Oil encapsulated in a natural plant-based material

Abstract

Encapsulated oil particles are provided herein, and the oil is encapsulated by a composition containing oatmeal. Also provided herein is a method of making encapsulated oil particles, the method comprising combining oatmeal and oil to form a first composition, mixing the first composition, homogenizing the mixed first composition to produce a second composition, and spray drying the second composition to produce encapsulated oil particles. Further provided are foods, food products (e.g., powdered milk for infants), or nutritional supplements containing the encapsulated oil particles.

Description

Technical Field

[0001] Cross - Reference to Related Applications This application claims priority to U.S. Provisional Application No. 63 / 352,190, filed on June 14, 2022, the entire content of which is incorporated herein by reference.

Background Art

[0002] Oils rich in essential fatty acids such as docosahexaenoic acid ("DHA") and eicosapentaenoic acid ("EPA") are prone to oxidation, producing aldehydes and other oxidation products that result in unpleasant tastes or odors. Thus, this oxidation affects the use of lipids and oils in foods, beverages, and nutritional supplements. It is necessary to avoid oxidation to extend the shelf life of oils or products containing oils.

Summary of the Invention

[0003] Encapsulated oil particles containing oil encapsulated by a plant - based composition containing oat flour such as hydrolyzed oat flour are provided herein. The composition containing oat flour may also contain fatty acids selected from the group consisting of alpha - linolenic acid, arachidonic acid, docosahexaenoic acid, docosapentaenoic acid, eicosapentaenoic acid, gamma - linolenic acid, linoleic acid, and any combination thereof. The oat flour may contain fatty acids, cholesterol, carbohydrates, ash, protein, calcium, sodium, potassium, and iron.

[0004] Optionally, the encapsulated oil contains up to 50% oil. The encapsulated oil particles may contain microbial oil, plant-based oil, fish oil, or any combination thereof. Optionally, the oil contains omega-3 fatty acids and / or triglycerides. The fatty acids can be selected from the group consisting of palmitic acid (C16:0), myristic acid (C14:0), palmitoleic acid (C16:1(n-7)), cis-vaccenic acid (C18:1(n-7)), docosapentaenoic acid (C22:5(n-6)), docosahexaenoic acid (C22:6(n-3)), and combinations thereof. Optionally, the oil contains fatty acids in ethyl ester form. The encapsulated oil containing fatty acids may contain less than 35% saturated fatty acids. Optionally, 10-30% of the fatty acids are omega-7 fatty acids, and more than 37% of the fatty acids are docosahexaenoic acid (DHA). The saturated fatty acids contained in the encapsulated oil can be myristic acid, palmitic acid, or a combination thereof. Optionally, 8-12% of the fatty acids are myristic acid. Optionally, 14-22% of the fatty acids are palmitic acid. The saturated fatty acids may contain less than 2% lauric acid, or pentadecanoic acid, margaric acid, stearic acid, or any combination thereof. Optionally, in the encapsulated oil, more than 95% of the triglycerides are composed of myristic acid (C14:0), palmitic acid (C16:0), docosapentaenoic acid n-6 (C22:5n-6, DPAn6), and docosahexaenoic acid (C22:6n-3, DHA). Optionally, the encapsulated oil contains less than 3% of each of lauric acid (C12:0), pentadecanoic acid (C15:0), palmitoleic acid (C16:1), margaric acid (C17:0), stearic acid (C18:0), vaccenic acid (C18:1n-7), oleic acid (C18:1n-9), gamma-linolenic acid (C18:3n-6), alpha-linolenic acid (C18:3n-3), stearidonic acid (C18:4), arachidic acid (C20:0), dihomo-gamma-linolenic acid (C20:3n-6), arachidonic acid (C20:4n-6, ARA), eicosapentaenoic acid (C20:5n-3, EPA), behenic acid (C22:0), docosatetraenoic acid (C22:4), docosapentaenoic acid n3 (C22:5n-3, DPAn3), and lignoceric acid (C24:0).Optionally, the oil contains less than 0.02% short-chain fatty acids. Optionally, the oil contains at least 35% C22:6n-3 (DHA) of the total fatty acids.

[0005] The encapsulated oil particles may also contain an emulsifier. The emulsifier can be, for example, a quillaja extract, lecithin, monoglyceride, diglyceride, polysorbate, gum, and protein. Both animal proteins such as those derived from milk and eggs, as well as plant-based proteins such as those derived from soy, wheat, pea, potato, oats and barley, or combinations thereof can be used for their emulsifying ability. Optionally, the emulsifier is an oat-based protein. Optionally, the emulsifier is located inside the encapsulation layer.

[0006] Compositions containing a plurality of encapsulated oil particles are provided herein. Optionally, at least 50% of the encapsulated oil particles in the composition have a diameter of less than 1 micron.

[0007] A method for producing encapsulated oil particles is also provided herein. The method includes combining oat flour and oil, and optionally other ingredients, to form a first composition, mixing the first composition, homogenizing the mixed first composition to produce a second composition, and spray drying the second composition to produce encapsulated oil particles. The mixing step optionally includes mechanical mixing such as high-shear mixing. High-shear mixing is optionally carried out at 5,000 - 15,000 rpm for 1 - 5 minutes (e.g., at 14,000 rpm for 3 minutes). Homogenization is optionally carried out at 2K - 5K psi using a microfluidizer. Optionally, the homogenization step is repeated at least twice before spray drying. Spray drying can be carried out in the presence of a gas (e.g., nitrogen) or with normal air.

Brief Description of the Drawings

[0008]

Figure 1

Figure 2

DETAILED DESCRIPTION OF THE INVENTION

[0009] Oils containing unsaturated fatty acids, particularly long-chain fatty acids, are prone to oxidation, which can result in unacceptable flavor and odor changes in the oil. Microencapsulation of oil droplets to form encapsulated oil particles can be used to reduce the oxidation of fatty acids in oils such as fish oil or microbial oil. Microencapsulation is a process in which small particles or droplets of a main component (e.g., oil) are surrounded by a coating material or embedded in a homogeneous or heterogeneous substrate, conventionally a polymeric material, to obtain small particles in a size range from submicron to several millimeters. Studies in Natural Products Chemistry: Volume 37. (eBook, 2012). Conventionally, microencapsulated oil particles are prepared using highly purified components such as maltodextrin or modified starch, or materials derived from genetically engineered microorganisms (such as corn-based starch). However, such materials typically contain high sugar content animal products (such as gelatin) or allergens (such as dairy products). In contrast, the disclosed encapsulated oil particles include a plant-based substrate (e.g., oat flour) that reduces or eliminates the sugar content, animal products, and allergens in the resulting encapsulated oil particles.

[0010] Encapsulated oil particles The encapsulated oil particles disclosed in this specification contain oil and a plant-based encapsulating material. Optionally, the composition containing oatmeal may also contain an oil-soluble nutrient selected from the group consisting of vitamin A, vitamin D, vitamin E, vitamin K, lycopene, coenzyme Q-10, and astaxanthin. Optionally, the particles further contain an emulsifier. Optionally, the encapsulated oil is rich in fatty acids. A fatty acid is a hydrocarbon chain terminated with a carboxyl group. An unsaturated fatty acid contains at least one carbon-carbon double bond, while an unsaturated fatty acid contains a plurality of carbon-carbon double bonds. Fatty acids include short-chain fatty acids (SCFAs) that are fatty acids having an aliphatic end of less than 6 carbons (e.g., butyric acid); medium-chain fatty acids (MCFAs) that are fatty acids having an aliphatic end of 6 to 12 carbons; long-chain fatty acids (LCFAs) that are fatty acids having an aliphatic end of 13 to 21 carbons; and very-long-chain fatty acids (VLCFAs) that are fatty acids having an aliphatic end longer than 22 carbons. Examples of long-chain fatty acids (LCFAs) include, but are not limited to, myristate (C14:0), palmitic acid (C16:0), docosapentaenoic acid n-6 (C22:5n-6, DPA n6), docosahexaenoic acid (C22:6n-3, DHA), lauric acid (C12:0), pentadecanoic acid (C15:0), palmitoleic acid (C16:1), margaric acid (C17:0), stearic acid (C18:0), vaccenic acid (C18:1n-7), oleic acid (C18:1n-9), gamma-linolenic acid (C18:3n-6), alpha-linolenic acid (C18:3n-3), stearidonic acid (C18:4), arachidic acid (C20:0), dihomo-gamma-linolenic acid (C20:3n-6), arachidonic acid (C20:4n-6, ARA), eicosapentaenoic acid (C20:5n-3, EPA), behenic acid (C22:0), docosatetraenoic acid (C22:4), docosapentaenoic acid n3 (C22:5n-3, DPA n3), and lignoceric acid (C24:0).

[0011] The oil may be fish oil, microbial oil, vegetable oil, or other oil that can be metabolized in the body of a human or non-human subject. Examples of non-human subjects include fish, livestock (e.g., cows, chickens, sheep), and domesticated animals (e.g., cats, dogs, guinea pigs, mice, etc.).

[0012] The fish oil for encapsulation can be selected from those rich in omega-3 fatty acid content. Examples of fish particularly rich in these oils include mackerel, herring, tuna, and salmon.

[0013] Vegetable oils can be derived from raw materials such as nuts, seeds, and grains. Exemplary vegetable oils for encapsulation include peanut oil, canola oil, soybean oil, coconut oil, olive oil, safflower oil, cottonseed oil, sunflower oil, sesame oil, grape seed oil, palm oil, and corn oil.

[0014] As the microbial oil described in this specification, there may be mentioned oils derived from single-celled organisms that grow naturally in an aquatic or terrestrial environment, or their laboratory types. Such organisms can be eukaryotic or prokaryotic microalgae. The microalgae can be selected from the genus Schizochytrium, Oblongichytrium, Aurantiochytrium, and Ulkenia, or any mixture thereof. Optionally, the microorganism is a thraustochytrid of the order Thraustochytriales, more specifically, Thraustochytriales of the genus Thraustochytrium. Exemplary microorganisms include Thraustochytriales as described in U.S. Pat. Nos. 5,340,594 and 5,340,742 (which are incorporated herein by reference in their entirety). The microorganism can be a Thraustochytrium species, for example, a Thraustochytrium species deposited as ATCC Accession No. PTA-6245 (i.e., T18) as described in U.S. Pat. No. 8,163,515 (which is incorporated herein by reference in its entirety). Thus, optionally, the microorganism is of the family Thraustochytriaceae. Optionally, the microorganism is of the genus Thraustochytrium. Optionally, the microorganism is T18 deposited at the ATCC as PTA-6245. The oil can also be produced as described in U.S. Pat. Nos. 10,385,370 and 11,198,891 (which are incorporated herein by reference in their entirety).

[0015] Optionally, the oil is derived from the G3 strain of thraustochytrid, particularly of the genus Aurantiochytrium, deposited with the International Depositary Authority of Canada (IDAC) and assigned accession number 220716-01. The G3 strain can accumulate a significant amount of biomass in a shorter time than other thraustochytrids. Further, the G3-1 strain can accumulate a high concentration of oil rich in docosahexaenoic acid (DHA) and palmitic acid (C16:0). Also, the G3 strain can accumulate protein up to a level that constitutes about 30% of its biomass dry weight. In summary, the G3 strain produces biomass rich in DHA, palmitic acid, and protein in a short time. The G3 strain can be cultivated and cultured as described in U.S. Patent No. 11,198,891, which is hereby incorporated by reference in its entirety.

[0016] The term "thraustochytrid", as used herein, refers to any member of the order Thraustochytriales, including the family Thraustochytriaceae. Strains described as thraustochytrids include the following organisms: the order Thraustochytriales; the family Thraustochytriaceae, the genus Thraustochytrium (species: sp., arudimentale, aureum, benthicola, globosum, kinnei, motivum, multirudimentale, pachydermum, proliferum, roseum, striatum), the genus Ulkenia (species: sp., amoeboidea, kerguelensis, minuta, profunda, radiate, sailens, sakariana, schizochytrops, visurgensis, yorkensis), the genus Schizochytrium (species: sp., aggregatum, limnaceum, mangrovei, minutum, octosporuni), the genus Japoniochytrium (species: sp., marinum), the genus Aplanochytrium (species: sp., haliotidis, kerguelensis, profunda, stocchinoi), the genus Althornia (species: sp., crouchii), or the genus Elina (species: sp., marisalba, sinorifica). The species described in Ulkenia are considered members of the genus Thraustochytrium. Strains described as being within the genus Thraustochytrium may share characteristics common to the genus Schizochytrium and may also be described as belonging to the genus Schizochytrium. For example, in some taxonomic classifications, T18 may be considered to be within the genus Thraustochytrium because it includes characteristics representative of both genera, while in other classifications, it may be described as being within the genus Schizochytrium.

[0017] The oil of the encapsulated oil may contain fatty acids selected from the group consisting of alpha-linolenic acid, arachidonic acid, docosahexaenoic acid (DHA) (C22:6(n-3)), docosapentaenoic acid C22:5(n-6)), eicosapentaenoic acid, gamma-linolenic acid, linoleic acid, and any combination thereof. Optionally, 30-35% of the total fatty acids in the encapsulated oil are DHA. Optionally, the oil contains triglycerides (i.e., molecules composed of three fatty acids covalently bonded to a glyceride molecule). The encapsulated oil may further contain fatty acids selected from the group consisting of palmitic acid (C16:0), myristic acid (C14:0), palmitoleic acid (C16:1(n-7)), vaccenic acid (C18:1(n-9)), cis-vaccenic acid (C18:1(n-7)), and combinations thereof. Optionally, the oil contains one or more fatty acids in ethyl ester form. The encapsulated oil may contain saturated fatty acids, where the saturated fatty acids are myristic acid, palmitic acid, or a combination thereof. Optionally, 8-12% of the fatty acids are myristic acid. Optionally, 14-22% of the fatty acids are palmitic acid. Optionally, the saturated fatty acids contain less than 2% lauric acid, or pentadecanoic acid, margaric acid, stearic acid, or any combination thereof.

[0018] The encapsulated oil may contain less than 35% saturated fatty acids, where 10 - 30% of the fatty acids are omega-7 fatty acids and more than 37% of the fatty acids are docosahexaenoic acid (DHA). Examples of omega-7 fatty acids include, for example, palmitoleic acid (C16:1(n-7)), cis-vaccenic acid (C18:1(n-7)), or combinations thereof. The oil encapsulated by the composition may optionally contain 30 - 35%, 25 - 35%, 25 - 30%, 20 - 30%, 20 - 25%, 15 - 25%, 15 - 20%, 10 - 20%, 10 - 15%, 5 - 15%, 5 - 10%, or less than 5% saturated fatty acids. In one approach, the oil encapsulated by a composition containing oatmeal may further contain 37 - 40%, 37 - 45%, 40 - 50%, 45 - 55%, 50 - 60%, 55 - 65%, 60 - 70%, 65 - 75%, 70 - 80%, 75 - 85%, 80 - 90%, 85 - 95%, or more DHA. Optionally, in the encapsulated oil, more than 95 - 99% of the triglycerides are composed of myristic acid (C14:0), palmitic acid (C16:0), docosapentaenoic acid n-6 (C22:5n-6, DPAn6), and docosahexaenoic acid (C22:6n-3, DHA).

[0019] The encapsulated oil may contain less than 3% each of lauric acid (C12:0), pentadecanoic acid (C15:0), palmitoleic acid (C16:1), margaric acid (C17:0), stearic acid (C18:0), vaccenic acid (C18:1n-7), oleic acid (C18:1n-9), gamma-linolenic acid (C18:3n-6), alpha-linolenic acid (C18:3n-3), stearidonic acid (C18:4), arachidic acid (C20:0), dihomo-gamma-linolenic acid (C20:3n-6), arachidonic acid (C20:4n-6, ARA), eicosapentaenoic acid (C20:5n-3, EPA), behenic acid (C22:0), docosatetraenoic acid (C22:4), docosapentaenoic acid n3 (C22:5n-3, DPAn3), and lignoceric acid (C24:0). Optionally, the oil contains less than 2% each of lauric acid (C12:0), pentadecanoic acid (C15:0), palmitoleic acid (C16:1), margaric acid (C17:0), stearic acid (C18:0), vaccenic acid (C18:1n-7), oleic acid (C18:1n-9), gamma-linolenic acid (C18:3n-6), alpha-linolenic acid (C18:3n-3), stearidonic acid (C18:4), arachidic acid (C20:0), dihomo-gamma-linolenic acid (C20:3n-6), arachidonic acid (C20:4n-6, ARA), eicosapentaenoic acid (C20:5n-3, EPA), behenic acid (C22:0), docosatetraenoic acid (C22:4), docosapentaenoic acid n3 (C22:5n-3, DPAn3), and lignoceric acid (C24:0). Optionally, the oil contains less than 1% each of lauric acid (C12:0), pentadecanoic acid (C15:0), palmitoleic acid (C16:1), margaric acid (C17:0), stearic acid (C18:0), vaccenic acid (C18:1n-7), oleic acid (C18:1n-9), gamma-linolenic acid (C18:3n-6), alpha-linolenic acid (C18:3n-3), stearidonic acid (C18:4), arachidic acid (C20:0), dihomo-gamma-linolenic acid (C20:3n-6), arachidonic acid (C20:4n-6, ARA), eicosapentaenoic acid (C20:5n-3, EPA), behenic acid (C22:0), docosatetraenoic acid (C22:4), docosapentaenoic acid n3 (C22:5n-3, DPAn3), and lignoceric acid (C24:0).

[0020] The encapsulated substrate is a plant-based material. As an example, the plant-based material is, optionally, oat flour that contains little allergen. Oat flour is also less expensive than encapsulating materials such as rubber. Oat flour requires only minimal processing. Oats are processed in an oven and dehulled to produce powder. Optionally, the oat flour is hydrolyzed.

[0021] Oat flour naturally contains vitamin E, phenolic compounds (e.g., ester-linked glycerol complexes, ester-linked alkyl complexes, ethers and ester-linked glycerides, anthranilic acid and avenanthramide), and polar lipids, which provide emulsifying ability and prevent oxidation of oil. Phenolic compounds have antioxidant activity like other antioxidants present in oat flour, such as tocopherol, L-ascorbic acid, thiol, and phenolic amino acids. However, most of the antioxidants in oat flour are bound to proteins or carbohydrates. Enzymes present in oats, such as amylase, can convert carbohydrates to sugars and release bound phenolic compounds from oats into the medium. Furthermore, both water solubility and emulsifying ability are significantly improved after hydrolysis of oats.

[0022] The oat flour used for encapsulation of oil is, optionally, hydrolyzed. The hydrolyzed oat flour may contain fatty acids, cholesterol, carbohydrates, ash, protein, calcium, sodium, potassium, and iron. Optionally, the hydrolyzed oat flour contains 5 - 10% fatty acids. Optionally, the hydrolyzed oat flour contains 70 - 75% carbohydrates. The hydrolyzed oat flour may contain 10 - 15% protein.

[0023] In addition to the oil and plant-based encapsulating material, the encapsulated oil particles optionally further comprise an emulsifier. Such an emulsifier is a non-heterologous emulsifier (i.e., an emulsifier that does not naturally occur in the plant-based encapsulating material) added to a mixture of the oil and the plant-based encapsulating material (e.g., oatmeal) to facilitate suspension or miscibility of the oil in the plant-based encapsulating material. The emulsifier can be selected from the group consisting of quillaia extract, lecithin, monoglycerides, diglycerides, polysorbates, gums, and proteins. The emulsifier can be further selected from the group consisting of mono- and diglycerides, fatty acid derivatives such as polyglycerol esters (PGE), propylene glycol esters (PGMS), stearoyl lactylates, sucrose esters, sorbitan esters, polysorbates, lecithin extracted from egg yolk, or vegetable oils such as soybean oil, sunflower oil, and canola oil.

[0024] Generally, an "emulsion" as used herein refers to a substance containing both a dispersed phase and a continuous phase. In many cases, the emulsion is either an oil suspended in an aqueous phase (o / w) or water suspended in an oil (w / o). An emulsifier is amphiphilic and contains a water-soluble head and an oil-soluble tail, whereby the emulsifier can bind to both polar and nonpolar compounds to achieve a stable emulsion. When added to an o / w emulsion, the emulsifier orientates such that the nonpolar tail extends into the oil while the polar head faces the water. Due to their amphiphilic nature, proteins make good emulsifiers. Proteins can stabilize an emulsion by adsorbing at the interface, coating the oil or air droplets, and forming a stable film. Both animal proteins such as those derived from milk and eggs, as well as plant-based proteins such as those derived from soy, wheat, peas, and potatoes, oats, and barley can be used with respect to their emulsifying ability.

[0025] Composition of Encapsulated Oil Particles Compositions containing oil particles are further disclosed herein. Compositions containing a plurality of encapsulated oil particles can be in powder form. Optionally, 50% of the encapsulated oil particles in the powder composition have a diameter of less than 1 micron, and the oil constitutes up to 50% of the powder composition. For example, the oil can be 0.001% - 50%, 1% - 50%, 5% - 50%, 10% - 50%, 20% - 50%, 25% - 50%, 30% - 50% or 40% - 50% of the powder composition. The encapsulated oil droplets in the composition can have a diameter of 0.4 - 100 μm.

[0026] The powder composition containing encapsulated oil particles can be mixed with other dry ingredients or liquid ingredients. The powder containing oil encapsulated in oatmeal is white to light brown and has a characteristic "oat - like" or neutral taste and aroma.

[0027] The powder can be used in a wide range of dry products (such as protein mixes, dry specially - prepared powdered milk, dry milk, dry cereals or grains, etc.). The powder can be mixed with a liquid or other diluent to produce confectioneries (such as chocolate, gummies, candies, jelly, and biscuits), beverages (such as milk, sports drinks, nutritional drinks, tea, smoothies, and juices), dairy products (such as yogurt), cereals and grains (such as porridge, oatmeal, and infant cereals), and nutritional supplements (such as vitamin or mineral products, medicinal plant products, amino acid products, and enzyme supplements).

[0028] The powder can be used in animal feed. Examples of animal feed include pet food (such as cat, dog, guinea pig, and hamster feed), fish feed (such as aquarium fish, cultured fish or crustaceans, farmed fish or crustaceans), and livestock (such as cows, sheep, goats, chickens, ducks, etc.). Such feed incorporated with the encapsulating material is designed to be palatable to the organism and provide the necessary nutrients.

[0029] The powder can be incorporated into nutritional supplements or pharmaceutical products. Examples of nutritional supplements or pharmaceutical products include various types of tablets, capsules, drinks, and the like.

[0030] Foods can be manufactured by methods known in the art. As an example, extrusion technology can be used to produce cereals, including breakfast cereals. Through the extrusion process, a mixture of grains, starch, sugar, and other ingredients is converted into the shape and texture of cereal. This technology involves forcing the cereal dough through a dedicated machine called an extruder that utilizes heat, pressure, and mechanical shear forces to cook the mixture and shape it into various forms such as flakes, loops, or puffs. The parameters of the extruder, including temperature, water content, and screw speed, are adjusted to achieve desired product attributes such as crunchiness, flavor, and appearance. Extrusion technology enables the efficient mass production of cereals, including breakfast cereals, ensures quality uniformity, and allows for a wide range of flavor options to satisfy diverse tastes and consumer preferences worldwide. The extrusion method is known to those skilled in the art and is described, for example, in Choton, et al., “Extrusion technology and its application in food processing: A review” The Pharma Innovation 9(2):162 - 68(2020), and Alam et al., “Extrusion and Extruded Products: Changes in Quality Attributes as Affected by Extrusion Process Parameters: A Review,” Critical Reviews in Food Science and Nutrition 56:3 445 - 73(2016), the entireties of which are incorporated herein by reference.

[0031] Method for producing encapsulated oil particles A method for producing encapsulated oil particles is provided herein, the method comprising combining a plant-based encapsulating material (e.g., oatmeal) and oil to form a first composition, mixing the first composition, homogenizing the mixed first composition to produce a second composition, and spray drying the second composition to produce encapsulated oil particles. The oatmeal is optionally hydrolyzed oatmeal. Hydrolyzed oatmeal can be produced, for example, by hydrating oats with water while stirring. The method optionally further comprises adding an emulsifier to the oil and oatmeal before or during mixing. Mixing the first composition can be carried out using mechanical forces such as high-shear mixing at 5,000 to 15,000 rpm for 1 to 5 minutes. Alternatively, the first composition can be carried out using mechanical forces at 5,000 to 20,000 rpm for 1 to 5 minutes. By way of example, high-shear mixing can be carried out at 14,000 rpm for 3 minutes, at greater than 15,000 rpm for less than 1 minute, at 15,000 or 20,000 rpm or less for 1 minute, at 15,000 or 20,000 rpm or less for 2 minutes, at 15,000 or 20,000 rpm or less for 3 minutes, at 15,000 or 20,000 rpm or less for 4 minutes, at 15,000 or 20,000 rpm or less for 5 minutes.

[0032] Homogenization is optionally carried out, for example, at 1,000 to 30,000 psi using a microfluidization device. Optionally, homogenization is carried out at 2,000 to 5,000 psi. By way of example, homogenization can be carried out at 2,000 to 3,000 psi, 2,000 to 4,000 psi, 3,000 to 4,000 psi, 3,000 to 5,000 psi, or 4,000 to 5,000 psi. Optionally, the homogenization step is repeated at least 2 times before spray drying, for example, 3, 4, or 5 times.

[0033] Next, the homogenized suspension is spray dried. Conventional spray drying is carried out at high heat and high oxygen levels to remove moisture. However, the spray drying process used herein is carried out at a lower temperature to avoid oxidation caused by high heat and high oxygen levels. The spray drying of the present method is carried out, for example, at a gas flow rate of 30 Nm 3 / hour. The spray drying can be carried out in the absence of oxygen or in a low oxygen atmosphere. Optionally, the spray drying is carried out under nitrogen. The resulting spray dried particles are optionally less than 5% moisture, less than 4% moisture, less than 3% moisture, less than 2% moisture, or less than 1% moisture.

[0034] Materials, compositions, and components are disclosed that can be used for, or in combination with, the disclosed methods and compositions, can be used in their preparation, or are products thereof. These and other materials are disclosed herein, and while specific mention of each and every individual and collective combination and permutation of these compounds may not be explicitly disclosed when combinations, subsets, interactions, groups, etc. of these materials are disclosed, it is to be understood that each is specifically contemplated and described herein. For example, if a method is disclosed and discussed and numerous modifications that can be made to a number of molecules including this method are discussed, each and every combination and permutation of this method, as well as possible modifications, are specifically contemplated unless specifically indicated to the contrary. Similarly, any subset or combination of these is also specifically contemplated and disclosed. This concept applies to all aspects of the present disclosure including, but not limited to, steps in methods using the disclosed compositions. Thus, if there are a variety of additional steps that can be carried out, each of these additional steps can be carried out with any specific method step or combination of method steps of the disclosed method, and each such combination or subset of combinations is to be specifically contemplated and considered disclosed.

[0035] Publications cited in this specification and the materials in which they are cited are hereby incorporated by reference in their entirety specifically into this specification.

Examples

[0036] The following examples are intended to further illustrate specific aspects of the methods and compositions described in this specification and are not intended to limit the scope of the claims.

[0037] Example 1: Materials and Methods Hydrolyzed oat flour was used as the encapsulation material, quillaja extract was used as the emulsifier, and algal oil containing 530 mg / g of DHA was used as the main component. The typical nutritional values of oat flour per 100 grams are as follows: Energy (kJ) = 1770 ± 354; Energy (kcal) = 419 ± 83.8; Fat (g) = 6.5 ± 1.3 (of which saturates (g) = 1.0, polyunsaturated fat (g) = 2.3, monounsaturated fat (g) = 1.9, trans fatty acids (g) = <0.01, Cholesterol (mg) = <0.5; Total carbohydrates (g) = 76.7 ± 15.3 (of which sugars (g) = 4 - 6.0, dietary fiber (g) = 5.1 - 7.7, beta-glucan (g) = 3.3 - 5.0; Ash (g) = 1.3 - 2.0; Protein = currently (N × 6.25) 11.0; Calcium (mg) = 70.5; Sodium (mg) = 8.2; Potassium (mg) = 330; and Iron (mg) = 3.3.

[0038] The oat flour was hydrated by stirring in water for about 2 hours. After hydration of the oat flour, the oat flour was sieved through a 170 mesh screen. The remaining ingredients were added slowly with stirring. After adding the remaining ingredients, the mixture was high-shear mixed at 14,000 rpm for 3 minutes. Next, the suspension was homogenized using a microfluidizer at 3,000 psi in one pass. Next, the emulsion was spray-dried at a gas flow rate of 30 nm 3 / hour, an inlet temperature of 110 °C, and an outlet temperature of 54 °C.

[0039] The volume measurement distributions of the oil droplet size and the particle size were analyzed. The powder morphology was evaluated using a scanning electron microscope. Table 1 below shows the Dv at 10%, 50%, and 90%, which means the points of the size distribution at which 10%, 50%, or 90% of the total volume of the material in the sample is encapsulated. Thus, Dv90 is 303 μm, meaning that 90% of the sample has a size of about 303 μm or less. Figure 1 shows that the oil droplet size (Dv50) was less than 1 μm. Next, the emulsion was dried to 15% solids, and the powder had a final moisture content of 2.13% and a water activity of 0.12. Overall, the particles had a relatively round shape as shown in the scanning electron micrograph of Figure 2.

Table 1

[0040] Example 2: Feasibility Experiment Algal oil was removed from the freezer and thawed in a water bath. Commercially available hydrolyzed oat flour (Hydrolyzed Oat Flour, Glanbia, Kilkenny, Ireland) was weighed into one or more beakers and hydrated for a minimum of 30 minutes and up to overnight to assist in the filtration process. After hydration, Oat16 was filtered through a 170-mesh sieve. During the filtration process, 1.5 - 2% of the solids were removed. To the filtered solids, 50.9 g of algal oil and 0.8 g of a commercially available antioxidant composition (RPT40, Kemin, Iowa) were added, and the beaker was covered to reduce oxidation. Subsequently, high-shear mixing was performed at 14 Krpm for 3 minutes. Next, using a microfluidizer, the mixture was homogenized at 4000 psi with 2 - 3 passes. After each pass, a small sample was collected for oil droplet size analysis. After obtaining the desired droplet size, spray drying was then carried out. The selected droplet size was less than 1 micron. If the oil droplet size was not achieved, the homogenization process was repeated at 20,000 psi using the microfluidizer while taking care to avoid excessive processing and emulsion breakage. Table 2 shows the components in three batches. In each batch, Q-Naturale® (a commercially available natural emulsifier extracted from quillaja wood) (Ingredion, Westchester, IL).

Table 2

[0041] Example 3: Cereal Containing Encapsulated Oil One of the challenges in incorporating DHA into an extrusion product is maintaining its stability during the extrusion process. DHA is sensitive to heat, oxygen, and light, which can cause a reduction and loss of its nutritional benefits. The high temperature and shear forces associated with extrusion can potentially affect the integrity of DHA.

[0042] As described in this example, encapsulated algal oil was incorporated into breakfast cereal using an extrusion process.

[0043] Encapsulated oil containing oat flour was prepared using the method described herein. Briefly, oat flour, oil, and other ingredients were mixed at 5,000 - 15,000 rpm for 1 - 5 minutes (e.g., at 14,000 rpm for 3 minutes), and then homogenized at 3000 - 5000 PSI. The resulting emulsion was spray-dried at an inlet temperature of 80 - 180 °C and an outlet temperature of 50 - 90 °C to form a powder.

[0044] To prepare breakfast cereal, the encapsulated oil powder was mixed with other dry ingredients (e.g., oat flour, pea starch, etc.), and then extruded using a Clextral EV32 twin-screw extruder at a feed rate of 30 - 31 kg / hour and a temperature in the range of 40 - 115 °C. Samples were collected and packed into nitrogen-flushed bags. A shelf-life study of the extruded cereal was conducted under ambient conditions.

Table 3

[0045] The DHA concentration in the breakfast cereal was 66.52 mg per 30 g serving size of the cereal. After storage at ambient temperature for 6 months, there was no oil deterioration. This example demonstrates that the encapsulated oil particles described herein can be incorporated into foods including breakfast cereal.

[0046] The intensity of seafood or fishy flavor in the cereal was evaluated using a trained sensory panel consisting of 3 sensory testers. For samples containing encapsulated oil powder, no fishy seafood odor was detected by the sensory testers even after storage under ambient conditions for 6 months.

Claims

1. Encapsulated oil particles comprising oil encapsulated by a composition comprising oat flour.

2. The encapsulated oil particles according to claim 1, wherein the oat flour is hydrolyzed oat flour.

3. The encapsulated oil particles according to claim 1 or 2, wherein the oil comprises microbial oil, plant-based oil, fish oil, or any combination thereof.

4. The encapsulated oil particles according to any one of claims 1 to 3, wherein the oil further comprises an oil-soluble nutrient selected from the group consisting of vitamin A, vitamin D, vitamin E, vitamin K, lycopene, coenzyme Q-10, and astaxanthin.

5. The encapsulated oil particles according to any one of claims 1 to 4, wherein the oil comprises omega-3 fatty acids.

6. The encapsulated oil particles according to any one of claims 1 to 5, wherein the oil comprises a fatty acid selected from the group consisting of alpha-linolenic acid, arachidonic acid, docosahexaenoic acid, docosapentaenoic acid, eicosapentaenoic acid, gamma-linolenic acid, linoleic acid, and any combination thereof.

7. The encapsulated oil particles according to any one of claims 1 to 6, wherein the oil comprises triglycerides.

8. The encapsulated oil particles according to any one of claims 1 to 7, wherein the oil comprises a fatty acid selected from the group consisting of palmitic acid (C16:0), myristic acid (C14:0), palmitoleic acid (C16:1(n-7)), cis-vaccenic acid (C18:1(n-7)), docosapentaenoic acid (C22:5(n-6)), docosahexaenoic acid (C22:6(n-3)), and combinations thereof.

9. The encapsulated oil particles according to any one of claims 1 to 8, wherein the oil comprises fatty acids in ethyl ester form.

10. The encapsulated oil particles according to any one of claims 1 to 9, wherein the oil comprises fatty acids, the oil comprises less than 35% saturated fatty acids, 10-30% of the fatty acids are omega-7 fatty acids, and more than 37% of the fatty acids are docosahexaenoic acid (DHA).

11. The encapsulated oil particles according to any one of claims 1 to 10, wherein the oil comprises saturated fatty acids, and the saturated fatty acids are myristic acid, palmitic acid, or a combination thereof.

12. The oil contains fatty acids, and 8 to 12% of the fatty acids are myristic acid. The encapsulated oil particles according to any one of claims 1 to 11.

13. The oil contains fatty acids, and 14 to 22% of the fatty acids are palmitic acid. The encapsulated oil particles according to any one of claims 1 to 12.

14. The saturated fatty acids contain less than 2% of lauric acid, pentadecanoic acid, margaric acid, stearic acid, or any combination thereof. The encapsulated oil particles according to any one of claims 11 to 13.

15. More than 95% of the triglycerides are composed of myristic acid (C14:0), palmitic acid (C16:0), docosapentaenoic acid n-6 (C22:5n-6, DPA n6), and docosahexaenoic acid (C22:6n-3, DHA). The encapsulated oil particles according to claim 7.

16. The oil contains less than 3% of each of lauric acid (C12:0), pentadecanoic acid (C15:0), palmitoleic acid (C16:1), margaric acid (C17:0), stearic acid (C18:0), vaccenic acid (C18:1n-7), oleic acid (C18:1n-9), γ-linolenic acid (C18:3n-6), α-linolenic acid (C18:3n-3), stearidonic acid (C18:4), arachidic acid (C20:0), dihomo-γ-linolenic acid (C20:3n-6), arachidonic acid (C20:4n-6, ARA), eicosapentaenoic acid (C20:5n-3, EPA), behenic acid (C22:0), docosatetraenoic acid (C22:4), docosapentaenoic acid n3 (C22:5n-3, DPA n3), and lignoceric acid (C24:0). The encapsulated oil particles according to any one of claims 1 to 15.

17. The oil contains less than 0.02% of short-chain fatty acids. The encapsulated oil particles according to any one of claims 1 to 16.

18. The oil contains at least 35% of C22:6n-3 (DHA) in the triglycerides in the total fatty acids. The encapsulated oil particles according to any one of claims 1 to 17.

19. The encapsulated oil particles according to any one of claims 1 to 18, further comprising an emulsifier.

20. The emulsifier is selected from the group consisting of quillaia extract, lecithin, monoglyceride, diglyceride, polysorbate, rubber, and protein. The encapsulated oil particles according to claim 21.

21. The hydrolyzed oat flour-containing encapsulated oil particles according to any one of claims 2 to 20, which contain 5 to 10% fatty acids, 10 to 15% proteins, 70 to 75% carbohydrates, cholesterol, ash, calcium, sodium, potassium, and iron.

22. The encapsulated oil particles according to any one of claims 1 to 21, which contain 40 to 50% oil.

23. A composition containing a plurality of encapsulated oil particles according to any one of claims 1 to 22, wherein at least 50% of the encapsulated oil particles have a diameter of less than 1 micron.

24. A method for producing encapsulated oil particles, comprising: (a) combining oat flour and oil to form a first composition; (b) mixing the first composition; (c) homogenizing the mixed first composition to produce a second composition; (d) spray-drying the second composition to produce encapsulated oil particles.

25. The method according to claim 24, wherein the oat flour is hydrolyzed oat flour.

26. The method according to claim 25, wherein the hydrolyzed oat flour is produced by hydrating oats with water while stirring.

27. The method according to any one of claims 24 to 26, wherein step (a) further comprises combining the hydrolyzed oat flour and the oil with an emulsifier.

28. The method according to any one of claims 24 to 27, wherein the mixing in step (b) is mechanical mixing.

29. The method according to claim 28, wherein the mechanical mixing is high-shear mixing.

30. The method according to claim 29, wherein the high-shear mixing is at 5K to 15K rpm.

31. The method according to claim 30, wherein the high-shear mixing is carried out for 1 to 5 minutes.

32. The method according to claim 29, wherein the high-shear mixing is carried out at 14K rpm for 3 minutes.

33. The method according to any one of claims 24 to 32, wherein the homogenization comprises homogenizing using a microfluidizer at 2K to 5K psi.

34. The method according to any one of claims 24 to 33, wherein the homogenization step is repeated two or more times before spray-drying.

35. The method according to any one of claims 24 to 34, wherein the spray-drying is carried out in the presence of a gas.

36. The method according to claim 35, wherein the gas is nitrogen. **Claim 37** A food, food product, or dietary supplement comprising the encapsulated oil particles according to any one of claims 1 to 22.

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