WO2009118282A2 - Encapsulation de composés labiles par oxydation - Google Patents

Encapsulation de composés labiles par oxydation Download PDF

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Publication number
WO2009118282A2
WO2009118282A2 PCT/EP2009/053358 EP2009053358W WO2009118282A2 WO 2009118282 A2 WO2009118282 A2 WO 2009118282A2 EP 2009053358 W EP2009053358 W EP 2009053358W WO 2009118282 A2 WO2009118282 A2 WO 2009118282A2
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WIPO (PCT)
Prior art keywords
oil
acid
product
oxidation
oxidation labile
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PCT/EP2009/053358
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English (en)
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WO2009118282A3 (fr
Inventor
Roar Hauch
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Novozymes A/S
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Publication of WO2009118282A2 publication Critical patent/WO2009118282A2/fr
Publication of WO2009118282A3 publication Critical patent/WO2009118282A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/79—Fixation, conservation, or encapsulation of flavouring agents in the form of films
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P20/00—Coating of foodstuffs; Coatings therefor; Making laminated, multi-layered, stuffed or hollow foodstuffs
    • A23P20/10—Coating with edible coatings, e.g. with oils or fats
    • A23P20/12—Apparatus or processes for applying powders or particles to foodstuffs, e.g. for breading; Such apparatus combined with means for pre-moistening or battering
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P20/00—Coating of foodstuffs; Coatings therefor; Making laminated, multi-layered, stuffed or hollow foodstuffs
    • A23P20/10—Coating with edible coatings, e.g. with oils or fats
    • A23P20/15—Apparatus or processes for coating with liquid or semi-liquid products
    • A23P20/18—Apparatus or processes for coating with liquid or semi-liquid products by spray-coating, fluidised-bed coating or coating by casting
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to a product and a method for producing a product with enhanced stability towards oxidation of oxidation labile compounds.
  • omega-3 polyunsaturated fatty acids has been associated with decreased cardiovascular death by decreasing plasma triglycerides, blood pressure, platelet aggregation, and inflammation.
  • seafood is the best source of omega- 3 acids, many individuals do not like the taste of seafood, do not have ready access to seafood, or cannot afford seafood.
  • One solution is to supplement the diet with cod liver oil or fish oil capsules, but this solution has low compliance.
  • Another solution is to add omega-3 rich fish oils directly to foods, such as dairy products, cereal products, baked goods, and nutrition bars.
  • a challenge with the latter approach is to provide the benefits of omega-3 fatty acids without imparting any offending fish flavors or fish odors, which are byproducts of lipid oxidation. Similar challenges exist for other oxidation labile compounds.
  • the invention in a first aspect relates to a method for preparing a product comprising an oxidation labile product having high oxidation stability comprising the steps of: a. Providing a slurry comprising i. An oxidation labile compound ii. A film forming protein b. Spray drying the slurry to provide the product.
  • the method of the invention provides a product comprising an oxidative labile compound, which product has surprisingly high oxidative stability.
  • the invention relates to a food or nutritional product comprising the product according to the invention.
  • Figure 1 shows Oxipres data for products of the invention prepared in examples 1-6, demonstrating the high oxidative stability.
  • the relative oxygen pressure over time is shown in the graph.
  • the drop in pressure corresponds to the time when oxidation in the sample accelerated and thus relative oxidative stabilities can be compared.
  • Figure 2 shows volatile Organic Compounds after 1 , 3, 6 and 15 weeks of storage at 25 0 C of the product prepared in example 1.
  • Figure 3 shown volatile organic compounds after 1 , 3, 6 and 15 weeks of storage at 25 0 C of the product prepared in example 2.
  • Figure 4 shows volatile organic compounds after 1 , 3, 6 and 15 weeks of storage at 25 0 C of the product prepared in example 3.
  • An oxidation labile compound having utility in the present invention includes a material comprising a molecule with a carbon backbone having at least one carbon-carbon double bond that is prone to oxidation. Removal of a labile hydrogen atom from a carbon adjacent to the double bond creates a free radical that is susceptible to attack by oxygen to form a free radical peroxide, which may serve as a catalyst for further oxidation.
  • oxidation labile compounds are suitable for use in this invention.
  • the oxidation labile compound comprises at least one oxidation labile lipid.
  • Oxidation labile lipids include fatty acids, fatty acid esters, fatty acid methyl esters (FAMEs), tri-, di- and/or mono- glycerides, glycolipids, phospholipids, sphingolipids, sterols, sterol esters, steroid hormones and polyisoprenoids.
  • the oxidation labile lipids may be neutral or polar and especially include unsaturated fatty acids.
  • the oxidation labile lipid contains polyunsaturated fatty acids.
  • neutral lipids are triacylglycerols, fat-soluble vitamins and waxes.
  • a typical polar lipid class is phospholipids.
  • a preferred oxidation labile compound may contain long chain polyunsaturated fatty acid, (i.e., fatty acids containing at least 2 unsaturated carbon- carbon bonds, e.g., double bonds and a carbon chain with 18 or more carbon atoms).
  • the long chain polyunsaturated fatty acids are in a particular embodiment omega-3 and/or omega-6 polyunsaturated fatty acids.
  • the polyunsaturated fatty acid may be present within triglycerides.
  • the oxidation labile compound may be a preparation of substantially unsaturated fats or substantially unsaturated oils.
  • fats and oils comprise monoglycerides, diglycerides, triglycerides, and free fatty acids.
  • the glycerides of fats and oils generally comprise fatty acids that are at least 4 carbons in length, and more preferably, unsaturated fatty acids that range in length from 16 to 24 carbons.
  • the unsaturated fatty acid may be monounsaturated or polyunsaturated.
  • the oxidation labile compound may be a polyunsaturated fatty acid (PUFA), which has at least two carbon-carbon double bonds generally in the cis- configuration.
  • the PUFA may be a long chain fatty acid having at least 18 carbons atoms.
  • the PUFA may be an omega-3 fatty acid in which the first double bond occurs in the third carbon-carbon bond from the methyl end of the carbon chain (i.e., opposite the carboxyl acid group).
  • omega-3 fatty acids examples include alpha-linolenic acid (18:3, ALA), stearidonic acid (18:4), eicosatetraenoic acid (20:4), eicosapentaenoic acid (20:5; EPA), docosatetraenoic acid (22:4), n-3 docosapentaenoic acid (22:5; n-3DPA), and docosahexaenoic acid (22:6; DHA).
  • the PUFA may also be an omega-6 fatty acid, in which the first double bond occurs in the sixth carbon-carbon bond from the methyl end.
  • omega-6 fatty acids examples include linoleic acid (18:2), gamma-linolenic acid (18:3), eicosadienoic acid (20:2), dihomo-gamma- linolenic acid (20:3), arachidonic acid (20:4), docosadienoic acid (22:2), adrenic acid (22:4), n-6 docosapentaenoic acid (22:5) and calendic acid (18:3).
  • the fatty acid may also be an omega-9 fatty acid, such as oleic acid (18:1 ), eicosenoic acid (20:1 ), mead acid (20:3), erucic acid (22:1 ), and nervonic acid (24:1 ).
  • the oxidation labile compound may be derived from a biological source, such that it may be a crude mixture of proteins, lipids, and carbohydrates.
  • the oxidation labile compound may be a mixture of lipids that is essentially devoid of proteins and/or carbohydrates.
  • the oxidation labile compound may be a purified lipid.
  • the oxidation labile compound may be a marine animal-derived oil.
  • the marine animal-derived oil may originate from a vertebrate, in-vertebrate or micro- or unicellular-organism fish or a marine organism, e.g. such that the oil may be a fish oil or a marine microorganism oil.
  • the long chain (2OC, 22C) omega-3 and omega-6 fatty acids are found in marine organisms. The ratio of omega-3 to omega-6 fatty acids in marine organisms ranges from about 8:1 to 20:1.
  • Aquatic organisms from which oil rich in omega-3 fatty acids may be derived include, but are not limited to tuna, abalone scallops, albacore tuna, anchovies, catfish, clams, cod, gem fish, herring, lake trout, mackerel, menhaden, orange roughy, salmon, sardines, sea mullet, sea perch, shark, shrimp, squid and trout.
  • the oxidation labile compound may be a plant-derived oil.
  • Plant and vegetable oils are rich in omega-6 fatty acids. Some plant-derived oils, such as flaxseed oil, are especially rich in omega-3 fatty acids.
  • Plant or vegetable oils are generally extracted from the seeds of a plant, but may also be extracted from other parts of the plant.
  • Plant or vegetable oils that are commonly used for cooking or flavoring include, but are not limited to, acai oil, almond oil, amaranth oil, apricot seed oil, argan oil, avocado seed oil, babassu oil, ben oil, blackcurrant seed oil, Borneo tallow nut oil, borage seed oil, buffalo gourd oil, canola oil, carob pod oil, cashew oil, castor oil, coconut oil, coriander seed oil, corn oil, cottonseed oil, evening primrose oil, false flax oil, flax seed oil, grapeseed oil, hazelnut oil, hemp seed oil, kapok seed oil, lallemantia oil, linseed oil, macadamia oil, meadowfoam seed oil, mustard seed oil, okra seed oil, olive oil, palm oil, palm kernel oil, peanut oil, pecan oil, pequi oil, perilla seed oil, pine nut oil, pistachio oil, poppy seed oil, prune kernel oil, pumpkin seed oil, quinoa
  • the oxidation labile compound may be derived from microorganisms such as algae, fungi and bacteria.
  • the fungi is Mortierella alpine.
  • the oxidation labile compound may be an algae derived oil.
  • algae-derived oils include those from and Suitable algae, from which oil is extracted, include Aphanizomenon, Bacilliarophy, Botryococcus, Chlorophyceae, Crypthecodinium, Dunaliella, Euglena, Isochrysis, Nannochloropsis, Nannochloris, Neochloris, Phaeodactylum, Pleurochrysis, Prymnesiumparvum, Scenedesmus, Schizochytrium, Spirulina and Tetraselmis.
  • Aphanizomenon Bacilliarophy, Botryococcus, Chlorophyceae, Crypthecodinium, Dunaliella, Euglena, Isochrysis, Nannochloropsis, Nannochloris, Neochloris, Phaeodactylum, Pleurochrysis, Prymnesiumparvum, Scenedesmus, Schizochytrium, Spirulina and Tetraselmis.
  • the algae, from which oil is extracted include Aphanizomenon flos-aquae, Bacilliarophy sp., Botryococcus braunii, Chlorophyceae sp., Crypthecodinium cohnii, Dunaliella tertiolecta, Euglena gracilis, Isochrysis galbana, Nannochloropsis salina, Nannochloris sp., Neochloris oleoabundans, Phaeodactylum tricornutum, Pleurochrysis carterae, Prymnesiumparvum, Scenedesmus dimorphus, Schizochytrium sp., Spirulina sp., and Tetraselmis chui.
  • the core comprising the oxidation labile compound is a lipid enriched biomass produced from a microorganism, in particular from an auxotrophic marine microorganism containing - at least in part - the antioxidants produced by said microorganism.
  • auxotrophic marine microorganism is an algae, in particular a micro algae or an algae-like microorganism, preferably a member of the Stramenopiles group, more preferably a Hamatores sp, a Proteromonads sp, a Opalines sp, a Developayella sp, a Diplophrys sp, a Labrinthulids sp, a Thraustochytrids sp, a
  • Biosecids sp an Oomycetes sp, a Hypochytridiomycetes sp, a Commation sp, a Reticulosphaera sp, a Pelagomonas sp, a Pelagococcus sp, an Ollicola sp, an Aureococcus sp, a Parmales sp, a Diatoms sp, a Xanthophytes sp, a Phaeophytes sp (brown algae), a Eustigmatophytes sp, a Raphidophytes sp, a Synurids sp, an Axodines sp, a Chrysomeridales sp, a Sarcinochrysidales sp, a Hydrurales sp, a Hibberdiales sp, or a Chromulinales sp.
  • the lipid enriched biomass may be produced as known in the art, e.g., as described in WO 2005/021735.
  • the oxidation labile compound may be a spice or fragrance oil.
  • suitable examples of spice or fragrant oils include angelica oil, anise oil, basil oil, bergamont oil, orange oil, black pepper oil, calamus oil, citronella oil, calendula oil, camphor oil, cardamom oil, celery oil, chamomile oil, cinnamon oil, clove oil, coriander oil, lemon grass oil, cypress oil, cumin seed oil, davana oil, dill seed oil, eucalyptus oil, fennel seed oil, garlic oil, geranium oil, ginger oil, grape seed oil, hyssop oil, jasmine oil, juniper berry oil, lavender oil, lemon oil, lime oil, myrrh oil, neroli oil, neem oil, nutmeg oil, palm Rosa oil, parsley oil, peppermint oil, rose oil, rosemary oil, rose wood oil, sage oil, sesame oil, spearmint oil,
  • the oxidation labile compound may be a pharmaceutical fo rm u l ati o n co m p ri s i n g a n oxi d ati ve ly u n sta bl e p h a rm a ce u ti ca l , s u ch a s arachadonic/arachidonic acid or a prostaglandin.
  • the formulation may also comprise an unstable oil as a carrier.
  • Suitable examples of pharmaceutical grade carrier oils include cod liver oil, corn oil, cottonseed oil, eucalyptus oil, lavender oil, olive oil, peanut oil, peppermint oil, safflower oil, sesame oil, and soybean oil.
  • the oxidation labile compound may also be a formulation comprising a fat-soluble vitamin, such as vitamin A, D, K, or E.
  • the oxidation labile compound may be preparation of fish materials or fish meal, which is the solid material that remains after most of the water and oil have been removed from the starting fish material.
  • fish or marine organism that may be used for the preparation of fish meal include anchovy, blue whiting, capelin, crab, herring, mackerel, menhaden, pollack, salmon, shrimp, squid, tuna, and whitefish.
  • the oxidation labile compound may be an animal-derived fat.
  • suitable animal-derived fats include poultry fat, beef tallow, mutton tallow, butter, pork lard, whale blubber, and yellow grease (which may be a mixture of vegetable and animal fats).
  • the oxidation labile compound is an oil from marine organisms comprising omega-3 and omega-6 fatty acids.
  • the oxidation labile compound is an omega-3 fish oil.
  • the oxidation labile compound is an omega-3 fatty acid.
  • the oxidation labile compound content of the core is in amounts of more thani O % w/w, in particular in amounts of 10-20% w/w. In one embodiment the oxidation labile compound is present in the core in amounts of more than 5%. In another embodiment the oxidation labile compound is present in the core in amounts of more than 10%. In a further embodiment the oxidation labile compound is present in the core in amounts of more than 15%. In a particular embodiment the oxidation labile compound is present in the core in amounts of more than 20%. In a further particular embodiment the oxidation labile compound is present in the core in amounts of more than 25%, more than 30%, more than 35%, more than 40%, more than 50%, more than 60% or even more than 75%.
  • a film forming compound is according to the invention intended to mean a protein capable of forming a film in aquatic environments.
  • Film forming compounds as such are know within the art.
  • the film forming compound is a water soluble and amphiphilic molecule with film forming properties due to their ability to make molecular interactions.
  • Such molecules are known for the skilled person as molecules capable of stabilizing oil in water emulsions and are generally known as emulsifying compounds, however the present inventors surprisingly have discovered that these film forming proteins can be used for encapsulation of oxidative labile compounds such as PUFA.
  • the film forming protein is an edible or organic compound, more preferred the film forming compound is a protein of plant or animal origin such as a milk protein.
  • the film forming compound may be a partly or fully water soluble protein; it may be an amphiphilic water soluble protein.
  • wheat gluten As examples can be mentioned wheat gluten, rye gluten, barley gluten, rice proteins, corn protein, zein, soy protein, casein and whey proteins, gelatin and collagen
  • the proteins can be naturally proteins i.e. not modified proteins, or it can be proteins modified by e.g. partly or fully deamidated, hydrolysed or denaturated or any combinations thereof.
  • the file forming compounds is a partly or fully deamidated cereal proteins, in particular wheat protein, and most preferred a deamidated and amphiphilic water soluble wheat protein.
  • a preferred film forming compound is the deamidated and amphiphilic water soluble wheat protein marketed under the name Meripro brand from Tate & LyIe.
  • the slurry may also contain other compounds such as antioxidants, vitamins, color etc.
  • the slurry comprises an antioxidant. These additional compounds are suitably added and mixed together with other ingredients of the slurry.
  • Antioxidants may be present in the core together with the oxidation labile compound.
  • the antioxidant may be natural or synthetic. Suitable antioxidants include, but are not limited to, ascorbic acid and its salts, ascorbyl palmitate, ascorbyl stearate, anoxomer, N- acetylcysteine, benzyl isothiocyanate, o-, m-or p-amino benzoic acid (o is anthranilic acid, p is PABA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), caffeic acid, canthaxantin, alpha-carotene, beta-carotene, beta-caraotene, beta-apo-carotenoic acid, camosol, carvacrol, cetyl gallate, chlorogenic acid, citric acid and its salts, clove extract, coffee bean extract, p-coumaric acid, 3,4-dihydroxybenzoic acid, N,N'-diphenyl-p- phenylenediamine (DP
  • Resveratrol is a polyphenol ⁇ phytoalexin. It is a stilbenoid, a derivative of stilbene. It exists as two structural isomers: cis-resveratrol and trans-resveratrol. Resveratrol is produced by plants. It is found in the skins of certain red grapes, in peanuts, blueberries, some pines, the roots and stalks of Japanese knotweed and giant knotweed. Further antioxidants are rice bran extract, rosemary extract, rosmarinic acid, sage extract, sesamol, silymarin, sinapic acid, succinic acid, stearyl citrate, syringic acid, tartaric acid, thymol, tocopherols, or vitamin E, is a fat-soluble vitamin.
  • Natural vitamin E exists in eight different forms or isomers four tocopherols (i.e., alpha-, beta-, gamma-and delta-tocopherol), and four tocotrienols (i.e., alpha-, beta-, gamma-and delta-tocotrienols).
  • antioxidants include tyrosol, vanilic acid, 2,6-di-tert-butyl-4-hydroxymethylphenol (i.e., lonox 100), 2,4- (tris-3',5'-bi-tert-butyl-4'-hydroxybenzyl)-mesitylene (i.e., lonox 330), 2,4,5- trihydroxybutyrophenone, ubiquinone, tertiary butyl hydroquinone (TBHQ), thiodipropionic acid, trihydroxy butyrophenone, tryptamine, tyramine, uric acid, vitamin K and derivates, vitamin Q10, wheat germ oil, zeaxanthin, and/or combinations thereof.
  • tyrosol vanilic acid
  • 2,6-di-tert-butyl-4-hydroxymethylphenol i.e., lonox 100
  • Preferred antioxidants include tocopherols, ascorbyl palmitate, propyl gallate and rosemary extracts.
  • concentration of the antioxidant or combination of antioxidants may range from about 0.001% to about 5% by weight. In a particular embodiment the concentration of the antioxidant or combination of antioxidants may range from about 0.01-1 %. In a most particular embodiment the concentration of the antioxidant or combination of antioxidants may range from about 0.03-0.3% by weight.
  • the antioxidant is selected from the group consisting of tocopherol, resveratrol and/or derivatives thereof, Propyl gallat, rosemary extracts, ascorbic acid, ascorbyl palmitate and combinations thereof.
  • Other preferred examples of suitable antioxidants according to the invention includes: Herbal extracts, e.g.
  • rosemary extract tocopherols or vitamin E, ascorbyl palmitate, astaxantin, canmthaxantin, ascorbic acid, butylated hydroxyanisole (BHA), butylates hydroxytoluene (BHT), tertiary butyl hydroquinone (TBHQ), alpha-carotene, beta-carotene, ethylele diamine tetraacetic acid (EDTA), dodecyl- & octyl & propylgallate, flavonoids e.g.
  • catechin epichatechin, epichatechin gallate, epigallocatechin (EGC), epigallocatechin gallate (EGCG) polyphenol epigallochatechin-3-gallate, flavones, apigenin, chrysin, luteolin, flavenols, datiscetin, myricetin, daemfero, flavanones and lecithin.
  • slurry is intended to be understood as a mixture comprising one or more oxidation labile compounds, one or more film forming compounds, water and other optional ingredients to form an oil in water emulsion.
  • the slurry may according to the invention be prepared using any suitable technology as the skilled person will appreciate and will generally be prepared by adding ingredients of the slurry in a suitable container and mixing thoroughly.
  • the slurry generally comprises film forming agents in an amount of between 10 and 60 % w/w based on the weight of the slurry except water, preferably between 20 and 60% w/w and most preferred around 50% w/w.
  • Water is added in a sufficient amount in order to provide a slurry having satisfactory rheological properties for the preparation of the slurry, optional homogenization and spray drying.
  • water is added in an amount of 10-90% w/w based on the total weight of the slurry, more preferred between 20 and 70% w/w and most preferred around 25-50% w/w.
  • the prepared slurry is spray dried using methods and equipment known per se in the art.
  • the spray drying should be performed under conditions that on one side provides for an adequate drying of the slurry to provide the desired product and on the other side is not so harsh to damage the product.
  • the desired product being a powder comprising a matrix with the oxidation labile compound is distributed evenly throughout the matrix in multiple compartments.
  • the conditions for the spray drying should be selected to provide a product having a particle size in the range on 10-1000 ⁇ m, preferably 20-100 ⁇ m. It is within the skills of the average practitioner to select suitable conditions for the spray drying based on general common knowledge with in the field and optionally routine experiments.
  • a further aspect of the present invention is the provision of a food product comprising an edible material and a product of the invention.
  • the food product may be a liquid beverage.
  • liquid beverages include milk, flavored milk drinks, goat milk, liquid yogurt, soy milk, rice milk, fruit drinks, fruit-flavored drinks, vegetable drinks, nutritional drinks, energy drinks, sports drinks, infant formula, teas, and coffee drinks.
  • the food product may also be a dairy or an egg product.
  • dairy products include, but are not limited to, cheese, ice cream, ice cream products, yogurt, whipping cream, sour cream, cottage cheese, buttermilk, egg whites, and egg substitutes.
  • the food product may be a cereal-based product.
  • Non-limiting examples of food products derived from cereals include breakfast cereals, pasta, breads, baked products (i.e., cakes, pies, rolls, cookies, crackers), tortillas, granola bars, nutrition bars, and energy bars.
  • the food product may be a nutritional supplement.
  • the food product may be a vegetable-derived product. Examples of vegetable-derived food products include textured vegetable proteins, tofu, corn chips, potato chips, vegetable chips, popcorn, and chocolate products.
  • the food product may be a meat product or a meat analog.
  • meat products include, but are not limited to, processed meats, comminuted meats, and whole muscle meat product.
  • the meat may be animal meat or seafood meat.
  • the meat analog may be a textured vegetable or dairy protein that mimics animal or seafood meat in texture.
  • the meat analog may be part or all of the meat in a food product.
  • the food product may also be a canned food product to which the microcapsule is added to prevent oxidation during the heating process.
  • the food product may be a product for animals.
  • the animal may be a companion animal, an agricultural animal, or an aquatic organism.
  • Non-limiting examples of animal food products include canned pet foods, dried pet foods, agricultural animal feeds, and agricultural animal feed supplements.
  • the feeds may be pelleted, extruded, or formed by other methods.
  • the feeds or feed supplements may be liquid. Examples include a nursery diets for monogastric animals, calf milk replacer, or fish and other oils used
  • compositions may be sprayed on or applied to a food product.
  • suitable food products include food bars, nutrition bars, snacks, nuts, oats, cookies, crackers, dried fish or seafood products, and pet foods or pet snacks.
  • the composition may be added directly to oxidation sensitive foods. Examples include, but are not limited to, cooking oils, frying oils, spray-on oils, salad dressings, margarines, nut oils, herb or spice oils, cream liquors, shelf-stable cream products, fish oils, fish sauce, nutritional supplements containing fat soluble vitamins and oils, and pharmaceutical preparations containing oxidation labile lipids or oils.
  • the PUFA compound is for human consumption with the purpose of supplying additional PUFA to the diet.
  • PU FA's are essential to humans because of inadequate synthesis in the human metabolism and the overall goal of supplying additional PUFA to the diet is to reach the Recommended Daily Intake for PUFA.
  • Several types of delivery routes exist such as a dietary supplement as capsules, as fortification of diary products, such as infant formula which is fortified products for infants ( 0-12 months of age) and growing up milk also fortified milk for children, or as fortified foods in general, examples being bread, cakes, chocolate, candy, canned food, cereals, spreads and drinks.
  • the particles of the invention are used in food products, as a nutritional supplement, as a dietary supplement and/or in feed products. The particles of the invention may even be incorporated into pharmaceuticals.
  • Nonfood Products A further aspect of the invention provides nonfood products comprising lipid-coated stabilized products comprising oxidative labile compounds.
  • the nonfood product may be a cosmetic, a body moisturizer, or an anti-aging cream for humans, or it may be a product to prevent pet coat oil oxidation or prevent pet odor.
  • the nonfood product may be a fragrance product or an air freshener product.
  • the nonfood product may be a paint or varnish.
  • the nonfood product may be a mineral oil, a synthetic oil, or a biodiesel.
  • the particles may be used in non food products such as cosmetics, body moisterizers, anti aging creams, fragrances, air freshener, paint and or varnish
  • PUFA-containing lipid was produced and recovered by the following process:
  • lipids were cultivated to obtain a culture broth using the method disclosed in WO 2005/021735 A1. Approx. 50 % (by weight) of the mature cells was lipids. 25-30 % of the lipid content was DHA (22:6(n-3)), and 50-60 % was palmitic acid (16:0).
  • the lipid in the algae was present mainly as lipid vesicles with triglycerides (3 fatty acids pr molecule), and as sterol esters (1 fatty acid) and phospholipids (2 fatty acids) in the cell and organelle membranes.
  • a 750 L pressure tank was heated to 75-8O 0 C with steam and flushed with nitrogen.
  • the culture broth was run through a bead mill with 0.6 mm SiLi beads (Zirconium
  • the pH in the pressure tank was regulated to pH 10 with 45% KOH, as soon as the fluid level reached the pH sensor in the tank.
  • a Westfalia SB-7 centrifuge was heated to 75 0 C with steam, and jerrycans were prepared for product reception by nitrogen-flushing.
  • the alkaline liquid still over 7O 0 C was run through the SB-7 oil centrifuge (200 L/h, 4.0-4.4 bars counter pressure), and the lipid emulsion was recovered as the top phase.
  • the lipid emulsion was collected in 25 L jerrycans.
  • the deamidated wheat protein was a commercial product (Meripro 71 1 ) from Tate & LyIe.
  • the maltodextrin "Glucidex IT 21" (powder, DE; 19-23 spec.) was purchased from Roquette.
  • the PUFA emulsion contained 36% (w/w) water, 57% (w/w) lipid (22-24% DHA) and 7% (w/w) non-lipid Nitrogen Free Extract.
  • the PUFA source used for spray drying example 4+5 was a pure lipid with a composition equal to the lipid fraction of the PUFA emulsion used for example 1-3.
  • the pure lipid used for these examples were provided by heating the emulsion to above 70 0 C and allowing for a phase separation. The resulting pure lipid top phase was used to further formulation.
  • the deamidated wheat protein and maltodextrin were the same as in example 1-3, and the "RPT40" was an antioxidant blend from Kemin Food Ingredients containing rosemary extract, ascorbyl palmitate and tocopherols.
  • Example 6 A commercial powder containing polyunsaturated lipids (mostly DHA) was included as a reference for stability analyses.
  • the product was "Martek DHA tm Powder KSF58" with lot # 7500004068HM was sold by Martek Bioscience Corporation.
  • Example 1-6 were analyzed in the Oxipres apparatus (www.mikrolab.dk) measuring the pressure over sealed 10 g replica samples of the powders from example 1 -6. This was done under accelerated conditions of pure oxygen at initially 5 bar and 50 0 C. The point in time when the pressure over the samples drastically dropped (Induction Period) was recorded in hours. The IP is seen as a measure of the relative stability of the samples, and corresponds to the time when oxidation in the sample accelerates. Induction Periods for the 6 formulations (ex. 1-6) calculated from the graphs seem in figure 1 were as follows;
  • Figure 2, 3 and 4 show the overlaid chromatograms (week 1 , 3, 6 and 15) for powder/example 1 , 2, 3 respectively.
  • VOCs A development of VOCs is seen over time for all 3 samples. The point in time when the formation of VOCs begins show a good fit to the IP's of the same samples. Powders from example 2 and 3 develop VOCs already between W3-W6 (IP's -37-39 hours) while the example 1 powder only develops VOCs somewhere between W6-W15.

Abstract

La présente invention concerne un procédé pour encapsuler des composés labiles par oxydation par préparation d’une suspension comprenant le composé labile par oxydation et un composé filmogène suivie par le séchage par pulvérisation pour obtenir un produit ayant une stabilité à l’oxydation améliorée.
PCT/EP2009/053358 2008-03-25 2009-03-23 Encapsulation de composés labiles par oxydation WO2009118282A2 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107223712A (zh) * 2017-07-11 2017-10-03 安徽牧龙湖食品有限公司 一种特浓杂粮羊乳饮料的加工方法
US10499663B2 (en) 2015-10-16 2019-12-10 Gold & Green Foods Oy Method of manufacturing a meat replacement product and a meat replacement food product
IT202200008018A1 (it) * 2022-04-22 2023-10-22 Calliero S P A Processo per la polverizzazione e stabilizzazione di oli essenziali comprendenti furanodieni

Citations (7)

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Publication number Priority date Publication date Assignee Title
GB878793A (en) * 1959-08-05 1961-10-04 Shinshiro Ohtaki Storage-stable sweet corn powder and the production thereof
US3851083A (en) * 1972-10-25 1974-11-26 Pillsbury Co Process for forming stable food pieces
WO1991006227A1 (fr) * 1989-11-06 1991-05-16 Opta Food Ingredients, Inc. Enduits comestibles a base de proteines
WO2001074175A1 (fr) * 2000-04-04 2001-10-11 Australian Food Industry Science Centre Encapsulation d'ingredients alimentaires
WO2004009054A2 (fr) * 2002-07-24 2004-01-29 General Mills, Inc. Encapsulation de composantes sensibles par pre-emulsification
WO2005048998A1 (fr) * 2003-11-21 2005-06-02 Commonwealth Scientific & Industrial Research Organisation Systemes gastro-intestinaux d'administration
WO2007065718A1 (fr) * 2005-12-08 2007-06-14 Dsm Ip Assets B.V. Hydrocolloide protecteur pour ingredients actifs

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB878793A (en) * 1959-08-05 1961-10-04 Shinshiro Ohtaki Storage-stable sweet corn powder and the production thereof
US3851083A (en) * 1972-10-25 1974-11-26 Pillsbury Co Process for forming stable food pieces
WO1991006227A1 (fr) * 1989-11-06 1991-05-16 Opta Food Ingredients, Inc. Enduits comestibles a base de proteines
WO2001074175A1 (fr) * 2000-04-04 2001-10-11 Australian Food Industry Science Centre Encapsulation d'ingredients alimentaires
WO2004009054A2 (fr) * 2002-07-24 2004-01-29 General Mills, Inc. Encapsulation de composantes sensibles par pre-emulsification
WO2005048998A1 (fr) * 2003-11-21 2005-06-02 Commonwealth Scientific & Industrial Research Organisation Systemes gastro-intestinaux d'administration
WO2007065718A1 (fr) * 2005-12-08 2007-06-14 Dsm Ip Assets B.V. Hydrocolloide protecteur pour ingredients actifs

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10499663B2 (en) 2015-10-16 2019-12-10 Gold & Green Foods Oy Method of manufacturing a meat replacement product and a meat replacement food product
CN107223712A (zh) * 2017-07-11 2017-10-03 安徽牧龙湖食品有限公司 一种特浓杂粮羊乳饮料的加工方法
IT202200008018A1 (it) * 2022-04-22 2023-10-22 Calliero S P A Processo per la polverizzazione e stabilizzazione di oli essenziali comprendenti furanodieni

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