Method for preparing nutritional oil comprising egg yolk phospholipids and 1,3-dioleoyl-2-palmitoylglycerol, and nutritional oil prepared by using same

By controlling the weight ratio of egg yolk phospholipids to OPO triglycerides and employing a specific dispersion process, the problem of poor dispersibility of egg yolk phospholipids in OPO oils was solved, achieving uniformity and stability of the nutritional oils, making them suitable for various oil formulations and simplifying the production process.

WO2026032361A1PCT designated stage Publication Date: 2026-02-12AAK ZHANGJIAGANG LTD
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Patent Information

Application Number
PCT/CN2025/113177
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-08-08
Filing Date
2025-08-07
Publication Date
2026-02-12

AI Technical Summary

Technical Problem

Egg yolk phospholipids exhibit poor dispersibility in 1,3-dioleoyl-2-palmitoylglycerol triglyceride, leading to precipitation and stratification of the mixture upon temperature changes, thus limiting its application in oil and fat products.

Method used

By controlling the weight ratio of egg yolk phospholipids to OPO-containing triglycerides within the range of 1:20 to 1:4, and employing specific dispersion processing techniques, including shearing at 3000-5000 rpm and high-pressure homogenization at 200-300 bar, the uniformity and oil-dissolving properties of egg yolk phospholipids in OPO nutrient oils are improved.

Benefits of technology

It achieves good uniformity and stability of egg yolk phospholipids in OPO nutritional oils, solves the problems of sedimentation and stratification, simplifies the production process, is applicable to a variety of oil formulations, and improves the applicability and flexibility of the food industry.

✦ Generated by Eureka AI based on patent content.

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    Figure PCTCN2025113177-FTAPPB-I100002
  • Figure PCTCN2025113177-FTAPPB-I100003
    Figure PCTCN2025113177-FTAPPB-I100003
Patent Text Reader

Abstract

Provided in the present invention are a method for preparing a nutritional oil comprising egg yolk phospholipids and 1,3-dioleoyl-2-palmitoylglycerol (OPO), and a nutritional oil prepared by using same. Specifically, the method comprises: (1) mixing egg yolk phospholipids, OPO-containing triglycerides and a base oil to obtain a dispersion, wherein the weight ratio of the egg yolk phospholipids to the OPO-containing triglycerides is in the range of 1:20 to 1:4; and (2) sequentially subjecting the dispersion to a shearing treatment and a homogenizing treatment, wherein the shearing treatment comprises shearing the dispersion under heating at a rotation speed of 3000-5000 rpm, and the homogenizing treatment comprises homogenizing the sheared dispersion under heating at a pressure of 200-300 bar. In the OPO-containing triglycerides, the proportion of 2-position palmitic acid in total palmitic acids is at least 52%, and the content of OPO is at least 40 wt%. By means of the method of the present invention, the content of egg yolk phospholipids in an OPO-containing nutritional oil can be increased, and the resulting nutritional oil containing egg yolk phospholipids and OPO has good uniformity and oil-dissolving properties.
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Description

Method for preparing nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride and nutritional oil prepared by the method TECHNICAL FIELD

[0001] The present application relates to the technical field of food processing, and in particular, the present application provides a method for preparing nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride (OPO) and nutritional oil prepared by the method. BACKGROUND

[0002] Egg yolk phospholipid, also known as lecithin, is a natural phospholipid mixture present in egg yolk, which has the property of amphiphilic molecules, i.e. one end is hydrophilic (contains nitrogen or phosphorus head), the other end is hydrophobic (oleophilic long hydrocarbon chain). Egg yolk phospholipid has important physiological functions and application value in edible oil. Specifically, egg yolk phospholipid has physiological activities such as antioxidant, antibacterial, anti-inflammatory, and nerve, cardio-cerebral vascular protection, etc. It can improve fat metabolism, protect the retina, improve intelligence and brain, etc. In addition, egg yolk lecithin can relieve blood aggregation, clarify blood fat, and avoid the hardening of arterial vascular membrane, preventing diseases such as arteriosclerosis, myocardial infarction and cerebral hemorrhage, etc. Choline in egg yolk lecithin is the precursor of neurotransmitter acetylcholine, which can improve memory and learning ability. In addition, egg yolk lecithin can promote the synthesis and regeneration of lipoprotein, improve alcoholic liver disorder, and protect the membranes of liver mitochondria, microsomes and lysosomes from damage. In summary, egg yolk phospholipid is considered as a natural resource with high added value due to its multifunctionality and wide application in the food industry. In edible oil, it not only can improve the nutritional value of food, but also can enhance the flavor and taste of food, which has important significance for promoting health and improving food quality.

[0003] On the other hand, 1,3-dioleoyl-2-palmitoyl triglyceride (OPO) is a structured fat, which is characterized by its palmitic acid mainly located at the sn-2 position of the triglyceride, while unsaturated fatty acids such as oleic acid are mainly located at the sn-1 and sn-3 positions. This structure is similar to the natural fat structure in breast milk. OPO structured fat can provide a variety of unique nutritional and health benefits, such as preventing constipation, optimizing calcium and fatty acid absorption, enhancing bone development, promoting the growth of beneficial bacteria, etc. The addition of OPO structured fat is considered as one of the latest developments in nutritional food, which helps better meet the natural nutritional needs of babies by simulating the fat structure of breast milk, supporting the healthy growth of babies. In summary, 1,3-dioleoyl-2-palmitoyl triglyceride (OPO) has become an important food ingredient due to its similarity to breast milk fat structure and various health benefits in infant formula.

[0004] Therefore, it is an effort direction in the current food processing field to develop nutritional food containing both egg yolk phospholipid and OPO.

[0005] Generally, phospholipids have poor dispersibility in liquid oil, and after adding 0.3% by weight of phospholipids to the liquid oil, the phospholipids will precipitate and separate, which greatly limits the application of phospholipids in oil products. The dispersibility of phospholipids can be significantly improved by adding emulsified soybean oil, and the uniform distribution of phospholipids in liquid oil is improved. The more emulsified soybean oil is added, the more obvious the effect is. However, in some mixed oils without the addition of emulsified soybean oil, the dispersibility of phospholipids is still a problem to be solved. In particular, for the mixed system of egg yolk phospholipids and OPO, the egg yolk phospholipids have poor dispersibility in OPO. The OPO nutritional oil is in a solidified state at room temperature. At high temperature, a small amount of egg yolk phospholipids can be well mixed with OPO, and only a small amount of precipitate is formed. However, as the temperature of the mixed system decreases to room temperature, the egg yolk phospholipids will precipitate and separate.

[0006] Therefore, it is of great significance to develop a method for preparing a nutritional oil containing egg yolk phospholipids and OPO with good uniformity. SUMMARY

[0007] From the above technical problems, the purpose of the present application is to provide a method for preparing a nutritional oil containing egg yolk phospholipids and 1,3-dioleic acid-2-palmitic acid triglyceride, and a nutritional oil prepared by the method. According to the method of the application, the content of egg yolk phospholipids in the OPO-containing nutritional oil can be increased, and the obtained nutritional oil containing egg yolk phospholipids and OPO has good uniformity and oiliness.

[0008] The present application is completed by the inventors through in-depth and meticulous research.

[0009] Specifically, in one aspect, the present application provides a method for preparing a nutritional oil containing egg yolk phospholipids and 1,3-dioleic acid-2-palmitic acid triglyceride, the method comprising the following steps:

[0010] (1) mixing egg yolk phospholipids, OPO-containing triglyceride and raw material oil to obtain a dispersion, wherein the weight ratio of egg yolk phospholipids to the OPO-containing triglyceride is in the range of 1:20 to 1:4; and

[0011] (2) sequentially performing shear treatment and homogenization treatment on the dispersion, wherein the shear treatment comprises shearing the dispersion at a speed of 3000-5000 rpm under heating, and the homogenization treatment comprises homogenizing the sheared dispersion under heating at a pressure of 200-300 bar, wherein

[0012] In the OPO-containing triglyceride, the proportion of 2-palmitic acid to the total palmitic acid is at least 52%, and the content of OPO is at least 40% by weight.

[0013] In another aspect, the present application provides a nutritional oil containing egg yolk phospholipid and 1,3-dioleic acid-2-palmitic acid triglyceride, which is prepared according to the method described above.

[0014] Compared with the prior art in the art, the present application has the advantages of:

[0015] 1. The processing technology of the present application significantly improves the uniformity of the OPO nutritional oil containing egg yolk phospholipid by specific raw material ratio and specific mixing steps, which solves the problem of egg yolk phospholipid precipitation and stratification in the prior art, thereby improving the appearance and stability of the oil.

[0016] 2. By using the specific high-speed shearing and high-pressure homogenization process, the present application improves the solubility of egg yolk phospholipid in the OPO nutritional oil, which can maintain the uniform distribution of the oil even under temperature changes.

[0017] 3. Compared with the traditional method which requires additional addition of emulsified soybean oil to improve the solubility of phospholipid, the process of the present application does not require additional pretreatment of the base oil, simplifying the production process.

[0018] 4. The processing technology of the present application is not only suitable for specific oil formula, but also effective for different mixed oil ratios, which increases its applicability and flexibility in the food industry. DETAILED DESCRIPTION

[0019] It should be understood that those skilled in the art can conceive other various embodiments and make modifications thereof according to the teachings of the present specification without departing from the scope or spirit of the present disclosure. Therefore, the following detailed description is not intended to be limiting in nature.

[0020] Unless otherwise indicated, all numbers expressing features, quantities and properties of the present disclosure are to be understood as being modified in all instances by the term "about." Accordingly, unless otherwise indicated, the numerical parameters set forth in the description and the claims are approximations that can vary depending upon the desired properties sought to be obtained by those skilled in the art utilizing the teachings of the present disclosure. At the very least, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques. Numerical ranges include all values from and including the lower and the upper values, in increments of one unit provided that there is a variation of less than 1 in the numerical value. The use of "about" with respect to a given numerical value or a given numerical range means that the value or range is approximately correct, and that slight deviations or variations are expected to be within the scope of the given value or range.

[0021] OPO nutritional oil is generally in solid state at room temperature and gradually melts when heated. In the present disclosure, "oil melting property" of OPO nutritional oil refers to the homogeneity of the oil after it is heated and melted from solid state at room temperature, unless otherwise specified.

[0022] As mentioned above, phospholipids, especially egg yolk phospholipids, have poor dispersibility in liquid oil. For a mixture of egg yolk phospholipids and OPO-containing triglycerides, at high temperature, a small amount of egg yolk phospholipids can be well mixed with the OPO-containing triglycerides, with only a small amount of precipitation. However, as the temperature of the mixture decreases to room temperature, the egg yolk phospholipids will precipitate and separate, which greatly limits the application of nutritional oil products containing both egg yolk phospholipids and OPO. The present application aims to solve the above technical problems.

[0023] Specifically, the present application provides a method for preparing a nutritional oil containing egg yolk phospholipids and 1,3-dioleic acid-2-palmitic acid triglyceride (OPO), the method comprising the following steps:

[0024] (1) mixing egg yolk phospholipids, OPO-containing triglycerides and raw oil to obtain a dispersion, wherein the weight ratio of egg yolk phospholipids to the OPO-containing triglycerides is in the range of 1:20 to 1:4; and

[0025] (2) sequentially subjecting the dispersion to shear treatment and homogenization treatment, wherein the shear treatment comprises shearing the dispersion at a speed of 3000-5000 rpm under heating, and the homogenization treatment comprises homogenizing the sheared dispersion at a pressure of 200-300 bar under heating, wherein

[0026] In the OPO-containing triglycerides, the proportion of 2-position palmitic acid to total palmitic acid is at least 52%, and the content of OPO is at least 40% by weight.

[0027] The inventors of the present application found in their research that by specifically controlling the weight ratio of egg yolk phospholipids to OPO-containing triglycerides in the nutritional oil and by a specific dispersion treatment process (including high-speed shear treatment and high-pressure homogenization treatment under specific conditions), a nutritional oil containing egg yolk phospholipids and OPO with high egg yolk phospholipid content and good homogeneity and oil melting property can be obtained.

[0028] According to certain embodiments of the present application, the weight ratio of egg yolk phospholipid to the OPO-containing triglyceride is in the range of 1:20 to 1:4. When the weight ratio of egg yolk phospholipid to the OPO-containing triglyceride is greater than 1:4, the content of egg yolk phospholipid is too high to achieve effective dispersion in the OPO nutritional oil, and a large amount of precipitation and serious stratification occurs after standing at room temperature for 24 hours. In order to further improve the uniformity and oiliness of the nutritional oil containing egg yolk phospholipid and OPO, the weight ratio of egg yolk phospholipid to the OPO-containing triglyceride is in the range of 1:19 to 1:5, preferably 1:19 to 1:8.

[0029] In addition, the inventors of the present application found that a specific dispersion treatment process (including high-speed shearing treatment and high-pressure homogenization treatment under specific conditions) is crucial for obtaining a nutritional oil containing egg yolk phospholipid and OPO with good uniformity and oiliness. Without being bound by theory, it is speculated that the specific dispersion treatment process according to the present application can efficiently disperse the poorly soluble egg yolk phospholipid in the OPO-containing oil system, thereby forming a uniformly and stably mixed egg yolk phospholipid-OPO-containing triglyceride oil system that remains in a completely uniformly mixed state when cooled to room temperature and then heated and melted again.

[0030] Specifically, in the shearing treatment of step (2) of the method according to the present application, the viscosity of the oil is reduced by applying shear force, promoting the uniform distribution of different components in the oil. Shear force helps to break up the dispersed phase in the oil, forming fine particles or droplets, thereby improving dispersibility and emulsifiability. There is no particular limitation on the specific type of device used for shearing treatment, which can be selected from conventional common shearing devices commonly used for oil food processing. Preferably, a high-speed shearing tank, a high-shear emulsifier, a colloid mill or a homogenizer, etc. can be used.

[0031] According to certain embodiments of the present application, in step (2), the shearing treatment comprises shearing the dispersion at a rotation speed of 3000-5000 rpm under heating. When the rotation speed used for shearing treatment is less than 3000 rpm, a small amount of precipitation exists in the obtained egg yolk phospholipid-OPO oil system, and the egg yolk phospholipid cannot be completely dispersed in the OPO oil system; on the other hand, when the rotation speed used for shearing treatment is greater than 5000 rpm, a small amount of precipitation exists in the obtained egg yolk phospholipid-OPO oil system (even a large amount of precipitation occurs in the case of using certain formulations), and the egg yolk phospholipid cannot be completely dispersed in the OPO oil system.

[0032] According to some embodiments of the present application, the shearing treatment is performed under heating. Preferably, in step (2), in order to improve the uniformity and oiliness of the nutritional oil containing egg yolk phospholipid and OPO, the shearing treatment is performed at a temperature range of 55-70°C. Preferably, in step (2), in order to improve the uniformity and oiliness of the nutritional oil containing egg yolk phospholipid and OPO, the shearing treatment is performed for 3-5 minutes.

[0033] Specifically, in the homogenization treatment of step (2) of the method according to the present application, by applying high shear force, large droplets in the oil are broken into smaller droplets, thereby reducing the average size of the droplets in the emulsion. The specific type of device used for homogenization treatment is not particularly limited, and can be selected from conventional common homogenization devices commonly used in oil food processing. Preferably, a high-pressure homogenizer or the like can be used.

[0034] According to some embodiments of the present application, in step (2), the homogenization treatment includes homogenizing the sheared dispersion under heating at a pressure of 200-300 bar. When the pressure used for homogenization treatment is less than 200 bar, the resulting egg yolk phospholipid-OPO oil system quickly appears a large amount of precipitate, and the egg yolk phospholipid cannot be dispersed in the OPO oil system; when the pressure used for homogenization treatment is greater than 300 bar, there is a small amount of precipitate in the resulting egg yolk phospholipid-OPO oil system (even a large amount of precipitate in the case of using some formulations), and the egg yolk phospholipid cannot be completely dispersed in the OPO oil system.

[0035] According to some embodiments of the present application, the homogenization treatment is performed under heating. Preferably, in step (2), in order to improve the uniformity and oiliness of the nutritional oil containing egg yolk phospholipid and OPO, the homogenization treatment is performed at a temperature range of 55-70°C. Preferably, in step (2), in order to improve the uniformity and oiliness of the nutritional oil containing egg yolk phospholipid and OPO, the homogenization treatment is performed for 5-10 minutes.

[0036] According to some embodiments of the present application, the sum of the weight of egg yolk phospholipid and the OPO-containing triglyceride accounts for 60%-95% of the total weight of the nutritional oil. In order to further improve the uniformity and oiliness of the nutritional oil containing egg yolk phospholipid and OPO, the sum of the weight of egg yolk phospholipid and the OPO-containing triglyceride preferably accounts for 65%-90%, more preferably 80%-90%, of the total weight of the nutritional oil.

[0037] There is no particular limitation on the specific type of raw oil that can be used in the present application. Preferably, the raw oil is selected from one or more of vegetable oil or animal oil. More preferably, the raw oil is selected from one or more of the group consisting of sunflower oil (including high oleic sunflower oil), medium-chain triglyceride, coconut oil, flaxseed oil, anhydrous butter, palm kernel oil, DHA algal oil, fish oil, walnut oil, camellia oil, perilla seed oil, sea buckthorn seed oil, avocado oil, wheat germ oil, blackcurrant seed oil, borage oil, eucommia seed oil, evening primrose oil, soybean oil, rapeseed oil (including low erucic rapeseed oil), corn oil, peanut oil, safflower seed oil, palm oil, rice bran oil, sesame oil, gamma-linolenic acid oil, tomato seed oil, peony seed oil, krill oil, king's delight seed oil, babassu oil, milk thistle seed oil, conjugated linoleic acid, MCT oil, and shea oil, etc. More preferably, the sunflower oil is high oleic sunflower oil (HOSO).

[0038] According to certain embodiments of the present application, in order to further improve the mixing property of the egg yolk phospholipid and the OPO-containing triglyceride, the egg yolk phospholipid and the raw oil can be mixed first to obtain a premix in step (1), and then the premix is mixed with the OPO-containing triglyceride to obtain the dispersion for step (2). Preferably, the raw oil comprises sunflower oil. More preferably, in order to further improve the uniformity and oiliness of the nutritional oil containing egg yolk phospholipid and OPO, the raw oil comprises high oleic sunflower oil.

[0039] The method according to the present application can improve the content of egg yolk phospholipid in the OPO-containing nutritional oil, and in the prepared nutritional oil containing egg yolk phospholipid and 1,3-dioleic acid-2-palmitic acid triglyceride, the weight of the egg yolk phospholipid accounts for 5%-10%, preferably 5%-8%, more preferably 6%-8% of the total weight of the nutritional oil.

[0040] According to certain embodiments of the present application, in the prepared nutritional oil containing egg yolk phospholipid and 1,3-dioleic acid-2-palmitic acid triglyceride, the weight of the OPO-containing triglyceride accounts for 30%-90%, preferably 50%-90%, more preferably 60%-90% of the total weight of the nutritional oil.

[0041] According to certain embodiments of the present application, the method further comprises the following steps:

[0042] (3) subjecting the product of step (2) to microfiltration treatment.

[0043] By filtering through a microporous filter, the oil can be reduced in stratification, ensuring that the oil remains uniform and consistent during storage and use.

[0044] The egg yolk phospholipid that can be used in the present application is not particularly limited and can be obtained by a conventional commercial route. Preferably, the egg yolk phospholipid is an egg yolk phospholipid having a phospholipid content of 75% or more. The egg yolk phospholipid contains phosphatidylcholine (PC), phosphatidylethanolamine (PE), sphingomyelin (SM), and lyso-phospholipid (LPC+LPE), etc. Alternatively, a specific example of the egg yolk phospholipid includes an ELIP 3020 product produced and sold by Ahu Skars Oil Co., Ltd., which is a complex of egg yolk phospholipid and high-oleic sunflower oil, wherein the mass ratio of the egg yolk phospholipid to the high-oleic sunflower oil is about 1:1. The ELIP 3020 product contains phospholipid-bound DHA and phospholipid-bound ARA, and specifically, the ELIP 3020 product contains about 59% by weight of phosphatidylcholine (PC), about 11% by weight of phosphatidylethanolamine (PE), about 2% by weight of sphingomyelin (SM), and about 8.5% by weight of lyso-phospholipid (LPC+LPE), etc., based on the dry weight thereof.

[0045] The OPO-containing triglyceride that can be used in the present application is not particularly limited and can be obtained by a conventional commercial route or synthesized by a conventional esterification reaction. The esterification reaction is a process in which glycerol and fatty acid react to form a triglyceride under the action of an acidic or basic catalyst. In addition to the esterification reaction, the OPO structure ester can also be prepared by an interesterification reaction. The interesterification reaction involves an existing triglyceride and free fatty acid, and under the action of a specific catalyst (usually an enzyme), the position of the fatty acid in the triglyceride molecule is adjusted. The selection of the catalyst is crucial in the esterification and interesterification reactions. The esterification reaction can be carried out using an acidic or basic catalyst, while the interesterification reaction usually requires a more specific enzyme catalyst.

[0046] Preferably, the OPO-containing triglyceride that can be used in the present application is a fraction of the interesterification product obtained by selective interesterification at the 1,3-position of a plant oil (e.g., palm oil) and oleic acid. Preferably, in the OPO-containing triglyceride that can be used in the present application, the proportion of 2-palmitic acid to the total palmitic acid is at least 52%, and the content of OPO is at least 40% by weight. The OPO-containing triglyceride can be commercially available as a food nutrient fortifier. The physicochemical indicators of the OPO-containing triglyceride meet the indicators specified in the Chinese National Food Safety Standard GB 30604-2015. Specifically, the OPO-containing triglyceride that can be used in the present application is 1,3-dioleic acid-2-palmitic acid triglyceride (product name: INFAT C250) produced by Ahu Skars Oil (Zhangjiagang) Co., Ltd.

[0047] In addition to the above-mentioned components, one or more additives conventionally used in the field of nutritional oil and fat can be added to the method for preparing a nutritional oil and fat containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to the present application, provided that the good mixing performance between the egg yolk phospholipid and the 1,3-dioleoyl-2-palmitoyl triglyceride and the oiling performance of the resulting nutritional oil and fat are not affected. Specific examples of the one or more additives that can be applicable include: antioxidants including, but not limited to, vitamin E (mixed tocopherols), AP (ascorbyl palmitate), BHA (butylated hydroxyanisole), BHT (butylated hydroxytoluene), and the like; emulsifiers including, but not limited to, caprylocaproyl glycerides, and the like; nutritional fortifiers including, but not limited to, vitamin A, vitamin D, DHA (docosahexaenoic acid), EPA (eicosapentaenoic acid), and the like; stabilizers including, but not limited to, EDTA, and the like; preservatives including, but not limited to, nisin, and the like; and functional ingredients including, but not limited to, oligosaccharides, and the like.

[0048] According to another aspect of the present application, there is provided a nutritional oil and fat containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride, which is prepared according to the above-described method.

[0049] The nutritional oil and fat prepared according to the method of the present application can contain at least 0.05 g / 100 g of phospholipid-bound arachidonic acid (ARA) and at least 0.03 g / 100 g of phospholipid-bound docosahexaenoic acid (DHA). For example, the nutritional oil and fat prepared according to the method of the present application can contain 0.05 to 0.20 g / 100 g, preferably 0.06 to 0.16 g / 100 g, for example 0.07 to 0.12 g / 100 g of phospholipid-bound ARA, and / or the nutritional oil and fat prepared according to the method of the present application can contain 0.03 to 0.20 g / 100 g, preferably 0.04 to 0.15 g / 100 g, for example 0.06 to 0.12 g / 100 g of phospholipid-bound DHA.

[0050] The following DETAILED DESCRIPTION is intended to illustrate, but not limit, the present disclosure.

[0051] DETAILED DESCRIPTION 1 is a method for preparing a nutritional oil and fat containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride, the method comprising the steps of:

[0052] (1) mixing egg yolk phospholipid, OPO-containing triglyceride, and a raw material oil to obtain a dispersion, wherein the weight ratio of the egg yolk phospholipid to the OPO-containing triglyceride is in the range of 1:20 to 1:4; and

[0053] (2) sequentially subjecting the dispersion to a shearing treatment and a homogenizing treatment, wherein the shearing treatment comprises shearing the dispersion at a rotation speed of 3000-5000 rpm under heating, and the homogenizing treatment comprises homogenizing the sheared dispersion under heating at a pressure of 200-300 bar, wherein

[0054] In the OPO-containing triglyceride, the proportion of palmitic acid at the 2-position to the total palmitic acid is at least 52%, and the content of OPO is at least 40% by weight.

[0055] Specific embodiment 2 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-diolein-2-palmitin according to specific embodiment 1, wherein the weight ratio of egg yolk phospholipid to the OPO-containing triglyceride is in the range of 1:19 to 1:5.

[0056] Specific embodiment 3 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-diolein-2-palmitin according to specific embodiment 1, wherein in step (2), the shearing treatment is carried out at a temperature in the range of 55-70°C.

[0057] Specific embodiment 4 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-diolein-2-palmitin according to specific embodiment 1, wherein in step (2), the shearing treatment is carried out for 3-5 minutes.

[0058] Specific embodiment 5 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-diolein-2-palmitin according to specific embodiment 1, wherein in step (2), the homogenizing treatment is carried out at a temperature in the range of 55-70°C.

[0059] Specific embodiment 6 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-diolein-2-palmitin according to specific embodiment 1, wherein in step (2), the homogenizing treatment is carried out for 5-10 minutes.

[0060] Specific embodiment 7 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-diolein-2-palmitin according to specific embodiment 1, wherein the sum of the weight of egg yolk phospholipid and the OPO-containing triglyceride accounts for 60%-95% of the total weight of the nutritional oil.

[0061] Specific embodiment 8 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-diolein-2-palmitin according to specific embodiment 1, wherein the raw material oil is selected from one or more of plant oil or animal oil.

[0062] Specific embodiment 9 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to specific embodiment 1, wherein the raw material oil is selected from one or more of the group consisting of sunflower oil (including high oleic sunflower oil), medium chain triglyceride, coconut oil, flaxseed oil, anhydrous butter, palm kernel oil, DHA algal oil, fish oil, walnut oil, camellia oil, perilla seed oil, sea buckthorn seed oil, avocado oil, wheat germ oil, black currant seed oil, borage oil, eucommia seed oil, evening primrose oil, soybean oil, rapeseed oil (including low erucic rapeseed oil), corn oil, peanut oil, safflower seed oil, palm oil, rice bran oil, sesame oil, gamma-linolenic acid oil, tomato seed oil, peony seed oil, krill oil, king's delight seed oil, babassu oil, milk thistle seed oil, conjugated linoleic acid, MCT oil, and shea oil, etc.

[0063] Specific embodiment 10 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to specific embodiment 9, wherein the sunflower oil is high oleic sunflower oil.

[0064] Specific embodiment 11 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to specific embodiment 1, wherein the step (1) comprises:

[0065] mixing the egg yolk phospholipid and the raw material oil to obtain a premix, and then mixing the premix with the OPO-containing triglyceride to obtain the dispersion.

[0066] Specific embodiment 12 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to specific embodiment 11, wherein the raw material oil contains high oleic sunflower oil.

[0067] Specific embodiment 13 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to specific embodiment 1, wherein the weight of the egg yolk phospholipid accounts for 5%-10% of the total weight of the nutritional oil.

[0068] Specific embodiment 14 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to specific embodiment 1, wherein the weight of the OPO-containing triglyceride accounts for 54%-90% of the total weight of the nutritional oil.

[0069] Specific embodiment 15 is the method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to specific embodiment 1, further comprising the following steps:

[0070] (3) subjecting the product of step (2) to a microfiltration treatment.

[0071] Embodiment 16 is a nutritional oil comprising egg yolk phospholipids and 1,3-dioleic-2-palmitic triglyceride, which is prepared according to the method of any one of embodiments 1-15.

[0072] Embodiment 17 is the nutritional oil comprising egg yolk phospholipids and 1,3-dioleic-2-palmitic triglyceride according to embodiment 16, wherein the nutritional oil comprises at least 0.05 g / 100 g of phospholipid-bound arachidonic acid (ARA) and at least 0.03 g / 100 g of phospholipid-bound docosahexaenoic acid (DHA).

[0073] The application will be described in more detail below with reference to the following examples. It should be noted that these descriptions and examples are intended to make the application more easily understood, and are not intended to limit the scope of the application. The scope of the application is defined by the appended claims.

[0074] Examples

[0075] In the present application, unless otherwise specified, the reagents used are commercially available products, which are used directly without further purification treatment.

[0076] Table 1 List of raw materials

[0077] Table 2 Fatty acid composition in OPO-containing triglycerides

[0078] Test methods

[0079] The nutritional oils prepared in the following examples and comparative examples were respectively tested for homogeneity and oiliness according to the test methods described below.

[0080] Test for homogeneity

[0081] 300 g of the nutritional oil prepared in each of the following examples and comparative examples was respectively taken and added into a 500 mL beaker. The sample was left standing at room temperature in the dark for 24 hours, and then its homogeneity was judged by observing the appearance of the sample.

[0082] The observation data came from ten evaluators in the field of nutritional oil production, who respectively observed the appearance of the samples by naked eye and scored on the following criteria:

[0083] 9-10 points: completely mixed and uniform;

[0084] 7-8 points: mostly mixed and uniform;

[0085] 5-6 points: a small amount of sediment;

[0086] 3-4 points: a large amount of sediment; and

[0087] 1-2 points: complete sedimentation.

[0088] Finally, the average score of the ten evaluators is taken as the evaluation score of the sample. Since sedimentation occurs in the sample, samples with less than 7 points are not suitable as nutritional oil products.

[0089] Test on oiliness

[0090] The "oiliness" of the OPO nutritional oil refers to the uniform state of the oil after it is heated and melted from a solid state at room temperature.

[0091] Specifically, 300 g of each of the nutritional oils prepared in the examples and comparative examples was taken and added to a 500 mL beaker. The sample was left to stand at room temperature until it reached room temperature and became solidified. Then, the sample was heated to 60°C to melt it, and then its appearance was observed at 1 hour, 2 hours, and 4 hours, respectively. Subsequently, the sample was cooled to 45°C and left to stand for 24 hours, and its appearance was observed. Finally, the sample at 45°C and left to stand for 24 hours was stirred at a rotation speed of 300 rpm for 1 minute, left to stand for 1 hour, and its appearance was observed again.

[0092] The observation data came from ten evaluators in the field of nutritional oil production, who scored the appearance of the samples on the following standards after observing them with the naked eye:

[0093] 9-10 points: completely mixed and uniform;

[0094] 7-8 points: mostly mixed and uniform;

[0095] 5-6 points: a small amount of sediment;

[0096] 3-4 points: a large amount of sediment; and

[0097] 1-2 points: complete sedimentation.

[0098] Finally, the average score of the ten evaluators is taken as the evaluation score of the sample.

[0099] Example 1 (E1)

[0100] 10 parts by weight of ELIP 3020 and 90 parts by weight of OPO-containing triglyceride were simultaneously added into a high-speed shearing tank (Model T50D, IKA, Germany) and dispersed at 70°C for 3 minutes at a rotation speed of 3000 rpm. Then, the high-speed shearing-treated mixture was transferred into a high-pressure homogenizer (Model PANDA PLUS 2000H, GEA, Germany) and homogenized at 55°C under a pressure of 200 bar for 5 minutes. The high-pressure homogenization-treated mixture was filtered through a microporous filter membrane with a pore size of 3 μm to obtain a nutritional oil 1.

[0101] The nutritional oil 1 was tested for homogeneity and oiliness according to the methods described in detail in the Test Method section above. The results for homogeneity are shown in Table 3 below, and the results for oiliness are shown in Table 4 below.

[0102] Examples 2-6 (E2-E6) and Comparative Examples 1-12 (CE1-CE12)

[0103] Examples 2-6 and Comparative Examples 1-12 were carried out in a similar manner to Example 1, except that the types of the individual raw materials and their ratios, the process conditions for shearing treatment, or the process conditions for homogenization treatment were changed as described in Table 3, to prepare nutritional oils 2-6 and comparative nutritional oils 1-12.

[0104] The nutritional oils 2-6 and comparative nutritional oils 1-12 were tested for homogeneity and oiliness, respectively, according to the methods described in detail in the Test Method section above. The results for homogeneity are shown in Table 3 below, and the results for oiliness are shown in Table 4 below.

[0105] Table 4 Oiliness test results of the nutritional oils of Examples 1-6 (E1-E6) and Comparative Examples 1-12 (CE1-CE12)

[0106] As can be seen from the results in Table 3 above, the nutritional oils containing egg yolk phospholipid and 1,3-dioleic-2-palmitic triglyceride prepared according to the technical solution of the present application have good homogeneity and remain in a good dispersed state after standing at room temperature for 24 hours.

[0107] In addition, as can be seen from the results in Table 4 above, the nutritional oils prepared according to Examples 1-6 of the technical solution of the present application have much superior oiliness performance compared to Comparative Examples 1-12.

[0108] It is known from the comparison of the data in Tables 3 and 4 that the specific weight ratio of egg yolk phospholipid to OPO-containing triglyceride and the specific dispersion process, including high shear treatment and high pressure homogenization under specific conditions, are essential for obtaining a nutritional oil containing egg yolk phospholipid and OPO with good homogeneity and oiliness. When the conditions defined in the present application with respect to the raw material ratio and the dispersion process are not met, a nutritional oil containing egg yolk phospholipid and OPO that meets the application requirements cannot be obtained.

[0109] While specific embodiments of the application have been shown and described herein, it is understood that various alternatives and / or equivalents can be used in place of the specific embodiments shown and described herein without departing from the scope of the application. The application intended to include any modifications or alterations to the specific embodiments discussed herein. It is understood that various modifications and changes can be made without departing from the scope of the present application. Such modifications and changes are intended to fall within the scope of the application as defined by the appended claims.

Claims

1. A method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride (OPO), the method comprising the steps of: (1) mixing egg yolk phospholipid, OPO-containing triglyceride and a raw material oil to obtain a dispersion, wherein the weight ratio of egg yolk phospholipid to the OPO-containing triglyceride is in the range of 1:20 to 1:4; and (2) sequentially subjecting the dispersion to shear treatment and homogenization treatment, wherein the shear treatment comprises shearing the dispersion at a rotation speed of 3000-5000 rpm under heating, and the homogenization treatment comprises homogenizing the sheared dispersion under heating at a pressure of 200-300 bar, wherein the proportion of 2-position palmitic acid in the total palmitic acid in the OPO-containing triglyceride is at least 52%, and the content of OPO is at least 40% by weight.

2. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein the weight ratio of egg yolk phospholipid to the OPO-containing triglyceride is in the range of 1:19 to 1:

5.

3. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein in step (2), the shear treatment is performed at a temperature in the range of 55°C-70°C.

4. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein in step (2), the shear treatment is performed for 3-5 minutes.

5. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein in step (2), the homogenization treatment is performed at a temperature in the range of 55°C-70°C.

6. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein in step (2), the homogenization treatment is performed for 5-10 minutes.

7. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein the sum of the weights of egg yolk phospholipid and the OPO-containing triglyceride accounts for 60%-95% of the total weight of the nutritional oil.

8. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein the raw material oil is selected from one or more of a plant oil or an animal oil. ​ ​ ​ 9. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein the raw material oil is selected from one or more of the group consisting of sunflower oil, medium chain triglyceride, coconut oil, flaxseed oil, anhydrous butter, palm kernel oil, DHA algal oil, fish oil, walnut oil, camellia oil, perilla seed oil, sea buckthorn seed oil, avocado oil, wheat germ oil, black currant seed oil, borage oil, eucommia seed oil, evening primrose oil, soybean oil, rapeseed oil, corn oil, peanut oil, safflower seed oil, palm oil, rice bran oil, sesame oil, gamma-linolenic acid oil, tomato seed oil, peony seed oil, krill oil, king's delight seed oil, milk thistle seed oil, conjugated linoleic acid, MCT oil, and shea oil.

10. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 9, wherein the sunflower oil is high-oleic sunflower oil.

11. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein the step (1) comprises: mixing the egg yolk phospholipid and the raw material oil to obtain a premix, and then mixing the premix with the OPO-containing triglyceride to obtain the dispersion.

12. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 11, wherein the raw material oil contains high-oleic sunflower oil.

13. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein the weight of the egg yolk phospholipid accounts for 5-10% of the total weight of the nutritional oil.

14. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein the weight of the OPO-containing triglyceride accounts for 30-90% of the total weight of the nutritional oil.

15. The method for preparing a nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 1, further comprising the following step: (3) subjecting the product of step (2) to microfiltration treatment.

16. A nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride, which is prepared according to the method of any one of claims 1-15.

17. The nutritional oil containing egg yolk phospholipid and 1,3-dioleoyl-2-palmitoyl triglyceride according to claim 16, wherein the nutritional oil contains at least 0.05 g / 100 g of phospholipid-bound arachidonic acid (ARA) and at least 0.03 g / 100 g of phospholipid-bound docosahexaenoic acid (DHA).

Citation Information

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