Method for producing vegetable ester oil comprising transesterification reaction step

Abstract

The present invention relates to a method for producing a vegetable ester oil, comprising a step of producing a vegetable ester oil by transesterifying a vegetable oil with an alcohol in the presence of a catalyst. The vegetable ester oil produced according to the method may exhibit antioxidant effects, anti-inflammatory effects, and skin-whitening effects.

Description

A method for producing vegetable ester oil including an ester exchange reaction step

[0001] The present invention relates to a method for preparing a vegetable ester oil comprising an ester exchange reaction step and a cosmetic composition comprising the vegetable ester oil prepared by the said method.

[0002] Natural oils are mainly composed of glycerol and fatty acids, and glycerol and fatty acids can be separated through catalytic reactions. The method traditionally used in the production of ester oils is esterification, which has been widely utilized mainly in the industrial and food sectors.

[0003] However, these existing methods have several limitations when applied to the production of cosmetic raw materials. For example, catalysts used in industrial production processes and reaction solvents such as methanol are often unsuitable for use as cosmetic raw materials. Additionally, ester oils produced in the food industry are primarily manufactured for biodiesel production and possess characteristics that make them unsuitable for use as cosmetic ingredients. Although the cosmetics industry also produces ester oils through esterification reactions, there is a limitation in that it is difficult to appeal to consumers as 'plant-derived' products because synthetic raw materials are used in most cases.

[0004] Accordingly, the inventors developed a method for producing plant-based ester oil suitable for the cosmetics industry using plant-based raw materials, and completed the present invention by confirming that the ester oil produced according to this method has antioxidant, anti-inflammatory, and skin whitening effects.

[0005] One aspect provides a method for producing vegetable ester oil, comprising the step of transesterifying vegetable oil with an alcohol under a catalyst to produce vegetable ester oil.

[0006] Another aspect is to provide a composition comprising vegetable ester oil prepared by the above method.

[0007] Another aspect is providing uses for plant ester oils for antioxidant, anti-inflammatory, or skin whitening purposes.

[0008] Another aspect is to provide an antioxidant, anti-inflammatory, or skin whitening method comprising the step of administering an effective amount of vegetable ester oil to an individual.

[0009] One aspect provides a method for producing vegetable ester oil, comprising the step of producing vegetable ester oil by transesterifying vegetable oil with alcohol under a catalyst.

[0010] The term "plant" means all organisms taxonomically belonging to the plant kingdom, and the plants include gymnosperms, angiosperms, alpine plants, ornamental plants, trees, succulents, bryophytes, ferns, aquatic plants, carnivorous plants, epiphytes, grasses, seagrasses, etc., and may be flowers, leaves, roots, vines, shoots, seeds, fruits, or stems of plants.

[0011] In one embodiment, the plant of the vegetable oil may be the fruit or seed of the plant.

[0012] In one embodiment, the plant of the vegetable oil may be rice or safflower, and specifically may be rice bran or safflower seeds.

[0013] The term "rice bran" refers to a crushed mixture of pericarp, seed coat, aleurone layer, etc., that is produced when brown rice is milled to make polished white rice, and is also called "rice bran."

[0014] The term "safflower seed" refers to the seeds of a plant called *Carthamus tinctorius* or *Carthamus tinctorius*, which belongs to the Asteraceae family. Rich in unsaturated fatty acids such as linoleic acid and oleic acid, it is used as a raw material for oil extraction and is widely known as a medicinal ingredient beneficial for bone health.

[0015] The term "vegetable oil" refers to oil extracted from the seeds or fruits of plants. The vegetable oil may be rice bran oil or safflower seed oil. The vegetable oil may be obtained by pressing, cold pressing, solvent extraction, carbon dioxide extraction, or hot maceration of the plants.

[0016] In one embodiment, the weight ratio of the vegetable oil to the alcohol is 1:0.0001 to 50, 1:0.0001 to 30, 1:0.0001 to 20, 1:0.0001 to 10, 1:0.0001 to 1, 1:0.0001 to 0.5, 1:0.0001 to 0.2, 1:0.001 to 50, 1:0.001 to 30, 1:0.001 to 20, 1:0.001 to 10, 1:0.001 to 1, 1:0.001 to 0.5, 1:0.001 to 0.2, 1:0.01 to 50, 1:0.01 to 30, 1:0.01 to 20, It may be 1:0.01 to 10, 1:0.01 to 1, 1:0.01 to 0.5, 1:0.01 to 0.2, 1:0.05 to 50, 1:0.05 to 30, 1:0.05 to 20, 1:0.05 to 10, 1:0.05 to 1, 1:0.05 to 0.5, 1:0.05 to 0.2, or 1:0.1.

[0017] In one embodiment, the alcohol may be a C1 to C12 alcohol. Specifically, the alcohol may be a polyhydric alcohol or an aliphatic alcohol.

[0018] In one embodiment, the alcohol may be spirit (ethanol) or fermented spirit.

[0019] The term "alcohol" refers to ethyl alcohol that can be diluted and consumed, and includes fermented alcohol or synthetic alcohol.

[0020] The term "fermented alcohol" refers to alcohol purified to a high purity by fermenting starchy or sugary raw materials using saccharifying enzymes and then distilling them using a continuous distillation method. Unlike synthetic alcohol, which is produced by synthesizing ethylene extracted from petroleum or coal and is unsuitable for food use because the safety of the ethylene has not been verified, the above-mentioned fermented alcohol can be primarily used as a raw material for food, medicine, or cosmetics.

[0021] In one embodiment, the catalyst may be a homogeneous catalyst, a heterogeneous catalyst, or an anion exchange resin.

[0022] The term "catalyst" refers to a substance that increases the reaction rate without being consumed or altered during the reaction process. Specifically, the catalyst may be a base catalyst or an anion exchange resin that promotes the reaction by providing electron pairs.

[0023] The weight ratio of the vegetable oil to the catalyst is 1:0.0000001 to 90, 1:0.000001 to 70, 1:0.00001 to 50, 1:0.00001 to 30, 1:0.00001 to 20, 1:0.00001 to 10, 1:0.00001 to 5, 1:0.00001 to 1, 1:0.00001 to 0.5, 1:0.00001 to 0.1, 1:0.00001 to 0.05, 1:0.00001 to 0.01, 1:0.0001 to 50, 1:0.0001 to 30, 1:0.0001 to 20, 1:0.0001 to 10, 1:0.0001 to 5, 1:0.0001 to 1, 1:0.0001 to 0.5, 1:0.0001 to 0.1, 1:0.0001 to 0.05, 1:0.0001 to 0.01, 1:0.0005 to 50, 1:0.0005 to 30, 1:0.0005 to 20, 1:0.0005 to 10, 1:0.0005 to 5, 1:0.0005 to 1, 1:0.0005 to 0.5, 1:0.0005 to 0.1, 1:0.0005 to 0.05, 1:0.0005 to 0.01, 1:0.001 to It may be 50, 1:0.001 to 30, 1:0.001 to 20, 1:0.001 to 10, 1:0.001 to 5, 1:0.001 to 1, 1:0.001 to 0.5, 1:0.001 to 0.1, 1:0.001 to 0.05, 1:0.001 to 0.01, or 1:0.005.

[0024] The term "homogeneous catalyst" refers to a catalyst in which the catalyst exists in the same phase as the reactants. The homogeneous catalyst may include, but is not limited to, sodium hydroxide (NaOH), sodium carbonate (Na2CO3), sodium bicarbonate (NaHCO3), potassium hydroxide (KOH), potassium carbonate (K2CO3), potassium bicarbonate (KHCO3), calcium hydroxide (CaOH2), calcium carbonate (CaCO3), calcium bicarbonate (CaHCO3), rice straw ash, etc.

[0025] The term "heterogeneous catalyst" refers to a catalyst and reactants existing in different phases, which may include, but are not limited to, calcium oxide (CaO), magnesium oxide (MgO), etc.

[0026] The term "anion exchange resin" refers to a synthetic resin that is added to another aqueous solution and plays the role of exchanging its own anions with specific anions in the aqueous solution.

[0027] The term "transesterification" refers to the process of exchanging the organic functional group R" of an ester with the organic functional group R' of an alcohol. Also called transesterification, this reaction is usually catalyzed by the addition of an acid catalyst or a base catalyst. The term "ester" can be used interchangeably with "ester."

[0028] As an example of an ester exchange reaction, triglycerides in vegetable oils react with alcohols in the presence of strong acids or bases to produce a mixture of fatty acid alkyl esters and glycerol, and this reaction is widely used to reduce the viscosity of triglycerides.

[0029] In one embodiment, the method for producing the vegetable ester oil may further include a step of purifying the produced vegetable ester oil after the step of producing the vegetable ester oil.

[0030] In one embodiment, the purification may be dehydrated, degummed, deacidified, neutralized, decolored, dewaxed, or deodorized.

[0031] In one embodiment, the above-mentioned refinement may be a dewaxing agent.

[0032] The term "refining" refers to the process of increasing purity by removing impurities mixed in a substance. The term "dehydration" refers to the removal of water; the term "degumming" refers to the removal of gums such as phospholipids; the terms "deacidification, neutralization" refer to the removal of free fatty acids; the term "decolorization" refers to the removal of pigments; the term "dewaxing" refers to the removal of solid oils; and the term "deodorization" refers to the removal of off-odors.

[0033] In one embodiment, the method for producing the vegetable ester oil may further include a step of filtering the purified reaction vegetable ester oil after the step of purifying the produced vegetable ester oil.

[0034] The term "filtration" refers to the selective removal of substances, and can utilize particle size, electromagnetic properties, etc.

[0035] In one embodiment, it was confirmed that in the case of a vegetable ester oil using fermented alcohol as a solvent, compared to a vegetable ester oil using synthetic alcohol as a solvent, the dewaxing and filtration time is reduced and the dispersibility for inorganic pigments is excellent (Fig. 1 and Table 1).

[0036] Another aspect provides a vegetable ester oil produced by the above method.

[0037] In the above vegetable ester oil, the terms or elements mentioned that are identical to those already mentioned are as described above.

[0038] In this specification, the term "vegetable ester oil" refers to a vegetable oil that has undergone an ester exchange reaction, and can be produced by the step of producing a vegetable ester oil by ester exchange reaction between a vegetable oil and an alcohol under a catalyst. The term "vegetable ester oil" may be used interchangeably with "vegetable ester oil," "ester oil," or "ester oil."

[0039] The above plant ester oil is a plant-based raw material with excellent effects such as antioxidant, anti-inflammatory, and skin whitening effects, and can be applied in various ways in the production of cosmetic raw materials.

[0040] Another aspect provides a composition comprising a vegetable ester oil prepared by the above method. In the composition, any terms or elements mentioned that are identical to those already mentioned are as described above.

[0041] The above composition comprises, based on the total weight of the composition, 0.000000001 wt% to 80 wt%, for example, 0.000000001 wt% to 60 wt%, 0.000000001 wt% to 40 wt%, 0.000000001 wt% to 30 wt%, 0.000000001 wt% to 20 wt%, 0.000000001 wt% to 10 wt%, 0.000000001 wt% to 5 wt%, 0.000000001 wt% to 0.001 wt%, 0.000000001 wt% to 0.0001 wt%, 0.00000001 wt% to 0.0001 wt%, and 0.0001 wt% to 80 wt%. wt%, 0.0001 wt% to 60 wt%, 0.0001 wt% to 40 wt%, 0.0001 wt% to 30 wt%, 0.0001 wt% to 20 wt%, 0.0001 wt% to 10 wt%, 0.0001 wt% to 5 wt%, 0.001 wt% to 80 wt%, 0.001 wt% to 60 wt%, 0.001 wt% to 40 wt%, 0.001 wt% to 30 wt%, 0.001 wt% to 20 wt%, 0.001 wt% to 10 wt%, 0.001 wt% to 5 wt%, 0.01 wt% to 80 wt%, 0.01 wt% to 60 wt%, 0.01 wt% to 40 wt%, 0.01 wt% to 30 wt%, 0.01 wt% to 20 wt%, 0.01 wt% to 10 wt%, 0.01 wt% to 5 wt%, 0.1 wt% to 80 wt%, 0.1 wt% to 60 wt%, 0.1 wt% to 40 wt%, 0.1 wt% to 30 wt%, 0.1 wt% to 20 wt%, 0.1 wt% to 10 wt%, 0.1 wt% to 5 wt%, 0.1 wt% to 1 wt%, 0.5 wt% to 5 wt%, 0.5 wt% to 3 wt%, 0.5 wt% to 2 wt%, 0.5 wt% to 1.5 wt%, 0.5 wt% to 1 wt%, 0.It may contain 7% to 5% by weight, 0.7% to 3% by weight, 0.7% to 2% by weight, 0.7% to 1.5% by weight, 0.8% to 5% by weight, 0.8% to 3% by weight, 0.8% to 2% by weight, 0.8% to 1% by weight, or 1% by weight of vegetable ester oil.

[0042] The concentration of vegetable ester oil in the above composition may be 0.01 ppm to 10,000 ppm, 0.05 ppm to 1,000 ppm, 0.1 ppm to 100 ppm, 0.5 ppm to 10 ppm, or 1 ppm.

[0043] The composition containing the above plant ester oil may have skin condition improvement effects such as anti-inflammatory, antioxidant, and skin whitening effects.

[0044] In one embodiment, the composition may be for antioxidant, anti-inflammatory, or skin whitening purposes.

[0045] The term "antioxidant" refers to the inhibition of oxidation and may include the action of eliminating free radicals, which attack normal cells in the body and act as a cause of aging or various diseases. For example, antioxidants can refer to any action that scavenges DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals.

[0046] In one embodiment, the composition may have DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging ability. Therefore, the composition may have an antioxidant effect.

[0047] The term "anti-inflammatory" refers to any action that suppresses inflammation.

[0048] In one embodiment, the composition may serve to inhibit the mRNA expression of IL-6β / β-actin. Accordingly, the composition may have an anti-inflammatory effect and a skin irritation soothing effect.

[0049] The term "skin whitening" may refer not only to brightening the skin tone by inhibiting the synthesis of melanin pigment, but also to improving skin hyperpigmentation such as melasma or freckles caused by ultraviolet rays, hormones, or genetics.

[0050] In one embodiment, the composition can reduce or inhibit melanin synthesis. Accordingly, the composition can have a skin whitening effect.

[0051] In one embodiment, it was confirmed that the vegetable ester oil prepared by the method according to the above aspect has significantly excellent antioxidant, anti-inflammatory, and skin whitening effects (Experimental Example 5).

[0052] In one embodiment, the composition may be a cosmetic composition.

[0053] The above cosmetic composition may be prepared in a formulation comprising a lotion (skin lotion), skin softener, skin toner, astringent, lotion, milk lotion, moisture lotion, nourishing lotion, massage cream, nourishing cream, moisture cream, eye cream, hand cream, foundation, essence, nourishing essence, eye essence, pack, soap, cleansing foam, cleansing lotion, cleansing cream, body lotion, body cream, body cleanser, suspension, gel, powder, paste, mask pack or sheet, or aerosol composition. Compositions of such formulations may be prepared according to methods conventional in the field.

[0054] The ingredients included in the above cosmetic composition may include ingredients commonly used in cosmetic compositions in addition to the above vegetable ester oil as active ingredients, and may include, for example, conventional auxiliary agents and carriers such as stabilizers, solubilizers, vitamins, pigments, and fragrances.

[0055] In one embodiment, the composition may be a skin external application composition.

[0056] In this specification, the term "external skin preparation" is a concept that generally encompasses all compositions used externally, and may refer to a wide range of products that can be applied to cosmetic compositions containing various cosmetics such as basic cosmetics, makeup cosmetics, hair cosmetics, shaving cosmetics, or various pharmaceuticals or quasi-pharmaceuticals such as ointments. For example, the above quasi-pharmaceuticals may be disinfectants, shower foams, mouthwash, wet wipes, detergent soaps, hand washes, humidifier fillers, masks, ointments, coating agents, or filter fillers.

[0057] The above-mentioned topical skin composition may additionally contain, in addition to the active ingredient, ingredients commonly incorporated in topical preparations according to the intended use and the properties of the topical composition, specifically moisturizers, UV absorbers, vitamins, animal and plant extracts, digestive agents, whitening agents, vasodilators, astringents, cooling agents, hormones, etc.

[0058] The formulation of the above-mentioned external skin composition may take an appropriate form depending on the intended use and the properties of the external composition, and specifically may be an aqueous solution type, a solubilization type, an emulsion type, a liquid type, a gel type, a paste type, an ointment type, an aerosol type, a water-oil two-layer type, or a water-oil-powder three-layer type, but the formulation and form of the external agent of the present invention are not limited by the above-mentioned formulation.

[0059] In addition, the above-mentioned topical skin preparation may further include a mechanism necessary to penetrate or transfer the active ingredient into the skin tissue.

[0060] Another aspect is providing uses for plant ester oils for antioxidant, anti-inflammatory, or skin whitening purposes.

[0061] Another aspect provides an antioxidant, anti-inflammatory, or skin whitening method comprising the step of administering an effective amount of vegetable ester oil to an individual. In the above aspects, any terms or elements mentioned that are identical to those already mentioned are as described above.

[0062] The above 'vegetable ester oil' may be a vegetable ester oil produced by a method according to one aspect.

[0063] In the above aspects, "effective amount" refers to the content of a composition in which the pharmacological component or active component within the composition is contained in an amount sufficient to provide a therapeutic, corrective, or preventive effect to an individual to whom the oil is to be administered. The effective amount may include the meaning of a "preventive effective amount," a "corrective effective amount," or a "therapeutic effective amount."

[0064] In the above aspects, "individual" may mean any individual requiring antioxidant, anti-inflammatory, or skin whitening. The individual may include or exclude humans, and may include mammals, and the mammals may include, for example, humans, dogs, cats, rats, mice, rats, guinea pigs, horses, cattle, pigs, sheep, monkeys, chimpanzees, etc.

[0065] In the above aspects, "administration" means administering an effective amount of the oil directly to an individual to form it within the individual's body. The administration may be oral or parenteral, and may include transdermal administration, subcutaneous administration, or application to the skin. Suitable dosages of the mixture or composition may be prescribed differently depending on factors such as the method of formulation, mode of administration, age, body weight, sex, pathological condition, diet, time of administration, route of administration, rate of excretion, and response sensitivity.

[0066] According to a method according to one aspect, a vegetable ester oil can be produced by undergoing an ester exchange reaction under a catalyst. The vegetable ester oil produced in this way possesses antioxidant, anti-inflammatory, and skin whitening effects, and can therefore be applied in various ways in the production of cosmetic raw materials.

[0067] Figure 1 is a figure showing the products of vegetable oils that have undergone an ester exchange reaction according to the type of solvent.

[0068] Figure 2 shows the change in molecular weight of vegetable oils that have undergone an ester exchange reaction, Figure 2a shows rice bran ester oil, and Figure 2b shows safflower seed ester oil.

[0069] Figure 3 shows the results of a compatibility test of vegetable ester oils that have undergone an ester exchange reaction, Figure 3a shows rice bran ester oil, and Figure 3b shows safflower seed ester oil.

[0070] Figure 4 shows the effect of improving the feel of vegetable ester oils that have undergone an ester exchange reaction, Figure 4a shows rice bran ester oil, and Figure 4b shows safflower seed ester oil.

[0071] Figure 5 shows the DPPH analysis results to confirm the antioxidant effect of vegetable oil subjected to an ester exchange reaction.**p<0.01,***p<0.001 vs None

[0072] Figure 6 shows the inhibitory effect of vegetable oil subjected to an ester exchange reaction on melanin production. #p<0.05 vs None,*p<0.05,**p<0.01 vs Control

[0073] Figure 7 shows the mRNA expression of IL-6β / β-actin to confirm the anti-inflammatory effect of vegetable oils subjected to an ester exchange reaction.***p<0.001 vs None,##p<0.01,###p<0.001 vs Control

[0074] The following examples will be explained in more detail. However, these examples are intended to illustrate one or more specific examples, and the scope of the present invention is not limited to these examples.

[0075] [Example]

[0076] Examples 1-2. Preparation of vegetable oil subjected to an ester exchange reaction using fermented alcohol as a solvent

[0077] Rice bran or safflower seeds were cold-pressed at 49°C or lower to obtain rice bran oil or safflower seed oil. Rice bran ester oil (Example 1) was prepared by subjecting the above oil to an ester exchange reaction using 99.5% purity fermented alcohol purchased from Korea Alcohol Industry as a solvent. Specifically, rice bran oil, fermented alcohol, and catalyst were mixed in a weight ratio of 1:0.1:0.005, and an ester exchange reaction was carried out at 55 to 75°C for 2 to 3 hours.

[0078] After the above ester exchange reaction, a dewaxing process was performed at -20°C to 20°C for 10 to 60 hours, specifically at 10°C for 20 hours. In addition, a filtration process was performed at a Nutsche filter under reduced or increased pressure for 0.5 to 6 hours, specifically for 2 hours, using a filter paper of 0.5 µm to 5.0 µm.

[0079] Safflower seed ester oil (Example 2) was prepared by undergoing an ester exchange reaction in the same manner as Example 1, except that safflower seeds were used as the plant instead of rice bran in Example 1.

[0080] [Comparative Example]

[0081] Comparative Examples 1–2. Preparation of vegetable oil subjected to an ester exchange reaction using synthetic ethanol as a solvent

[0082] Rice bran ester oil (Comparative Example 1) was prepared by undergoing an ester exchange reaction using synthetic alcohol as a solvent instead of the fermented alcohol of Examples 1 and 2 above; and safflower seed ester oil (Comparative Example 2) was prepared by undergoing an ester exchange reaction in the same manner as Comparative Example 1, except that safflower seeds were used instead of rice bran as the plant in Comparative Example 1.

[0083] [Experimental Example]

[0084] Experimental Example 1. Comparative analysis of vegetable oils subjected to ester exchange reaction according to solvent type

[0085] 1-1. Comparison of Dewaxing and Filtration Processes

[0086] To compare the dewaxing and filtration processes of vegetable oils that underwent ester exchange reactions according to the type of solvent, the GC / MS (Gas Chromatography / Mass Spectrometry) method was used for analysis.

[0087] After the dewaxing process was carried out at 10°C for 20 hours, the filtration process time was compared by using a 0.5 µm to 5.0 µm filter paper in a Nutsche filter under reduced or increased pressure.

[0088] As a result, it was confirmed that in the rice bran ester oil subjected to an ester exchange reaction using fermented alcohol as a solvent (Example 1), the major fatty acids oleic acid and linoleic acid underwent an ester reaction to produce ethyl oleate and ethyl linoleate, whereas in the rice bran ester oil subjected to an ester reaction using synthetic alcohol as a solvent (Comparative Example 1), glyceryl monooleate was also produced in addition to ethyl oleate and ethyl linoleate (Fig. 1).

[0089] Glyceryl monooleate precipitates at low temperatures, just like wax, during the dewaxing process, causing the filtration to clog. Accordingly, it was confirmed that the rice bran ester oil of Comparative Example 1, which underwent an ester exchange reaction using synthetic alcohol as a solvent, took approximately 1.4 times longer to undergo the dewaxing and filtration processes than the rice bran ester oil of Example 1, which underwent an ester exchange reaction using fermented alcohol as a solvent.

[0090] 1-2. Comparison of Inorganic Pigment Dispersibility

[0091] To compare the dispersibility of inorganic pigments in vegetable oils that have undergone an ester exchange reaction according to the type of solvent, the oils of Examples 1-2 or Comparative Examples 1-2 were added little by little to inorganic pigments of titanium dioxide and zinc oxide at room temperature and mixed, and the minimum amount of oil (g) required until the entire inorganic pigment became a single mass was indicated as the Wet point (g / 100g). Specifically, the oils of Examples 1-2 or Comparative Examples 1-2 were added dropwise to 100 g of inorganic pigment, mixed with a spatula, and the weights were added up until a single mass was formed to make a comparison.

[0092] As a result, as shown in Table 1 below, rice bran ester oil (Example 1), which underwent an ester exchange reaction using fermented alcohol as a solvent, showed dispersibility 1.093 times higher in titanium dioxide and 1.064 times higher in zinc oxide than rice bran ester oil (Comparative Example 1), which underwent an ester reaction using synthetic alcohol as a solvent, confirming that both inorganic pigments have excellent dispersibility when fermented alcohol is used as a solvent. Similarly, safflower seed ester oil (Example 2), which underwent an ester exchange reaction using fermented alcohol as a solvent, showed dispersibility 1.124 times higher in titanium dioxide and 1.12 times higher in zinc oxide than safflower seed ester oil (Comparative Example 2), which underwent an ester reaction using synthetic alcohol as a solvent, confirming that both inorganic pigments have excellent dispersibility when fermented alcohol is used as a solvent.

[0093] In addition, in Examples 1 and 2, it exhibited dispersibility similar to that of dimethicone (6cs), a silicone oil, confirming that the vegetable ester oil using fermented alcohol as a solvent has excellent dispersibility capable of replacing silicone oil.

[0094] [Table 1]

[0095]

[0096]

[0097] Experimental Example 2. Analysis of Molecular Weight Change of Vegetable Oil After Ester Exchange Reaction

[0098] To confirm the change in molecular weight of vegetable ester oils that underwent an ester exchange reaction, an experiment was conducted as follows.

[0099] 2-1. Rice bran ester oil

[0100] Rice bran oil that had not undergone an ester exchange reaction was used as the experimental control group, and rice bran phytosyl ester oil that had undergone an ester exchange reaction using fermented alcohol was used as the experimental group. TM Using ), the change in molecular weight was measured by the GPC (Gel Permeation Chromatography) method.

[0101] Specifically, the sample was passed through a column embedded in the GPC instrument and detected according to molecular size using a refractive index detector to determine the molecular weight, which was then calculated as the Weight-Average Molecular Weight (Mw).

[0102] As a result, the molecular weight of the experimental group was 1,298 Da and the molecular weight of the control group was 414 Da, confirming that the molecular weight of the rice bran ester oil subjected to the ester exchange reaction decreased by approximately 31.9% compared to the rice bran oil produced through the conventional process (Fig. 2a).

[0103] 2-2. Safflower Seed Ester Oil

[0104] Safflower oil that had not undergone the ester exchange reaction was used as the experimental control group, and safflower phytosily oil that had undergone the ester exchange reaction was used as the experimental group. TM Using ), the change in molecular weight was measured by the GPC (Gel Permeation Chromatography) method.

[0105] Specifically, the sample was passed through a column embedded in the GPC instrument and detected according to molecular size using a refractive index detector to determine the molecular weight, which was then calculated as the Weight-Average Molecular Weight (Mw).

[0106] As a result, the molecular weight of the experimental group was 1,303 Da and the molecular weight of the control group was 400 Da, confirming that the molecular weight of the safflower seed ester oil subjected to the ester exchange reaction decreased by approximately 30.6% compared to the safflower seed oil produced through the conventional process (Fig. 2b).

[0107] Experimental Example 3. Compatibility test of vegetable oil subjected to ester exchange reaction

[0108] To confirm the compatibility of vegetable ester oils that have undergone an ester exchange reaction, an experiment was conducted as follows.

[0109] Compatibility tests were performed by setting the sample-to-solvent ratio to 1:99, 5:95, and 10:90 at 1%, 5%, and 10%, respectively, shaking at 400 rpm for 5 minutes, heating from room temperature 25°C to 80°C, and then cooling back to room temperature 25°C. The results were evaluated by classifying them into soluble, suspended, partly soluble, and insoluble.

[0110] 3-1. Rice bran ester oil

[0111] Rice bran oil that had not undergone an ester exchange reaction was used as the experimental control group, and rice bran ester oil that had undergone an ester exchange reaction (rice bran phytosily) was used as the experimental group. TM ) was used.

[0112] As a result, unlike the control group, it was confirmed that the solubility increased and compatibility improved in the experimental group when dimethicone (6cs, 100cs), 1,3-butylene glycol, 1-3-pentylene glycol, and glycerin were used in the solvent (Fig. 3a).

[0113] 3-2. Safflower Seed Ester Oil

[0114] Safflower oil that had not undergone an ester exchange reaction was used as the experimental control group, and safflower phytosyl oil that had undergone an ester exchange reaction was used as the experimental group. TM ) was used.

[0115] As a result, unlike the control group, it was confirmed that the solubility increased and compatibility improved when dimethicone (6cs, 100cs), 1-3-pentylene glycol, glycerin, and ethanol were used in the solvent in the experimental group (Fig. 3b).

[0116] Experimental Example 4. Test of usability of vegetable oil subjected to ester exchange reaction

[0117] To confirm the effect of improving the user experience of vegetable ester oils that have undergone an ester exchange reaction, an experiment was conducted as follows.

[0118] The user experience test was conducted using a blind use test method with 25 general panelists. As a sensory evaluation, the user experience (gloss, lightness, absorbency, stickiness, greasiness) was measured by rubbing the experimental group and dimethicone (6cs, 100cs) on the back of the hand, and responses were given using a Likert scale on a scale of 1 point (not at all), 2 points (not), 3 points (average), 4 points (yes), and 5 points (very much so).

[0119] 4-1. Rice bran ester oil

[0120] Dimethicone (6cs, 100cs) was used as the experimental control group, and rice bran ester oil (rice bran phytosily) that underwent an ester exchange reaction was used as the experimental group. TM ) was used.

[0121] As a result, unlike the control group dimethicone (6cs, 100cs), it was confirmed that the experimental group maintained gloss and absorption while improving stickiness and oiliness, thereby enhancing the user experience (Fig. 4a).

[0122] 4-2. Safflower Seed Ester Oil

[0123] Dimethicone (6cs, 100cs) was used as the experimental control group, and safflower seed ester oil (safflower phytosily) was used as the experimental group. TM ) was used.

[0124] As a result, unlike the control group dimethicone (6cs, 100cs), it was confirmed that the experimental group maintained gloss, absorption, and a light texture, while improving stickiness and oiliness, thereby enhancing the user experience (Fig. 4b).

[0125] Experimental Example 5. Changes in skin efficacy of vegetable oil subjected to ester exchange reaction

[0126] 5-1. Antioxidant Effects

[0127] To confirm the antioxidant effect of vegetable oil that has undergone an ester exchange reaction, an experiment was conducted as follows.

[0128] The antioxidant capacity of the samples (safflower seed oil, safflower seed ester oil obtained through esterification) was evaluated by measuring the radical scavenging ability of the samples to be tested after initiating oxidation with an oxidizing agent called DPPH, and a spectrophotometer was used as the equipment. After preparing 0.1 mM DPPH / 80% MeOH, 0.01 ml of the sample and ascorbic acid were added to 0.99 ml of DPPH solution, mixed by vortexing, and then left in a dark room at room temperature for 30 minutes, after which the absorbance was measured at 517 nm.

[0129] As a result, unlike safflower seed oil that had not undergone an ester exchange reaction or safflower seed ester oil that had undergone an ester reaction using synthetic alcohol as a solvent (Comparative Example 2), which had no or little antioxidant effect, it was confirmed that safflower seed ester oil that had undergone an ester exchange reaction using fermented alcohol as a solvent (Example 2) had an excellent antioxidant effect, and in particular, when safflower seed ester oil that had undergone an ester exchange reaction using fermented alcohol as a solvent was included at a content of 1.00%, the antioxidant effect was found to be significantly superior (Fig. 5).

[0130] 5-2. Melanin production inhibitory effect

[0131] To confirm the melanin production inhibitory effect of vegetable oils that have undergone an ester exchange reaction, an experiment was conducted as follows.

[0132] Specifically, the whitening effect of the samples was confirmed by numerically comparing the amount of melanin produced within melanocyte cells by treatment with raw materials. Equipment used included a CO2 incubator, ELISA reader, and centrifuge.

[0133] Murine melanoma (B16-F10) cells were seeded into a 6-well plate at a density of 1 x 10⁵ cells per well in medium containing an appropriate amount of FBS (fetal bovine serum) and cultured under 5% CO₂ at 37°C until cells attached. Subsequently, the medium was replaced with a medium diluted to an appropriate concentration with the sample (safflower seed oil, safflower seed ester oil obtained through ester exchange reaction), and the cells were cultured under 5% CO₂ at 37°C for 72 hours. The cells were then washed with PBS and treated with trpysin-EDTA to harvest them. Afterward, the cells were centrifuged at 5,000 rpm for 10 minutes, and the supernatant was removed to obtain a pellet. The pellet was dried at 80°C for 1 hour, and then 300 µl of 1N sodium hydroxide solution containing 10% DMSO was added and reacted in an 80°C bath to obtain intracellular melanin. The absorbance was then measured at 490 nm using a microplate reader.

[0134] As a result, it was confirmed that unlike safflower seed oil that did not undergo an ester exchange reaction, which had a low melanin production inhibitory effect, safflower seed ester oil that underwent an ester exchange reaction had a significantly superior antioxidant effect in inhibiting melanin production (Fig. 6).

[0135] 5-3. Inflammatory Suppressing Effect

[0136] To confirm the anti-inflammatory effect of vegetable oils that have undergone an ester exchange reaction, an experiment was conducted as follows.

[0137] Specifically, to confirm the anti-inflammatory efficacy, the gene expression of IL-6β was analyzed. Human keratinocyte cell lines (HaCaT) were inoculated into a 6-well plate at a concentration of 1 x 10⁵ cells / mL and cultured under 5% carbon dioxide (CO₂) at 37°C for 18 hours. After adding the immunostimulant Poly I:C 10 μg / ml and IL-4 protein 10 ng / ml to the culture medium, dexamethasone, which has an anti-inflammatory effect, was used at a concentration of 1 μM as a positive control.

[0138] After culture, cells were harvested, washed with phosphate buffer (PBS), and total RNA was extracted using the PureLink® RNA Mini Kit (Thermo Fisher Scientific).

[0139] Changes in the expression of the inflammation-related gene IL-6β were measured using qRT-PCR (quantitative real-time PCR), which involves attaching a fluorescent substance to the DNA product amplified in a polymerase chain reaction (PCR) and continuously detecting the fluorescent substance. The fluorescence intensity of the IL-6β gene was standardized to the actin value, the control group was converted to 100%, and the difference was compared to measure the expression levels of each gene. The results are shown in Figure 7.

[0140] As a result, rice bran phytosily obtained through an ester exchange reaction TM In the case of ), the level of IL-6β / β-actin mRNA expression is significantly reduced, indicating excellent anti-inflammatory and skin irritation soothing effects (Fig. 7).

[0141] In summary, vegetable oils subjected to ester exchange reactions exhibit reduced molecular weight, improved compatibility and usability, and excellent antioxidant, anti-inflammatory, and skin whitening effects. Furthermore, using fermented alcohol as the solvent for the ester exchange reaction can shorten the time required for dewaxing and filtration processes; when mixed with inorganic pigments, it demonstrates excellent dispersibility and significantly enhanced antioxidant effects. Therefore, having confirmed the excellent antioxidant, anti-inflammatory, and skin whitening effects of vegetable ester oils produced through ester exchange reactions using fermented alcohol as a solvent, these natural plant-based raw materials can be applied in various ways for the production of cosmetic ingredients.

Claims

1. A method for producing vegetable ester oil, comprising the step of transesterifying vegetable oil with alcohol under a catalyst to produce vegetable ester oil.

2. A method for producing a vegetable ester oil according to claim 1, wherein the plant is the fruit or seed of a plant.

3. A method for producing vegetable ester oil according to claim 1, wherein the plant is rice bran or safflower seeds.

4. A method for producing a vegetable ester oil according to claim 1, wherein the weight ratio of the vegetable oil to the alcohol is 1:0.001 to 10.

5. A method for producing vegetable ester oil according to claim 1, wherein the alcohol is a fermented alcohol.

6. A method for producing vegetable ester oil according to claim 1, wherein the catalyst is a homogeneous catalyst, a heterogeneous catalyst, a base catalyst, or an anion exchange resin.

7. A method for producing a vegetable ester oil according to claim 1, further comprising, after the step of producing the vegetable ester oil, a step of purifying the produced vegetable ester oil.

8. A method for producing vegetable ester oil according to claim 7, wherein the purification is dehydration, degumming, deacidification, neutralization, decolorization, dewaxing, or deodorization.

9. A cosmetic composition comprising a vegetable ester oil prepared by the method of any one of claims 1 to 8.

10. A cosmetic composition according to claim 9, wherein the cosmetic composition is for antioxidant, anti-inflammatory, or skin whitening purposes.

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