Oleogel and method for its preparation and use

Abstract

An oleogel and its preparation method and its use. The oleogel comprises 60-90 wt% liquid oil, 6-35 wt% structuring agent, and 4-15 wt% water. The liquid oil comprises unsaturated fatty acids, and the structuring agent is protein modified particles. The oleogel is an antioxidant edible oil composition containing unsaturated fatty acids, no further stabilizers need to be added, the use of thickeners, emulsifiers, and organic reagents is avoided, and the oleogel has antioxidant properties, which is beneficial for the long-term storage of the product. The oleogel can be used as an oral medicine to achieve various therapeutic effects.

Description

[Technical field]

[0001] The present disclosure is in the field of functional foods, and specifically relates to functional compositions rich in unsaturated fatty acids for use as oral pharmaceuticals to improve the health status of a subject and to prevent or treat associated diseases or conditions. [Background technology]

[0002] Unsaturated fatty acids are fatty acids that make up fat in the body and are essential fatty acids for the human body. Unsaturated fatty acids are divided into two types: monounsaturated fatty acids and polyunsaturated fatty acids, depending on the number of double bonds. As a common animal-derived unsaturated fatty acid, fish oil contains unsaturated fatty acids, which combine with cholesterol to form esters, which are decomposed into cholic acid and excreted from the body. It has the ability to significantly reduce blood cholesterol and triglycerides and increase high-density lipoprotein, which can be used for antihyperlipidemia. In addition, fish oil also has functions such as antiplatelet aggregation, anticoagulation, and the ability to prevent the occurrence of thrombotic diseases.

[0003] However, oxidation of unsaturated fatty acids has been a significant problem for some time, which has attracted much attention, especially in the oil and fat industry, pharmaceutical and food industries, which are heavily involved in the oxidation of unsaturated fatty acids. Addressing the problem of unsaturated fatty acid oxidation in the prior art often involves the use of antioxidants. However, due to production costs and health, many methods have been attempted in the art to avoid the use of antioxidants. Among these methods, one option is to treat unsaturated fatty acids with structuring agents to form oleogels.

[0004] According to the size of molecular weight, the structuring agents that can be used for fats and oils are divided into small molecule gelling agents and biopolymer gelling agents. Small molecule gelling agents (such as glyceryl mono- and distearate, wax, lecithin, fatty acids, and their derivatives) usually self-assemble by heating and cooling to form a crystalline network structure, thereby structuring liquid oils to prepare fat and oil compositions. However, this type of processing requires a heating temperature higher than the melting point of the small molecule gelling agent, and higher operating temperatures are prone to cause rancidity of unsaturated fatty acids. Biopolymers, especially proteins, have become the best choice as lipid structuring agents due to their high nutritional value and high consumer acceptance. Hydrophilic proteins are not soluble in fats and oils, which limits the direct application of proteins in the field of fat and oil structuring. Fat and oil structuring using proteins as structuring agents is usually prepared by indirect methods, which mainly include Pickering emulsion template method, bubble template method, and solvent replacement method.

[0005] A Chinese invention patent application (published as CN107950684) discloses a method for preparing an oil composition rich in unsaturated fatty acids using Pickering emulsion as a template. The method involves first preparing a gelatin-polyphenol complex solution, then shearing and homogenizing it with a vegetable oil rich in unsaturated fatty acids to prepare a mixed emulsion, which is then dried and sheared to obtain a solid oil composition. This method requires complex processing such as homogenization, drying, and shearing, and is cumbersome. The oil composition finally obtained by this patent contains gelatin, which is not accepted by consumers for various reasons, and contains antioxidant polyphenols and polysaccharides, forming a protein-polyphenol-polysaccharide that is particulate and adsorbs on the surface of the oil. Furthermore, although this method produces an oleogel by shearing, the viscoelasticity is difficult to control and the amount of oil contained is not high (less than 60%).

[0006] China Invention Patent Application (Publication No. CN112063002A) discloses a porous material for adsorbing organic solvent to prepare organogel, which is prepared from rice bran protein by bubble template method. However, the gel uses organic solvent and cannot meet the requirements for preparing oleogel. The product contains more air, which is unfavorable to the protection of oil and fat.

[0007] China Invention Patent Application (Publication No. CN105228461A) discloses a method for continuously preparing an oil and fat composition with ethyl cellulose. This method utilizes the property of ethyl cellulose melting at high temperatures, which is mixed with oils and fats in an extruder, and the mixture is cooled to form the oil and fat composition. However, this method requires the temperature of the melting part of the extruder to be 100-200°C, and high temperature processing accelerates the oxidation of unsaturated fatty acids.

[0008] There remains a need in the art to optimize structuring agents to ameliorate the shortcomings of existing oleogels. Summary of the Invention

[0009] Focusing on the existing problems of oleogel, namely low oil content, poor and difficult to control rheological properties, and oxidation of unsaturated fatty acids due to factors such as heating during processing, the present inventors provide a new oleogel. The preparation process of oleogel is simple and does not include a heating step that may cause oxidation of unsaturated fatty acids. The oleogel of the present disclosure has the following characteristics: high oil content (more than 60%), suitable rheological properties (1x10 3 Pa~1x10 5 It also has a storage modulus of 0.2 Pa and a loss factor of 0.08-0.5), and high antioxidant properties (peroxide value below 2.5 mmol / kg).

[0010] In one embodiment, the present disclosure provides an oleogel comprising 60-90 wt. % liquid oil, 6-35 wt. % structuring agent, and 4-15 wt. % water, wherein said liquid oil comprises unsaturated fatty acids, said structuring agent is protein modified particles, and said liquid oil is the continuous phase.

[0011] In one embodiment, the liquid oil content is from 63 to 85 wt% and / or the structuring agent content is from 6 to 25 wt%.

[0012] In one embodiment, the unsaturated fatty acid is one or more of monounsaturated fatty acid and polyunsaturated fatty acid.The monounsaturated fatty acid may include one or more of myristic acid, palmitoleic acid, oleic acid, transoleic acid, lysine oleic acid, erucic acid, and cetoleic acid.The polyunsaturated fatty acid may include one or more of omega-3 and omega-6 polyunsaturated fatty acid.

[0013] In one embodiment, the protein is one or more of an animal protein and a vegetable protein. The animal protein may include one or more of whey protein, casein, collagen, and gelatin.

[0014] In one embodiment, the protein denatured particles are obtained by preparing a protein suspension, denaturing by heating, homogenizing, and drying.Homogenizing may be performed by one or more of mechanical stirring homogenizing, ultrasonic homogenizing, microfluidic homogenizing, colloid mill homogenizing, and ball mill homogenizing.Drying may be performed by one or more of vacuum drying, vacuum freeze drying, electric heat blow drying, and spray drying.

[0015] In one embodiment, the protein suspension is a 2-25 wt% whey protein aqueous suspension. In one embodiment, the liquid oil is one or more of olive oil, canola oil, peanut oil, algae oil, fish oil, linseed oil, perilla oil, chia seed oil, and krill oil.

[0016] In one embodiment, the oleogel contains or does not contain an antioxidant, which may be one or more of an oil-soluble antioxidant and a water-soluble antioxidant.

[0017] In one embodiment, the oil-soluble antioxidant is one or more of rosmanol, carnosol, sesamol, vitamin E, butylated hydroxyanisole, dibutylated hydroxytoluene, propyl gallate, and tert-butylhydroquinone, and the water-soluble antioxidant is one or more of vitamin C, sodium isoascorbate, tea polyphenols, epigallocatechin gallate, sugars, and sugar alcohols, where the sugars include sucrose and the sugar alcohols are one or more of xylitol, sorbitol, erythritol, and maltitol.

[0018] In one embodiment, the oleogel has the following characteristics as measured by a rheometer: (1) 1x10 3 Pa~1x10 5 has a storage modulus of 1 Pa; (2) having a loss factor of 0.08 to 0.5; has one or more of the following:

[0019] In another embodiment, the present disclosure provides use of an oleogel of the present disclosure in a food, health food, or cosmetic product, or in the preparation of an oral pharmaceutical product, wherein said oral pharmaceutical product is used for one or more of the following: (1) regulating blood lipids and / or removing blood clots; (2) preventing Alzheimer's disease, nourishing the brain and / or improving memory; (3) preventing arthritis, relieving gout and asthma, and temporarily reducing swelling and pain caused by arthritis; (4) improving vision and / or preventing and treating presbyopia; and (5) maintaining the retina.

[0020] In another aspect, the present disclosure provides an oral pharmaceutical preparation comprising an oleogel of the present disclosure.

[0021] In another embodiment, (1) adding a structurant to a liquid oil and mixing them to obtain a suspension of said structurant in the oil phase; and (2) adding water to the suspension of structurant in oil phase and homogenizing them to obtain an oleogel; There is provided a method for preparing the oleogel of the present application comprising:

[0022] In one embodiment, the method further comprises the step of adding an oil soluble antioxidant, a water soluble antioxidant, or both, to the oil phase, the water phase, or both, respectively.

[0023] In one embodiment, the method does not include the step of heating the liquid oil.

[0024] Advantages of the present disclosure include: 1. The oleogel of the present disclosure has an oil content of more than 60%, which meets the need in the art for high oil content products. The oleogel of the present disclosure has solid / semi-solid nature and good rheological properties such as plasticity, spreadability, and shear rheology, and can be widely used in food systems. 2. The oleogel of the present disclosure has suitable rheological properties (1x10 3 Pa~1x10 5 It has a storage modulus of 0.2 Pa and a loss factor of 0.08 to 0.5. 3. The oleogel of the present disclosure has high antioxidant properties (peroxide value below 2.5 mmol / kg) and can be stored for long periods of time in an easily oxidized environment. 4. The process of preparing the oleogel of the present disclosure is simple and can be obtained by just homogenizing and mixing the ingredients, without the need for a heating step. An oleogel having a uniform appearance, not lamellar, and high content of unsaturated fatty acids is prepared. The process of the present disclosure allows for high speed and continuous production on a large scale, and oil and fat composition products with different viscoelastic properties can be prepared by simply controlling the process conditions, satisfying the applications in different foods, health foods, medicines, and cosmetics. 5. The compositions of the present disclosure have simple ingredients and do not require the addition of additional stabilizers, thereby avoiding the use of thickeners, emulsifiers, and organic agents. [Brief description of the drawings]

[0025] [Figure 1] Figure 1 shows photographs of the appearance of oleogel. Panel A shows ++++: transparent, not cloudy. Panel B shows +++: semi-transparent, not substantially cloudy. Panel C shows ++: substantially opaque, slightly cloudy. Panel D shows +: opaque, cloudy. The more plus signs, the more favorable the appearance of the oleogel. The transparency of the oleogel is related to the stability of the product structure; the more transparent, the more stable the gel. The principle is that the more dispersed the protein network in the oleogel, the smaller the size of the protein aggregates, and therefore the smaller the angle of light scattering in the gel, the more transparent the gel. [Diagram 2] FIG. 2 shows a micrograph of the stained oleogel. [Diagram 3] FIG. 3 shows water solubility experiment 1 of oleogels prepared by different methods. [Figure 4]FIG. 4 shows water solubility experiment 2 of oleogels prepared by different methods. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0026] In order to further understand the present disclosure, the preferred embodiments of the present disclosure are described below in combination with examples, but it should be understood that these descriptions are not intended to limit the scope of the claims of the present invention, but are only intended to further describe the features and advantages of the present disclosure. Those skilled in the art can refer to the contents of this specification and appropriately improve the process parameters to achieve it. It is particularly important to point out that all similar replacements and modifications are obvious to those skilled in the art, and all of them are considered to be included in the present disclosure. The method and use of the present disclosure have been described through preferred embodiments, and it is clear that those involved can modify or appropriately change and combine the method and use described herein to realize and apply the technology of the present disclosure without departing from the content, spirit and scope of the present disclosure. Although it is believed that those skilled in the art will fully understand the following terms, the following definitions are still provided to help explain the invention disclosed by the present disclosure.

[0027] The term "comprising" as used herein is synonymous with "including," "contain," or "characterized by," and is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. "Comprising" is a term of art used in claims to mean that elements are present, but that other elements may also be added and still form a structure or method within the scope of the claim.

[0028] As used herein, "liquid oil" refers to oil in a fluid state, such as oil in a fluid state at room temperature. Liquid oils include, but are not limited to, olive oil, canola oil, peanut oil, algae oil, fish oil, linseed oil, perilla oil, chia seed oil, and krill oil. As used herein, the content of liquid oil is 60-90 wt%, such as 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, 89 wt%, etc., based on the weight of the oleogel.

[0029] As used herein, "unsaturated fatty acid" refers to a straight-chain fatty acid containing one or more double bonds and a carbon chain that is generally 18-22 carbon chain length. Unsaturated fatty acids may include monounsaturated fatty acids and polyunsaturated fatty acids. Polyunsaturated fatty acids are divided into omega-6 and omega-3 polyunsaturated fatty acids according to the position and function of the double bonds. For example, linoleic acid and arachidonic acid belong to the omega-6 series, while linolenic acid, DHA, or EPA belong to the omega-3 series. Preferably, the unsaturated fatty acid is an omega-3 polyunsaturated fatty acid. The amount of unsaturated fatty acid contained in the liquid oil may vary. For example, the unsaturated fatty acid content can be 1%, 2%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95%, or any range or value therebetween.

[0030] As used herein, "structuring agent" refers to an ingredient that causes oil to aggregate through a polymeric network resulting from strong interactions between molecules. The structuring agent may be a protein denatured particle. The protein may be one or more of animal protein and vegetable protein. For example, the animal protein is one or more of whey protein, casein, collagen, and gelatin. Preferably, the structuring agent is a protein denatured particle. The protein denatured particle may be obtained by preparing a protein suspension, denaturing by heating, homogenizing, and drying. In one embodiment, homogenization may be performed by one or more of mechanical stirring homogenization, ultrasonic homogenization, microfluidic homogenization, colloid mill homogenization, and ball mill homogenization. In one embodiment, drying may be performed by one or more of vacuum drying, vacuum freeze drying, electric heat blow drying, and spray drying. Preferably, the protein suspension is a whey protein suspension, such as a 2-25 wt% whey protein aqueous suspension. For example, the whey protein denatured particle powder can be prepared by preparing a whey protein suspension with a concentration of 2% to 25%, magnetically stirring the whey protein suspension to completely dissolve it, heating at 75 to 100°C for 30 to 100 minutes to prepare a protein denatured particle liquid, and drying the protein denatured particle liquid. As used herein, the content of structurant is from 6 to 35 wt%, such as 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, 19 wt%, 20 wt%, 21 wt%, 22 wt%, 23 wt%, 24 wt%, 25 wt%, 26 wt%, 27 wt%, 28 wt%, 29 wt%, 30 wt%, 31 wt%, 32 wt%, 33 wt%, or 34 wt%, and any range therebetween, based on the weight of the oleogel.

[0031] "Continuous phase" as used herein refers to a substance that disperses other substances in a dispersion system. In the oleogels described herein, the continuous phase may be a liquid oil.

[0032] The oleogel of the present disclosure may also contain a suitable amount of water, for example, 4-15 wt% water, such as 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, or 14 wt%, and any range therebetween. In one embodiment, the weight ratio of structuring agent to water is 1:3 to 5:1, such as 5:12, 1:2, 7:12, 8:12, 9:12, 10:12, 1:1, 20:12, 25:12, 35:12, or 40:12.

[0033] The oleogel of the present disclosure may or may not include other ingredients other than the liquid oil, structurant, and water. Preferably, the oleogel of the present disclosure does not include other ingredients. The other ingredients include, but are not limited to, antioxidants, gels, stabilizers, thickeners, or emulsifiers. The antioxidants may include one or more of an oil-soluble antioxidant and a water-soluble antioxidant. The oil-soluble antioxidants may include one or more of rosmanol, carnosol, sesamol, vitamin E, butylated hydroxyanisole, dibutylated hydroxytoluene, propyl gallate, and tert-butylhydroquinone, and the water-soluble antioxidants may include one or more of vitamin C, sodium isoascorbate, tea polyphenols, epigallocatechin gallate, sugar, and sugar alcohol. Preferably, the sugar is sucrose. Preferably, the sugar alcohol is one or more of xylitol, sorbitol, erythritol, and maltitol.

[0034] As used herein, the "peroxide value" is an index of the degree of oxidation of oils and fatty acids, usually the content of active oxygen in millimoles of peroxide in 1 kg of sample, and indicates whether the sample has deteriorated due to oxidation. Generally, the higher the peroxide value, the higher the degree of rancidity. The peroxide value is the upper limit set by food standards for food oxidation. If the value is exceeded, the food will be rejected. If the peroxide value exceeds the standard, it means the food has deteriorated, and deteriorated food may have adverse effects on the human body. The peroxide value can be determined by titration and colorimetry as described in China Food Quality Standard GB / T 5009.37-2003, which is the analytical method for the hygiene standard of edible oils. Different oils have different peroxide value standards. For example, for DHA algae oil, the peroxide value / (mmol / kg) should be less than 7.5 (as specified in the People's Republic of China Food Industry Standard LS / T 3243-2015); for edible crude vegetable oil, the peroxide value / (g / 100g) should be less than 0.25 (as specified in the National Food Safety Standard for Vegetable Oils GB2716-2018); for edible hydrogenated oil, the peroxide value / (g / 100g) should be less than 0.1; for margarine, shortening, cocoa substitutes, vegetable cream, powdered oils and fats, etc., the peroxide value / (g / 100g) should be less than 0.13 (as specified in the National Food Safety Standard for Edible Oils and Fat Products GB15196-2015). For confectionery and bread, biscuits, instant noodles, and quick-frozen prepared products, the peroxide value / (g / 100g) should be less than 0.25 (as specified in the corresponding national food safety standard). Most of the products in the prior art focus on the oleogel-forming properties of the structurant, and little focus on whether the oleogel formed meets the food standard of peroxide value. During long-term research, the inventors have found that the oleogel of the present disclosure has a lower peroxide value and meets the national peroxide value requirements in various types of food. For example, the oleogel of the present disclosure can be used as a nutritional supplement in confectionery and bread. When appropriate, it can also be used as a nutritional supplement in the above and other types of products.

[0035] In this specification, viscoelasticity can be characterized by a plurality of parameters such as storage modulus (G') and / or loss factor (tanδ). Preferably, viscoelasticity can be characterized by the loss factor (tanδ), indicating whether the research sample exhibits solidity (elasticity) or liquidity (viscosity). For a perfectly elastic material, the tanδ value is 0. When 0 < tanδ < 1, the research sample shows more elasticity than viscosity. When tanδ = 1, the research sample is below the critical strain used to measure ductility. When tanδ > 1, the research sample shows more viscosity than elasticity. In this specification, the desired result is 1x10 3 Pa ≤ G’ ≤ 1x10 5 Pa, 0.08 ≤ tanδ ≤ 0.5, and an oleogel with greater elasticity than viscosity can be obtained. In this specification, the loss factor is calculated as loss modulus (G”) / storage modulus (G’), where the storage modulus (G’) and loss modulus (G”) can be measured by a rheometer.

[0036] How to prepare the product The oleogel of the present disclosure may be prepared by mixing a structuring agent such as whey protein denatured particles with a liquid oil, homogenizing them to form an oil phase suspension, and adding water. For whey protein denatured particles, a whey protein suspension with a concentration of 2% to 25% may be prepared, which may be completely dissolved by magnetic stirring, and then heated at 75 to 100°C for 30 to 100 minutes to prepare a protein denatured particle liquid, which may be dried to obtain a protein denatured particle powder. 6 to 35% whey protein denatured particles may be mixed with a liquid oil such as algae oil rich in omega-3 polyunsaturated fatty acids, and homogenized to obtain an oil phase suspension of whey protein. Then, 4 to 15% water may be added to the suspension, followed by homogenization to obtain the oleogel of the present disclosure. The method may not include a step of heating the liquid oil. As used herein, heating can be at a temperature above room temperature for a period of time, such as 40° C., 45° C., 50° C., 55° C., 60° C., 65° C., 70° C., 75° C., 80° C., 85° C., 90° C., 95° C., 100° C. or higher, for 30 minutes, 35 minutes, 40 minutes, 45 minutes, 50 minutes, 55 minutes, or 60 minutes or more.

[0037] Product Application The oleogels of the present disclosure may have different effects depending on the type of unsaturated fatty acid contained therein. For example, the oleogels of the present disclosure may contain one or more of fish oil, squalene, ethyl polyenoate, or evening primrose oil and have the effects of these ingredients. The oleogels of the present disclosure may be formulated into oral pharmaceuticals to achieve various therapeutic effects.

[0038] Fish oil is a common animal source of omega-3 and contains a lot of DHA and EPA, which are essential fatty acids beneficial to humans. As a functional oil, fish oil can be used in medicine. Its main functions and effects include regulating blood lipids, removing blood clots, preventing blood clotting, preventing cerebral thrombosis, cerebral hemorrhage, and stroke; preventing arthritis, relieving gout and asthma, and temporarily reducing swelling and pain caused by arthritis; preventing Alzheimer's disease, nourishing the brain, and improving memory; improving eyesight, preventing and treating presbyopia; and maintaining the retina. In addition, it can also be used as an adjunct treatment for diseases. It is suitable for patients with thrombosis, cerebral hemorrhage, or stroke; people with three highs (high blood pressure, high blood lipids, and high cholesterol); people with poor eyesight and presbyopia; people with symptoms of heart disease and arteriosclerosis; people with arthritis, gout, and asthma; and patients who need to prevent and treat diabetic complications.

[0039] Squalene is a natural compound found in shark liver oil. It has multiple physiological functions, such as improving the activity of superoxide dismutase (SOD) in the body, enhancing the immune function of the body, improving sexual function, anti-aging, anti-fatigue, and anti-tumor. Among marine fish oil products, squalene is the only drug that has been confirmed to have the effect of preventing and treating tumors, and is widely used in tumor patients. The main effects of squalene are hepatoprotection, promoting liver cell regeneration, and protecting liver cells, thereby improving liver function; anti-fatigue and enhancing the body's resistance to diseases, improving the immune function of the human body; protecting the adrenal cortex function and improving stress resistance; anti-tumor (especially after cancer resection or when using radiation therapy and chemotherapy). The effect is remarkable, and its greatest feature is to prevent cancer from metastasizing to the lungs; and to enhance the effect of white blood cells. The applications of squalene include improving the immune system; regulating the acid-base balance of the human body (alkaline products); and using it as an antioxidant to effectively improve skin color and alleviate skin diseases such as psoriasis and dermatitis. Squalene helps treat heart disease, high and low blood pressure, diabetes, stomach disease, kidney disease, conjunctivitis, empyema, gynecological diseases, and rheumatoid arthritis. Squalene helps restore normal blood cholesterol levels in people who eat a lot of fatty foods. Squalene is a fitness tonic.

[0040] Ethyl polyenoate is a product of polyunsaturated fatty acid ethyl ester obtained by refining and esterifying fish oil extracted from marine fish. The main components are ethyl eicosapentaenoate and ethyl docosahexaenoate, both of which contain more unsaturated bonds. It is a light yellow to yellow transparent oily liquid with a slight fishy smell. It has the effect of lowering serum triglycerides and total cholesterol, and is used for hyperlipidemia.

[0041] The main components of evening primrose oil are r-linolenic acid, magnesium, zinc, copper, vitamins C, E, B6, and B5. It can be blended with base oils and essential oils and has multiple therapeutic and whitening capabilities. It can be made into capsules for oral administration to treat cardiovascular diseases, premenstrual syndrome, and menopausal syndrome. It can be blended with lotions and creams and used in aromatherapy to improve eczema, psoriasis, aid in wound healing and nail growth, and solve hair problems. It is commonly used at a 10% dosage.

[0042] The present disclosure will be further described in detail with reference to the following examples. However, it should be understood by those skilled in the art that these examples are provided for illustrative purposes only and are not intended to limit the present disclosure. EXAMPLES

[0043] Specific embodiments of the present application are described in detail with reference to examples as follows. Those skilled in the art will understand that the following examples are used only to illustrate the present application and should not be considered as limiting the scope of the present application. If specific conditions are not specified in the examples, they are carried out under conventional conditions or conditions recommended by the manufacturer. All reagents or equipment for which the manufacturer is not indicated are conventional products that are commercially available. Unless otherwise stated, all amounts listed are stated in weight percentages based on the total weight. The present application should not be construed as being limited to the specific examples described.

[0044] 1. Preparation method Step 1: A whey protein suspension with a concentration of 2% to 25% was prepared, completely dissolved by magnetic stirring, and heated at 75 to 100°C for 30 to 100 minutes to prepare a protein denatured particle liquid. After drying the protein denatured particle liquid, a protein denatured particle powder was obtained.

[0045] Step 2: 6 - 35% whey protein denatured particles were mixed with algal oil rich in omega-3 polyunsaturated fatty acids and homogenized to obtain an oil phase suspension of whey protein.

[0046] Step 3: 4 - 15% water was added to the above suspension and then homogenized to obtain an oleogel rich in omega-3 polyunsaturated fatty acids with an oil content of up to 60 - 90%.

[0047] 2. Test Method 1. Rheological properties Equipment used: Rheometer Test procedure: The rheological properties of the oleogel were analyzed by small amplitude oscillatory shear analysis. The oleogel was placed on the sample stage of a rheometer (HAAKE MARS 60), and a sawtooth plate (P35TI / SE) was selected for the test. The gap between the sample stage and the parallel plate was 1 mm. First, the sample was strain scanned at 25°C, and the storage modulus (G’), loss modulus (G”), and loss factor (tanδ) were recorded to characterize the rheological properties of the oil-based composition.

[0048] Regarding the rheology test, the storage modulus (G’) can evaluate the elastic measurement or stored energy, and the loss modulus (G”) can evaluate the viscous measurement or dissipated energy. Loss factor tanδ = G” / G’

[0049] The storage modulus (G’) reflects the elasticity of the composition.

[0050] Viscoelasticity can be characterized by the loss factor (tanδ), which represents whether the research sample exhibits the properties of a solid (elasticity) or a liquid (viscosity). For a perfectly elastic material, the tanδ value is 0. When 0 < tanδ < 1, the research sample shows more elasticity than viscosity. When tanδ = 1, the research sample is below the critical strain and can be used to measure ductility. When tanδ > 1, the research sample shows more viscosity than elasticity.

[0051] 2. Oxidation properties Equipment used: acid buret, iodine flask, rotary evaporator Test procedure: (1) Sampling The prepared sample was crushed, mixed thoroughly, and then placed in a jar. Petroleum ether, 2-3 times the volume of the sample, was added to the jar. The jar was shaken well to mix thoroughly and left for at least 12 hours. Filtration was performed through a funnel filled with anhydrous sodium sulfate to obtain the filtrate. The petroleum ether was evaporated under reduced pressure using a rotary evaporator in a water bath below 40°C. The residue was the sample to be tested.

[0052] (2) Sample measurement Sample measurements were performed away from direct sunlight. 2-3g of sample was weighed (to the nearest 0.001g) and placed in a 250mL iodine flask. 30mL of chloroform-glacial acetic acid mixture was added and the flask was gently shaken to completely dissolve the sample. 1.00mL of saturated potassium iodide solution was added exactly. The bottle was tightly capped. The flask was gently shaken for 0.5 minutes and left in the dark for 3 minutes. The flask was removed and 100mL of water was added. The flask was shaken well. The precipitated iodine was immediately titrated with sodium thiosulfate standard solution until a pale yellow color was obtained (if the peroxide value was estimated to be less than 5.91mmol / kg, a 0.002mol / L standard solution was used, and if the peroxide value was estimated to be greater than 5.91mmol / kg, a 0.01mol / L standard solution was used). 1mL of starch indicator was added. The titration was continued. The flask was vigorously shaken until the blue color of the solution disappeared. A blank test was performed at the same time. The volume V0 of the 0.01 mol / L sodium thiosulfate solution consumed in the blank test should not exceed 0.1 mL.

[0053] (3) Display of analysis results When the peroxide value is expressed in millimoles of active oxygen in 1 kg of sample, it is calculated by the formula: X = (V - V0) x c / (2 x m) x 1000. During the ceremony: X: peroxide value, millimoles per kilogram (mmol / kg); V: volume of sodium thiosulfate standard solution consumed by the sample, in milliliters (mL); V0: Volume of sodium thiosulfate standard solution consumed by the blank test, milliliters (mL); c: concentration of sodium thiosulfate standard solution, moles per liter (mol / L); m: mass of the sample, grams (g); 1000: Conversion factor

[0054] The calculation result is expressed as the arithmetic mean of two independent measurements obtained under reproducible conditions, with significant figures retained to two decimal places.

[0055] Evaluation criteria: The antioxidant capacity of an oil or fat composition is characterized by its peroxide value: the lower the peroxide value, the better the antioxidant properties.

[0056] 3.Appearance evaluation As shown in Figure 1, panel A shows ++++: transparent, not turbid; Panel B: +++: Translucent, essentially not turbid; Panel C: ++: practically opaque, slightly hazy; Panel D shows +: opaque, cloudy.

[0057] Example 1: Structural characteristics of the oil composition 1. An oleogel was prepared according to the recipe in Table 1. Specifically, 18 wt% of whey protein denatured particles was added to 70 wt% of algal oil rich in omega-3 polyunsaturated fatty acids and mixed for 0.5 to 3 hours to obtain a protein oil phase suspension. Next, 12 wt% of purified water was added to the oil phase suspension and homogenized for 3 to 30 minutes to obtain an oleogel rich in omega-3 polyunsaturated fatty acids. [Table 1]

[0058] The oleogels were observed under a microscope to reveal their structural features (staining scheme). The protein particles were fluorescently stained with Thioflavin T (Th T) during the preparation process. Images of the protein particles or networks were taken using a Leica TCS SP5 confocal laser microscope (Leica Microsystems Inc., Heidelberg, Germany) at an excitation wavelength of 458 nm.

[0059] FIG. 2 shows the results of protein particles forming a permeable network in the oil composition. As shown in FIG. 2, the black parts are oil, and the proteins have fluorescent absorption by staining and show bright green dots under confocal laser microscope. According to the micrograph, the protein particles showing green fluorescence are linked and aggregated into chains, and this structure can condense liquid oil into a semi-solid / solid oil composition, i.e., oleogel. The oleogel with this special structure can effectively block oxygen and delay the rancidity of oils rich in omega-3 polyunsaturated fatty acids, as shown below. According to FIG. 2, in the oleogel, the algae oil is the continuous phase and the protein particles are the dispersed phase.

[0060] 2. Comparative Example of Glyceryl Mono- and Distearate Structured Oils 90 wt% algal oil and 10 wt% glycerol mono- and distearate were thoroughly mixed, and the mixture was heated at 70-100° C. for 30-60 minutes, then cooled to obtain an oil composition.

[0061] Glyceryl mono- and distearate was heated and subsequently cooled to crystallize, resulting in a solid / semi-solid fat composition. Heat treatment accelerates rancidity of fats and oils rich in omega-3 polyunsaturated fatty acids, so that the peroxide value measured by measuring the oxidation properties is 5.2 mmol / kg. In contrast, the preparation process of the oleogel of the present disclosure does not require a heating step, thus avoiding the oxidation of fats and oils caused by heat treatment.

[0062] Example 2: Study of protein-modified particles with different loadings The content of whey protein modified particles in the oleogel formulation was evaluated on the rheological properties and peroxide value of the oleogel. Specifically, the mass of algal oil and water was controlled (70 g and 12 g, respectively). The mass of protein modified particles was varied (g). The rheological properties and peroxide value were measured by the methods described above. The results are shown in Table 2. [Table 2] Not Formed: Refers to the composition prepared being a liquid or visibly mobile oil in suspension and unable to solidify into a solid or semi-solid.

[0063] As shown in Table 2, when the content of protein modified particles is 6-35%, oleogel can be prepared, and when the content of protein modified particles is less than 6% or more than 35%, oleogel cannot be formed. The prepared oleogel has better antioxidant properties, and the peroxide value is less than 2.5mmol / kg, which is suitable for use as food. The inventors found that the protein modified particles affect the appearance of the oleogel. When the content of protein modified particles is 10.8%, the appearance of the oleogel is transparent and not cloudy. As the content of protein modified particles is further increased, the appearance of the oleogel gradually becomes cloudy.

[0064] Within a certain range of 6-35%, as the content of protein microparticles increases, the gel strength also increases. When the content of protein microparticles exceeds a certain range, the protein microparticles are supersaturated and cannot be sufficiently dispersed in the oil and fat, causing the precipitation of the protein microparticles. When the ratio of protein denatured particles to purified water is 3:12 or 45:12, no oleogel can be formed. Surprisingly, as the ratio of protein denatured particles to purified water increases from 3:12 to 25:12, the peroxide value tends to decrease gradually, and when it further increases from 25:12 to 45:12, the peroxide value increases gradually again. When the ratio of protein denatured particles to purified water is 25:12, the peroxide value of the oleogel is the lowest.

[0065] Example 3: Study of algae oil at different dosages The rheological properties and peroxide value of the oleogel were evaluated depending on the content of algal oil in the oleogel formulation. The combination with the lower peroxide value was selected. The ratio of protein modified particles to purified water was 20:12, and the amount of algal oil added was determined. Specifically, the mass of protein modified particles and water was controlled (20 g and 12 g, respectively). The mass of algal oil was changed (g). The rheological properties and peroxide value were measured by the above methods. The results are shown in Table 3. [Table 3]

[0066] As shown in Table 3, when the algal oil content is 60-90%, an oil composition can be prepared and the prepared oleogel has excellent antioxidant properties. As the algal oil content increases, the oleogel becomes more transparent. When the ratio of protein denatured particles to purified water is 20:12, the algal oil content is as high as 89%.

[0067] Example 4: Study of different amounts of added water The effect of water content in the oleogel formulation on the rheological properties and peroxide value of the oleogel was evaluated. Specifically, the mass of protein modified particles and algal oil were controlled (20 g and 70 g, respectively). The mass of water was varied (g) and the rheological properties and peroxide value were measured by the methods described above. The results are shown in Table 4. [Table 4]

[0068] As shown in Table 4, when the water content is between 4 and 15%, an oil and fat composition can be prepared and the prepared oleogel has excellent antioxidant properties. Surprisingly, the inventors have noticed that the water content affects the appearance of the oleogel. When the water content is 4.3%, the oleogel is translucent and not substantially cloudy. When the water content is increased to 15.1%, the oleogel tends to become more cloudy, being substantially opaque and cloudy.

[0069] Example 5: Study of oleogels prepared with different fats and oils The applicability of the oleogel of the present disclosure to different liquid oils was also investigated. Specifically, the formulation of the oleogel is shown in Table 5 and the preparation method was the same as above except that different liquid oils were added. [Table 5]

[0070] As shown in Table 5, in addition to algal oil, linseed oil and fish oil can also be used to prepare the oil composition in the same manner, and the prepared oleogels have excellent antioxidant properties.

[0071] Example 6: Study of added antioxidants The effect of antioxidant addition on the rheological properties and peroxide value of the oleogel of the present disclosure was also investigated. Specifically, the formulation of the oleogel was shown in Table 6, and the preparation method was the same as the above method, except that antioxidants Vitamin C (VC), sucrose, and erythritol were further added. The results are shown in Table 6. [Table 6] *Accelerated test conditions: Temperature 40℃, humidity 75%, sample stability for 1 month

[0072] As shown in Table 6, the oleogel of the present application has superior antioxidant properties to Control 1 (algal oil only) and Control 2 (algal oil and monoglycerides). After the addition of antioxidants, the antioxidant capacity of the oleogel was improved, however, even without the addition of antioxidants, the oleogel of the present disclosure achieves the same order of peroxide value and can be used directly as a food product.

[0073] Example 7: Differences in properties between krill oil oleogel with oil phase as the continuous phase and krill oil emulsion gel with water phase as the continuous phase A: Krill oil oleogel was prepared according to the composition ratios in Table 1, except using krill oil instead of algal oil. B: A krill oil emulsion gel was prepared using whey protein as a gelling agent. Specifically, the krill oil emulsion gel was prepared as follows: 1. 300g of 8% whey protein solution was prepared. 2. The aqueous phase was high sheared at a speed of 18000 rpm. 200g of krill oil was added. The shear rate was maintained for 5 minutes to form a uniform krill oil emulsion. 3. The emulsion was heated at 85°C for 30 minutes, then cooled in ice water to form a krill oil emulsion gel.

[0074] 0.5 g each of Gels A and B was placed in 50 mL of purified water at 60°C and thoroughly stirred at a rotation speed of 500 rpm for 10 minutes. The states of the two gels were observed and compared.

[0075] As shown in Figures 3 and 4, krill oil oleogel (Tube A) and emulsion gel (Tube B) have similar appearance, but krill oil oleogel is insoluble in water and floats on the water. Conversely, krill oil emulsion gel can dissolve in water again to form an emulsion. From the structure analysis, the continuous phase of oleogel is oil and fat, while the continuous phase of emulsion gel is water. When a fat-soluble dye is added for dyeing, oleogel can be dyed. Emulsion gel is an oil-in-water type system, and fat-soluble dye cannot penetrate it and therefore cannot be dyed, which is clearly different from oleogel in this respect.

[0076] Example 8: Rheological properties and peroxide values ​​of oleogels prepared with different types of proteins The applicability of different proteins to the oleogel of the present disclosure was also investigated. Specifically, the formulation of the oleogel was shown in Table 7 and the preparation method was the same as that described above except that different kinds of proteins were used. [Table 7]

[0077] In addition to whey protein, casein, collagen, gelatin, zein, and mung bean protein can also be used to prepare the oil and fat composition in the same manner, and the prepared oleogel has excellent antioxidant properties, as shown in Table 7. In the present application, various proteins such as casein, collagen, gelatin, zein, and mung bean protein can be used in place of whey protein.

[0078] The above embodiments are preferred embodiments of the present disclosure, but the embodiments of the present disclosure are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present disclosure should be considered as equivalent substitutions and fall within the scope of protection of the present disclosure.

Claims

1. 1. An oleogel comprising 60-90 wt % liquid oil, 6-35 wt % structuring agent, and 4-15 wt % water, wherein the liquid oil comprises unsaturated fatty acids, the structuring agent is a protein modified particle, and the liquid oil is the continuous phase.

2. 2. The oleogel of claim 1, wherein the liquid oil content is from 63 to 85 wt % and / or the structuring agent content is from 6 to 25 wt %.

3. 2. The oleogel of claim 1, wherein the unsaturated fatty acids are one or more of monounsaturated and polyunsaturated fatty acids, the monounsaturated fatty acids comprising one or more of myristic acid, palmitoleic acid, oleic acid, transoleic acid, lysine oleic acid, erucic acid, and cetoleic acid, and the polyunsaturated fatty acids comprising one or more of omega-3 and omega-6 polyunsaturated fatty acids.

4. 10. The oleogel of claim 1, wherein the protein is one or more of an animal protein and a vegetable protein, the animal protein comprising one or more of whey protein, casein, collagen, and gelatin.

5. 2. The oleogel of claim 1, wherein the protein denatured particles are obtained by preparing a protein suspension, denaturing by heating, homogenizing and drying, wherein the homogenization is done by one or more of mechanical stirring homogenization, ultrasonic homogenization, microfluidic homogenization, colloid mill homogenization and ball mill homogenization, and the drying is done by one or more of vacuum drying, vacuum freeze drying, electric heated air drying and spray drying.

6. 6. The oleogel of claim 5, wherein said protein suspension is a 2-25 wt% aqueous whey protein suspension.

7. 10. The oleogel of claim 1, wherein the liquid oil is one or more of olive oil, canola oil, peanut oil, algae oil, fish oil, linseed oil, perilla oil, chia seed oil, and krill oil.

8. 10. The oleogel of claim 1 with or without an antioxidant, said antioxidant being one or more of an oil soluble antioxidant and a water soluble antioxidant.

9. 9. The oleogel of claim 8, wherein the oil soluble antioxidant is one or more of rosmanol, carnosol, sesamol, vitamin E, butylated hydroxyanisole, dibutylated hydroxytoluene, propyl gallate, and tert-butylhydroquinone, and the water soluble antioxidant is one or more of vitamin C, sodium isoascorbate, tea polyphenols, epigallocatechin gallate, sugars, and sugar alcohols, wherein the sugar comprises sucrose and the sugar alcohol is one or more of xylitol, sorbitol, erythritol, and maltitol.

10. The following characteristics are measured by rheometer: (1) 1x10 ３ Pa ~ 1 x 10 ５ 2) having a storage modulus of 0.02 Pa; and (1) having a loss factor of 0.08 to 0.

5.

11. 13. Use of the oleogel of claim 1 in a food, health food, or cosmetic product, or in the preparation of an oral medicinal product for one or more of the following: (1) regulating blood lipids and / or removing blood clots; (2) preventing Alzheimer's disease, nourishing the brain and / or improving memory; (3) preventing arthritis, relieving gout and asthma, and temporarily reducing swelling and pain caused by arthritis; (4) improving vision and / or preventing and treating presbyopia; and (5) maintaining the retina.

12. 13. An oral pharmaceutical preparation comprising the oleogel of claim 1.

13. (1) adding a structurant to a liquid oil and mixing them to obtain a suspension of the structurant in the oil phase; and (2) adding water to the suspension of structuring agent in oil phase and homogenizing them to obtain an oleogel.

14. 14. The method of claim 13, further comprising adding an oil-soluble antioxidant, a water-soluble antioxidant, or both, to the oil phase, the water phase, or both, respectively, and not including the step of heating the liquid oil.

Images