generated by natural active components such as oryzanol and phytosterols in rice bran oil; at the same time, the device has minimal absorbance fluctuations in the complex system of multi-component and multi-polarity rice bran oil, and can also effectively eliminate the shear thinning effect caused by pseudoplastic components, making it suitable for viscosity monitoring needs of both edible and industrial grade rice bran oil in various scenarios. Furthermore, the raw materials for this molecular device are all derived from natural products or natural equivalents, which are inexpensive and readily available. The preparation process employs a one-step dehydration coupling reaction, which is environmentally friendly and the post-processing is simple and easy to implement. It boasts both high yield and low cost, and meets the requirements of low-carbon industrial production. These advantages fully highlight the enormous potential of this damascene ketone-based hybrid fragrance molecular device in optimizing rice bran oil refining processes, grading product quality, and expanding high-value applications.

[0074] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A damascene-based hybrid fragrance molecule device, characterized in that, It has the structure shown in Equation I: Equation I.

2. The method for preparing the damascene ketone-based hybrid fragrance molecular device according to claim 1, characterized in that, Includes the following steps: Damascone is dissolved in the first solvent to obtain a damascone solution; Dissolve trans-2-hexene-4-oxo-aldehyde in a second solvent to obtain a trans-2-hexene-4-oxo-aldehyde solution; A metal inorganic salt is dissolved in a third solvent to obtain a metal inorganic salt solution; an organic base is dissolved in a fourth solvent to obtain an organic base solution; the metal inorganic salt solution and the organic base solution are mixed to obtain a composite base solution. The damascone solution, the trans-2-hexene-4-oxo-aldehyde solution, and the composite alkaline solution are mixed and subjected to a dehydration condensation reaction to obtain a damascone-based hybrid fragrance molecule device with the structure shown in Formula I.

3. The preparation method according to claim 2, characterized in that, The inorganic metal salt includes one or more of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, potassium hydroxide, and calcium hydroxide. The organic base includes one or more of trimethylamine, N,N-diisopropylethylamine, pyridine, imidazole, 4-dimethylaminopyridine, N,N,N',N'-tetramethylethylenediamine, and triethylamine.

4. The preparation method according to claim 3, characterized in that, The molar ratio of damascone, trans-2-hexene-4-oxo-aldehyde, metal inorganic salt and organic base is 1~3:1~5:1~6:1~5.

5. The preparation method according to claim 1 or 4, characterized in that, The first solvent is an alcohol-polar solvent, wherein the volume ratio of alcohol solvent to polar solvent in the alcohol-polar solvent is 1~6:1, the alcohol solvent includes anhydrous ethanol, and the polar solvent includes N,N-dimethylformamide; the concentration of the damascone solution is 1~3 mol / L; The second solvent is a tetrahydrofuran-alcohol mixture, wherein the volume ratio of tetrahydrofuran to alcohol solvent in the tetrahydrofuran-alcohol mixture is 1:1 to 6, and the alcohol solvent includes one or more of methanol, anhydrous ethanol, propanol, ethylene glycol, and 1,2-propanediol; the concentration of the trans-2-hexene-4-oxo-aldehyde solution is 1 to 6 mol / L. The third solvent is a mixture of alcohol and water, with a volume ratio of alcohol to water of 1 to 6:

1. The alcohol includes one or more of methanol, anhydrous ethanol, propanol, ethylene glycol, and 1,2-propanediol. The concentration of the metal inorganic salt solution is 1 to 3 mol / L. The fourth solvent includes one or more of N,N-dimethylformamide, anhydrous ethanol, dimethyl sulfoxide, and methanol; the concentration of the organic base solution is 1~5 mol / L.

6. The preparation method according to claim 5, characterized in that, The dehydration condensation reaction is carried out at a temperature of 80~120℃ for 2~4 hours.

7. The application of the damastone-based hybrid fragrance molecular device according to claim 1 or the damastone-based hybrid fragrance molecular device prepared by the preparation method according to any one of claims 2 to 6 in measuring the micro-region viscosity of rice bran oil, characterized in that, The method of application includes the following steps: Damask ketone-based hybrid fragrance molecular devices are mixed with organic solvents to obtain a damask ketone-based hybrid fragrance molecular device solution. The solution of the damascene-based hybrid fragrance molecule device was mixed with natural rice bran oil. The resulting test solution was subjected to optical signal intensity measurement. The micro-area viscosity of the rice bran oil was obtained based on the correspondence between optical signal intensity and rice bran oil viscosity value.

8. The application according to claim 7, characterized in that, The organic solvents include oleic acid, linoleic acid, palmitic acid, stearic acid, or linolenic acid.

9. The application according to claim 7, characterized in that, The volume ratio of the damascena ketone-based hybrid fragrance molecular device solution to natural rice bran oil is 1:

99. The concentration of the damascene-based hybrid fragrance molecule device in the test solution is 10 μmol / L.

10. The application according to claim 9, characterized in that, The excitation wavelength for the optical signal intensity measurement is 275~320 nm, and the emission wavelength is 350~600 nm.

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