An oregano essential oil inclusion complex with high encapsulation efficiency, high stability and anti-inflammatory and soothing effects, and its preparation method and application

Abstract

The present invention provides an oregano essential oil inclusion complex with high encapsulation rate, high stability and anti-inflammatory and soothing effects, a preparation method and applications thereof. The composition of the oregano essential oil inclusion complex includes oregano essential oil, an encapsulating agent and an emulsifier. The emulsifier includes poloxamer, PPG-13-decyltetradeceth-24 and sodium bis(lauroylglutamyl)lysinate. The present invention does not use organic reagents such as absolute ethanol and ethyl acetate to participate in the encapsulation of oregano essential oil, which greatly ensures the safety of the oregano essential oil inclusion complex. Instead, it creatively uses common emulsifiers in cosmetics to participate in the essential oil encapsulation. The three emulsifiers cooperate with each other and have a synergistic effect in improving the encapsulation rate of oregano essential oil, enhancing the product stability and safety, so that the final encapsulation rate of oregano essential oil is as high as over 95%, and it has outstanding performance in terms of stability, safety, anti-inflammatory and soothing effects, water solubility and formulation compatibility.

Description

Technical Field

[0001] The invention belongs to the field of daily chemical products and relates to an oregano essential oil inclusion compound with high embedding rate, high stability and anti-inflammatory and soothing effects, as well as a preparation method and application thereof. Background Art

[0002] Oregano (Origanum vulgare L.) is a perennial semishrub or herbaceous plant in the Lamiaceae family and genus Origanum, found throughout most of my country. It is pungent and non-toxic, and the entire plant is used medicinally, surpassing mint in its cold-dispelling and relieving effects.

[0003] Oregano essential oil (Origanum vulgare L. essential oil) is often obtained from the whole plant or leaves of oregano, often through steam distillation. It contains terpenes and phenolic compounds, primarily thymol, carvacrol, and linalool. Currently, reports on the anti-inflammatory effects of oregano essential oil include:

[0004] The study "Research Progress on Oregano Essential Oil and Its Biological Function Application" by Guo Jie et al. was published in Henan Agriculture, 2022, (14): 56-58. The study showed that oregano essential oil has good anti-inflammatory effects because it is rich in rosmarinic acid, a recognized anti-inflammatory component. Studies have confirmed that rosmarinic acid can relieve asthma and allergy symptoms by reducing the number of eosinophils and neutrophils. In addition to rosmarinic acid, an anti-inflammatory component, β-caryophyllene and thymol also have certain anti-inflammatory functions.

[0005] Feed Industry, 2021, 42(04): 15-20. Zheng Yunfeng et al. published "Research Progress on the Biological Functions of Oregano and Its Essential Oil." The study showed that thymol, a component of oregano essential oil, can inhibit inflammation both in vivo and in vitro. Thymol can inhibit pancreatic elastase released by human immune cells, which is one of the hallmarks of inflammatory responses.

[0006] This shows that oregano essential oil does have potential anti-inflammatory effects. However, the composition of oregano essential oil varies greatly from region to region or from source to source, for example:

[0007] "Analysis of the Components of Origanum vulgare Essential Oil and Its Antioxidant and Antibacterial Activities" by Li Na et al. was published in China Condiments, 2020, 45(09): 29-33+54. The research shows that: Origanum vulgare essential oil obtained by processing Origanum vulgare purchased from Bozhou Xianyang Yushan Pharmaceutical Co., Ltd. was detected by GC-MS to contain 54 components, accounting for 91.04% of the total essential oil content. Thymol (26.63%), carvacrol (14.44%), 2-isopropyl-1-methoxy-4-methylbenzene (11.75%) and terpinene (9.23%) are the components with relatively high relative contents, and the main prominent effects are antioxidant and antibacterial.

[0008] "Stability of Antibacterial Active Components of Origanum vulgare Essential Oil and Its Sustained Release Characteristics in Antibacterial Cartons" by Zhao Yazhu et al. was published in Food and Fermentation Industries, 2020, 46(20): 114-119. The research shows that: Origanum vulgare essential oil purchased from Changsha Gelen Biotechnology Co., Ltd. was identified by GC-MS to contain 14 chemical components, among which o-cresol is 4.94%, thymol is 1.941%, carvacrol is 83.06%, 3-methyl-4-isopropylphenol is 1.02%, and 1,3-diisopropyl-2-methoxybenzene is 6.82%. The main prominent effect is antibacterial.

[0009] It can be seen that the components of Origanum vulgare essential oil from different sources vary greatly, and there are also significant differences in the prominent effects. In addition, the main compound components of Origanum vulgare essential oil have small molecular weights and are easily absorbed by the human body, but they also have disadvantages such as easy volatilization, easy oxidation, and easy photodegradation, resulting in quite limited storage and practical applications. Therefore, the industry often uses some cyclodextrin encapsulation technologies to endow essential oil raw materials with characteristics such as antioxidant, anti-light, anti-heat, anti-volatilization, and solid-phase.

[0010] "Preparation of Origanum vulgare Essential Oil Microcapsules and Their Application in Antibacterial Food Packaging Paper" by Pan Gaofeng et al. was published in China Pulp & Paper, 2022, 41(12): 16-23. Its main process involves steps of dissolving in absolute ethanol and extracting with a small amount of ethyl acetate. Finally, the core material inclusion rate of Origanum vulgare essential oil-HP-β-CD microcapsules is 83.69%.

[0011] "Study on the Preparation Process of Origanum vulgare Essential Oil-β-Cyclodextrin Microcapsules" by Yin Cheng et al. was published in Cereals & Oils, 2021, 34(02): 51-54. Its main process involves steps of dissolving in absolute ethanol and using 1% sucrose fatty acid ester. Finally, the embedding rate of the prepared Origanum vulgare essential oil-β-cyclodextrin microcapsules is 55.14%.

[0012] "Preparation and antibacterial effect of oregano essential oil β-cyclodextrin microcapsules" by Lu Yanxia et al. was published in Packaging Engineering, 2016, 37(05): 84-88. Its main process involves the steps of dissolving in absolute ethanol and washing with absolute ethanol. The encapsulation efficiency is 73%, and the encapsulated product has good antibacterial effects.

[0013] Thus, the potential problems that may exist when the existing oregano essential oil encapsulation technology is applied to the cosmetics field are as follows:

[0014] 01 The use of organic reagents such as absolute ethanol and ethyl acetate poses a risk of residue, and such organic reagents are well-known in the cosmetics industry to have risks of skin irritation and even inflammation induction.

[0015] 02 The encapsulation efficiency of oregano essential oil is generally not very high, and its application may be restricted.

[0016] Therefore, it is of practical significance to develop an oregano essential oil inclusion compound with soothing effects for cosmetics, improve the encapsulation efficiency of oregano essential oil, and enable it to be used safely and stably in the cosmetics field. Summary of the Invention

[0017] Aiming at the deficiencies of the existing technology, the purpose of the present invention is to provide an oregano essential oil inclusion compound with high encapsulation efficiency, high stability and anti-inflammatory and soothing effects, and its preparation method and application.

[0018] The high encapsulation efficiency described in the present invention means that the encapsulation efficiency of oregano essential oil in the oregano essential oil inclusion compound (the mass of oregano essential oil in the oregano essential oil inclusion compound / the added amount of oregano essential oil during preparation) reaches more than 95%. The high stability means that: an essence is prepared with the oregano essential oil inclusion compound at a mass fraction of 0.2%. The essence is stable for 90 days at -15 to 49 °C and has no smell of oregano essential oil.

[0019] To achieve the purpose of this invention, the following technical solutions are adopted in the present invention:

[0020] In the first aspect, the present invention provides an oregano essential oil inclusion compound with high encapsulation efficiency, high stability and anti-inflammatory and soothing effects. The composition of the oregano essential oil inclusion compound includes oregano essential oil, a complexing agent and an emulsifier. The emulsifier includes poloxamer, PPG-13-decyltetradeceth-24 and sodium bis(lauroylglutamyl)lysinate.

[0021] Preferably, the composition of the oregano essential oil inclusion compound includes 1 part of oregano essential oil, 2-4 parts of emulsifier and 12-20 parts of complexing agent by weight.

[0022] Specific values in the above 2-4 parts are, for example, 2 parts, 2.2 parts, 2.5 parts, 2.7 parts, 3 parts, 3.2 parts, 3.5 parts, 3.7 parts, 4 parts, etc.

[0023] Specific numerical values in the above 12 to 20 parts include 12 parts, 13 parts, 14 parts, 15 parts, 16 parts, 17 parts, 18 parts, 19 parts, 20 parts, etc.

[0024] Preferably, the emulsifier comprises, by weight, 1 to 5 parts of poloxamer, 1 to 5 parts of PPG-13-decyltetradecyl ether-24, and 1 to 5 parts of sodium di(laurylamide glutamine) lysine.

[0025] Specific numerical values in the above 1 to 5 parts include, for example, 1 part, 1.5 parts, 2 parts, 2.5 parts, 3 parts, 3.5 parts, 4 parts, 4.5 parts, 5 parts, and the like.

[0026] Preferably, the inclusion agent comprises any one of cyclodextrin, methylcyclodextrin or hydroxypropylcyclodextrin, or a combination of at least two thereof.

[0027] Preferably, the oregano essential oil is extracted from oregano leaves.

[0028] Preferably, the oregano leaves are produced in Tengchong, Yunnan.

[0029] Preferably, the oregano essential oil is prepared by steam distillation, which comprises: crushing oregano leaves to obtain oregano leaf powder, then mixing with water, and distilling to obtain oregano essential oil.

[0030] Preferably, the steam outlet temperature during the distillation is 80-85°C, for example, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, etc., and the distillation time is 1.5-2.5h, for example, 1.5h, 1.6h, 1.7h, 1.8h, 1.9h, 2h, 2.1h, 2.2h, 2.3h, 2.4h, 2.5h, etc.

[0031] Preferably, the weight of the water is 8 to 12 times the weight of the oregano leaf powder, for example, 8 times, 8.5 times, 9 times, 9.5 times, 10 times, 10.5 times, 11 times, 11.5 times, 12 times, etc.

[0032] Preferably, the particle size of the oregano leaf powder is 60-100 mesh, for example, 60 mesh, 65 mesh, 70 mesh, 75 mesh, 80 mesh, 85 mesh, 90 mesh, 95 mesh, 100 mesh, etc.

[0033] In a second aspect, the present invention provides a method for preparing the oregano essential oil inclusion compound having high encapsulation rate, high stability and anti-inflammatory and soothing effects as described in the first aspect, the preparation method comprising: mixing oregano essential oil, an emulsifier, an inclusion agent and water to obtain a mixed liquid, and drying the mixed liquid.

[0034] Preferably, in the mixed solution, based on 1 part by weight of oregano essential oil, the weight of the emulsifier is 2 - 4 parts, the weight of the complexing agent is 12 - 20 parts, and the weight of water is 80 - 120 parts.

[0035] Specific values in the above 2 - 4 parts are, for example, 2 parts, 2.2 parts, 2.5 parts, 2.7 parts, 3 parts, 3.2 parts, 3.5 parts, 3.7 parts, 4 parts, etc.

[0036] Specific values in the above 12 - 20 parts are, for example, 12 parts, 13 parts, 14 parts, 15 parts, 16 parts, 17 parts, 18 parts, 19 parts, 20 parts, etc.

[0037] Specific values in the above 80 - 120 parts are, for example, 80 parts, 85 parts, 90 parts, 95 parts, 100 parts, 105 parts, 110 parts, 115 parts, 120 parts, etc.

[0038] Preferably, the temperature of the mixing is 30 - 50 °C, such as 30 °C, 35 °C, 40 °C, 45 °C, 50 °C, etc., and the time of the mixing is 2 - 4 h, such as 2 h, 2.2 h, 2.5 h, 2.8 h, 3 h, 3.2 h, 3.5 h, 3.8 h, 4 h, etc.

[0039] Preferably, the mixing is carried out under stirring.

[0040] Preferably, the rotation speed of the stirring is 200 - 500 r / min, such as 200 r / min, 250 r / min, 300 r / min, 350 r / min, 400 r / min, 450 r / min, 500 r / min, etc.

[0041] Preferably, the drying method includes any one of spray drying, freeze drying or vacuum drying.

[0042] Preferably, the parameter settings of the spray drying are as follows: the inlet air temperature is 140 - 160 °C, such as 140 °C, 142 °C, 144 °C, 146 °C, 148 °C, 150 °C, 152 °C, 154 °C, 156 °C, 158 °C, 160 °C, etc., the compressed air flow rate is 400 - 600 L / h, such as 400 L / h, 420 L / h, 440 L / h, 460 L / h, 480 L / h, 500 L / h, 520 L / h, 540 L / h, 560 L / h, 580 L / h, 600 L / h, etc., and the feeding rate is 0.8 - 1.2 L / h, such as 0.8 L / h, 0.9 L / h, 1 L / h, 1.1 L / h, 1.2 L / h, etc.

[0043] Preferably, the temperature of the freeze drying is -60 - -40 °C, such as -60 °C, -55 °C, -50 °C, -45 °C, -40 °C, etc.

[0044] Preferably, the temperature of the vacuum drying is 30 to 60 °C, such as 30 °C, 35 °C, 40 °C, 45 °C, 50 °C, 55 °C, 60 °C, etc., and the vacuum degree is 0.01 to 0.1 Mpa, such as 0.01 Mpa, 0.02 Mpa, 0.03 Mpa, 0.04 Mpa, 0.05 Mpa, 0.06 Mpa, 0.07 Mpa, 0.08 Mpa, 0.09 Mpa, 0.1 Mpa, etc.

[0045] In a third aspect, the present invention provides the use of the oregano essential oil inclusion complex with high encapsulation rate, high stability and anti-inflammatory and soothing effects as described in the first aspect in the preparation of cosmetics.

[0046] Preferably, the cosmetics include any one of toner, essence, skin care lotion, cream or mask.

[0047] Preferably, the oregano essential oil inclusion complex accounts for 0.1% to 1% of the total mass of the cosmetics, such as 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, etc.

[0048] The numerical ranges described in the present invention not only include the above-listed point values, but also include any point values between the above numerical ranges not listed. Due to space limitations and for the sake of brevity, the present invention does not exhaustively list the specific point values included in the ranges.

[0049] Compared with the prior art, the present invention has the following beneficial effects:

[0050] The present invention does not use organic reagents such as absolute ethanol and ethyl acetate to participate in the encapsulation of oregano essential oil, which greatly ensures the safety of the oregano essential oil inclusion complex. Instead, it creatively uses common emulsifiers in cosmetics to participate in the essential oil inclusion. Poloxamer, PPG-13-decyltetradeceth-24 and sodium bis(lauroylglutamyl)lysinate cooperate with each other, and have a synergistic effect in improving the encapsulation rate of oregano essential oil, improving the product stability, safety and anti-inflammatory and soothing effects. The effects achieved by the three-component compounding of the present invention cannot be achieved by using other common emulsifiers in the art, so that the final encapsulation rate of oregano essential oil is as high as more than 95%, and it has outstanding performance in terms of stability (the prepared essence product is stable for 90 days at -15 to 49 °C without the smell of oregano essential oil), safety, anti-inflammatory and soothing effects, water solubility and formulation compatibility.

[0051] In terms of oregano essential oil, in the present invention, oregano from Tengchong, Yunnan is selected for the first time, and oregano essential oil is obtained by steam distillation to ensure stable supply and stable composition. Through GC-MS analysis, the main components of the obtained oregano essential oil are identified. At the same time, an LPS-induced mouse macrophage inflammation model and a copper sulfate-induced zebrafish animal model are used to verify that it clearly has prominent anti-inflammatory activity, and its anti-inflammatory and soothing effect is significantly better than that of oregano essential oil from other producing areas. Description of the Drawings

[0052] Figure 1 It is a graph showing the inhibitory effect of three kinds of oregano essential oils on TNF-α.

[0053] Figure 2 It is a graph showing the inhibitory effect of three kinds of oregano essential oils on IL-6.

[0054] Figure 3 It is a graph showing the inhibitory effect of three kinds of oregano essential oils on NO.

[0055] Figure 4 It is a graph showing the effect of oregano essential oil from Tengchong, Yunnan on neutrophil aggregation in zebrafish.

[0056] Figure 5 It is a fluorescence quantification graph of neutrophils in zebrafish by oregano essential oil from Tengchong, Yunnan.

[0057] Figure 6 It is a total ion chromatogram of oregano essential oil by GC-MS. Detailed Embodiments

[0058] The technical solutions of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0059] In the following embodiments, unless otherwise specified, all reagents and consumables are purchased from conventional reagent manufacturers in the art; unless otherwise specified, the experimental methods and technical means used are conventional methods and means in the art.

[0060] Poloxamer: BASF (China) Co., Ltd., model Pluracare L64 G.

[0061] PPG-13-decyltetradeceth-24: Kelsi Hair International Trade (Shanghai) Co., Ltd., model SOLUBULEGS-01.

[0062] Sodium bis(lauroylglutamyl)lysinate: Asahi Kasei Fine Chemical Co., Ltd., model PELLICER TM L-30.

[0063] Hydroxypropyl cyclodextrin: Shanghai Aladdin Biochemical Technology Co., Ltd., model H108813.

[0064] Methyl cyclodextrin: Shanghai Aladdin Biochemical Technology Co., Ltd., model M102038.

[0065] Cyclodextrin: Shanghai Aladdin Biochemical Technology Co., Ltd., model C104384.

[0066] Experiment 1: Obtaining Origanum vulgare essential oil from different origins

[0067] Process for obtaining Origanum vulgare essential oil: Take dried Origanum vulgare leaves, remove sand and stones, crush and sieve to obtain fine Origanum vulgare leaf powder with a particle size of 60 mesh. Steam-distill the fine Origanum vulgare leaf powder with water being 10 times the weight of the fine Origanum vulgare leaf powder, the steam outlet temperature being 85°C, and the distillation time being 2h to obtain Origanum vulgare essential oil.

[0068] Select the origins as: Tengchong, Yunnan; Kunming, Yunnan; Nanning, Guangxi. The corresponding Origanum vulgare essential oils obtained from these three places (prepared uniformly according to the above process) are denoted as essential oil A, essential oil B, and essential oil C.

[0069] Experiment 2: Determination of the viability of macrophage RAW264.7

[0070] Cell viability was determined by the thiazolyl blue (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, MTT) colorimetric method. RAW264.7 cells with good morphology and in the logarithmic growth phase were selected and inoculated into a 96-well plate and incubated in an incubator for 24h. Then, they were treated with different concentrations for 24h, with 3 replicates set for each concentration. The original supernatant was removed, and MTT test solution was added to each well and incubated in an incubator for 4h. The absorbance at an absorption wavelength of 490nm was measured with an enzyme-linked immunosorbent assay (ELISA) reader to calculate the cell viability. The cell viability was calculated according to the following method, as shown below:

[0071]

[0072] After testing, when the concentrations of essential oil A, essential oil B, and essential oil C were 100μg / mL, the cell viability was ≥80%. For the convenience of subsequent anti-inflammatory tests and comparisons, the test concentration was selected as 100μg / mL.

[0073] Experiment 3: LPS-induced inflammation experiment of macrophage RAW264.7

[0074] RAW264.7 cells in the logarithmic growth phase with good morphology were seeded in a 24-well plate and incubated in an incubator for 24 h. A blank control group, an LPS-induced stimulation group, a positive control group (dexamethasone, dex), and a sample group were set up and incubated in an incubator at 37 °C and 5% CO2 for 2 h. Except for the blank control group, LPS was added to each well and incubated in the incubator for 24 h. The cell supernatants were detected according to the instructions of the ELISA kit (Thermo Fisher Scientific (China) Co., Ltd.) and the nitric oxide detection kit (Thermo Fisher Scientific (China) Co., Ltd.), and the contents of TNF-α, IL-6, and NO in the collected cell supernatants were detected respectively. The experimental results were analyzed by data processing software, and the evaluation criteria are shown in Table 1.

[0075] Table 1

[0076]

[0077] After testing, the inhibitory effects of essential oil A, essential oil B, and essential oil C on the secretion of TNF-α, IL-6, and NO are shown in Table 2 below. The specific inhibition graphs of essential oils A, B, and C against these three inflammatory factors are shown in Figure 1 、 Figure 2 、 Figure 3 。

[0078] Table 2

[0079] Essential oil number TNF-α score IL-6 score NO score Total score Essential oil A 1 1 1 3 Essential oil B 1 0.3 0.3 1.6 Essential oil C 0.3 0.7 1 2

[0080] According to the above results, it can be found that essential oil A has the most obvious inhibitory effect on the secretion of TNF-α, IL-6, and NO. Therefore, oregano essential oil from Tengchong, Yunnan was used for subsequent research and analysis, and the copper sulfate-induced zebrafish inflammation experiment was used to verify again that it has good anti-inflammatory efficacy.

[0081] Experiment 4 Copper sulfate-induced zebrafish inflammation experiment

[0082] The zebrafish breeding method was carried out according to "The zebrafish book". The breeding water temperature was maintained at about 28.5 °C, with 14 h of light and 10 h of darkness every day, and feeding was carried out once in the morning and once in the evening. One female fish and two male fish were placed in the spawning tank the night before collecting the embryos. The next morning, the embryos were collected. On the day of collecting the embryos, about 7-8 hours post-fertilization (7-8 hpf (hour post-fertilization)), the embryos in poor condition were removed, and fresh egg water was replaced, and the culture was continued in an incubator at 28.5 °C.

[0083] Zebrafish at 72 hpf with consistent development were randomly divided into 4 groups, with 15 individuals in each group, namely the normal control group, the model control group, the positive control group, and the sample group. The normal control group did not ingest copper sulfate, while the model control group, the positive control group, and the sample group all ingested copper sulfate (copper sulfate was ingested into the zebrafish by dissolving it in the fish-raising water). Before ingesting copper sulfate, the positive control group and the sample group respectively ingested 5 μg / mL dexamethasone and 100 μg / mL oregano essential oil. After incubating in the dark for 2 h, zebrafish were randomly selected from those with normal phenotypes and behaviors, anesthetized with tricaine, fixed with 3% methylcellulose, observed and photographed under stereomicroscopic fluorescence. The photographing results of all zebrafish must be completed under the same instrument and environmental conditions, and the body positions of the zebrafish should be kept consistent. Image Pro Plus 6.0 software was used to analyze the fluorescence intensity of individual zebrafish larvae to quantify neutrophil recruitment.

[0084] The fluorescence intensity of oregano essential oil from Tengchong, Yunnan, against zebrafish larvae was used to quantify neutrophil recruitment. For details, see Figure 4 、 Figure 5 . The results showed that 100 μg / mL oregano essential oil could achieve the same effect as the positive control dexamethasone, with a significant anti-inflammatory effect.

[0085] Experiment 5 GC-MS Component Analysis of Oregano Essential Oil

[0086] Through GC–MS detection, the total ion current chromatogram is as shown in Figure 6 . It was detected that there were 15 main components with a relative content above 0.1% in the oregano essential oil from Tengchong, Yunnan, accounting for 92.37%. The specific details are shown in Table 3. According to the component analysis, it can be found that the main compounds in the oregano essential oil from Tengchong, Yunnan, are thymol (3.74%), carvacrol (52.68%), and eucalyptol (11.4%).

[0087] Table 3

[0088]

[0089] Currently, there are many research reports on the anti-inflammatory efficacy of carvacrol. For example, it was reported in Phytother Res, 2021.35(1):95-121 that carvacrol can down-regulate the secretion of TNF-α, IL-1β, IL-6, and IL-8; it was reported in Pharm Biol, 2010.48(1):1130-1136 that carvacrol inhibits the activities of nicotinamide adenine dinucleotide phosphate (NADPH) oxidase and ROS, thus having anti-inflammatory potential. Through GC-MS analysis, the main compounds in the oregano essential oil from Tengchong, Yunnan, can be clarified, which directly verifies the reason for its excellent anti-inflammatory effect.

[0090] Experiment 6 Safety Analysis of Origanum vulgare L. Essential Oil

[0091] To verify whether the obtained Origanum vulgare L. essential oil can be safely applied to cosmetic formulations, heavy metal and pesticide residue tests were carried out according to the "Technical Specifications for Cosmetics Safety (2015 Edition)", and the specific test results are shown in Table 4 below.

[0092] Table 4

[0093]

[0094]

[0095] Therefore, the Origanum vulgare L. essential oil from Tengchong, Yunnan can be safely applied to cosmetic formulations.

[0096] At present, Origanum vulgare L. essential oil has characteristics such as strong volatility, strong odor, and poor water solubility. When directly added to cosmetic formulations, the following problems may occur:

[0097] 01. Strong volatility, resulting in a sharp reduction in ingredients within the shelf life and a decline in soothing efficacy;

[0098] 02. Strong odor, resulting in more restrictions on the application of cosmetic formulations;

[0099] 03. Poor water solubility, resulting in poor compatibility of the formulation and even oil separation and other situations.

[0100] To solve the above problems, specific examples and comparative examples will be described below.

[0101] Example 1

[0102] This example provides an Origanum vulgare L. essential oil inclusion complex with cosmetic soothing efficacy, and the specific preparation process is as follows:

[0103] S1 Crushing step: Take dry Origanum vulgare L. leaves from Tengchong, Yunnan, remove sand and stones, crush and sieve to obtain Origanum vulgare L. leaf fine powder of 60 mesh;

[0104] S2 Distillation step: Steam-distill the Origanum vulgare L. leaf fine powder, and the water used is 10 times the weight of the Origanum vulgare L. leaf fine powder, the steam outlet temperature is 85 °C, and the distillation time is 2 h to obtain Origanum vulgare L. essential oil;

[0105] S3 Inclusion step: Add the obtained Origanum vulgare L. essential oil, the combined emulsifier is poloxamer: PPG-13-decyltetradeceth-24: sodium bis(lauramidoglutamyl)lysinate = 1:1:1, the clathrating agent is: hydroxypropyl cyclodextrin, and water. The ratio of the four is: Origanum vulgare L. essential oil: combined emulsifier: clathrating agent: water = 1:3:16:100, and carry out sufficient heating and stirring for a time of: 2 h, a temperature of: 50 °C, and a rotation speed of: 300 r / min to obtain the Origanum vulgare L. essential oil inclusion liquid;

[0106] S4 Drying step: Spray-dry the obtained oregano essential oil inclusion complex solution (inlet air temperature 150 °C, compressed air flow rate 500 L / h, feed rate 1 L / h) to obtain the final oregano essential oil inclusion complex, denoted as inclusion complex A.

[0107] Example 2

[0108] This example provides an oregano essential oil inclusion complex with cosmetic soothing efficacy, and the specific preparation process is as follows:

[0109] S1 Crushing step: Take dried oregano leaves from Tengchong, Yunnan, remove sand and stones, crush and sieve to obtain 80-mesh oregano leaf fine powder;

[0110] S2 Distillation step: Subject the oregano leaf fine powder to steam distillation. The water used is 12 times the weight of the medicinal material, the steam outlet temperature is 80 °C, and the distillation time is 2.5 h to obtain oregano essential oil;

[0111] S3 Inclusion step: Add the obtained oregano essential oil, with the combined emulsifier being poloxamer: PPG-13-decyltetradeceth-24: sodium bis (lauroyl glutamine) lysinate = 5:1:1, the clathrating agent being methyl cyclodextrin, and water. The ratio of the four is: oregano essential oil: combined emulsifier: clathrating agent: water = 1:4:14:90. Carry out sufficient heating and stirring for 3 h at a temperature of 40 °C and a rotation speed of 500 r / min to obtain the oregano essential oil inclusion complex solution;

[0112] S4 Drying step: Freeze-dry the obtained oregano essential oil inclusion complex solution at -50 °C to obtain the final oregano essential oil inclusion complex, denoted as inclusion complex B.

[0113] Example 3

[0114] This example provides an oregano essential oil inclusion complex with cosmetic soothing efficacy, and the specific preparation process is as follows:

[0115] S1 Crushing step: Take dried oregano leaves from Tengchong, Yunnan, remove sand and stones, crush and sieve to obtain 70-mesh oregano leaf fine powder;

[0116] S2 Distillation step: Subject the oregano leaf fine powder to steam distillation. The water used is 8 times the weight of the medicinal material, the steam outlet temperature is 85 °C, and the distillation time is 1.5 h to obtain oregano essential oil;

[0117] S3 inclusion step: adding the obtained oregano essential oil, a combined emulsifier of poloxamer:PPG-13-decyltetradecyl alcohol polyether-24:sodium di(laurylamide glutamine) lysine in a ratio of 1:5:1, an inclusion agent of cyclodextrin, and water in a ratio of oregano essential oil:combination emulsifier:inclusion agent:water in a ratio of 1:2:18:110, and heating and stirring thoroughly for 4 hours at a temperature of 30°C and a rotation speed of 200 rpm to obtain an oregano essential oil inclusion solution;

[0118] S4 Drying step: The obtained oregano essential oil inclusion liquid is dried under vacuum at 45° C. and 0.03 MPa to obtain the final oregano essential oil inclusion complex, which is recorded as inclusion complex C.

[0119] Example 4

[0120] This embodiment provides an oregano essential oil inclusion complex with cosmetic soothing efficacy. Compared with Example 1, the only difference is the S3 inclusion step: the combined emulsifier is poloxamer: PPG-13-decyltetradecyl ether-24: sodium di(laurylamide glutamine) lysine = 1:1:5. Other conditions refer to Example 1.

[0121] The obtained oregano essential oil inclusion complex was recorded as inclusion complex D.

[0122] Example 5

[0123] This example provides a cosmetic soothing oregano essential oil inclusion complex. The only difference between this example and Example 1 is the inclusion complex S3: the combined emulsifier ratio is poloxamer:PPG-13-decyltetradeceth-24:sodium di(laurylamideglutamine)lysine (5:5:1). Other conditions are similar to those in Example 1.

[0124] The obtained oregano essential oil inclusion complex is recorded as inclusion complex E.

[0125] Example 6

[0126] This example provides a cosmetic soothing oregano essential oil inclusion complex. The only difference between this example and Example 1 is the inclusion step S3: the combined emulsifier ratio is poloxamer:PPG-13-decyltetradeceth-24:sodium di(laurylamideglutamine)lysine (5:1:5). Other conditions are similar to those in Example 1.

[0127] The obtained oregano essential oil inclusion complex was recorded as inclusion complex F.

[0128] Example 7

[0129] This embodiment provides an oregano essential oil inclusion complex with cosmetic soothing efficacy. Compared with Embodiment 1, the only difference lies in the S3 inclusion step: the combined emulsifier is poloxamer:PPG-13-decyltetradeceth-24:disodium lauroyl glutamyl lysinate = 1:5:5. Other conditions refer to Embodiment 1.

[0130] The obtained oregano essential oil inclusion complex is denoted as inclusion complex G.

[0131] Comparative Example 1

[0132] This comparative example provides an oregano essential oil inclusion complex with cosmetic soothing efficacy. Compared with Embodiment 1, the only difference lies in the S3 inclusion step, and the combined emulsifier used is the composite emulsifier used in Example 1 of CN106071074A: monoglyceride:sucrose ester = 2:8. Other conditions refer to Embodiment 1.

[0133] The obtained oregano essential oil inclusion complex is denoted as inclusion complex H.

[0134] Comparative Example 2

[0135] This comparative example provides an oregano essential oil inclusion complex with cosmetic soothing efficacy. Compared with Embodiment 1, the only difference lies in the S3 inclusion step, and the emulsifier used is Tween 20 used in the example of CN114365742A. Other conditions refer to Embodiment 1. Other conditions refer to Embodiment 1.

[0136] The obtained oregano essential oil inclusion complex is denoted as inclusion complex I.

[0137] Comparative Example 3

[0138] This comparative example provides an oregano essential oil inclusion complex with cosmetic soothing efficacy. Compared with Embodiment 1, the only difference lies in the S3 inclusion step: the combined emulsifier is poloxamer:PPG-13-decyltetradeceth-24 = 1:1. Other conditions refer to Embodiment 1.

[0139] The obtained oregano essential oil inclusion complex is denoted as inclusion complex J.

[0140] Comparative Example 4

[0141] This comparative example provides an oregano essential oil inclusion complex with cosmetic soothing efficacy. Compared with Embodiment 1, the only difference lies in the S3 inclusion step: the combined emulsifier is poloxamer:disodium lauroyl glutamyl lysinate = 1:1. Other conditions refer to Embodiment 1.

[0142] The obtained oregano essential oil inclusion complex is denoted as inclusion complex K.

[0143] Comparative Example 5

[0144] This comparative example provides an oregano essential oil inclusion complex with cosmetic soothing effects. Compared with Example 1, the difference lies only in the S3 inclusion step: the combined emulsifier is PPG-13-decyltetradeceth-24: sodium bis(lauroylglutamyl)lysinate = 1:1. Other conditions refer to Example 1.

[0145] The obtained oregano essential oil inclusion complex is denoted as inclusion complex L.

[0146] Entrapment efficiency test

[0147] The basis for determining the entrapment efficiency of each inclusion complex: It was determined according to the method described in "Study on the Preparation Process of Oregano Essential Oil-β-Cyclodextrin Microcapsules" by Yin Cheng et al. published in Cereals and Oils, 2021, 34(02): 51-54. The specific results are shown in Table 5 below.

[0148] Table 5

[0149]

[0150]

[0151] According to the above entrapment efficiency situation, it can be found that the entrapment efficiencies of the inclusion complexes obtained in Examples 1 to 7 are all relatively excellent, all greater than 95%. In the comparative examples, emulsifiers used in the references, such as a mixed emulsifier of monoglyceride and sucrose ester and Tween 20, and removing any one component from the combined emulsifier, all showed varying degrees of decline in entrapment efficiency and also could not reach the expected value of greater than 95%. This result shows that poloxamer, PPG-13-decyltetradeceth-24 and sodium bis(lauroylglutamyl)lysinate cooperate with each other and have a synergistic effect in improving the entrapment efficiency of oregano essential oil. Using other common emulsifiers in the art cannot achieve the high entrapment efficiency effect achieved by the three-component compounding of the present invention.

[0152] Application example - Application of oregano essential oil inclusion complex in cosmetics

[0153] To better verify the actual application potential of the obtained oregano essential oil inclusion complex, a serum with relatively higher requirements for odor and solubility was selected for application description later.

[0154] The serum formula is shown in Table 6.

[0155] Table 6

[0156]

[0157]

[0158] Twelve kinds of essence were obtained according to the formula in Table 6, and were respectively denoted as Sample A - L (the oregano essential oil clathrates used corresponded to Clathrate A - L respectively).

[0159] (1) Stability test

[0160] The 12 kinds of essence obtained above were respectively placed under different temperature conditions (-15°C, 5°C, 40°C, 49°C), and the pH value and stability of the samples were observed. The results are shown in Table 7.

[0161] Table 7

[0162]

[0163]

[0164] According to the above situation, it can be found that the essence products prepared from the clathrates of each example are always very stable. For the oregano essential oil clathrates obtained in the comparative example, when the temperature is high, a very weak or weak smell of oregano essential oil can be smelled. Although the overall formulation system is very stable, the samples obtained in the comparative example may have a relatively smaller consumer audience due to the odor problem during use.

[0165] (2) Patch safety experiment

[0166] Test samples: Essence samples A - L.

[0167] Test method:

[0168] 100 volunteers were randomly recruited, with a male - female ratio of 1:1, no history of allergies, and an age distribution of 20 - 50 years old. The above samples A - L were respectively weighed, 12 samples for each person, 0.01 g for each portion, and then 0.01 g of pure water was added and mixed evenly. They were put into patch tapes, and then pressed on the designated upper back of the volunteers, and then gently pressed to expel air. During the experiment, the volunteers were instructed not to exercise vigorously, scratch, or take a bath, and the skin reactions were observed at 0.5 h, 24 h, and 48 h.

[0169] Skin adverse reaction evaluation criteria: See Table 8.

[0170] Table 8

[0171]

[0172]

[0173] The patch test results are summarized in Table 9.

[0174] Table 9

[0175]

[0176] From the results of the above patch tests, although according to the "Hygiene Standard for Cosmetics", none of the above samples will cause adverse reactions to human skin. However, based on the above data, some differences can still be found. When the encapsulation rate of oregano essential oil obtained in the comparative example is relatively low, there is a small proportion that causes a weak positive reaction (erythema reaction), which further confirms that if the encapsulation rate of oregano essential oil is high, it is relatively more stable and safer.

[0177] In summary, the oregano essential oil clathrate provided by the present invention has a clear composition, anti-inflammatory and soothing effects, and outstanding performance in terms of safety, stability, water solubility and formulation compatibility, and has good application potential in the field of cosmetics.

[0178] The applicant declares that the present invention uses the above embodiments to illustrate an oregano essential oil clathrate with a high encapsulation rate, high stability and anti-inflammatory and soothing effects, its preparation method and application. However, the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of each raw material of the product of the present invention, the addition of auxiliary components, and the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

[0179] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

[0180] In addition, it should be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. To avoid unnecessary repetition, the present invention will not separately describe various possible combination methods.

Claims

1. An oregano essential oil inclusion complex with high encapsulation rate, high stability and anti-inflammatory and soothing effects, characterized in that, The composition of the oregano essential oil inclusion complex includes oregano essential oil, a complexing agent, and an emulsifier. The emulsifier is 1 - 5 parts by weight of poloxamer, 1 - 5 parts by weight of PPG - 13 - decyltetradeceth - 24, and 1 - 5 parts by weight of sodium bis(lauramidoglutamate); The complexing agent is any one or a combination of at least two of cyclodextrin, methylcyclodextrin, or hydroxypropyl cyclodextrin; The oregano essential oil inclusion complex is prepared by a method comprising the following steps: Mix 1 part of oregano essential oil, 2 - 4 parts of an emulsifier, 12 - 20 parts of a complexing agent, and 80 - 120 parts of water to obtain a mixed solution, and then dry it to obtain the product; The temperature of the mixing is 30 - 50°C, and the time of the mixing is 2 - 4 h; The mixing is carried out under stirring, and the stirring speed is 200 - 500 r / min.

2. The oregano essential oil inclusion complex with high embedding rate, high stability and anti-inflammatory and soothing effects as described in claim 1, wherein, The oregano essential oil is extracted from oregano leaves.

3. The oregano essential oil inclusion complex with high embedding rate, high stability and anti-inflammatory and soothing effects as described in claim 2, characterized in that, The origin of the oregano leaves is Tengchong, Yunnan.

4. The oregano essential oil inclusion complex with high encapsulation rate, high stability and anti-inflammatory and soothing effects as described in claim 1, wherein, The oregano essential oil is obtained by steam distillation. The steam distillation method includes: Crushing oregano leaves to obtain oregano leaf powder, then mixing it with water and carrying out distillation to obtain oregano essential oil.

5. The oregano essential oil inclusion complex with high embedding rate, high stability and anti-inflammatory and soothing effects as described in claim 4, wherein, The steam outlet temperature during the distillation is 80 - 85°C, and the time of the distillation is 1.5 - 2.5 h.

6. The oregano essential oil inclusion complex with high embedding rate, high stability and anti-inflammatory and soothing effects according to claim 4, characterized in that, The weight of the water is 8 - 12 times the weight of the oregano leaf powder.

7. The oregano essential oil inclusion complex with high encapsulation rate, high stability and anti-inflammatory and soothing effects as described in claim 4, wherein, The particle size of the oregano leaf powder is 60 - 100 mesh.

8. The preparation method of the oregano essential oil inclusion complex with high embedding rate, high stability and anti-inflammatory and soothing effects according to any one of claims 1-7, characterized in that, The preparation method includes: Mix 1 part of oregano essential oil, 2 - 4 parts of an emulsifier, 12 - 20 parts of a complexing agent, and 80 - 120 parts of water to obtain a mixed solution, and then dry it to obtain the product; The temperature of the mixing is 30 - 50°C, and the time of the mixing is 2 - 4 h; The mixing is carried out under stirring, and the stirring speed is 200 - 500 r / min.

9. The preparation method according to claim 8, characterized in that, The drying method includes any one of spray drying, freeze drying, or vacuum drying.

10. The preparation method according to claim 9, characterized in that, The parameter settings for the spray drying are: inlet air temperature 140 - 160°C, compressed air flow rate 400 - 600 L / h, and feed rate 0.8 - 1.2 L / h.

11. The preparation method according to claim 9, characterized in that, [[ID= 12. The preparation method according to claim 9, wherein ​ ​ 14. The application according to claim 13, wherein ​ 15. The application according to claim 13, characterized in that, ​

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