WO2012033523A1 - Procédés d'amélioration de la stabilité d'aliments, de boissons et de produits cosmétiques faisant appel à des mélanges d'arômes naturels - Google Patents

Procédés d'amélioration de la stabilité d'aliments, de boissons et de produits cosmétiques faisant appel à des mélanges d'arômes naturels Download PDF

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Publication number
WO2012033523A1
WO2012033523A1 PCT/US2011/001551 US2011001551W WO2012033523A1 WO 2012033523 A1 WO2012033523 A1 WO 2012033523A1 US 2011001551 W US2011001551 W US 2011001551W WO 2012033523 A1 WO2012033523 A1 WO 2012033523A1
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food
antioxidant
antioxidant composition
foods
sugar
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PCT/US2011/001551
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English (en)
Inventor
Roger Nahas
Anita E. Uhlir
Peter Collins Vanalstyne
Elizabeth Barren
Donald Berdahl
James Barren
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Kalamazoo Holding, Inc.
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Publication of WO2012033523A1 publication Critical patent/WO2012033523A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; 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
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/215—Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3526—Organic compounds containing nitrogen
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3562—Sugars; 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
    • 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
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the instant invention relates to improved methods for enhancing the stability of foods, beverages, nutritional supplements and/or cosmetics by incorporating into them effective amounts of naturally derived compositions of a Maillard reaction product resulting from reacting an amino acid and a sugar, optionally containing one or more chelating or non-chelating antioxidant components derived from edible herbs, spices, fruits, vegetables and/or grains, and/or further optionally combined with one or more synthetic food grade antioxidants.
  • Enhanced stability includes flavor stability, color stability, textural stability and/or component stability (such as lipid, vitamin, carotenoid, protein or other constituent).
  • the present invention further relates to processes for preparing antioxidant flavoring compositions with specific activities and solubility characteristics tailored to deliver the antioxidant components to sites within the foods, beverages, nutritional supplements or cosmetics where they operate most effectively.
  • the present invention further relates to foods, beverages, nutritional supplements and cosmetics treated with the inventive compositions.
  • Food antioxidants [0002] Substances that serve to protect foods from the deleterious effects of oxidation are commonly added to foods and are called antioxidants or stabilizers. These substances can be naturally or synthetically derived, although consumers generally prefer those materials from natural sources. The performance of a given antioxidant is dependent upon many things, including its chemical nature (stability, reactivity, functionality and the like) and its physical properties (volatility, solubility, polarity and the like). Antioxidant substances can have different modes of action, interfering with oxidation processes in a number of ways. Substances can function as antioxidants if they:
  • radical scavengers are phenolic compounds such as carnosic acid, carnosol, rosmarinic acid, tocopherols, tocotrienols, and oleorupins.
  • oxygen scavengers • React preferentially with oxygen, removing it from the environment of the substrate being stabilized.
  • oxygen scavengers include ascorbic acid.
  • quenchers • Absorb, and render less harmful, energy from incident radiation or energy from excited chemical species (quenchers). Examples of quenchers include carotenoids.
  • AO regenerators • Reduce and thereby regenerate oxidized antioxidants (AO regenerators). Examples also include ascorbic acid regenerating tocopherols.
  • antioxidant substances in order to be effective in a complex food, beverage, nutritional supplement and / or cosmetic, antioxidant substances must possess the right solubility properties to allow them to migrate to the site in the substrate matrix where the oxidation or its initiation is taking place.
  • EDTA ethylenediamine tetraacetic acid
  • EDTA's structure makes for a very powerful metal chelator.
  • EDTA is particularly useful in stabilizing oil and water-containing emulsion systems, such as mayonnaise, salad dressings, emulsified beverages, and the like. Since EDTA has many industrial applications, it has become widespread in the environment and is the most abundant man-made compound in many European surface waters. Although the isolated molecule does not present a risk of bioaccumulation, the ligand-metal complexes may significantly increase the bioavailability of extremely dangerous heavy metals (Oviedo and Rodriguez, 2003). Because of these concerns and the consumer preference for natural as opposed to synthetic additives, there is a need to find a natural, preferably GRAS (Generally Recognized As Safe) replacement for this important and highly functional food additive.
  • GRAS Generally Recognized As Safe
  • Model systems that are simpler representations of foods, beverages, nutritional supplements and cosmetics can be used to test the performance of antioxidant compositions.
  • Food systems that contain polyunsaturated fats are particularly subject to lipid oxidation leading to food quality deterioration and formation of off-flavors. Oxidation can be monitored by measuring the primary oxidation products (hydroperoxides) as well as secondary oxidation products (aldehydes and ketones).
  • Hydroperoxide monitoring tests include spectroscopic methods that allow the assessment of the oxidative stability of a bulk oil system or oil and water emulsion system and the efficacy of antioxidant treatments by measuring the hydroperoxides in a system in cumene hydroperoxide equivalents, via the conversion of iron (II) to iron (III) (Bou et al., 2008) or by simply monitoring the emulsion absorbance at 234 nm which is the absorbance of the conjugated dienes (precursors or hydroperoxides).
  • Most of the emulsion models established to mimic food systems and used as matrices to test the performance of various antioxidants consist of oil-in-water emulsions (O/W).
  • Foods containing O/W emulsions include mayonnaise, milk, cream, etc while others like butter and margarine, are water in oil emulsions (W/O) where the oil (the continuous phase) surrounds droplets of water (the discontinuous phase).
  • W/O oil emulsions
  • the Maillard reaction is probably the most important reaction that takes place in food during processing.
  • the heating of amino acids and reducing sugars results in a cascade of complicated reactions resulting in pigments responsible for food coloring as well as chemical structures that constitute what we perceive as processed, or cooked food taste and aroma.
  • MRP Maillard reaction products'
  • buffer in such an aqueous system requires a dialysis or desalination step following by a drying step (freeze-drying, spray-drying, etc.), which is not convenient from a commercial perspective if antioxidative MRP flavoring preparations are to be used as intentional food additives.
  • MRP fractions can be separated by dialysis from Maillard reaction products based on molecular size generated in an aqueous model system after 4 hours of reaction time, and pure single MRPs can be isolated in order to screen the fractions as well as the single pure MRPs for their antioxidant activity (Monti et al., 1999).
  • Using such a method for generating antioxidant additives would not be efficient on a large scale, and would involve relatively lengthy and expensive steps such as dialysis, fractionation and purification. These processing steps would affect the yield and the cost of the product.
  • This invention presents a simple, easy, inexpensive and efficient method to prepare and incorporate antioxidative MRP flavorings into foods as intentional antioxidant food additives.
  • the current invention solves the problems preventing the use of methods known in the art to prepare and use antioxidative Maillard reaction flavoring preparations as intentional food additives.
  • Naturally-derived antioxidants are used with good effect as stabilizers in many food, beverage, nutritional supplements and cosmetics products. There are many products and ingredients, however, that are highly oxidatively unstable and for which the current state of the art antioxidants are insufficient to provide the degree of increased oxidative stability required or desired.
  • This invention allows the use of Maillard reaction products produced in a controlled, polar system as flavoring food additives with antioxidant properties.
  • Dairy products and their corresponding non-dairy vegetable fat substituted products undergo accelerated oxidation because of the high water content in the matrices (oil-in-water).
  • the presence of small-sized oil droplets results in a high water contact surface area and therefore larger interface areas where the oil molecules are prone to oxidation.
  • EDTA is a very powerful chelating agent and is very effective in preserving the flavor of mayonnaise in storage. In Germany, EDTA is not allowed in mayonnaise. Absent the ability to use this highly effective stabilizer, German mayonnaise with sufficient shelf life must be manufactured with oils that are inherently more stable than the oils often used in other countries, namely oils that are relatively more saturated. The use of more saturated fats runs counter to the wish to include more unsaturated fats in the diet, and there is a desire to make and sell mayonnaise in Germany that incorporates more highly unsaturated and less inherently stable oils.
  • mayonnaise preparations containing highly unsaturated fish and algal-derived oils are desired.
  • the current stabilizing agents allowed by German regulations are not sufficiently effective to stabilize mayonnaise made with higher levels of unsaturation.
  • One purpose of this invention is to provide materials and methods to enhance the stabilization of mayonnaise and related oil-in-water emulsions such as salad dressings, dairy products, creamers and the like, beyond what is now practiced in the art.
  • Cured Meats are subject to oxidation processes that result in the loss of desirable flavors, the formation of off-flavors, the loss of desirable cured meat pigment color, and the formation of undesirable colors, among other effects that cause a decrease in the shelf life of the product. Cured meats are also subject to the growth of bacteria, yeasts and molds that also shorten the shelf life of the product. Another purpose of this invention is to provide materials and methods to enhance the stabilization of cured meats beyond what is now achievable in the prior art.
  • the frying process subjects the frying oil and the article being fried to severe oxidative stress.
  • Another purpose of this invention is to provide materials and methods to improve the shelf life and quality of frying oils and of fried foods.
  • Meat products especially, including baby food preparations, that are retorted in metal, glass or plastic containers often suffer oxidative damage leading to off color formation particularly at the surface of the product.
  • the development of off flavors can also occur during the retort process and in the period during which the product is stored prior to use. It is a further purpose of this invention to provide materials and methods to stabilize potted meat products against oxidation resulting in flavor and color changes.
  • Coffee extracts or concentrates are replacing freshly brewed coffee in many retail settings. Freshly brewed coffee and coffee extracts or concentrates are susceptible to oxidative process leading to unwanted flavor changes. It is a further purpose of this invention to provide materials and methods to stabilize coffee and coffee extracts or concentrates against oxidatively induced flavor changes.
  • Beer and other malt beverages undergo undesirable flavor changes as a result of oxidative processes during the brewing process and in storage. It is a further purpose of this invention to provide materials and methods to increase the flavor stability and shelf life of beer and malt beverages.
  • flavor compositions with utility as antioxidants in food, beverages, nutritional supplements and cosmetics can be prepared by reacting a sugar with an amino acid in a natural, semi-natural or artificial food grade carrier, (such as glycerine, alkylene diols or a liquid emulsifier).
  • a natural, semi-natural or artificial food grade carrier such as glycerine, alkylene diols or a liquid emulsifier.
  • compositions are obtained without any necessary pH control, nor subsequent purification or isolation steps, and in most cases can be added directly to the food in the carrier where the reaction has been performed.
  • the antioxidative Maillard reaction flavoring compositions is surprisingly effective at low doses and hence it delivers an antioxidant protection without affecting the taste, odor and color of the food system to which it is being added. This will extend the benefit of the antioxidative effect of the endogenous Maillard reaction in cooked food to a controlled use of the latter as a flavoring additive with antioxidant capacity.
  • the present invention further relates to highly effective antioxidant compositions made by the Maillard reaction from at least one monosaccharide with at least one amino acid.
  • a combination of the Maillard reaction antioxidative flavors can be mixed together with metal chelating elements derived from herbs, spices, fruits and / or vegetables, radical scavengers, oxygen scavengers, secondary antioxidants, quenchers and/or antioxidant regenerators derived from natural and /or synthetic sources.
  • the present invention thus provides methods for stabilizing foods, beverages, cosmetics and/or nutritional supplements by the application vegetable and/or grain-derived metal chelating compositions, optionally containing additional natural and/or synthetic antioxidants to the said food, beverage, cosmetic and or nutritional supplement, in an amount sufficient to have a measurable stabilizing effect.
  • the present invention further provides stabilized foods, beverages, cosmetics and / or nutritional supplements comprising a food, beverage, cosmetic and / or nutritional supplement, together with a stabilizing composition consisting of metal chelating elements derived vegetables and/or grains, optionally combined with synthetic and / or natural antioxidants of the radical scavenger, oxygen scavenger, secondary antioxidant, quencher and / or antioxidant regenerator types.
  • This invention provides a method for stabilizing the fresh flavor and preventing the formation of off-flavors in dairy products and corresponding non- dairy products (where the animal fat is substituted with vegetable fat), salad dressings and other oil-in-water emulsion-based food systems by treating these materials at an effective stage in their production with an effective amount of a antioxidative MRP flavoring preparation, optionally containing one or more antioxidant components also derived from edible herbs, spices, fruits, vegetables and/or grains, and/or further optionally combined with one or more synthetic food grade antioxidants, in a manner that does not impact the taste or color of oil-in- water emulsion-based foods.
  • This invention provides a method for stabilizing the fresh flavor and color and preventing the formation of off-flavors and off-colors in cured meats, including ham, bacon, salt pork, sausage, kippered herring, beef jerky, salami, summer sausage, cold cuts, bologna, pastrami, pepperoni, corned beef, roast beef, hot dogs, dried beef, bratwurst, polish sausage, barbecued pork, pork loin, beef brisket, salmon, liverwurst, pork char sui, prosciutto, culatello, lomo, coppa, bresaola, lardo, guanciale, mocetta, qadid, and the like, by incorporating into these materials at an effective stage in their production, an effective amount of an antioxidative MRP flavoring composition consisting of said antioxidant composition, optionally containing one or more antioxidant components also derived from edible herbs, spices, fruits, vegetables and/or grains, and/or further optionally combined with one or more
  • This invention provides a method for stabilizing the fresh flavor and preventing the formation of off-flavors in frying oils and in the foods fried in that oil by treating the frying oil prior to or during the frying operation with an effective amount of an antioxidative MRP flavoring composition, said antioxidant composition, optionally containing one or more antioxidant components also derived from edible herbs, spices, fruits, vegetables and/or grains, and/or further optionally combined with one or more synthetic food grade antioxidants.
  • This invention provides a method for slowing the rate of oxidation, stabilizing the fresh flavor and preventing the formation of off-flavors in fats and oils containing polyunsaturated lipids by treating these materials at an effective stage in their production or use with an effective amount of an antioxidative MRP flavoring preparation, optionally containing one or more antioxidant components also derived from edible herbs, spices, fruits, vegetables and/or grains, and/or further optionally combined with one or more synthetic food grade antioxidants.
  • This invention provides a method for slowing the rate of oxidation, stabilizing the fresh flavor and preventing the formation of off-flavors in extruded human and animal foods by incorporating into them at an effective stage in their production or use, an effective amount of an antioxidative MRP flavoring composition, said antioxidant composition, optionally containing one or more antioxidant components also derived from edible herbs, spices, fruits, vegetables and/or grains, and/or further optionally combined with one or more synthetic food grade antioxidants.
  • antioxidative, natural flavoring compositions useful for stabilizing foods, cosmetics, beverages and nutritional supplements can be prepared by the Maillard reaction of an amino acid and a sugar reacted at a ratio of amino acid to sugar 1 :20 to 20:1 , including 5:1 -1 :5, for at least 15 min for at least 100° C, for 1-2 hr, or for 2-20 hr in a polar carrier such as glycerin and / or alkylene glycol and /or lecithin and / or any other inert or minimally reactive carrier that allows its direct addition to a food.
  • a polar carrier such as glycerin and / or alkylene glycol and /or lecithin and / or any other inert or minimally reactive carrier that allows its direct addition to a food.
  • Antioxidative, natural flavoring compositions can be obtained from the Maillard reaction of any triose, pentose or hexose with a variety of commercially available amino acids derived from natural sources including but not limited to serine, phenylalanine, histidine, methionine, cysteine, arginine, proline, glutamic acid, or hydrolyzed protein alternatively.
  • the antioxidant substances obtained from the Maillard reaction can be combined to form more complex antioxidant compositions.
  • the antioxidant compositions can be obtained in a variety of ways.
  • One method of obtaining the antioxidant compositions is by a one-step process by adding the amino acid and the sugar to the carrier at 1 -99% by weight (weight of total reactants per 100 g of carrier), including at 5-75%, and subsequently heating and stirring the solution to at least 100° C and holding it for at least 15 minutes before cooling it down to room temperature and using it directly as a food additive without any further processing.
  • Carriers include but are not limited to glycerine and propylene glycol.
  • the MRP flavoring preparations providing antioxidative utility were obtained through direct reaction of the amino acid(s) and sugar (s) in a polar food grade carrier without the need of conventional reaction solvent such as water, fat or a complex food matrix such as bread or meat.
  • antioxidative MRP flavoring preparations can be added directly to foods whenever the carrier is permitted, and carriers can be interchanged based on which one is more favorable in a certain food.
  • Another feature of the present invention involves the combination of antioxidative Maillard reaction flavoring compositions derived from naturally derived amino acids and sugars with other natural antioxidants, including, but not limited to, tocopherols, tocotrienols, ascorbic acid, ascorbates, natural gallates, catechins, epigallocatechin gallate, grape seed extract, olive leaf extract, resveratrol, carbazoles, erythorbic acid, erythorbates, carnosol, carnosic acid, rosmarinic acid, rosmanol, xanthohumol, rosemary extract, sage extract, oregano extract, and other spice and herb extracts.
  • natural antioxidants including, but not limited to, tocopherols, tocotrienols, ascorbic acid, ascorbates, natural gallates, catechins, epigallocatechin gallate, grape seed extract, olive leaf extract, resveratrol, carbazoles, erythorbic acid, erythorbates, car
  • antioxidant formulations that contain a complete contingent of oil soluble or dispersible radical scavenging agents, water soluble or dispersible radical scavenging agents, oil soluble or dispersible chelating agents, and water soluble or dispersible chelating agents, or any combination thereof.
  • oil soluble or dispersible radical scavenging agents water soluble or dispersible radical scavenging agents
  • oil soluble or dispersible chelating agents oil soluble or dispersible chelating agents
  • water soluble or dispersible chelating agents or any combination thereof.
  • Another feature of the present invention involves the combination of chelating compositions derived from herbs, spices, fruits and/or vegetables with synthetic antioxidants such as propyl gallate, BHA, BHT, ethoxyquin, TROLOX ® , TBHQ, ascorbyl palmitate, EDTA. While these compositions are not as preferred as their all-natural counterparts, they are contemplated as part of the present invention in a manner as described in the previous paragraph.
  • Another feature of the present invention involves the use of the antioxidative MRP flavoring compositions, alone, or in combination with other natural or synthetic antioxidants in the stabilization of foods, beverages, cosmetics and nutritional supplements.
  • Another feature of the present invention involves foods, beverages, cosmetics, and nutritional supplements treated with the antioxidative MRP flavoring compositions, alone, or in combination with other natural or synthetic antioxidants.
  • the antioxidative MRP flavoring preparations may be added directly to foods, where their solubility characteristics permit. They may be dissolved in an additional amount of carrier, such as an alkylene diol, glycerin, any food grade surfactants (such as glycerol mono-oleate, lecithin, glycerol monostearate, etc .), benzyl alcohol, and the like, and then added to foods. They may be dispersed onto solid carriers, such as salt, flour, sugars, maltodextrin, silica (such as cabosil), cyclodextrins, starches, gelatins, lactose, whey powders, proteins, and the like and then added to foods.
  • carrier such as an alkylene diol, glycerin, any food grade surfactants (such as glycerol mono-oleate, lecithin, glycerol monostearate, etc .), benzyl alcohol, and the like, and then
  • cosmetics we include as examples, but are not limited to:
  • Lip balm Lip gloss, lipstick, lip stains, lip tint, blush, bronzers & highlighters, concealers & neutralizers, foundations, foundation primer, glimmers & shimmers, powders, eye shadow, eye color, eye liner, mascara, nail polish, nail treatments-strengtheners, make-up, body creams, moisturizers, suntan preparations, sunless tan formulations, body butter, body scrubs, make-up remover, shampoos, conditioners, dandruff control formulations, anti frizz formulations, straightening formulations, volumizing formulations, styling aids, hairsprays, hair gels, hair colors and tinting formulations, anti-aging creams, body gels, essential oils, creams, cleansers, soaps.
  • beverages we include as examples, but are not limited to:
  • Meat wild and domestic; fresh and cured, processed and unprocessed, dried, canned
  • Poultry fish, vegetable protein, dairy products (milk, cheese, yogurt, ice cream), ground spices, vegetables, pickles, mayonnaise, sauces (pasta sauces, tomato-based sauces), salad dressings, dried fruits, nuts, potato flakes, soups, baked goods (breads, pastries, pie crusts, rolls, cookies, crackers, cakes, pies, bagels), vegetable oils, frying oil, rendered fats and oils, fried foods (potato chips, corn chips), prepared cereals (breakfast cereals), cereal grain meals, condiments (ketchup, mustard, cocktail sauce, candies, confectionary, chocolates, baby foods).
  • animal foods we include as examples, but are not limited to: extruded pet food, kibble, dry pet food, semi-dry pet food, animal meals, fish meals and wet pet food.
  • nutritional supplements we include as examples, but are not limited to: eye health supplements, vitamins, nutrition boosters, carotenoid supplements, protein supplements, energy bars, nutritional bars, algal oils, fish oils, oils containing polyunsaturated fatty acids.
  • metal ions we mean those metal ions that promote or initiate lipid or other oxidation processes, including, but not limited to Fe +2 , Fe +3 , Cu + , Cu +2 , Ni +2 .
  • HERBALOX ® Seasoning is a registered trademark of KALSEC ® , Inc.
  • HERBALOX ® Seasoning 41-19-34 comprises a water soluble rosemary extract containing rosmarinic acid.
  • HERBALOX ® Seasoning Type HT-O comprises an oil soluble rosemary extract, with a portion of the volatile oils removed, and comprising carnosic acid and carnosol.
  • HERBALOX ® Seasoning 41.088319 comprises an oil soluble rosemary extract, with a portion of the volatile oils removed, and comprising carnosic acid and carnosol.
  • HERBALOX ® Seasoning QS is a rosemary extract formulation containing carnosic and carnosol that is dispersible in oil and dispersible in water.
  • HERBALOX ® Seasoning Type 25 is an oil soluble rosemary extract containing carnosic acid and carnosol.
  • Example 1 Preparation of antioxidative Maillard reaction solution from xylose and lysine in propylene glycol.
  • D-xylose (15.00 g) and L-lysine (14.60 g) powders were mixed by stirring in 100 g of propylene glycol (PG) heated to at least 65° C and stirred. The temperature was brought to 100° C and held at that temperature for one hour. At one hour, heating was turned off, and the antioxidant MRP solution was allowed to cool to about 65° C, at which time it was transferred to a glass storage vessel, and allowed to complete cooling to room temperature.
  • PG propylene glycol
  • Example 2 Preparation of antioxidative Maillard reaction product solution from xylose and glutamic acid in kosher glycerin.
  • D-xylose (19.50 g) and L-glutamic acid (14.70 g) were added to kosher glycerin (100 g) heated to 65° C, the temperature was brought to 100° C and held at for one hour. At one hour, the heating was turned off, and the antioxidant MRP solution was allowed to cool to about 65° C, at which time it was transferred to a glass storage vessel, and allowed to complete cooling to room temperature.
  • Preparation of the emulsion 780g of distilled water was mixed with 20 g of polysorbate 20 (TWEEN 20) and 200 g of canola oil using a High Sheer blender for 5 minutes at 4500rpm. This mixture was then passed thru a PVA two-stage homogenizer 6 times, attaining a consistent particle size distribution centered on 0.7 ⁇ .
  • polysorbate 20 TWEEN 20
  • canola oil canola oil
  • 20,000 ppm aqueous stock solutions were made for each antioxidative MRP solution to be tested by dissolving 0.2 g of the material in 10ml_ of distilled water.
  • a 1000 ppm stock solution of CaNa2-EDTA (ETDA) was made by dissolving 0.01 g of the EDTA in 10ml_ of distilled water.
  • 50 g aliquots of the emulsion were mixed with 125, 250 or 500 ⁇ _ of the MRP stock solutions to attain 50, 100, or 200 ppm test mixtures.
  • a 50 g aliquot of the emulsion was mixed with 500uL of the EDTA stock solution to attain a 10ppm standard test mixture.
  • a control mixture was made in this manner using 500 ⁇ _ of distilled water as the additive.
  • the treated emulsions were incubated at 60° C.
  • Antioxidant activity was determined by slightly modified method (Shantha and Decker, 1994) by monitoring the progression of hydroperoxides. Comparisons of the curves for the samples to the EDTA and control curves indicate the relative antioxidant activity of the materials.
  • One set of data is presented in Figure 1.
  • a control sample is prepared by mixing 100 ml_ of deionized water with 400 g of unfortified canola oil, 8.0 g of ATMOS 300 K and 1 g of TWEEN 20 using a WARING ® Blender. The blended emulsion is passed through a single stage homogenizer 10 times, and then stored refrigerated at 6° C.
  • Test samples containing the inventive antioxidant MRP flavoring compositions, optionally containing one or more antioxidant component also derived from edible herbs, spices, fruits, vegetables and/or grains, and/or further optionally combined with one or more synthetic food grade antioxidants are prepared by adding the antioxidant to the water or the oil used to make the emulsion, and the W/O emulsions are prepared as described above.
  • the W/O emulsions are allowed to age, aliquots are taken a various times and dissolved in methanol or ethanol with sonication. The absorbance at 234 nm is measured and it is found that conjugate diene hydroperoxide formation occurs much more slowly in the antioxidant- treated emulsions than in the controls.
  • Example 6 The effect of antioxidant composition on the prevention of warmed over flavor and enhancement of microbiological shelf life of cooked meats.
  • the meat was ground on a Biro # 812 grinder through a 3/16" plate and 4-winged knife.
  • Burger patties were portioned using a stainless steel patty former into 130 g portions, cooked at 300° F to an internal temperature of 160-165° F.
  • the cooked portions were chilled at 38 ° F and then placed into non-barrier polyethylene bags and stored at 38° F for 11 days for microbiological evaluation; and, for 48 hr for evaluation for lipid oxidation.
  • Two portions from each treatment were frozen in a sharp freezer at -25 °F, vacuum packaged and stored at -15° F as samples for time zero.
  • Lipid oxidation (as measured by TBARS) and microbiological assays (aerobic and psychrotrophic plate counts) were conducted.
  • Thiobarbituric Acid Reactive Substance (TBAR) testing was done to measure the extent of oxidation.
  • An identical sample of ground beef was prepared, cooked and stored, except that the additive was HERBALOX ® Seasoning Type 25 at 2000 ppm.
  • Absorbance readings for the TRAR test were made in duplicate at 531 nm. These reading were averaged and used to calculate the TBAR value. Oxidation occurs slower in the antioxidative MRP flavoring treatments than the untreated control samples.
  • Bacterial levels determined by aerobic and psychrotroph counting, are lower on a composite sample of all ground beef treatments at time zero and on the individual samples after incubation in the treated samples, compared to the control.
  • Example 7 The stabilizing effect of chelating compositions on cured meat oxidation (flavor) and color.
  • Fresh ground beef (75% lean) is purchased from a local supermarket in four, 101b. chubs. The ground beef is stored at 32-35° F in a reach in cooler for 12 hr before processing. Forty pounds of the ground beef is ground on a Biro # 812 grinder through a 1/8" plate and 4-winged knife. Twenty pounds of re- ground beef is placed in a clean, pre-chilled stainless steel MAINCA RM#35 paddle/ribbon mixer, 0.20 % by weight of maltodextrin M100 (GPC) was added to the ground beef (control), and the ground beef was mixed for 3 minutes. The mixed meat was placed into a plastic tote, placed in 32-35° F KELVINATOR® reach-in cooler.
  • GPC maltodextrin M100
  • a second 20 lb. batch of re-ground beef is placed into the MAINCA mixer, and 0.04 pounds of maltodextrin upon which 2.86 g of antioxidative MRP preparation from lysine and xylose is added and the composition was mixed for 3 minutes. All processing (grinding, mixing, stuffing) is conducted in a 38° F processing room.
  • Four, six pound lots of ground beef from the control and treatment groups are weighed into 10.5" X 1 1" ZIPLOCK® freezer storage bags and labeled. Three bags from each treatment are placed on coated wire racks in a 10° F TYLER® walk-in freezer, one bag from treatment and control group are processed into bologna.
  • the bologna is processed in a programmable, atmosphere controlled RATIONAL® Oven to an internal temperature of 155° F, chilled to below 40° F overnight then sliced to 3/16" on a WARING Pro food slicer and sliced in a 38° F processing room.
  • Five to seven slices from each treatment are placed in a polyethylene non-barrier ZIPLOCK® bag and 7"X1 1" barrier (3 mil, Nylon/PE) pouch (PRIME SOURCE® ) or a gas flushed (70% nitrogen and 30% carbon dioxide) sealed pouch.
  • Modified atmosphere packages are tested for gas ratios and residual oxygen using a Dansensor Checkmate 9900 gas analyzer.
  • Packages of sliced bologna are then placed into a 35° F reach-in TRUE® cooler and stored for evaluation (the a * /b * ratios for color are determined at time zero).
  • Example 8 Stabilizing Mayonnaise.
  • the mayonnaise recipe consisted of 80% oil, 8% egg yolk, 6.6% vinegar (at 5% acidity), 3.9% water, 1 % sugar and 0.5% salt.
  • a control mayonnaise was prepared by first combining the egg yolk, sugar, salt and water in the mixing bowl for a stand mixer. This was hand-whisked until well mixed. The bowl was then placed on the stand mixer and the mixer set to the second speed. Oil was slowly added while mixing. Vinegar was then added and the mayonnaise was mixed for an additional 2 minutes. Finally, the entire mixture was transferred to a food processor and blended until the desired consistency was achieved.
  • the following test mayonnaise samples were prepared. All test materials were dissolved in either the oil or the vinegar, according to their solubility, for incorporation into the mayonnaise, using the process described for the control.
  • Test 1 0.05% MRP from xylose and lysine
  • HERBALOX ® Seasoning 41.088319 is a commercially available, deflavorized, oil soluble rosemary extract containing carnosic acid and carnosol. It is anticipated that the combination of chelator antioxidants with water soluble rosemary extracts containing rosmarinic acid will also be highly
  • oil and water dispersible chelator antioxidants together with oil and water soluble radical scavengers (such as a mixture of oil and water soluble rosemary extracts) will be highly antioxidative and useful in this and other applications.
  • Example 9 Stable lipstick formulation.
  • a lipstick is prepared by combining 6g beeswax, 3g carnauba wax, 7g candelilla wax, 4g ozokerite, 30g polyisobutylene. 3g cosmetic grade mica, 2.25g red 7 lake and 44.75 g castor oil. The mixture is heated to 80° C with stirring. 0.3 g of peppermint oil flavoring, 0.03 g of BHT and 0.05 g of tocopherol is added. The mixture is stirred and poured into molds and allowed to cool.
  • a second lipstick is made using the same recipe, but in place of BHT, 0.10 g of MRP of xylose and lysine added and in place of tocopherol, 0.1 g of HERBALOX® Seasoning 41.088319 is added.
  • the lipstick is allowed to age and the quality of the lipstick is monitored over time using chemical analysis, sensory analysis and microbiological analysis.
  • the lipstick containing an antioxidative MRP flavoring composition from lysine and xylose is found to have a longer shelf life and continuously lower microbial count than the lipstick containing BHT.
  • Example 10 Stabilizing an Eye Health Nutritional Supplement Formulation.
  • Beadlets containing 5% zeaxanthin are prepared commercially using a modified food starch. Incorporation of MRP preparations enhances zeaxanthin storage stability.
  • frying oils are prepared using canola oil.
  • One is treated with 2000 ppm of HERBALOX® Seasoning Type HT-O.
  • Another is treated with 500 ppm of the MRP of xylose and lysine.
  • Another is treated with 2000 ppm of HERBALOX® Seasoning Type HT-O and 500 ppm of the MRP of xylose and lysine.
  • Another is the untreated control.
  • Multiple batches of previously par-fried sliced potatoes are fried, separately in each of the oils.
  • the quality of the frying oil and the quality of the fried potatoes are monitored as a function of time using chemical analysis and sensory analysis.
  • the treated oils are found to last longer (remain of higher quality) than the untreated oil.
  • the fried potatoes are found to be of higher quality and have a longer shelf life when fried in the treated oils versus the control oil.
  • the highest performing oil and fried food resulted from the treatment package consisting of a combination of 2000 ppm of HERBALOX® Seasoning Type HT-0 and 500 ppm of the total MRP. It is a matter of simple experiment to optimize the oil performance using antioxidative MRP flavoring preparations, in combination with added natural and / or synthetic antioxidants.
  • Example 12 Stabilizing Coffee Extracts.
  • a fresh, commercial coffee extract is divided into three portions. One portion serves as the control. A second portion is treated with MRP of xylose and lysine. A third portion is treated with calcium disodium EDTA.
  • the coffee extracts are allowed to age and are analyzed using chemical analysis and sensory analysis. The performance, in terms of flavor stability, follows the increasing order: control ⁇ MRP and EDTA.
  • Beer is brewed, optionally adding 100 ppm MRP of xylose and lysine to the mash.
  • the finished treated beer has higher flavor stability than the same beer absent the antioxidative MRP flavoring composition.
  • Example 14 Stabilizing an anthocyanin-containing beverage.
  • a flavored beverage colored with an anthocyanin-based food color is found to be more stable when it also contains 100 ppm of MRP of xylose and lysine.
  • Example 15 Stabilization of Potted Meat Babyfood [0074] A meat emulsion product suitable for use as a baby food is retorted in glass jars. No provision is made to eliminate oxygen from the headspace of the containers. Meat product without added MRP of xylose and lysine shows a discoloration of the surface of the meat after a storage time. Meat product prepared with 100 ppm of MRP of xylose and lysine remains free from the discoloration at an identical storage time and under similar storage conditions.
  • Example 16 Stabilizing Fish oil Emulsions.

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Abstract

La présente invention concerne des procédés améliorés de renforcement de la stabilité d'aliments, de boissons, de compléments alimentaires et/ou de produits cosmétiques, consistant à incorporer, dans lesdits produits, des quantités efficaces de compositions d'origine naturelle contenant le produit d'une réaction de Maillard résultant de la réaction d'un acide aminé et d'un sucre, éventuellement un ou plusieurs composants antioxydants chélateurs ou non-chélateurs issus d'herbes, d'épices, de fruits, de légumes et/ou de graines comestibles, et/ou éventuellement encore un ou plusieurs antioxydants de synthèse de qualité alimentaire. La présente invention concerne, en outre, des procédés de préparation de compositions anti-oxydantes aromatiques présentant une activité et des caractéristiques de solubilité spécifiques conçues sur mesure pour amener les composants antioxydants jusqu'aux sites où ils agissent le plus efficacement dans les aliments, boissons, compléments alimentaires ou produits cosmétiques. La présente invention concerne, en outre, des aliments, des boissons, des compléments alimentaires et des produits cosmétiques traités au moyen des compositions de l'invention.
PCT/US2011/001551 2010-09-10 2011-09-07 Procédés d'amélioration de la stabilité d'aliments, de boissons et de produits cosmétiques faisant appel à des mélanges d'arômes naturels WO2012033523A1 (fr)

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JP2012144457A (ja) * 2011-01-07 2012-08-02 Kracie Home Products Ltd 抗酸化剤、化粧料、飲食品組成物及び医薬品組成物
JP5632555B1 (ja) * 2014-06-17 2014-11-26 株式会社えがお アントシアニン安定化剤及びアントシアニンの安定化方法
EP3157346A4 (fr) * 2014-06-19 2018-01-10 Kemin Industries, Inc. Ingrédients pour retarder l'oxydation des matières grasses du lait
CN110169563A (zh) * 2019-05-28 2019-08-27 江南大学 一种具有抗氧化功能的美拉德风味肽及其制备方法
WO2021202989A1 (fr) * 2020-04-03 2021-10-07 Atomo Coffee, Inc. Substrats végétaux soumis à la réaction de maillard croisée
WO2022251529A1 (fr) * 2021-05-26 2022-12-01 Atomo Coffee, Inc. Substrats végétaux soumis à une réaction de maillard croisée

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012144457A (ja) * 2011-01-07 2012-08-02 Kracie Home Products Ltd 抗酸化剤、化粧料、飲食品組成物及び医薬品組成物
JP5632555B1 (ja) * 2014-06-17 2014-11-26 株式会社えがお アントシアニン安定化剤及びアントシアニンの安定化方法
JP2016003210A (ja) * 2014-06-17 2016-01-12 株式会社えがお アントシアニン安定化剤及びアントシアニンの安定化方法
EP3157346A4 (fr) * 2014-06-19 2018-01-10 Kemin Industries, Inc. Ingrédients pour retarder l'oxydation des matières grasses du lait
CN110169563A (zh) * 2019-05-28 2019-08-27 江南大学 一种具有抗氧化功能的美拉德风味肽及其制备方法
WO2021202989A1 (fr) * 2020-04-03 2021-10-07 Atomo Coffee, Inc. Substrats végétaux soumis à la réaction de maillard croisée
WO2022251529A1 (fr) * 2021-05-26 2022-12-01 Atomo Coffee, Inc. Substrats végétaux soumis à une réaction de maillard croisée

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