WO2025238190A1

WO2025238190A1 - Spray-dried powders having high pufa content

Info

Publication number: WO2025238190A1
Application number: PCT/EP2025/063484
Authority: WO
Inventors: Fabiola PORTA; Gabriela BADOLATO BÖNISCH; Bernd Schlegel
Original assignee: DSM IP Assets BV
Current assignee: DSM IP Assets BV
Priority date: 2024-05-15
Filing date: 2025-05-15
Publication date: 2025-11-20
Anticipated expiration: 2026-11-15

Abstract

The present disclosure spray-dried powders including from 30% to 60% by weight of an oil including polyunsaturated fatty acids (PUFAs) based on a total weight of the spray-dried powder. The spray-dried powder can further include a wall material comprising a monosaccharide, a disaccharide, an oligosaccharide, a polysaccharide, or mixtures thereof, where the weight ratio of oil to wall material is from 0.5 to 2 oil/wall material. The spray-dried powder can also include from 1% to 35% by weight of plant protein isolate, based on the total weight of the spray-dried powder.

Description

SPRAY-DRIED POWDERS HAVING HIGH PUFA CONTENT

CROSS-REFERENCE TO RELATED APPLICATION

[0001] This international application claims the benefit of U.S. Provisional Application No. 63/648,015, filed 15 MAY 2024, which is incorporated herein by reference in its entirety.

TECHNICAL FIELD

[0002] The present disclosure relates to spray-dried powders having high mg/g polyunsaturated fatty acid (PUFA) content, methods of making the same, and associated products and uses.

BACKGROUND

[0003] Flavors, essential oils, fragrances, and the like are valuable ingredients in a variety of end-use applications, such as food, perfumery, cosmetic, and pharmaceutical products. In many cases, these ingredients are volatile, minimally soluble in water, and are subject to degradation in the presence of oxygen, light, moisture, and/or heat. A variety of microencapsulation techniques have been developed to help preserve, solubilize, and protect these ingredients. Microencapsulation generally refers to a process of forming a small spheroidal material including a “core” - the internal material - having a “wall” or shell surrounding the core.

[0004] One example of a microencapsulation technique is spray drying. This method typically involves atomization of emulsions in a drying medium at a high temperature to promote rapid evaporation of water to form a surface crust entrapping the core material inside. A commonly used parameter in this microencapsulation method is the core:wall material ratio, which is typically around 1 :10 to 1 :2, depending on the core material, so as to provide high retention of the core material.

[0005] The typical need for a high ratio of wall material relative to core material can present a variety of challenges when attempting to incorporate high amounts (e.g., greater than 30% or 35%) of core material into the powder. For example, if the microcapsule is not able to effectively hold the core material, high levels of surface oil can result. High levels of surface oil can lead to loss of the core material, oxidation of the core material, self-heating, and/or poor performance of the microcapsules.

[0006] An alternative technique for microencapsulation is complex coacervation. This form of microencapsulation technology employs a phase separation process based on the formation of a coacervate between oppositely charged polymers. In further detail, an aqueous solution of two different polymers - typically a protein and a polysaccharide or other suitable polyanion - can be prepared in a variety of ways. For example, where gelatine is used as the protein, the coacervate can be prepared at a temperature above the gelling point of the protein. In contrast, where another protein is used, it may be preferable to prepare the coacervate at low temperature when the protein is still native. A “native” protein can be described as a protein in its functional form and having its natural folding configuration. Upon denaturation, such as by increased temperature, the structure can loosen and unfold. Consequently, protein molecules can aggregate, which can lead to a precipitate or a gel at sufficiently high concentrations. Additionally, coacervates are typically prepared at a pH that is above or below the isoelectric point of the protein. The core material can then be emulsified into the aqueous solution including the oppositely charged polymers. The pH of the solution can then be lowered below or raised above the isoelectric point of the protein, as the case may be, to separate the composition into two liquid phases - an insoluble polymer-rich phase and an aqueous phase that is depleted in both polymers - due to the electrostatic interactions between the oppositely charged polymers. In the case where gelatine is the protein, the temperature of the composition can then be lowered below the gelling temperature of the protein to form a wall around the core material. For other proteins, the temperature of the composition may be raised to form a wall around the core material. A cross-linking agent (e.g., chemically, for instance by glutaraldehyde, or enzymatically, for instance by transglutaminase) can then be added to harden and stabilize the microcapsule walls. A variety of factors affect the success of a particular complex coacervate method, including pH, ionic strength, protein-polyanion ratio, nature of the core material, and the core:wall ratio. Also, not all proteins are necessarily suitable for complex coacervation, especially where a high amount of core material is desired. Further, gelatine is the most commonly used protein in complex coacervation technology, which is not suitable for vegan products.

BRIEF SUMMARY

[0007] The present disclosure describes a spray-dried powder including from 30% to 60% by weight of an oil including polyunsaturated fatty acids (PUFAs) based on the total weight of the spray-dried powder. The spray-dried powder can also include a wall material including a monosaccharide, a disaccharide, an oligosaccharide, a polysaccharide, or a mixture thereof, where the weight ratio of oil to wall material is from 0.5 to 2 oil/wal I material. The spray-dried powder can also include 1% to 35% by weight of a plant protein isolate, based on the total weight of the spray-dried powder. [0008] The present disclosure also describes a gelled confection including the spray-dried powder disclosed herein and a gelling substance. The gelled confection can include from 1 mg/g to 200 mg/g of omega-3 fatty acids, omega-6 fatty acids, or a combination thereof based on the total weight of the gelled confection.

[0009] The present disclosure also describes a powder blend including the spray-dried powder disclosed herein and a powder base. The powder blend can include from 1 mg/g to 200 mg/g of omega-3 fatty acids, omega-6 fatty acids, or a combination thereof based on the total weight of the powder blend.

DETAILED DESCRIPTION

[0010] Although the following detailed description contains many specifics for the purpose of illustration, a person of ordinary skill in the art will appreciate that many variations and alterations to the following details can be made and are considered to be included herein. Accordingly, the following embodiments are set forth without any loss of generality to, and without imposing limitations upon, any claims set forth. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to be limiting. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs.

[0011] As used in this written description, the singular forms “a,” “an,” and “the” include express support for plural referents unless the context clearly dictates otherwise. Thus, for example, reference to “a fatty acid” or “the fatty acid” can include a plurality of such fatty acids.

[0012] Unless otherwise specified, all numerical parameters are to be understood as being prefaced and modified in all instances by the term “about,” in which the numerical parameters possess the inherent variability characteristic of the underlying measurement techniques used to determine the numerical value of the parameter.

[0013] Concentrations, amounts, and other numerical data may be expressed or presented herein in a range format. It is to be understood that such a range format is used merely for convenience and brevity and thus should be interpreted flexibly to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range is explicitly recited. As an illustration, a numerical range of “1 to 5” should be interpreted to include not only the explicitly recited values of 1 to 5, but also include individual values and subranges within the indicated range. Thus, included in this numerical range are individual values such as 1, 2, 3, 4, and 5 and sub-ranges such as from 1 to 3, from 2 to 4, from 3 to 5, etc. This same principle applies to ranges reciting only one numerical value as a minimum or a maximum. Furthermore, such an interpretation should apply regardless of the breadth of the range or the characteristics being described.

[0014] Reference throughout this written description to “an example” means that a particular feature, component, or characteristic described in connection with the example is included in at least one embodiment. Thus, appearances of the phrases “in an example” or “in one example” in various places throughout this written description are not necessarily all referring to the same embodiment.

PUFA Oils

[0015] The present disclosure describes spray-dried powders having a high amount of oil content that can optionally be used for vegan applications. In particular, the spray-dried powders typically have from 30% to 60% by weight of an oil including polyunsaturated fatty acids (PLIFAs) based on the total weight of the spray-dried powder.

[0016] As used herein, PLIFAs generally refer to omega fatty acids, such as omega-3 fatty acids, and omega-6 fatty acids, for example. Many omega fatty acids have been studied extensively and are believed to provide a number of positive health benefits.

[0017] For example, omega-3 fatty acids are essential fatty acids that the human body cannot make. Therefore, humans must obtain omega-3 fatty acids from their diet. Omega-3 fatty acids are believed to be important components of human cell membranes. In further detail, docosahexaenoic acid (DHA) is believed to reduce the risk of heart disease, promote normal brain and eye development in babies, and provide a variety of other health benefits.

Eicosapentaenoic acid (EPA) is believed to lower the risk of heart disease, reduce symptoms of depression, provide some anti-inflammatory effects, and provide a variety of other health benefits.

[0018] Omega-6 fatty acids are also considered essential fatty acids that humans must obtain from their diet. Omega-6 fatty acids, such as gamma-linolenic acid (GLA), dihomo-gamma- I inoleic acid (DGLA), and arachidonic acid (ARA), may provide a variety of health benefits, including anti-inflammatory effects. Also, ARA is believed to support a healthy immune system and inflammatory response in developing babies.

[0019] As these PLIFAs are believed to provide a variety of health benefits, there is a desire to provide a spray-dried powder having high levels of these PLIFAs. In some examples, the spray- dried powder can include from 30% to 60% by weight of an oil including PLIFAs, based on the total weight of the spray-dried powder. In additional examples, the spray-dried powder can include 30% to 45% by weight, 35% to 50% by weight, 40% to 55% by weight, or 45% to 60% by weight of an oil including PLIFAs, based on the total weight of the spray-dried powder. [0020] In some examples, the oil can include omega-3 fatty acids, omega-6 fatty acids or a combination thereof. In some examples, the oil can include omega-3 fatty acids. In some specific examples, the oil can include docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), or a combination thereof. In some examples, the oil can include DHA. In some examples, the oil can include EPA. In some examples, the oil can include DHA and EPA, where the amount of DHA is greater than the amount of EPA. In some examples, the oil can include DHA and EPA, where the amount of EPA is greater than the amount of DHA. In some further examples, the oil can include omega-6 fatty acids. In some specific examples, the oil can include ARA. In some examples, the oil can include DHA and ARA. In some examples, the oil can include EPA and ARA. In some examples, the oil can include DHA, EPA, and ARA.

[0021] In some specific examples, the oil can include both DHA and EPA where the weight ratio of EPA to DHA is greater than or equal to 1 , greater than 1.2, or greater than 1.5 EPA/DHA. In some additional examples, the oil can include both DHA and EPA where the weight ratio of EPA to DHA is less than 1, less than 0.7, or less than 0.5 EPA/DHA. In some examples, the oil can include DHA, EPA, and ARA where DHA, EPA, and ARA are present at a weight ratio of >1 : 1 : <1 DHA:EPA:ARA. In some examples, the oil can include DHA, EPA, and ARA where DHA, EPA, and ARA are present at a weight ratio of 1 : >1: <1 DHA:EPA:ARA.

[0022] In some examples, the spray-dried powder can include omega-3 fatty acids in an amount from 12% to 30% by weight based on the total weight of the spray-dried powder. In still additional examples, the spray dried-powder can include omega-3 fatty acids in an amount from 15% to 25% by weight based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include DHA in an amount from 5% to 30% by weight based on the total weight of the spray-dried powder. In some additional examples, the spray-dried powder can include DHA in an amount from 7% to 25% by weight, from 5% to 15% by weight, from 10% to 20% by weight, or from 15% to 25% by weight based on the total weight of the spray-dried powder. In some examples, the spray-dried powder includes EPA in an amount from 1.5% to 25% by weight based on the total weight of the spray-dried powder. In some additional examples, the spray dried powder can include EPA in an amount from 1.5% to 10% by weight, from 5% to 15% by weight, from 10% to 20% by weight, or from 15% to 25% by weight based on the total weight of the spray-dried powder. [0023] In some examples, the spray-dried powder can include omega-3 fatty acids in an amount from 75 mg/g to 350 mg/g, based on the total weight of the spray-dried powder. In still additional examples, the spray dried-powder can include omega-3 fatty acids in an amount from 100 mg/g to 200 mg/g, from 150 mg/g to 330 mg/g, or from 175 mg/g to 250 mg/g, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include DHA in an amount from 15 mg/g to 200 mg/g, based on the total weight of the spray-dried powder. In some additional examples, the spray-dried powder can include DHA in an amount from 30 mg/g to 100 mg/g, from 70 mg/g to 150 mg/g, from 90 mg/g to 130 mg/g, or from 100 mg/g to 150 mg/g, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder includes EPA in an amount from 15 mg/g to 200 mg/g, based on the total weight of the spray-dried powder. In some additional examples, the spray dried powder can include EPA in an amount from 30 mg/g to 100 mg/g, from 70 mg/g to 150 mg/g, from 90 mg/g to 130 mg/g, or from 100 mg/g to 150 mg/g, by weight based on the total weight of the spray- dried powder.

[0024] In some examples, the spray-dried powder can include omega-6 fatty acids in an amount from 0.1% to 25% by weight based on the total amount of the spray-dried powder. In some additional examples, the spray-dried powder can include omega-6 fatty acids in an amount from 0.1% to 10% by weight or from 10% to 25% by weight based on the total weight of the spray-dried powder.

[0025] The amount of PLIFA oil in the spray-dried powder can be determined as follows:

- Accurately weigh 5 grams of spray-dried powder into a suitable flask or beaker and mix with 200 mg amylase and 5 mL of 2.5% NH₄OH and 20 mL deionized water. Place flask or beaker in a water bath at 40 °C for 1 hour while stirring the mixture;

- Add 150 mL pentane, followed by 30 mL ethanol p.a.;

Stir the mixture for 5 minutes. Add 2 x 10 mL ethanol p.a., stirring for 2-5 minutes between each addition;

- Allow the mixture to stand for approximately 10 minutes to obtain good separation of phases;

Concentrate 50 mL of the upper pentane phase in a suitable dry and fared round-bottom flask in a Rotavapor at 40 °C and 730-750 bar;

- Add approximately 5 mL ethanol p.a. and mix the oil residue with the ethanol by swirling the flask, mix and concentrate to constant weight at about 10 mbar; and

Calculate the oil content in the powder as follows:

Content of oil in powder (%) = (Oil in flask(g) x 151.1 x 100)/(SW(g) x 50), where Oil in flask(g) = residual oil in round-bottom flask, 151.1 = volume of pentane and oil in the upper phase (mL), 50 = volume of the pentane phase removed (mL), SW(g) = weight of powder sample (g).

[0026] The fatty acids in the oil, such as DHA, EPA, or ARA, can be identified and quantified using GC-MS and GC-FID, respectively. For example, American Oil Chemists’ Society (AOCS) Official Method Ce 1b-89 can be used to obtain Fatty Acid Methyl Ester (FAME) data on the oils. As is well understood in the art, the FAME data reports the identified fatty acids in relative area % of all of the fatty acid peaks in the GO chromatogram. Wt.% or mg/g values can be calculated by comparing the peak area for a particular fatty acid against a peak area or standard curve obtained using one or more quantitative reference standards.

Oil Sources

[0027] The PLIFA oils described herein can be obtained from a variety of sources. In some examples, the PLIFA oil can be obtained from fish, such as salmon, mackerel, tuna, herring, sardines, or a combination thereof, for example. In other examples, such as for vegan applications, the PLIFA oil can be obtained from a microorganism or a plant. For example, PLIFA oils can be produced and/or obtained from plants, plant seeds, microalgae, fungi (including yeast), bacteria, and/or protists.

[0028] In some specific examples, the PLIFA oils can be extracted or otherwise obtained from a plant genetically modified to produce, or increase production of, at least one PLIFA, such as a PUFA-containing coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, rapeseed oil (canola oil), safflower oil, sesame oil, soybean oil, sunflower oil, camelina oil, etc. Additional examples and description can be found in U.S. Patent Publication Nos. 2015/0152450, 2013/0101723, 2013/0150599, 2010/0313309, 2008/0050505, and 2007/0220634, each of which is incorporated herein by reference. Plants can be grown and the oil extracted from the plants, or seeds thereof, using methods known in the art.

[0029] In some specific examples, the PUFA oils described herein can be produced, or largely produced, by a fungus. In some additional specific examples, the microbial oils described herein can be produced, or largely produced, by a fungus of the order Mortierellales.

[0030] In some specific examples, the PUFA oils described herein can be produced, or largely produced, by a fungus of the genus Mortierella. In some examples, the PUFA oils described herein can be produced, or largely produced by a fungus comprising Mortierella alpina, Mortierella vinacea, Mortierella polycephala, Mortierella elongata, or a combination thereof. [0031] In some specific examples, the PLIFA oils described herein can be produced, or largely produced, by a microalgae. In some examples, the microalgae can be or include a dinoflagellate, such as Crypthecodinium cohnii, for example.

[0032] In some additional specific examples, the PLIFA oils described herein can be produced, or largely produced, by a Thraustochytrid, which, at the time of this disclosure, is classified as a type of microalgae.

[0033] For purposes of the present disclosure, strains described as Thraustochytrids include organisms of the taxonomic order Thraustochytrialies. In some further examples, Thraustochytrids can include organisms of the taxonomic family Thraustochytriidae (or Thraustochytriaceae). In still further examples, Thraustochytrids can include organisms of the taxonomic genus Thraustochytrium, Ulkenia, Schizochytrium, Japonochytrium, Aplanochytrium, Althornia, Elina, Aurantiochytrium, Oblongichytrium, Botryochytrium, Parietichytrium, Sicyoidochytrium, or a combination thereof.

[0034] In some further examples, the PLIFA oils described herein can be produced, or at least largely produced, from a microorganism of a species, or a microorganism derived from a species, of the genus Thraustochytrium, Ulkenia, Schizochytrium, Aurantiochytrium, Japonochytrium, and/or Aplanochytrium.

[0035] Additional species of microorganisms that can be used to produce microbial oils can be found in U.S. Patent No. 8486267, which is incorporated herein by reference.

[0036] In some examples, the PUFA oil can include a blend of oils derived from different sources, such as a plant oil and a microbial oil, a plurality of plant oils, a plurality of microbial oils, a fish oil and a plant oil, a fish oil and a microbial oil, etc.

Wall Materials

[0037] Wall materials refer to the materials forming a matrix that encapsulates or otherwise protects the oil of the spray-dried powder. General considerations for selecting an appropriate wall material can include the ability of the wall material to withstand mechanical stress and environmental conditions that the oil will encounter during the encapsulation process and subsequent handling of the spray-dried powder. A variety of wall materials can be employed. Non-limiting examples of suitable wall materials can include a carbohydrate, a gum, or a combination thereof.

[0038] Carbohydrates can include monosaccharides, disaccharides, oligosaccharides, polysaccharides, or combinations thereof. In some examples, the carbohydrate can include a monosaccharide. Non-limiting examples of monosaccharides can include glucose, fructose, galactose, ribose, mannose, the like, or a combination thereof. In some additional examples, the carbohydrate can include a disaccharide. Non-limiting examples of disaccharides can include sucrose, lactose (for non-vegan applications), maltose, trehalose, the like, or a combination thereof. In some examples, the carbohydrate can include an oligosaccharide. Non-limiting examples of oligosaccharides can include fructo-oligosaccharides, gluco-oligosaccharides, galacto-oligosaccharides, arabinoxylan-oligosaccharids, raffinose, the like, or combinations thereof. In some examples, the carbohydrate can include a polysaccharide. Non-limiting examples of polysaccharides can include a starch, a maltodextrin, a chitosan (vegan or nonvegan, depending on application), a dextran, a carrageenan, a pectin, an alginate, or the like, or combinations thereof.

[0039] Gums are water-soluble polysaccharides that are recognized for producing viscous dispersions at low concentrations. Non-limiting examples of gums can include agar, alginate, guar gum, gellan gum, xanthan gum, Arabic gum (gum acacia), arabinogalactan, the like, or combinations thereof.

[0040] In some examples, the wall material can include a carbohydrate. In some specific examples, the carbohydrate can include a monosaccharide, a disaccharide, an oligosaccharide, a polysaccharide, or a combination thereof. In some examples, the wall material can include a monosaccharide and a polysaccharide. In some examples, the wall material can include a disaccharide and a polysaccharide. In some examples, the wall material can include an oligosaccharide and a polysaccharide. In some examples, the wall material can include a monosaccharide and an oligosaccharide. In additional examples, the wall material can include a disaccharide and an oligosaccharide. In additional examples, the wall material can include a monosaccharide, an oligosaccharide, and a polysaccharide. In yet additional examples, the wall material can include a disaccharide, an oligosaccharide, and a polysaccharide. In still additional examples, the wall material can include a monosaccharide, a disaccharide, and a polysaccharide. In some further examples, the wall material can include a gum. In still further examples, the wall material can include a carbohydrate and a gum. In some examples, the wall material can include a monosaccharide, a disaccharide, an oligosaccharide, a polysaccharide, or a combination thereof and a gum. In some examples, the wall material can include a disaccharide, a polysaccharide, and a gum. In some additional examples, the wall material can include an oligosaccharide, a polysaccharide, and a gum. In additional examples, the wall material can include a disaccharide, an oligosaccharide, and a gum. In additional examples, the wall material can include a polysaccharide and a gum. In further examples, the wall material can include a disaccharide and a gum. In some examples, the wall material can include a monosaccharide and a gum. In yet additional examples, the wall material can include an oligosaccharide and a gum.

[0041] The amount and type of wall material employed will vary based on the amount of oil incorporated into the spray dried powder and the ability of the wall material to encapsulate or otherwise protect the oil. As the spray-dried powders disclosed herein include high amounts of oil, the weight ratio of oil to wall material can typically be from 0.5 to 2 oil/wall material. In some further examples, the weight ratio of oil to wall material can be from 0.5 to 1.5, from 1 to 2, from 0.7 to 1.3, or from 1 to 1.8 oil/wall material.

[0042] In some specific examples, the spray-dried powder can include a carbohydrate in an amount of 10% to 45% by weight based on the total weight of the spray-dried powder. In still additional examples, the spray-dried powder can include a carbohydrate in an amount of 15% to 25% by weight, from 20% to 30% by weight, from 25% to 35% by weight, or from 30% to 40% by weight based on the total weight of the spray-dried powder.

[0043] In some examples, the carbohydrate can include a polysaccharide. In some examples, the polysaccharide can be present in the spray-dried powder in an amount of from 10% to 35% by weight based on the total weight of the spray-dried powder. In additional examples, the polysaccharide can be present in the spray-dried powder in an amount of from 15% to 25%, from 20% to 30%, or from 25% to 35%, based on the total weight of the spray-dried powder. [0044] In some examples, the polysaccharide can be a modified starch. In some examples, the modified starch can be a hydrophobically-modified starch. In some specific examples, the starch can be an octenyl succinic anhydride (OSA) starch. In some further examples, the carbohydrate can include a disaccharide. In some examples, the disaccharide can be sucrose, trehalose, maltose, or a combination thereof. In some specific examples, the disaccharide can be sucrose. In some examples, the carbohydrate can include a hydrophobically modified starch and a disaccharide.

[0045] In some examples, the spray-dried powder can include from 0% to 10% by weight, from 0% to 5% by weight, from 0% to 1% by weight, from 5% to 20% by weight, from 7% to 18% by weight, from 8% to 16% by weight, from 10% to 14%, or 0% by weight of a monosaccharide, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include from 0% to 20% by weight, from 0% to 5% by weight, from 5% to 20% by weight, or from 7% to 18% by weight of a disaccharide, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include from 5% to 20% by weight, from 7% to 18% by weight, from 8% to 16% by weight, or from 10% to 14% by weight of sucrose, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include from 0% to 10% by weight, from 0% to 5% by weight, from 0% to 1% by weight, or 0% by weight of glucose, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include from 0% to 10% by weight, from 0% to 5% by weight, from 0% to 1 % by weight, or 0% by weight of fructose, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include from 0% to 10% by weight, from 0% to 5% by weight, from 0% to 1% by weight, or 0% by weight of mannitol, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include from 0% to 10% by weight, from 0% to 5% by weight, from 0% to 1 % by weight, or 0% by weight of sorbitol, based on the total weight of the spray-dried powder. In some examples, the spray-dried powder can include from 0% to 10% by weight, from 0% to 5% by weight, from 0% to 1 % by weight, or 0% by weight of xylitol, lactitol, isomalt, maltitol, or combinations thereof, based on the total weight of the spray-dried powder. In some examples, monosaccharides and disaccharides used in the wall material can have a glass transition temperature (Tg) above room temperature and below the spray drying temperature used to prepare the spray-dried powder. For example, sucrose has a Tg of about 60° to 70° C, which is above room temperature, but below a typical spray drying temperature.

[0046] In some additional specific examples, the spray-dried powder can include a gum in an amount from 5% to 30% by weight, based on the total weight of the spray-dried powder. In some further examples, the spray-dried powder can include a gum in an amount from 5% to 15% by weight, 10% to 20% by weight, from 15% to 25% by weight, or from 20% to 30% by weight based on the total weight of the spray-dried powder.

Proteins

[0047] Proteins are macromolecular structures composed of amino acids that may assist as emulsifiers, in forming gels, and/or in forming rigid matrices. While proteins may form part of the wall material, for purposes of this disclosure, proteins will be considered and discussed separately from the wall material.

[0048] Proteins can be derived from plants or animals. Non-limiting examples of plant proteins can include rapeseed protein, fava bean protein, chickpea protein, pea protein, lupin protein, lentil protein, mung bean protein, peanut protein, cotton seed protein, sunflower seed protein, sesame seed protein, oat protein, rice protein, corn protein, gluten, soy protein, sorghum protein, quinoa protein, chia protein, hemp protein, buckwheat protein, alfalfa protein, clover protein, duckweed protein, grass protein, potato protein, sweet potato protein, cassava protein, yam protein, taro protein, almond protein, hazelnut protein, walnut protein, cashew protein, coconut protein, or the like. Non-limiting examples of animal proteins can include casein, gelatine, whey, egg protein, or the like.

[0049] Plant proteins may be obtained in their native form, but, in some cases, can be mixed with other components that come from the plant source. To obtain a relatively pure product, a wet isolation process is often used, which can cause the protein to denature and reduce the gelation properties of the protein.

[0050] Gelatine (a proteinaceous animal-based material) exhibits exceptional behavior as compared to many other proteins. Specifically, in a solution, gelatine is liquid at high temperatures and forms a gel upon cooling. In contrast, many other proteins are typically native at lower temperature and are denatured upon heating, causing the protein molecules to aggregate to form a gel at elevated temperatures.

[0051] Additionally, proteins typically have low solubility at their isoelectric point. As such, when the pH is adjusted to the isoelectric point, proteins typically aggregate to form a gel when the protein concentration is sufficiently high. However, the isoelectric point for many proteins is within a low pH range typically used for microbiological safety during the preparation of spray- dried powders. This can present a challenge to overcome when preparing a functional encapsulate using a native protein at low pH, as the solubility of the protein can be low at the same pH used for microbiological safety.

[0052] Typically, the spray-dried powders disclosed herein can include a plant protein. Commercial proteins can have various levels of purity. For example, protein concentrates can typically include up to 70%, by weight, of protein. Protein isolates can typically include at least 70%, by weight, or at least 80%, by weight, of protein. The spray-dried powders disclosed herein typically include a plant protein isolate. In some examples, the spray-dried powders may include a plant protein concentrate where the lower level of purity does not detectably impact the performance of the spray-dried powder in an adverse manner.

[0053] With this in mind, the plant protein isolate can typically have a solubility in water of at least 60% over a pH range of 2 to 5 at a temperature of 23 +1-2 °C. In some additional examples, the plant protein isolate can have a solubility in water of at least 70%, at least 75%, at least 80%, or at least 85% over a pH range of 2 to 5 at a temperature of 23 +1-2 °C.

[0054] In some additional examples, the plant protein isolate has a solubility of at least 88% over a pH range from 2 to 10 at a temperature of 23 +1-2 °C. In some further examples, the plant protein isolate has a solubility of at least 90%, at least 91%, at least 92%, at least 93%, at least 94%, at least 95%, at least 96%, at least 97%, at least 98% or at least 99% over a pH range from 2 to 10 at a temperature of 23 +1-2 °C. [0055] As is understood in the art, protein solubility is not typically measured in the same way as solubility of a sugar or salt is typically measured, for example. Proteins are typically not composed of a single pure compound. Additionally, the protein may include native and damaged/denatured fractions. As such, there is typically a fraction of the protein that will be less soluble than another fraction of the protein. Accordingly, traditional solubility tests, such as for salts and sugars, for example, do not adequately represent the solubility of proteins. With this in mind, protein solubility, as used herein, is calculated by the following equation:

Protein solubility (%) = (concentration of protein in supernatant (in g/l) I concentration of protein in total dispersion (in g/l)) x 100.

[0056] In further detail, protein solubility is measured using the following test: -sufficient protein to supply 0.8 g of protein is weighed into a beaker; -a small amount of demineralized water is added to the powder and the mixture is stirred until a smooth paste is formed;

-additional demineralized water is then added to make a total weight of 40 g (yielding a 2% (w/w) protein dispersion);

-the dispersion is slowly stirred for at least 30 min using a magnetic stirrer;

-afterwards the pH is determined and adjusted to the desired level (2, 3, 4, 5, for example) with NaOH or HCI;

-the pH of the dispersion is measured and corrected periodically during 60 minutes stirring;

-after 60 minutes of stirring, an aliquot of the protein dispersion is reserved for protein concentration determination (Dumas analysis; Dumas N x 6.25), another portion of the sample is centrifuged at 20,000 G for 2 min;

-the supernatant and pellet are separated after centrifugation;

-the protein concentration of the supernatant is also determined by Dumas analysis (Dumas N x 6.25);

- and protein solubility is calculated by:

[0057] In some examples, the spray-dried powder can include from 1% to 35% by weight of a plant protein isolate, based on the total weight of the spray-dried powder. In additional examples, the spray-dried powders can include from 2% to 30% by weight, from 3% to 25% by weight, from 4% to 20% by weight, from 5% to 15% by weight, or from 8% to 14% by weight of plant protein isolate, based on the total weight of the spray-dried powder. In still further examples, the spray-dried powder can include from 1% to 10% by weight or from 3% to 12% by weight of plant protein isolate, based on the total weight of the spray-dried powder.

[0058] In some examples, the plant protein isolate can be or include rapeseed protein, chickpea protein, pea protein, soy protein, rice protein, chia protein, hemp protein, a sunflower protein, or a combination thereof. In some specific examples, the plant protein can be or include rapeseed protein. In some examples, the plant protein can be or include chickpea protein. In some additional examples, the plant protein can be or include pea protein. In still additional examples, the plant protein can be or include soy protein. In further examples, the plant protein can be or include rice protein. In still further examples, the plant protein can be or include chia protein. In yet additional examples, the plant protein can be or include hemp protein.

[0059] In some specific examples, the plant protein isolate can be or include a rapeseed protein. Rapeseed protein isolate may be prepared from cold-pressed rapeseed oil seed meal as described in WO 2018/007492, for example. In some examples, the rapeseed protein isolate can have a protein content of from 70% to 98% (w/w), or from 80% to 95% (w/w), or from 85% to 95% (w/w). In some further examples, the rapeseed protein isolate can have from 40% to 65% (w/w) cruciferins and from 25% to 60% (w/w) napins as verified by Blue Native PAGE, for example as described in WO 2018/007492. In some additional examples, the rapeseed protein isolate can have at least 50% (w/w), at least 60% (w/w), at least 70% (w/w), at least 80% (w/w), at least 85% (w/w), at least 90% (w/w), or at least 95% (w/w) cruciferins, as verified by Blue Native PAGE, for example as described in WO 2018/007492. In still additional examples, the rapeseed protein isolate can have at least 50% (w/w), at least 60% (w/w), at least 70% (w/w), at least 80% (w/w), at least 85% (w/w), at least 90% (w/w), or at least 95% (w/w) napins, as verified by Blue Native PAGE, for example as described in WO 2018/007492. In some specific examples, the rapeseed protein isolate can include 10-40% (w/w) napins and 40-60% (w/w) cruciferins, as verified by Blue Native PAGE, for example as described in WO 2018/007492. In some additional specific examples, the rapeseed protein isolate can include 25-35% (w/w) napins and 40-55% (w/w) cruciferins, as verified by Blue Native PAGE, for example as described in WO 2018/007492. It is noted that the designation (w/w) is used interchangeably herein with “by weight”.

[0060] In some examples, the weight ratio of cruciferins to napins in the rapeseed protein isolate can be in the range of 1:99 to 99:1 , 5:95 to 95:5, or 10:90 to 80:20. In some further examples, the weight ratio of cruciferins to napins in the rapeseed protein isolate can be in the range of 20:80 to 80:20, or from 30:70 to 80:20. In still further examples, the weight ratio of cruciferins to napins in the rapeseed protein isolate can be in the range of 40:60 to 60:40 (w/w) such as 45:55 to 59:41. In yet further examples, the weight ratio of cruciferins to napins in the rapeseed protein isolate can be in the range 60:40 to 80:20, or 60:40 to 75:25, or 65:35 to 75:25. An example of such a rapeseed protein isolate is Puratein®, commercially available from Burcon NutraScience Corporation.

[0061] The amount of cruciferins and napins can be determined by Blue Native Page, HP-SEC or by sedimentation velocity (SV-ALIC). In further detail, the amounts of cruciferins and napins can be calculated in a variety of ways. For example, in some cases, the amount of cruciferins and napins can be calculated based on the total amount of rapeseed protein isolate. In other examples, the amounts of cruciferins and napins can be calcuated based on the sum of cruciferins and napins present in the rapeseed protein isolate. In additional examples, the amounts of cruciferins and napins are determined by size exclusion chromatography (SEC). In a specifice example, the amounts of cruciderins and napins are determined by size exclusion chromatography (SEC) using the following test:

[0062] Samples of protein isolate are dissolved in a 500 mM NaCI saline solution and analyzed by High Performance SEC using the same solution as the mobile phase, followed by detection using UV absorbance at 280 nm, wherein the relative contribution of cruciferin and napin (wt. %) is calculated as the ratio of the peak area of each protein with respect to the sum of both peak areas.

[0063] In some examples, such as for vegan applications, the amount of animal protein employed can be limited or eliminated entirely. Thus, in some examples, the spray-dried powder can include less than 1% by weight, less than 0.5% by weight, less than 0.1% by weight, or 0% by weight of animal protein based on the total weight of the spray-dried powder.

Additional Components

[0064] The spray-dried powder can include a variety of additional components as desired, and as can typically be found in spray-dried materials. Non-limiting examples can include antioxidants, preservatives, flow aids, pH modifiers, water, emulsifiers, flavors, colorants, the like, or a combination thereof.

Methods of Making

[0065] The spray-dried powders disclosed herein can be made in a variety of ways. Typically, the wall material is dissolved in an aqueous solvent at a pH suitable for forming an emulsion. In some examples, the pH can be a pH less than 7. In some further examples, the pH can be from 2-5. pH can be measured in any suitable way. As is known in the art, a suitable electrode can be selected and calibrated against calibration buffers prior to measuring the pH of a sample. [0066] In some examples, this initial mixture can be heated, optionally to a temperature suitable for pasteurization without adversely affecting the wall material. In some examples, the aqueous solvent is heated prior to adding the wall material. In some other examples, the wall material can be dispersed in ambient or cooled aqueous solvent and subsequently heated. In either case, in some examples, the initial mixture can be heated to a temperature of from 30 °C to 50 °C. In other examples, where pasteurization is used, the initial mixture can be heated to a temperature of from 60 °C to 90 °C, or from 60 °C to 70 °C, for example. Where pasteurization is used, the initial mixture can typically be cooled, or allowed to cool, after pasteurization to a temperature of from 30 °C to 50 °C.

[0067] The plant protein can then be added and mixed into the initial mixture to form a second mixture. Typically, the plant protein is added and mixed at a temperature of from 30 °C to 50 °C and a pH below 7, such as a pH from 2-5.

[0068] The PLIFA oil is typically heated to a temperature of from 30 °C to 50 °C prior to adding to the second mixture to form an oily mixture with high solids content. Typically, the oily mixture has a solids content (including the PLIFA oil) of greater than 50% by weight (e.g., 50%-70%, by weight). Once the PLIFA oil is added, the mixture is emulsified using a rotor stator or other suitable mixing device to achieve a D50 emulsion droplet size of < 1 pm. The emulsion droplet size can be determined using a MALVERN MASTERSIZER 3000 particle size analyzer using a redispersed powder method based on MIE diffraction theory of calculation. The instrument parameters for the measurement are disclosed in Table 1 below.

[0069] Once a suitable emulsion is achieved, the emulsion can be diluted with water and spray dried using standard spray drying techniques to form the spray-dried powder.

Table 1: Instrument parameters for measuring emulsion droplet size

Surface Oil

[0070] Typically, spray-drying provides a large amount of potentially flammable and explosive material. Although the formulation to be spray-dried enters the dryer as a wet spray, the material dries quickly to become more sensitive to ignition. Various sources of ignition can be possible, including incoming burning particles, electrostatic charge, a heater, downstream process components, or even autoignition of the material itself from self-heating.

[0071] While the amount of surface oil is typically not a primary factor leading to self-heating of a spray-dried powder, excessive amounts of surface oil (e.g., greater than 5% or 10% surface oil) can be a risk factor. Accordingly, minimizing the amount of surface oil of the spray-dried powder can, in some cases, help minimize the potential risk of the spray-dried powder with respect to auto-ignition or other sources of ignition in the drying equipment.

[0072] Additionally, PLIFA oils are highly susceptible to oxidation. Accordingly, high levels of surface oil can also lead to a poor sensory profile of the powder. As surface oil is not encapsulated by the wall material, it is exposed to ambient air potentially leading to degradation of PLIFA oils and other materials prone to oxidation, which can cause an increased concentration of off flavors in the powder.

[0073] Accordingly, the spray-dried powders described herein typically have a low level of surface oil to minimize the risk of self-heating and to improve the sensory profile of the powder. However, minimizing the surface oil in a spray-dried powder having high amounts of oil (e.g., at least 30% by weight, at least 40% by weight, or at least 50% by weight, for example) can be challenging.

[0074] Typically, the spray-dried powders described herein can include a surface oil content of less than 2% by weight as gravimetrically determined. In still further examples, the spray-dried powders can have a surface oil content of less than 1.5% by weight, less than 1% by weight, or less than 0.5% by weight as gravimetrically determined.

[0075] The surface oil of the spray-dried powder can be gravimetrically determined by transferring an accurately weighed amount of spray-dried powder (e.g., 7-8 grams) to a container and adding a suitable solvent (e.g., cyclohexane) in an amount (e.g., 50 mL) to extract and dissolve the surface oil. The spray-dried powder + solvent can be shaken for 5 minutes at 1000 shakes per minute and then filtered over a pleated filter. An accurate volume (e.g., 25 mL) of the solvate can be transferred to a tared round bottom flask. After rotary evaporating, the tare weight of the round bottom flask can be subtracted from the gross weight of the flask + residue to determine the amount of surface oil of the spray-dried powder.

Particle Size

[0076] One factor that can help minimize self-heating of the spray-dried powder can be the average particle size of the spray-dried powder. Finer powders generally ignite more easily and self-heat more easily due to their higher surface area to volume ratio. Accordingly, in some cases, a larger particle size can help provide a reduced risk of self-heating. Thus, in some examples, the spray-dried powder can have a D(50) particle size of 50 microns to 150 microns. In still additional examples, the spray-dried powder can have a D(50) particle size of from 80 microns to 95 microns, from 85 microns to 105 microns, or from 90 microns to 100 microns.

[0077] The D(50) particle size (Fraunhofer, 0.2 bar) can be determined using a MALVERN MASTERSIZER 3000 particle size analyzer at an air pressure 0.2 bar. The analysis can be performed using the following parameters:

Table 2: Instrument parameters for measuring powder D(50) particle size

Self-Heating

[0078] As discussed elsewhere herein, spray dried powders provide a large amount of potentially flammable and explosive material. As such, it is prudent to assess the self-heating characteristics of spray-dried powders to prevent equipment, and even facility, damage or destruction. The self-heating characteristics of a particular spray-dried powder are determined by the macro formulation of the spray-dried powder, including the formulation components and concentrations, the particle size of the powder, the amount of surface oil (if excessive), etc. [0079] One way to characterize the self-heating properties of a spray-dried powder is to measure the critical self-heating temperature (CSHT), which is a measurement of the highest temperature at which the powder does not ignite due to exothermic conditions. The critical selfheating temperature can be measured using the Hot Storage Test as follows:

[0080] A 400 ml wire basket is filled with powder (e.g., 200 g) and placed under air flow (in Grewer oven, for example). The sample is exposed to 1.2 °C/min increase from 20 °C, then hold at target temperature in the range of 80 - 100 °C for 24 hours with a gas air flow of 2.0 L/min. The internal temperature of sample is measured with a temperature probe. If the temperature increase is > 5 °C at the target temperature, the sample is considered to be self-heating at that temperature. The critical self-heating temperature is the temperature below which the sample internal temperature does not increase by 5 °C. If the sample is not self-heating at a particular target temperature, the test is repeated from the start and held at the next isothermal temperature (in 5 or 10 °C increments) until the temperature at which it will self-heat is reached. The test is stopped at 24 hours, or before 24 hours if the sample is already burning.

[0081] In some examples, the spray-dried powder disclosed herein has a critical self-heating temperature of at least 85 °C. In still additional examples, the spray-dried powder has a critical self-heating temperature of at least 90 °C. In still further examples, the spray-dried powder has a critical self-heating temperature of at least 95 °C, at least 100 °C, at least 105 °C, or at least 110 °C. Gelled Confection

[0082] The spray-dried powder described herein can be incorporated into a gelled confection. The gelled confection can include the spray-dried powder described herein and a gelling substance.

[0083] A variety of gelling substances can be used. In some cases, the gelling substance can be plant-based. Non-limiting examples of plant based gelling substances can include pectin, modified starch, carrageenan, agar-agar, guar gum, or the like. In some examples, the gelling substance can be an animal-based gelling substance, such as gelatin.

[0084] The gelled confection can also include a variety of other ingredients, such as a sugar, a sweetener, water, a flavor, a colorant, a pH adjuster, an antioxidant, a preservative, or the like. [0085] The spray-dried powder can be incorporated in the gelled confection in an amount to provide a suitable level of PLIFA in the gelled confection. In some examples, the gelled confection can include from 2% to 20% by weight of an omega-3 fatty acid, an omega-6 fatty acid, or a combination thereof, based on the total weight of the gelled confection. In some additional examples, the gelled confection can include from 2% to 10% by weight, from 5% to 15% by weight, or from 10% to 20% by weight of an omega-3 fatty acid, an omega-6 fatty acid, or a combination thereof based on the total weight of the gelled confection.

[0086] In some further examples, the gelled confection can include from 1% to 20% by weight of an omega-3 fatty acid based on the total weight of the gelled confection. In some additional examples, the gelled confection can include from 1% to 10% by weight, from 5% to 15% by weight, or from 10% to 20% by weight of an omega-3 fatty acid based on the total weight of the gelled confection. In some additional examples, the gelled confection can include from 1% to 20% by weight of DHA based on the total weight of the gelled confection. In still additional examples, the gelled confection can include from 1% to 10% by weight, from 2% to 8%, from 5% to 15% by weight, or from 10% to 20% by weight of DHA based on the total weight of the gelled confection. In some additional examples, the gelled confection can include from 1% to 20% by weight of EPA based on the total weight of the gelled confection. In still additional examples, the gelled confection can include from 1% to 10% by weight, from 2% to 8%, from 5% to 15% by weight, or from 10% to 20% by weight of EPA based on the total weight of the gelled confection.

[0087] In some further examples, the gelled confection can include from 1% to 20% by weight of an omega-6 fatty acid based on the total weight of the gelled confection. In some additional examples, the gelled confection can include from 1% to 10% by weight, from 2% to 8%, from 5% to 15% by weight, or from 10% to 20% by weight of an omega-6 fatty acid based on the total weight of the gelled confection. In some examples, the gelled confection can include from 1% to 20% by weight of ARA based on the total weight of the gelled confection. In still additional examples, the gelled confection can include from 1% to 10% by weight, from 2% to 8%, from 5% to 15% by weight, or from 10% to 20% by weight of ARA based on the total weight of the gelled confection.

Powder Blends

[0088] The spray-dried powder described herein can be incorporated into a powder blend. The powder blend can include the spray-dried powder described herein and a base powder.

[0089] A variety of substances can be used to formulate the base powder. In some cases, the base powder can include a protein, a carbohydrate, a sweetener, a flavor, a vitamin, a mineral, a fiber, an antioxidant, a colorant, an anti-caking agent, a pH adjuster, a texture enhancer, a solubility enhancer, the like, or a combination thereof.

[0090] Any suitable protein can be used in the powder base. Proteins can include animal-based or plant-based proteins. Non-limiting examples of animal proteins can include whey, casein, gelatin, egg protein, or the like. Non-limiting examples of plant proteins can include rapeseed protein, fava bean protein, chickpea protein, pea protein, lupin protein, lentil protein, mung bean protein, peanut protein, cotton seed protein, sunflower seed protein, sesame seed protein, oat protein, rice protein, corn protein, gluten, soy protein, sorghum protein, quinoa protein, chia protein, hemp protein, buckwheat protein, alfalfa protein, clover protein, duckweed protein, grass protein, potato protein, sweet potato protein, cassava protein, yam protein, taro protein, almond protein, hazelnut protein, walnut protein, cashew protein, coconut protein, or the like. In some examples, the protein can be or include an animal protein. In other examples, the protein can be or include a plant protein. In still other examples, the protein can include an animal protein and a plant protein.

[0091] Any suitable carbohydrate can be used in the powder base. Carbohydrates can include monosaccharides, disaccharides, oligosaccharides, polysaccharides, or a combination thereof. Non-limiting examples can include maltodextrins, dextrose, fructose, glucose, sucrose, or the like, for example. Other carbohydrates listed elsewhere herein can also be used.

[0092] Any suitable vitamins and or minerals can be used in the powder base. Non-limiting examples can include vitamin A, vitamin C, vitamin D, vitamin E, calcium, iron, magnesium, or the like.

[0093] Any suitable fiber can be included in the powder base. Non-limiting examples can include psyllium husk, inulin, or the like. [0094] Any suitable natural and/or artificial sweeteners and flavors can be used in the powder base. Non-limiting examples can include aspartame, acesulfame K, sucralose, saccharin, xylitol, honey coconut sugar, molasses, agave nectar, sucrose, or the like. Natural flavors are known in the art and can typically include chemical flavor compounds that are extracted from natural sources, such as plants or plant products as found in nature. Artificial flavors are also known in the art and can include any of a variety of suitable synthetic flavors useful for powder blends. [0095] Any suitable antioxidant can be included in the powder blend. Non-limiting examples can include resveratrol, green tea extract, quercetin, or the like.

[0096] Any suitable anti-caking agent can be included in the powder base to help prevent the powder blend from sticking together. One non-limiting example is silicon dioxide.

[0097] Any suitable texture enhancer can be included in the powder base to help minimize clumping and improve consistency of the powder. Non-limiting examples can include gums, such as xanthan gum, guar gum, or the like.

[0098] Any suitable solubility enhancer can be included in the powder base to help increase the solubility of the specific components of the blend in a target liquid or other suitable composition, for example. Non-limiting examples can include lecithin, sunflower oil, or the like.

[0099] The spray-dried powder can be incorporated in the powder blend in an amount to provide a suitable level of PLIFA in the powder blend. In some examples, the powder blend can include from 1 mg/g to 200 mg/g of an omega-3 fatty acid, an omega-6 fatty acid, or a combination thereof based on the total weight of the powder blend. In some additional examples, the powder blend can include from 1 mg/g to 20 mg/g, from 10 mg/g to 100 mg/g, from 50 mg/g to 150 mg/g, or from 100 mg/g to 200 mg/g of an omega-3 fatty acid, an omega-6 fatty acid, or a combination thereof based on the total weight of the powder blend.

[0100] In some further examples, the powder blend can include from 10 mg/g to 200 mg/g of an omega-3 fatty acid based on the total weight of the powder blend. In some additional examples, the powder blend can include from 10 mg/g to 100 mg/g, from 50 mg/g to 150 mg/g, or from 100 mg/g to 200 mg/g of an omega-3 fatty acid based on the total weight of the powder blend. In some additional examples, the powder blend can include from 10 mg/g to 200 mg/g of DHA based on the total weight of the powder blend. In still additional examples, the powder blend can include from 10 mg/g to 100 mg/g, from 20 mg/g to 200 mg/g, from 50 mg/g to 150 mg/g, or from 100 mg/g to 200 mg/g of DHA based on the total weight of the powder blend. In some additional examples, the powder blend can include from 10 mg/g to 200 mg/g of EPA based on the total weight of the powder blend. In still additional examples, the powder blend can include from 10 mg/g to 100 mg/g, from 20 mg/g to 80 mg/g, from 50 mg/g to 150 mg/g, or from 100 mg/g to 200 mg/g of EPA based on the total weight of the powder blend.

[0101] In some further examples, the powder blend can include from 10 mg/g to 200 mg/g of an omega-6 fatty acid based on the total weight of the powder blend. In some additional examples, the powder blend can include from 10 mg/g to 100 mg/g, from 20 mg/g to 80 mg/g, from 50 mg/g to 150 mg/g, or from 100 mg/g to 200 mg/g of an omega-6 fatty acid based on the total weight of the powder blend. In some examples, the powder blend can include from 10 mg/g to 200 mg/g of ARA based on the total weight of the powder blend. In still additional examples, the powder blend can include from 10 mg/g to 100 mg/g, from 20 mg/g to 80 mg/g, from 50 mg/g to 150 mg/g, or from 100 mg/g to 200 mg/g of ARA based on the total weight of the powder blend.

Other Applications

[0102] The spray-dried powders or powder blends disclosed herein can be included in a variety of products. As non-limiting examples, the spray-dried powders or powder blends disclosed herein can be included in a nutritional bar, a sports bar, a meal replacement product, yoghurt, milk, chocolate milk, fruit juice, a coffee product, a coffee creamer, tea, or the like. Such products can be formulated as known in the art, and can incorporate the spray-dried powders or powder blends disclosed herein at appropriate concentrations to provide a source of omega fatty acids.

Example Embodiments

[0103] Various compositions and methods are disclosed herein. To aid in the understanding of these compositions and methods, a number of non-limiting example embodiments are provided in the following numbered clauses for illustration purposes only. The following example embodiments can be combined together in any suitable combination, unless the context clearly suggests otherwise.

[0104] Clause 1. A spray-dried powder, comprising: from 30% to 60% by weight of an oil comprising polyunsaturated fatty acids (PLIFAs) based on a total weight of the spray-dried powder; a wall material, wherein a weight ratio of oil/wall material is from 0.5 to 2; and from 1 % to 35% by weight of plant protein isolate based on the total weight of the spray- dried powder. [0105] Clause 2. The spray-dried powder of clause 1, comprising from 35% to 55% by weight, preferably 40% to 55% by weight, more preferably 35% to 45% by weight of the oil based on the total weight of the spray-dried powder.

[0106] Clause 3. The spray-dried powder of clause 1 or clause 2, wherein the PLIFAs comprise omega-3 fatty acids, omega-6 fatty acids, or a combination thereof.

[0107] Clause 4. The spray-dried powder of any one of the preceding clauses, comprising omega-3 fatty acids in an amount from 12% to 35% by weight, preferably 15% to 25% by weight based on the total weight of the spray-dried powder.

[0108] Clause 5. The spray-dried powder of any one of the preceding clauses, comprising omega-6 fatty acids in an amount from 0.1% to 25% by weight, preferably 10% to 25% by weight, more preferably 0.5% to 10% based on the total weight of the spray-dried powder.

[0109] Clause 6. The spray-dried powder of any one of the preceding clauses, wherein the omega-3 fatty acid comprises docosahexaenoic acid (DHA).

[0110] Clause 7. The spray-dried powder of any one of the preceding clauses, wherein the omega-3 fatty acids comprises eicosapentaenoic acid (EPA).

[0111] Clause 8. The spray-dried powder of any one of the preceding clauses, comprising EPA and DHA, wherein DHA is present at a concentration greater than the concentration of EPA.

[0112] Clause 9. The spray-dried powder of any one of the preceding clauses, comprising a weight ratio of EPA to DHA of less than 1, preferably less than 0.7, more preferably less than 0.5 EPA/DHA.

[0113] Clause 10. The spray-dried powder of any one of clauses 1 to 7, comprising EPA and DHA, wherein EPA is present at a concentration greater than the concentration of DHA.

[0114] Clause 11. The spray-dried powder of clause 10, comprising a weight ratio of EPA to DHA of greater than or equal to 1 , preferably greater than 1.2, more preferably greater than 1.5 EPA/DHA.

[0115] Clause 12. The spray-dried powder of any one of the preceding clauses, wherein the omega-6 fatty acid comprises arachidonic acid (ARA).

[0116] Clause 13. The spray dried powder of any one of the preceding clauses, comprising

ARA and DHA, wherein DHA is present at a concentration greater than the concentration of ARA. [0117] Clause 14. The spray dried powder of any one of the preceding clauses, comprising ARA and EPA, wherein EPA is present at a concentration greater than the concentration of ARA.

[0118] Clause 15. The spray-dried powder of any one of the preceding clauses, wherein the wall material comprises a carbohydrate, a gum, or a combination thereof.

[0119] Clause 16. The spray-dried powder of any one of the preceding clauses, wherein the wall material comprises a polysaccharide.

[0120] Clause 17. The spray-dried powder of any one of the preceding clauses, wherein the wall material comprises a disaccharide, optionally wherein the disaccharide is sucrose.

[0121] Clause 18. The spray-dried powder of any one of the preceding clauses, wherein the wall material comprises a modified starch, optionally wherein the modified starch is a hydrophobically modified starch.

[0122] Clause 19. The spray-dried powder of any one of the preceding clauses, wherein the wall material comprises a gum.

[0123] Clause 20. The spray-dried powder of any one of the preceding clauses, wherein the weight ratio of oil to wall material is from 0.5 to 1.5, preferably 1 to 2, more preferably 1 to 1.8 oil/wall material.

[0124] Clause 21. The spray-dried powder of any one of the preceding clauses, comprising from 1% to 30% by weight, preferably 3% to 25% by weight, more preferably 5% to 20% by weight plant protein isolate based on the total weight of the spray-dried powder.

[0125] Clause 22. The spray-dried powder of any one of the preceding clauses, wherein the plant protein isolate comprises rapeseed protein, chickpea protein, pea protein, soy protein, rice protein, chia protein, hemp protein, or a combination thereof.

[0126] Clause 23. The spray-dried powder of any one of the preceding clauses, wherein the plant protein isolate has a solubility in water of at least 60%, preferably at least 70%, preferably at least 75%, more preferably at least 80% over a pH range of 2 to 5 at a temperature of 23° C.

[0127] Clause 24. The spray-dried powder of any one of the preceding clauses, wherein the plant protein comprises rapeseed protein isolate.

[0128] Clause 25. The spray-dried powder of any one of the preceding clauses, comprising less than 1% by weight, preferably less than 0.5% by weight, more preferably 0% by weight animal protein based on the total weight of the spray-dried powder. [0129] Clause 26. The spray-dried powder of any one of the preceding clauses, comprising less than 2.0% by weight, preferably less than 1.5% by weight, preferably less than 1% by weight, more preferably less than 0.5% by weight surface oil.

[0130] Clause 27. The spray-dried powder of any one of the preceding clauses, wherein the powder has a D(50) particle size of from 50 microns to 150 microns, preferably 60 microns to 130 microns, more preferably 90 microns to 120 microns, based on Fraunhofer diffraction theory at an air pressure of 0.2 bar.

[0131] Clause 28. The spray-dried powder of any one of the preceding claims, comprising from 5% to 20% by weight, preferably from 7% to 18% by weight, more preferably from 8% to 16% by weight, even more preferably from 10% to 14% by weight of a monosaccharide based on the total weight of the spray-dried powder.

[0132] Clause 29. The spray-dried powder of any one of the preceding claims, comprising from 5% to 20% by weight, preferably from 7% to 18% by weight, more preferably from 8% to 16% by weight, even more preferably from 10% to 14% by weight of a di-saccharide, optionally sucrose, based on the total weight of the spray-dried powder.

[0133] Clause 30. A gelled confection, comprising: the spray-dried powder of any one of the preceding clauses; and a gelling substance, wherein the gelled confection comprises from 1% to 20% by weight, preferably 1% to 10% by weight, more preferably 5% to 15% by weight, still more preferably 10% to 20% by weight of omega-3 fatty acids, omega-6 fatty acids, or a combination thereof based on a total weight of the gelled confection.

[0134] Clause 31. The gelled confection of clause 30, comprising from 1% to 20% by weight, preferably 1% to 10% by weight, more preferably 2% to 8% by weight, still more preferably 5% to 15% by weight DHA based on the total weight of the gelled confection.

[0135] Clause 32. The gelled confection of any one of clauses 30 to 31, comprising from 1% to 20% by weight, preferably 1% to 10% by weight, more preferably 2% to 8% by weight, still more preferably 5% to 15% by weight EPA based on the total weight of the gelled confection.

[0136] Clause 33. The gelled confection of any one of clauses 30 to 32, wherein the gelling substance is a plant-based gelling substance.

[0137] Clause 34. The gelled confection of any one of clauses 30 to 33, wherein the gelling substance is an animal-based gelling substance.

[0138] Clause 35. A powder blend, comprising: the spray-dried powder of any one of clauses 1 to 29; and a powder base, wherein the powder blend comprises from 1 mg/g to 200 mg/g, preferably 1 mg/g to 20 mg/g, more preferably 10 mg/g to 100 mg/g, still more preferably 50 mg/g to 150 mg/g of omega-3 fatty acids, omega-6 fatty acids, or a combination thereof based on a total weight of the powder blend.

Experimental Examples

[0139] Having generally described the spray-dried powders and associated methods and uses, a further understanding can be obtained by reference to the following experimental examples provided herein. The following experimental examples are provided for purposes of illustration only and are not intended to be limiting.

Example 1 - Spray-Dried Powders having > 40% (w/w) PUFA Oil

[0140] Modified starch, sucrose, citric acid, and sodium ascorbate were dissolved in water by mixing and heating to 65 °C. The mixtures were held at 65 °C to pasteurize the samples, after which the samples were cooled to 40 °C. The pH was monitored to ensure low pH (between 2 and 5) for both microbiological safety and suitable emulsion properties of the modified starch. VERTIS™ CanolaPRO® (hereinafter “CanolaPRO”) was then added to the composition and mixed. Life’s® Omega 60 (pre-heated to 40 °C) was then added to the composition and mixed. The composition was emulsified with a rotor stator at high solids (e.g., at least 50% (w/w)) to obtain an emulsion D(50) droplet size < 1 pm (MIE diffraction theory). The emulsion was then diluted with water and mixed.

[0141] The diluted emulsion was then spray dried using a single stage spray-dry tower configuration with a Niro air distributor and a Niro plate rotary atomizer at 11500 rpm. The tower inlet air was fed at 1800 m³/hour at a temperature of 155 °C with a moisture content of < 5 g/m³, using a bottom air outlet at a measured air temperature of from 82 to 88 °C.

[0142] The various physical properties presented in Table 3 were measured as described elsewhere herein. Table 3: Formulations and Physical Properties of Samples 1-5

1. commercially available from DSM Nutritional Products

Example 2 - Sensory Evaluation of Spray-Dried Powders having > 40% PUFA Oil

[0143] Additional spray-dried powders were prepared under good manufacturing practices (GMP) in the same manner as described in Example 1. Samples 6 and 7 both included CanolaPRO, whereas Sample 8 was a comparative example excluding CanolaPRO. The formulations are presented in Table 3 below.

Table 4: Formulations and Physical Properties of Samples 6-8

1. commercially available from DSM Nutritional Products

[0144] In addition to the physical property data presented in Table 4, Samples 6-8 were evaluated by a sensory panel as follows:

[0145] 10 trained sensory panelists evaluated Samples 6-8 for fishy smell and fishy taste on a scale from 0 (least intense) to 6 (most intense). For stability studies, the powders were placed in airtight containers and left at ambient temperature.

[0146] The results are presented below in Table 5.

Table 5: Sensory Results of Samples 6-8

[0147] As can be seen in Table 5, Samples 6 and 7 including CanolaPro had a less intense fishy smell as compared to Sample 8 without CanolaPro. Also, at the 3-month timepoint, the Samples 6 and 7 performed better in both fishy smell and fishy taste as compared to Sample 8.

Example 3 - Sensory Profile of Gummies Including Spray-Dried Powder

[0148] Gelled confections (gummies) were prepared including the spray dried powders of Samples 6 and 7. The formulation of these gummies is depicted in Table 6 below. Table 6: Formulation of Gummies for Sensory Stability Study of Samples 6 and 7

[0149] An additional gummy was prepared using the commercially available coacervate powder life’sOmega 033-P100, commercially available from DSM Nutritional Products, LLC. While the same PUFA oil was used to produce the spray dried powders in Samples 6-8 and the commercially available reference powder, the concentrations of the oil in each powder is slightly different and the overall composition of the powders is somewhat different. For example, life’sOmega 033-P100 does not include VERTIS™ CanolaPRO®. As such, the gummy including the commercially available powder has a slightly different formulation as depicted in Table 7 below.

Table 7: Formulation of Reference Gummy for Sensory Stability Study

[0150] Gummies were prepared by dry blending pectin with a portion of the sucrose (10 wt%, based on total formulation weight). The dry blend was added to boiling water while stirring with high speed mixer at 9000 rpm until the pectin was completely dissolved.

[0151] The pectin solution was combined with additional sucrose (4 wt%, based on total formulation weight) and the glucose syrup. The mixture is slowly heated to 106 °C with gentle mixing.

[0152] Separately, a slurry was prepared by mixing the PLIFA powder (spray-dried or coacervate) with an additional portion of sucrose (6 wt%, based on total formulation weight) and water. The slurry was added to the pectin mixture once the temperature of the pectin mixture reached 106 °C for 1 minute. The rest of the formulation ingredients were also added at this time. The mixture was stirred until homogeneous.

[0153] The homogeneous mixture was then poored into silicon molds and allowed to solidify for 24 hours at room temperature. The gummies were then demolded, coated with a glazing agent, and allowed to dry under ambient conditions for 24 hours.

[0154] For stability studies, the gummies were placed in airtight containers and left at ambient temperature.

[0155] At each timepoint, from 9 to 12 trained panelists evaluated each of the gummies to assess fishy smell, fishy taste, and flavor intensity (mango) on a scale from 0-6, with 0 being the least intense and 6 being the most intense. The results are presented below in Tables 8-10.

Table 8: Sensory Data for Gummy Formulated with Sample 6 Spray-Dried Powder

Table 9: Sensory Data for Gummy Formulated with Sample 7 Spray-Dried Powder Table 10: Sensory Data for Gummy Formulated with life’sOmega 033-P100

[0156] As can be seen from Tables 8-10, the gummies prepared with Sample 6 and Sample 7 spray-dried powders had less intense fishy smell and fishy taste as compared to the gummies prepared with the reference coacervate powder. Furthermore, the mango flavor was more intense over the 6-month stability period for the gummies prepared with Sample 6 and Sample 7 spray-dired powders as compared to the gummy prepared with the reference coacervate powder.

Example 4 - Comparative Spray-Dried Powders having > 40% PUFA Oil

[0157] Samples 9 and 10 were prepared using the same process as described above in Example 1, with the exception that the spray drying was performed using a two fluid nozzle spray dryer instead of a Niro Disc spray dryer. Specifically, spray drying was performed using a tower with a single stage configuration using an FSD air distributor and a 2-fluid nozzle atomizer at an atomizing air pressure of 1.5 bar. The tower inlet air was introduced at a flow rate of 1500 m³/hour at a temperature of 155 °C and a moisture content of < 4 g/m³. A bottom air outlet was used with a measured outlet air temperature of from 78 to 79 °C.

[0158] The formulations of these samples are presented in Table 11 below.

Table 11 : Formulations and Physical Properties of Comparative Samples 9 and 10

1 . commercially available from DSM Nutritional Products

[0159] As can be seen from Table 11, the emulsion droplet size was comparatively large, suggesting that the formulations did not emulsify well. Furthermore, each of these samples had a surface oil content of greater than 2% by weight, which can lead to poor sensory data. Furthermore, the low particle size further increases the risk of self-heating and reduces the encapsulating efficacy of the powder.

Example 5 -Spray-Dried Powders having > 30% PUFA Oil

[0160] Additional spray-dried powders were prepared having lower oil content as compared to those in Examples 1-3. These spray-dried powders had formulations according to Table 12 below. Generally, the samples were prepared in the same manner as described in Example 1, except that Sample 11 was prepared using a 2-fluid nozzle atomizer as described in Example 4.

Table 12: Formulations and Physical Properties of Samples 11-15

[0161] Like Samples 9 and 10 in Example 4 above, Sample 11 had a high emulsion droplet size, suggesting the formulation did not emulsify well. In contrast, Samples 12-15 had better emulsion properties, but were not prepared using citric acid to get a pH between 3-5. While the surface oil for Samples 12-15 was low, and the particle size was acceptable, the overall physical properties were not as good as those exhibited by Samples 1-7. One observation from this data set is that Sample 13, including sucrose, had the best self-heating properties, suggesting that a suitable mono- or di-saccharide can improve the quality of the spray-dried powder, in some examples.

Example 6 - Additional Spray-Dried Powders having > 30% PUFA Oil

[0162] Additional examples were prepared with an alternative emulsifier and with varying amounts of rapeseed protein in the same general manner as described in Example 1. The formulation details of these samples are shown in Table 13 below.

Table 13: Formulations and Physical Properties of Samples 16-18

1 . commercially available from DSM Nutritional Products

[0163] As can be seen from Table 13, the emulsions were prepared using an acid (citric acid) to keep the pH of the emulsion between 3-5. Good emulsion droplet size was achieved in each of Samples 16-18. While the absence of protein from the emulsion improved the self-heating temperature, the presence of CanolaPRO reduced the surface oil content.

Claims

What is claimed is:

1 ) A spray-dried powder, comprising: from 30% to 60% by weight of an oil comprising polyunsaturated fatty acids (PUFAs) based on a total weight of the spray-dried powder; a wall material comprising a monosaccharide, a disaccharide, an oligosaccharide, a polysaccharide, or mixtures thereof, wherein a weight ratio of oil to wall material is from 0.5 to 2 oil/wall material; and from 1 % to 35% by weight of plant protein isolate, based on the total weight of the spray-dried powder.

2) The spray-dried powder of claim 1 , comprising from 35% to 60% by weight, preferably 35% to 55% by weight, more preferably 30% to 45% by weight of the oil based on the total weight of the spray-dried powder.

3) The spray-dried powder of claim 1 or claim 2, wherein the PUFAs comprise omega-3 fatty acids, omega-6 fatty acids, or a combination thereof.

4) The spray-dried powder of any one of the preceding claims, comprising omega- 3 fatty acids in an amount from 12% to 35% by weight, preferably 15% to 25% by weight based on the total weight of the spray-dried powder.

5) The spray-dried powder of any one of the preceding claims, comprising omega- 6 fatty acids in an amount from 0.1% to 25% by weight, preferably 10% to 25% by weight, more preferably 0.5% to 10% based on the total weight of the spray- dried powder.

6) The spray-dried powder of any one of the preceding claims, wherein the omega-3 fatty acid comprises docosahexaenoic acid (DHA).

7) The spray-dried powder of any one of the preceding claims, wherein the omega-3 fatty acids comprises eicosapentaenoic acid (EPA).

8) The spray-dried powder of any one of the preceding claims, comprising EPA and DHA, wherein DHA is present at a concentration greater than the concentration of EPA. ) The spray-dried powder of any one of the preceding claims, comprising a weight ratio of EPA to DHA of less than 1 , preferably less than 0.7, more preferably less than 0.5 EPA/DHA. 0)The spray-dried powder of any one of claims 1 to 7, comprising EPA and DHA, wherein EPA is present at a concentration greater than the concentration of DHA. 1 )The spray-dried powder of claim 10, comprising a weight ratio of EPA to DHA of greater than or equal to 1 , preferably greater than 1 .2, more preferably greater than 1.5 EPA/DHA. 2)The spray-dried powder of any one of the preceding claims, wherein the omega-6 fatty acid comprises arachidonic acid (ARA). 3)The spray dried powder of any one of the preceding claims, comprising ARA and DHA, wherein DHA is present at a concentration greater than the concentration of ARA. 4)The spray dried powder of any one of the preceding claims, comprising ARA and EPA, wherein EPA is present at a concentration greater than the concentration of ARA. 5)The spray-dried powder of any one of the preceding claims, wherein the wall material comprises a carbohydrate, a gum, or a combination thereof. 6)The spray-dried powder of any one of the preceding claims, wherein the wall material comprises a polysaccharide. 7)The spray-dried powder of any one of the preceding claims, wherein the wall material comprises a disaccharide, optionally wherein the disaccharide is sucrose. 8)The spray-dried powder of any one of the preceding claims, wherein the wall material comprises a modified starch, optionally wherein the modified starch is a hydrophobically modified starch. 9)The spray-dried powder of any one of the preceding claims, wherein the wall material comprises a gum. )The spray-dried powder of any one of the preceding claims, wherein the weight ratio of oil to wall material is from 0.5 to 1 .5, preferably 1 to 2, more preferably 1 to 1.8 oil/wall material. )The spray-dried powder of any one of the preceding claims, comprising from 1 % to 30% by weight, preferably 3% to 25% by weight, more preferably 5% to 20% by weight plant protein based on the total weight of the spray-dried powder. )The spray-dried powder of any one of the preceding claims, wherein the plant protein isolate comprises rapeseed protein, chickpea protein, pea protein, soy protein, rice protein, chia protein, hemp protein, or a combination thereof. )The spray-dried powder of any one of the preceding claims, wherein the plant protein isolate has a solubility in water of at least 60%, preferably at least 70%, more preferably at least 75%, still more preferably at least 80% over a pH range of 2 to 5 at a temperature of 23° C. )The spray-dried powder of any one of the preceding claims, wherein the plant protein comprises a rapeseed protein isolate. )The spray-dried powder of any one of the preceding claims, comprising less than 1 % by weight, preferably less than 0.5% by weight, more preferably 0% by weight animal protein based on the total weight of the spray-dried powder.)The spray-dried powder of any one of the preceding claims, comprising less than 2% by weight, preferably less than 1 .5% by weight, preferably less than 1 % by weight, more preferably less than 0.5% by weight surface oil. )The spray-dried powder of any one of the preceding claims, wherein the powder has an D(50) particle size of from 50 microns to 150 microns, preferably 60 microns to 130 microns, more preferably 90 microns to 120 microns, based on Fraunhofer diffraction theory at an air pressure of 0.2 bar.)The spray-dried powder of any one of the preceding claims, comprising from 0% to 10% by weight, preferably from 0% to 5% by weight, more preferably 0% to 1 % by weight, even more preferably 0% by weight of a monosaccharide based on the total weight of the spray-dried powder. 9)The spray-dried powder of any one of the preceding claims, comprising from 5% to 20% by weight, preferably from 7% to 18% by weight, more preferably 8% to 16% by weight, even more preferably 10% to 14% by weight of a disaccharide, optionally sucrose, based on the total weight of the spray-dried powder. 0)A gelled confection, comprising: the spray-dried powder of any one of the preceding claims; and a gelling substance, wherein the gelled confection comprises from 1 % to 20% by weight, preferably 1 % to 10% by weight, more preferably 5% to 15% by weight, still more preferably 10% to 20% by weight of omega-3 fatty acids, omega-6 fatty acids, or a combination thereof based on a total weight of the gelled confection. 1 )The gelled confection of claim 29, comprising from 1 % to 20% by weight, preferably 1% to 10% by weight, more preferably 2% to 8% by weight, still more preferably 5% to 15% by weight DHA based on the total weight of the gelled confection. 2)The gelled confection of any one of claims 29 to 30, comprising from 1 % to 20% by weight, preferably 1 % to 10% by weight, more preferably 2% to 8% by weight, still more preferably 5% to 15% by weight EPA based on the total weight of the gelled confection. 3)The gelled confection of any one of claims 29 to 31 , wherein the gelling substance is a plant-based gelling substance. 4)The gelled confection of any one of claims 29 to 31 , wherein the gelling substance is an animal-based gelling substance. 5)A powder blend, comprising: the spray-dried powder of any one of claims 1 to 28; and a powder base, wherein the powder blend comprises from 1 mg/g to 200 mg/g, preferably 1 mg/g to 100mg/g, more preferably 50mg/g to 160 mg/g, still more preferably 100mg/g to 200mg/g of omega-3 fatty acids, omega-6 fatty acids, or a combination thereof based on a total weight of the powder blend.