WO2009013757A1 - Composition for protecting oils and fat - Google Patents

Composition for protecting oils and fat Download PDF

Info

Publication number
WO2009013757A1
WO2009013757A1 PCT/IL2008/001037 IL2008001037W WO2009013757A1 WO 2009013757 A1 WO2009013757 A1 WO 2009013757A1 IL 2008001037 W IL2008001037 W IL 2008001037W WO 2009013757 A1 WO2009013757 A1 WO 2009013757A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
water
antioxidant
composition according
antioxidant composition
Prior art date
Application number
PCT/IL2008/001037
Other languages
French (fr)
Inventor
Rena Reznik
Original Assignee
Frutarom Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Frutarom Ltd. filed Critical Frutarom Ltd.
Publication of WO2009013757A1 publication Critical patent/WO2009013757A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0053—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/011—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0028—Carboxylic acids; Their derivates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0085—Substances of natural origin of unknown constitution, f.i. plant extracts
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0092—Mixtures
    • 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 the field of protecting oils and fatty substances.
  • the invention relates to compositions and methods for improving the stability and quality of cooking oils, specifically oils for frying and baking foods.
  • Cooking or frying at elevated temperatures is a complex process during which simultaneous heat and mass transfer take place.
  • compositions and methods for protecting oils and fatty substances have been previously described, for example:
  • US Published Application No. 20030026887 discloses water-in-oil emulsions as additive for frying or boiling fat, wherein the water-in-oil emulsion includes antioxidants in combination with water soluble carboxylic acids.
  • the amount of oil (fat) in the emulsion is in the range of 70-90% weight.
  • the emulsion preferably comprises one or more water soluble carboxylic acids (for example citric acid) in an amount of approximately 0.5-4% weight, and one or more antioxidation agents (antioxidants), for example tocopherol extract and/or ascorbyl palmitate, in an amount of about 0.1-1% weight.
  • water soluble carboxylic acids for example citric acid
  • antioxidants for example tocopherol extract and/or ascorbyl palmitate
  • PCT Publication No WO 03/082021 discloses a process for stabilizing hot cooking oil, comprising periodically introducing into hot cooking oil an aqueous composition comprising at least one antioxidant.
  • the composition can be prepared by mixing an antioxidant and water-soluble or water-dispersible emulsif ⁇ er in water.
  • the aqueous composition does not comprise oil as one of its components.
  • US Patent No. 5,084,289 discloses a method for inhibiting the oxidation of edible oils and fats by admixing an aqueous solution containing a water-soluble antioxidant and a surfactant with the oils or fats.
  • the aqueous composition does not comprise oil as one of its components.
  • the present invention provides compositions and methods for improving the stability and quality of oils, fat and fatty substances.
  • composition of the invention comprises an antioxidant water-in-oil emulsion having exceptionally high water content.
  • the present invention provides a water-in-oil antioxidant composition
  • a water-in-oil antioxidant composition comprising: (i) water; (ii) at least one water-soluble antioxidant; (iii) at least one oil-soluble and water insoluble emulsifier; and (iv) oil.
  • said water-in-oil antioxidant composition comprises at least 20% weight per weight (w/w) water. In another embodiment said water-in-oil antioxidant composition comprises from about 20% to about 30% (w/w) water. In another embodiment said water-in-oil antioxidant composition comprises from about 24% to about 28% (w/w) water.
  • the water-in-oil antioxidant composition may further include glycerol and/or propylene glycol.
  • said at least one water soluble antioxidant in the water-in-oil antioxidant composition of the invention is selected from the group consisting of ascorbic acid, citric acid, L-ascorbate (Vitamin C), erythrobic acid, lactic acid, ellagitannin, chlorogenic acid, anthocyanin, water soluble antioxidant herb or plant extract and combinations thereof.
  • said water-in-oil antioxidant composition comprises from about 5% to about 40% w/w water-soluble antioxidant. According to another embodiment said water-in-oil antioxidant composition comprises from about 10% to about 30% w/w water-soluble antioxidant.
  • said at least one water-soluble antioxidant is ascorbic acid.
  • said water-in-oil antioxidant composition comprises as water-soluble antioxidants a combination of ascorbic acid and a water soluble antioxidant herb extract.
  • said herb is selected from the group consisting of basil, lemon balm (Melissa officinalis), mint, rosemary, sage, savory, marjoram, oregano, thyme, lavender, perilla extracts, and combinations thereof.
  • said water soluble antioxidant herb extract is present at a concentration of from about 0.1% to about 10% w/w, more preferably from about 0.5% to about 5%.
  • said water-soluble antioxidant herb extract is a lemon balm (Melissa officinalis) extract.
  • said lemon balm extract is present at a concentration of about 0.5% w/w, or about 1% w/w or about 5% w/w.
  • the water-in-oil antioxidant composition of the invention comprises from about 10% to about 30% w/w ascorbic acid. In another embodiment the water-in-oil antioxidant composition of the invention comprises from about 15% to about 28% w/w ascorbic acid.
  • said at least one oil soluble and water insoluble emulsifier in the water-in-oil antioxidant composition of the invention is selected from the group consisting of mono and di glycerides, glycerol, Tween® 40, Tween® 80, Span 80, Polyglycerol Polyricinoleate (PGPR), lecithin, propylene glycol, linoleic acid and combinations thereof.
  • PGPR Polyglycerol Polyricinoleate
  • the water-in-oil antioxidant composition of the invention comprises from about 0.5% to about 30% w/w emulsifier. In another specific embodiment, the water-in-oil antioxidant composition of the invention comprises from about 2% to about 20% w/w emulsifier.
  • said at least one oil-soluble and water insoluble emulsifier is a mono or di-glycerid.
  • said at least one oil-soluble and water insoluble emulsifier is Polyglycerol Polyricinoleate (PGPR).
  • PGPR Polyglycerol Polyricinoleate
  • the water-in-oil antioxidant composition of the invention comprises from about 2% to about 15% w/w PGPR.
  • the water-in-oil antioxidant composition comprises a combination of PGPR and Span 80.
  • the water-in-oil antioxidant composition comprises about 2% w/w PGPR and from about 0.1% to about 2% w/w Span 80.
  • said oil in the water-in-oil antioxidant composition of the invention is animal fat or plant oil.
  • said plant oil is selected from the group consisting of palm oil, olive oil, soybean oil, canola oil, pumpkin seed oil, corn oil, sunflower oil, peanut oil, grape seed oil, sesame oil, argan oil, rice bran oil, and combinations thereof.
  • said water-in-oil antioxidant composition comprises from about 10% to about 60% (w/w) oil. In another embodiment said water-in-oil antioxidant composition comprises from about 15% to about 50% (w/w) oil.
  • said water-in-oil antioxidant composition comprises canola oil.
  • said water-in-oil antioxidant composition comprises from about 15% to about 41% (w/w) canola oil.
  • the composition of the invention additionally comprises at least one fat-soluble antioxidant.
  • said fat-soluble antioxidant is selected from the group consisting of tocopherols, tocotrienols, retinol, rosemary oil, ascorbyl-palmitate and combinations thereof.
  • said water-in-oil antioxidant composition comprises from about 5% to about 35% w/w fat-soluble antioxidant.
  • said fat-soluble antioxidants are tocopherols.
  • Non- limiting examples of such tocopherols are Natural Mixed Tocopherols 50% or Natural Mixed Tocopherols 70%.
  • said water-in-oil antioxidant composition comprises Natural
  • the present invention provides a method of inhibiting oxidation and enhancing the stability and quality of fats and oils that comprises adding to said fats or oils an antioxidant effective amount of the water-in-oil antioxidant composition of the invention.
  • the present invention provides use of the water-in-oil antioxidant composition of the invention as an additive to fats and oils, in order to inhibit oxidation and enhance the stability and quality of fats and oils.
  • said fats and oils may be of plant or animal origin.
  • said oils are cooking or frying oils.
  • said oils are essential oils.
  • the present invention provides fried products, wherein said fried products were fried in oil comprising the water-in-oil antioxidant composition of the invention.
  • Said fried products include, for example fried potato chips and fried peanuts.
  • the present invention provides baked products, wherein said baked products were baked using oil comprising the water-in-oil antioxidant composition of the invention.
  • Said baked products include, include for example crackers and waffles.
  • Figure IA is a graph showing the amount of hexanal generated in Crown Waffles over time.
  • the Crown Waffles were baked with oil containing either 0.03% OS-MX or 0.03% Rosemary oil (HerbaloxTM). Time is indicated as days after production in closed packaging.
  • Figure IB is a graph showing the amount of aldehydes generated in Crackers over time. The Crackers were baked with oil containing either 150ppm (parts per million) OS-MX, 150ppm Rosemary oil (HerbaloxTM), or with no anti-oxidant (Control).
  • Figure 2 is a graph showing the amount of hexanal generated in fried potato chips. The potato chips were fried in oil containing either 0.1% OS-A, 0.2% OS-A, or with no anti- oxidant (Control).
  • Figure 3 is a graph showing the amount of hexanal generated in fried peanuts after 15 and 30 days of accelerated conditions (storage at 60°C), as measured by HS-GC. 0.07% OriganoxTM OS (OS-A) was dissolved in the frying oil. Control - no anti-oxidant added. DETAILED DESCRIPTION OF THE INVENTION
  • the present invention provides a water-in-oil antioxidant composition intended for use in protecting oils, fats and fatty substances.
  • the terms “oils”, “fats” and “fatty substances” are used interchangeably to denote any oil or fat which is liquid, solid or pasty at room temperature, whether it is of plant, animal, mineral or synthetic origin or whether it is used as it is or chemically modified, as well as any extract resulting from one of these fatty substances such as, for example, phytosterols, cholesterol, undecylenic acid or alternatively a mixture of a number of these compounds.
  • the terms include edible fatty substances in a general sense, including but not limited to digestible and non- digestible fats, oils, and fat substitutes.
  • relatively high load denotes that the load of the water soluble antioxidants in the composition is at least about 5% by weight and the load of water in the compositions is at least about 20% by weight.
  • the efficiency of the water-in-oil antioxidant composition of the invention can be attributed to the high content of water soluble antioxidants and water, since most of the deteriorative / oxidative reactions that lead to progressive deterioration of fats and oils occur at the oil-water interface.
  • the water-in-oil antioxidant composition of the present invention can be used in protecting any oils, fats and fatty substances of plant, animal, mineral or synthetic origin.
  • the oils are cooking and frying oils, including oils used in deep-frying.
  • cooking oil and frying oil are used interchangebly throughout this specification and should be understood to encompass any organic cooking media which is liquid at cooking temperature (normally around 100-250 0 C) but may not be liquid at lower temperatures.
  • Frying oils decompose over time and use, due to the formation and acquisition of various contaminants during the cooking process. Soaps, polar compounds, polymers, free fatty acids (FFA), color bodies and trace metals are the major contaminants which contribute to oil degradation through increased instability. The cooking process and the accumulation of these contaminants also result in a visibly darker color of the oil that can be displeasing in appearance.
  • FFA free fatty acids
  • composition of the invention will vary depending on the type of oil, the use of the specific oil and the conditions (e.g. temperature, pattern of use, exposure pattern, duration of use) to which the specific oil is subjected.
  • a water-in-oil antioxidant composition of the subject invention is accomplished by combining (i) water; (ii) at least one water-soluble antioxidant; (iii) at least one oil-soluble and water insoluble emulsif ⁇ er; and (iv) oil.
  • the water-in- oil antioxidant composition of the invention may further comprise at least one oil soluble antioxidant.
  • the water-in-oil antioxidant composition of the invention comprises water as one of the components of the novel composition.
  • the water content is relatively high and the composition preferably comprises above 20% water.
  • said water-in-oil antioxidant composition comprises from about 20% to about 30% (w/w) water.
  • said water-in-oil antioxidant composition comprises from about 24% to about 28% (w/w) water.
  • the water-in-oil antioxidant composition of the invention also comprises at least one water-soluble antioxidant.
  • the water-soluble antioxidant of the present invention can be any suitable antioxidant having a relatively good solubility in water. Examples of such water soluble antioxidants include, but are not limited to, ascorbic acid, citric acid, L- ascorbate (Vitamin C), erythrobic acid, lactic acid, ellagitannin, chlorogenic acid, anthocyanin, water soluble extract of plant origin (e.g. Labiate herb extracts), and combinations thereof.
  • the term "relatively good solubility in water” should be understood to encompass solubility that is sufficiently high to load the desired amount of the antioxidant in the water-in-oil antioxidant composition.
  • the desired amount of the water soluble antioxidant follows from the required/desired load that needs to be present in order to obtain the desired antioxidant effect and is dependant on the type of the oil to be protected, the use of the specific oil and the conditions (e.g. temperature, pattern of use, exposure pattern, duration of use) to which the specific oil is subjected.
  • said water-in-oil antioxidant composition comprises from about 5% to about 40% w/w water-soluble antioxidant. According to another embodiment said water-in-oil antioxidant composition comprises from about 10% to about 30% w/w water-soluble antioxidant.
  • the water-soluble antioxidant is ascorbic acid. In another specific embodiment of the present invention, the water soluble antioxidant is a combination of ascorbic acid and citric acid.
  • said water-in-oil antioxidant composition comprises as water-soluble antioxidants a combination of ascorbic acid and a water soluble antioxidant extract of plant origin.
  • the natural water soluble antioxidant extract of plant origin may be, but is not limited to a Lamiaceae family or Labiatae family herb.
  • An example of a water soluble extract of a Lamiaceae family or a Labiatae family of herbs as contemplated to be incorporated into the water-in-oil antioxidant composition of the present invention is described in WO 0039066 and the corresponding US patent No. 6,383,543 and in WO 0039248.
  • Examples of herbs of a Lamiaceae family or a Labiatae family include, but are not limited to basil, lemon balm ⁇ Melissa officinalis), mint, rosemary, sage, savory, marjoram, oregano, thyme, lavender, perilla. Other plant origins include tea and grape seeds.
  • the natural water soluble antioxidant extract o ⁇ ⁇ Lamiaceae family or a Labiatae family of herbs is present in the novel water- in-oil antioxidant composition at about 0.1-10% by weight.
  • the natural water soluble antioxidant composition comprises a lemon balm ⁇ Melissa officinalis) extract.
  • natural water soluble antioxidant lemon balm ⁇ Melissa officinalis) extract is present in the water-in-oil antioxidant composition of the invention at about 0.1-10% by weight.
  • natural water soluble antioxidant lemon balm ⁇ Melissa officinalis) extract is present in the water-in-oil antioxidant composition of the invention at about 0.5% by weight.
  • natural water soluble antioxidant lemon balm ⁇ Melissa officinalis) extract is present in the water-in-oil antioxidant composition of the invention at about 1% or about 5% by weight.
  • the water-in-oil antioxidant composition of the invention also comprises at least one oil-soluble and water insoluble emulsifier as one of the components of the novel composition.
  • the at least one oil-soluble and water insoluble emulsifier of the subject invention can be any suitable emulsifier having a relatively good solubility in oil and relatively poor solubility in water.
  • emulsifiers include, but are not limited to mono and di glycerides, glycerol, Tween® 40 (Polyoxyethylene sorbitan mono-palmitate), Tween® 80 (Polyoxyethylene sorbitan monooleate), Span 80 (Sorbitan monooleate), Polyglycerol Polyricinoleate (PGPR), lecithin, propylene glycol, linoleic acid and combinations thereof.
  • PGPR Polyglycerol Polyricinoleate
  • the term "relatively poor solubility in water” should be understood to encompass solubility of the emulsifier that is lower than 1% by weight.
  • the emulsifier is present in the novel water-in-oil antioxidant composition at about 0.5% to about 30% but preferable at about 2 - 20 % by weight.
  • the emulsifier is Polyglycerol Polyricinoleate (PGPR).
  • PGPR is present in the water-in-oil antioxidant composition of the invention at about 2 - 15 % by weight
  • the emulsifier is a combination of Polyglycerol Polyricinoleate (PGPR) and Span 80.
  • PGPR is present in the water-in-oil antioxidant composition of the invention at about 2 % by weight and Span 80 is present in the water-in-oil antioxidant composition of the invention at about 0.1 - 2 % by weight. In one specific embodiment of the present invention, PGPR is present in the water-in-oil antioxidant composition of the invention at about 1-3% by weight and mono and diglycerids are present in about 0.5-2% by weight.
  • the water-in-oil antioxidant composition of the invention also comprises oil as one of the components of the novel composition.
  • the oil can be any suitable animal fat or plant oil. Examples of such plant oils include, but are not limited to palm oil, olive oil, soybean oil, canola oil, pumpkin seed oil, corn oil, sunflower oil, safflower oil, peanut oil, grape seed oil, sesame oil, argan oil, rice bran oil and combinations thereof.
  • suitable oil should be understood as any oil that can be utilized successfully in the preparation of an emulsion.
  • oil is present in the novel water-in-oil antioxidant composition at about 10-60% by weight and preferably at about 15-50% by weight.
  • the oil is Canola oil.
  • Canola oil is present in the water-in-oil antioxidant composition of the invention at about 15 -41 % by weight.
  • the water-in-oil antioxidant composition of the invention may also additionally contain as one of its components at least one fat soluble antioxidant.
  • the at least one fat soluble antioxidant of the subject invention can be any suitable antioxidant having a relatively good solubility in oil and relatively poor solubility in water. Examples of such antioxidants include, but are not limited to tocopherols, tocotrienols, retinol, rosemary oil, ascorbyl-palmitate, and combinations thereof.
  • Tocopherols refers to a class of chemical compounds of which many have vitamin E activity, tocopherols are a series of organic compounds consisting of various methylated phenols. Tocopherols are fat-soluble antioxidants.
  • the at least one fat soluble antioxidant is present in the novel water-in-oil antioxidant composition at about 5-35% by weight.
  • the fat soluble antioxidants are tocopherols.
  • the tocopherols are Natural Mixed Tocopherols 50%.
  • Mixed Tocopherols 50% are present in the water-in-oil antioxidant composition of the invention at about 20 - 30 % by weight.
  • Another object of present invention is to provide a method of inhibiting oxidation of fats and oils, which comprises adding to said fats and oils an antioxidant effective amount of the water-in-oil antioxidant composition of the invention.
  • inhibiting oxidation also encompasses the consequences of such inhibition namely enhancement of the stability and quality of said fats and oils.
  • the water-in-oil antioxidant composition of the subject invention can be used in protecting any oils, fats, and fatty substances of plant, animal, mineral or synthetic origin.
  • the oils are essential oils.
  • the oils are cooking and frying oils.
  • the stability (usability) of a frying fat can be increased by a multiple (for example, extended at least by 1.5-fold as compared to the frying medium in the absence of the composition of the invention).
  • antioxidant effective amount refers to the amount of the composition which is sufficient to reduce the oxidation of a frying medium.
  • the antioxidant effective amount may be determined using procedures well described in the art, for example, by the Oil Stability Index (OSI), an American Oil Chemists Society (AOCS) approved method Cd 12B-92.
  • OSI Oil Stability Index
  • AOCS American Oil Chemists Society
  • the quantity by weight of the water-in-oil antioxidant composition of the invention is added in amounts of 0.02% to 0.5% by weight of the frying medium.
  • the invention further provides a method of improving the quality of a fried product which comprises cooking the product in a frying medium that contains an antioxidant effective amount of the water-in-oil antioxidant composition of the invention.
  • fried product refers to fried food products such as for example fabricated crisps, tortillas, wheat thins, crackers, rice cakes, cereals, extruded snacks, potato chips, granola bars, etc.
  • the fried food products may be sweet, salty, or savory.
  • the invention further provides a method of improving the quality of a baked product which comprises baking the product using oil that contains an antioxidant effective amount of the water-in-oil antioxidant composition of the invention.
  • baked product refers to baked food products such as for example, crackers, waffles, pretzels, biscuits, cookies, Bars.
  • the water-in-oil antioxidant composition of the invention can be used as an additive to fats, oils and fatty substances, to inhibit oxidation and enhance the stability and quality thereof.
  • the subject invention encompasses a use of a water-in-oil antioxidant composition of the invention as an additive to essential oils.
  • the subject invention also provides a use of a water-in-oil antioxidant composition of the invention as an additive to cooking and frying oils, such as for example deep-frying oils.
  • the water-in-oil antioxidant compositions of the invention are characterized by being an emulsion, having a shelf life of about one year, having an off white/beige to yellow/brown color, and a tea like oily taste.
  • Origanox TM WS-LB is a water-soluble powder of natural extract from lemon balm, an edible herb species belonging to the Labiatae family, available from RAD Natural Technologies Ltd. (Israel), and having the following specifications:
  • Aroma and flavor Extra mild, tea like flavor
  • Antioxidant activity > 90 units (Standardized by an in-house method)
  • Solubility Soluble in cold water Toxicity: Non toxic Shelf life 3 years when stored unopened according to specified conditions in original sealed packaging
  • the following formulations were prepared by mixing the aqueous phase (including water and water soluble components) with the oil phase, followed by homogenizing the mixture using a piston type homogenizer.
  • Formulations IV-VI which include Tocopherols the Tocopherols were mixed with the Canola oil prior to mixing the oil component with the water and emulsifier.
  • Antioxidant activity of Formulations I to VI was determined according to the Oil Stability Index (OSI), an American Oil Chemists Society (AOCS) approved method Cd 12B-92.
  • OSI Oil Stability Index
  • AOCS American Oil Chemists Society
  • Formulation I As shown in Table 2 Formulation IV that contains tocopherols (in the oil before mixing with water and emulsifier) has a superior effect as compared to
  • OriganoxTM OS-MX is an anti-oxidant composition comprising the following components: 15% Ascorbic acid 1% Origanox WS-LB
  • OriganoxTM OS-MX 40% oil (vegetable oil) OriganoxTM OS-MX was added to the oil prior to mixing of the oil with water and flour. Two types of products, Crown waffles and crackers were then prepared according to conventional baking procedures.
  • the degree of oxidation in the baked products was determined by measuring the level of aldehydes that are generated upon decomposition of the oil and are thus used as an indication of the degree of the oxidation.
  • Hexanal (an alkyl aldehyde) level was measured as shown in St. Angelo, et al (1980) Lipids 15, 45-49 using Headspace Gas chromatography (HS-GC).
  • HS-GC Headspace Gas chromatography
  • HS-GC is used for the analysis of volatiles and semi-volatile organics in solid, liquid, and gas samples.
  • OriganoxTM OS-MX inhibits the formation of hexanal (Figure IA) and other aldehydes (off flavor, Figure IB) and therefore maintains the freshness longer.
  • OriganoxTM OS-A is an anti-oxidant composition comprising the following components: 10% Ascorbic acid 5% Origanox WS- LB (Lemon balm extract) 20% water 15% PGPR 50% oil (Vegetable oil)
  • OriganoxTM OS-A was added to oil used for frying potato chips. OriganoxTM OS- A was used in the frying oil in order to increase shelf life and reduce rancidity of the fried potato chips.
  • Fried products may absorb around 30% of the frying oil, which is the main cause for rancidity development of the fried product.
  • OriganoxTM OS-A was dissolved in the frying oil used for flying peanuts.
  • the level of oxidation of the peanuts was measured by the Hexanal method using HS- GC. The test was carried out at accelerated conditions, namely the peanuts were stored at 6O 0 C for 30 days.

Abstract

A water-in-oil antioxidant composition for use as an additive to cooking oils, for inhibiting their oxidation and subsequent loss of stability and quality, wherein the water-in-oil composition comprises an exceptionally high water content, water soluble anti-oxidants, specifically ascorbic acid and anti-oxidant extracts of plants of the Labiate family, oil and an emulsifier.

Description

COMPOSITION FOR PROTECTING OILS AND FATS
FIELD OF THE INVENTION
The present invention relates to the field of protecting oils and fatty substances. In particular, the invention relates to compositions and methods for improving the stability and quality of cooking oils, specifically oils for frying and baking foods.
BACKGROUND
Cooking or frying at elevated temperatures (normally carried out at 100-250 0C) is a complex process during which simultaneous heat and mass transfer take place.
During the frying process a variety of chemical reactions occur that cause progressive deterioration of the frying medium (i.e. oxidation, hydrolysis and/or polymerization) and the quality, nutritional profile and cooking performance of the oil quickly diminishes.
Certain compositions and methods for protecting oils and fatty substances have been previously described, for example:
US Published Application No. 20030026887 discloses water-in-oil emulsions as additive for frying or boiling fat, wherein the water-in-oil emulsion includes antioxidants in combination with water soluble carboxylic acids. The amount of oil (fat) in the emulsion is in the range of 70-90% weight. The emulsion preferably comprises one or more water soluble carboxylic acids (for example citric acid) in an amount of approximately 0.5-4% weight, and one or more antioxidation agents (antioxidants), for example tocopherol extract and/or ascorbyl palmitate, in an amount of about 0.1-1% weight.
PCT Publication No WO 03/082021 discloses a process for stabilizing hot cooking oil, comprising periodically introducing into hot cooking oil an aqueous composition comprising at least one antioxidant. Typically, the composition can be prepared by mixing an antioxidant and water-soluble or water-dispersible emulsifϊer in water. The aqueous composition does not comprise oil as one of its components.
US Patent No. 5,084,289 discloses a method for inhibiting the oxidation of edible oils and fats by admixing an aqueous solution containing a water-soluble antioxidant and a surfactant with the oils or fats. The aqueous composition does not comprise oil as one of its components.
SUMMARY OF THE INVENTION The present invention provides compositions and methods for improving the stability and quality of oils, fat and fatty substances.
The composition of the invention comprises an antioxidant water-in-oil emulsion having exceptionally high water content.
Accordingly, in a first of its aspects the present invention provides a water-in-oil antioxidant composition comprising: (i) water; (ii) at least one water-soluble antioxidant; (iii) at least one oil-soluble and water insoluble emulsifier; and (iv) oil.
According to one embodiment, said water-in-oil antioxidant composition comprises at least 20% weight per weight (w/w) water. In another embodiment said water-in-oil antioxidant composition comprises from about 20% to about 30% (w/w) water. In another embodiment said water-in-oil antioxidant composition comprises from about 24% to about 28% (w/w) water.
The water-in-oil antioxidant composition may further include glycerol and/or propylene glycol.
According to one embodiment, said at least one water soluble antioxidant in the water-in-oil antioxidant composition of the invention is selected from the group consisting of ascorbic acid, citric acid, L-ascorbate (Vitamin C), erythrobic acid, lactic acid, ellagitannin, chlorogenic acid, anthocyanin, water soluble antioxidant herb or plant extract and combinations thereof.
According to one embodiment, said water-in-oil antioxidant composition comprises from about 5% to about 40% w/w water-soluble antioxidant. According to another embodiment said water-in-oil antioxidant composition comprises from about 10% to about 30% w/w water-soluble antioxidant.
According to one specific embodiment, said at least one water-soluble antioxidant is ascorbic acid. According to another specific embodiment, said water-in-oil antioxidant composition comprises as water-soluble antioxidants a combination of ascorbic acid and a water soluble antioxidant herb extract.
In one embodiment, said herb is selected from the group consisting of basil, lemon balm (Melissa officinalis), mint, rosemary, sage, savory, marjoram, oregano, thyme, lavender, perilla extracts, and combinations thereof.
In one embodiment, said water soluble antioxidant herb extract is present at a concentration of from about 0.1% to about 10% w/w, more preferably from about 0.5% to about 5%. In one specific embodiment, said water-soluble antioxidant herb extract is a lemon balm (Melissa officinalis) extract. In one embodiment, said lemon balm extract is present at a concentration of about 0.5% w/w, or about 1% w/w or about 5% w/w.
According to one embodiment, the water-in-oil antioxidant composition of the invention comprises from about 10% to about 30% w/w ascorbic acid. In another embodiment the water-in-oil antioxidant composition of the invention comprises from about 15% to about 28% w/w ascorbic acid.
According to one embodiment, said at least one oil soluble and water insoluble emulsifier in the water-in-oil antioxidant composition of the invention is selected from the group consisting of mono and di glycerides, glycerol, Tween® 40, Tween® 80, Span 80, Polyglycerol Polyricinoleate (PGPR), lecithin, propylene glycol, linoleic acid and combinations thereof.
According to one embodiment, the water-in-oil antioxidant composition of the invention comprises from about 0.5% to about 30% w/w emulsifier. In another specific embodiment, the water-in-oil antioxidant composition of the invention comprises from about 2% to about 20% w/w emulsifier.
According to one specific embodiment, said at least one oil-soluble and water insoluble emulsifier is a mono or di-glycerid.
According to another specific embodiment, said at least one oil-soluble and water insoluble emulsifier is Polyglycerol Polyricinoleate (PGPR). According to one embodiment, the water-in-oil antioxidant composition of the invention comprises from about 2% to about 15% w/w PGPR. In another embodiment, the water-in-oil antioxidant composition comprises a combination of PGPR and Span 80. In one embodiment, the water-in-oil antioxidant composition comprises about 2% w/w PGPR and from about 0.1% to about 2% w/w Span 80.
According to one embodiment, said oil in the water-in-oil antioxidant composition of the invention is animal fat or plant oil. hi one embodiment, said plant oil is selected from the group consisting of palm oil, olive oil, soybean oil, canola oil, pumpkin seed oil, corn oil, sunflower oil, peanut oil, grape seed oil, sesame oil, argan oil, rice bran oil, and combinations thereof.
In another embodiment said water-in-oil antioxidant composition comprises from about 10% to about 60% (w/w) oil. In another embodiment said water-in-oil antioxidant composition comprises from about 15% to about 50% (w/w) oil.
In one embodiment, said water-in-oil antioxidant composition comprises canola oil. hi one specific embodiment, said water-in-oil antioxidant composition comprises from about 15% to about 41% (w/w) canola oil. According to another embodiment the composition of the invention additionally comprises at least one fat-soluble antioxidant.
According to certain embodiments said fat-soluble antioxidant is selected from the group consisting of tocopherols, tocotrienols, retinol, rosemary oil, ascorbyl-palmitate and combinations thereof. According to one embodiment, said water-in-oil antioxidant composition comprises from about 5% to about 35% w/w fat-soluble antioxidant.
In one specific embodiment, said fat-soluble antioxidants are tocopherols. Non- limiting examples of such tocopherols are Natural Mixed Tocopherols 50% or Natural Mixed Tocopherols 70%. hi one embodiment, said water-in-oil antioxidant composition comprises Natural
Mixed Tocopherols 50% at a concentration of about 20% to about 30 % w/w.
By another of its aspects the present invention provides a method of inhibiting oxidation and enhancing the stability and quality of fats and oils that comprises adding to said fats or oils an antioxidant effective amount of the water-in-oil antioxidant composition of the invention. By yet another of its aspects the present invention provides use of the water-in-oil antioxidant composition of the invention as an additive to fats and oils, in order to inhibit oxidation and enhance the stability and quality of fats and oils.
In accordance with the invention, said fats and oils may be of plant or animal origin.
In accordance with one specific embodiment, said oils are cooking or frying oils.
In accordance with another specific embodiment, said oils are essential oils.
In yet another aspect, the present invention provides fried products, wherein said fried products were fried in oil comprising the water-in-oil antioxidant composition of the invention. Said fried products include, for example fried potato chips and fried peanuts.
In yet another aspect, the present invention provides baked products, wherein said baked products were baked using oil comprising the water-in-oil antioxidant composition of the invention. Said baked products include, include for example crackers and waffles.
BRIRF DESCRIPTION OF THE FIGURES
Figure IA is a graph showing the amount of hexanal generated in Crown Waffles over time. The Crown Waffles were baked with oil containing either 0.03% OS-MX or 0.03% Rosemary oil (Herbalox™). Time is indicated as days after production in closed packaging. Figure IB is a graph showing the amount of aldehydes generated in Crackers over time. The Crackers were baked with oil containing either 150ppm (parts per million) OS-MX, 150ppm Rosemary oil (Herbalox™), or with no anti-oxidant (Control). Figure 2 is a graph showing the amount of hexanal generated in fried potato chips. The potato chips were fried in oil containing either 0.1% OS-A, 0.2% OS-A, or with no anti- oxidant (Control).
Figure 3 is a graph showing the amount of hexanal generated in fried peanuts after 15 and 30 days of accelerated conditions (storage at 60°C), as measured by HS-GC. 0.07% Origanox™ OS (OS-A) was dissolved in the frying oil. Control - no anti-oxidant added. DETAILED DESCRIPTION OF THE INVENTION
The present invention provides a water-in-oil antioxidant composition intended for use in protecting oils, fats and fatty substances. Within the context of the present invention, the terms "oils", "fats" and "fatty substances" are used interchangeably to denote any oil or fat which is liquid, solid or pasty at room temperature, whether it is of plant, animal, mineral or synthetic origin or whether it is used as it is or chemically modified, as well as any extract resulting from one of these fatty substances such as, for example, phytosterols, cholesterol, undecylenic acid or alternatively a mixture of a number of these compounds. The terms include edible fatty substances in a general sense, including but not limited to digestible and non- digestible fats, oils, and fat substitutes.
The essence of this novel water-in-oil antioxidant composition of the subject invention lies in the provision of water-in oil composition containing a relatively high load of water-soluble antioxidants and water.
The term "relatively high load" as used herein denotes that the load of the water soluble antioxidants in the composition is at least about 5% by weight and the load of water in the compositions is at least about 20% by weight.
As used herein the term "about" refers to a value of +/- 10% of the indicated number.
Without wishing to be bound by theory, it is believed that the efficiency of the water-in-oil antioxidant composition of the invention can be attributed to the high content of water soluble antioxidants and water, since most of the deteriorative / oxidative reactions that lead to progressive deterioration of fats and oils occur at the oil-water interface.
The water-in-oil antioxidant composition of the present invention can be used in protecting any oils, fats and fatty substances of plant, animal, mineral or synthetic origin. In one specific embodiment the oils are cooking and frying oils, including oils used in deep-frying. The terms "cooking oil" and "frying oil" are used interchangebly throughout this specification and should be understood to encompass any organic cooking media which is liquid at cooking temperature (normally around 100-250 0C) but may not be liquid at lower temperatures.
Frying oils decompose over time and use, due to the formation and acquisition of various contaminants during the cooking process. Soaps, polar compounds, polymers, free fatty acids (FFA), color bodies and trace metals are the major contaminants which contribute to oil degradation through increased instability. The cooking process and the accumulation of these contaminants also result in a visibly darker color of the oil that can be displeasing in appearance.
The exact formulation of the composition of the invention will vary depending on the type of oil, the use of the specific oil and the conditions (e.g. temperature, pattern of use, exposure pattern, duration of use) to which the specific oil is subjected.
The provision of a water-in-oil antioxidant composition of the subject invention is accomplished by combining (i) water; (ii) at least one water-soluble antioxidant; (iii) at least one oil-soluble and water insoluble emulsifϊer; and (iv) oil. Optionally, the water-in- oil antioxidant composition of the invention may further comprise at least one oil soluble antioxidant.
The water-in-oil antioxidant composition of the invention comprises water as one of the components of the novel composition. The water content is relatively high and the composition preferably comprises above 20% water. In one embodiment said water-in-oil antioxidant composition comprises from about 20% to about 30% (w/w) water. In another embodiment said water-in-oil antioxidant composition comprises from about 24% to about 28% (w/w) water.
The water-in-oil antioxidant composition of the invention also comprises at least one water-soluble antioxidant. The water-soluble antioxidant of the present invention can be any suitable antioxidant having a relatively good solubility in water. Examples of such water soluble antioxidants include, but are not limited to, ascorbic acid, citric acid, L- ascorbate (Vitamin C), erythrobic acid, lactic acid, ellagitannin, chlorogenic acid, anthocyanin, water soluble extract of plant origin (e.g. Labiate herb extracts), and combinations thereof. The term "relatively good solubility in water" should be understood to encompass solubility that is sufficiently high to load the desired amount of the antioxidant in the water-in-oil antioxidant composition. The desired amount of the water soluble antioxidant follows from the required/desired load that needs to be present in order to obtain the desired antioxidant effect and is dependant on the type of the oil to be protected, the use of the specific oil and the conditions (e.g. temperature, pattern of use, exposure pattern, duration of use) to which the specific oil is subjected.
According to one embodiment, said water-in-oil antioxidant composition comprises from about 5% to about 40% w/w water-soluble antioxidant. According to another embodiment said water-in-oil antioxidant composition comprises from about 10% to about 30% w/w water-soluble antioxidant. In one specific embodiment of the present invention, the water-soluble antioxidant is ascorbic acid. In another specific embodiment of the present invention, the water soluble antioxidant is a combination of ascorbic acid and citric acid.
According to another specific embodiment, said water-in-oil antioxidant composition comprises as water-soluble antioxidants a combination of ascorbic acid and a water soluble antioxidant extract of plant origin.
The natural water soluble antioxidant extract of plant origin (also termed "herb extract"), may be, but is not limited to a Lamiaceae family or Labiatae family herb. An example of a water soluble extract of a Lamiaceae family or a Labiatae family of herbs as contemplated to be incorporated into the water-in-oil antioxidant composition of the present invention is described in WO 0039066 and the corresponding US patent No. 6,383,543 and in WO 0039248. Examples of herbs of a Lamiaceae family or a Labiatae family include, but are not limited to basil, lemon balm {Melissa officinalis), mint, rosemary, sage, savory, marjoram, oregano, thyme, lavender, perilla. Other plant origins include tea and grape seeds. In one embodiment of the subject invention, the natural water soluble antioxidant extract oϊ Ά Lamiaceae family or a Labiatae family of herbs is present in the novel water- in-oil antioxidant composition at about 0.1-10% by weight. In a specific embodiment of the subject invention, the natural water soluble antioxidant composition comprises a lemon balm {Melissa officinalis) extract. In one specific embodiment of the subject invention, natural water soluble antioxidant lemon balm {Melissa officinalis) extract is present in the water-in-oil antioxidant composition of the invention at about 0.1-10% by weight. In another specific embodiment of the subject invention, natural water soluble antioxidant lemon balm {Melissa officinalis) extract is present in the water-in-oil antioxidant composition of the invention at about 0.5% by weight. In yet another specific embodiment of the subject invention, natural water soluble antioxidant lemon balm {Melissa officinalis) extract is present in the water-in-oil antioxidant composition of the invention at about 1% or about 5% by weight.
The water-in-oil antioxidant composition of the invention also comprises at least one oil-soluble and water insoluble emulsifier as one of the components of the novel composition. The at least one oil-soluble and water insoluble emulsifier of the subject invention can be any suitable emulsifier having a relatively good solubility in oil and relatively poor solubility in water. Examples of such emulsifiers include, but are not limited to mono and di glycerides, glycerol, Tween® 40 (Polyoxyethylene sorbitan mono-palmitate), Tween® 80 (Polyoxyethylene sorbitan monooleate), Span 80 (Sorbitan monooleate), Polyglycerol Polyricinoleate (PGPR), lecithin, propylene glycol, linoleic acid and combinations thereof.
The term "relatively good solubility in oil" should be understood to encompass solubility of the emulsifier between 0.5%-30% by weight.
The term "relatively poor solubility in water" should be understood to encompass solubility of the emulsifier that is lower than 1% by weight. In one embodiment of the subject invention, the emulsifier is present in the novel water-in-oil antioxidant composition at about 0.5% to about 30% but preferable at about 2 - 20 % by weight. In a specific embodiment of the subject invention, the emulsifier is Polyglycerol Polyricinoleate (PGPR). In one specific embodiment of the subject invention, PGPR is present in the water-in-oil antioxidant composition of the invention at about 2 - 15 % by weight, hi another specific embodiment of the subject invention, the emulsifier is a combination of Polyglycerol Polyricinoleate (PGPR) and Span 80.
In one specific embodiment of the subject invention, PGPR is present in the water-in-oil antioxidant composition of the invention at about 2 % by weight and Span 80 is present in the water-in-oil antioxidant composition of the invention at about 0.1 - 2 % by weight. In one specific embodiment of the present invention, PGPR is present in the water-in-oil antioxidant composition of the invention at about 1-3% by weight and mono and diglycerids are present in about 0.5-2% by weight.
The water-in-oil antioxidant composition of the invention also comprises oil as one of the components of the novel composition. The oil can be any suitable animal fat or plant oil. Examples of such plant oils include, but are not limited to palm oil, olive oil, soybean oil, canola oil, pumpkin seed oil, corn oil, sunflower oil, safflower oil, peanut oil, grape seed oil, sesame oil, argan oil, rice bran oil and combinations thereof.
The term "suitable oil" should be understood as any oil that can be utilized successfully in the preparation of an emulsion. In one embodiment of the subject invention, oil is present in the novel water-in-oil antioxidant composition at about 10-60% by weight and preferably at about 15-50% by weight. In a specific embodiment of the subject invention, the oil is Canola oil. In one specific embodiment of the subject invention, Canola oil is present in the water-in-oil antioxidant composition of the invention at about 15 -41 % by weight. The water-in-oil antioxidant composition of the invention may also additionally contain as one of its components at least one fat soluble antioxidant. The at least one fat soluble antioxidant of the subject invention can be any suitable antioxidant having a relatively good solubility in oil and relatively poor solubility in water. Examples of such antioxidants include, but are not limited to tocopherols, tocotrienols, retinol, rosemary oil, ascorbyl-palmitate, and combinations thereof.
The term "Tocopherols " refers to a class of chemical compounds of which many have vitamin E activity, tocopherols are a series of organic compounds consisting of various methylated phenols. Tocopherols are fat-soluble antioxidants.
The term "relatively good solubility in oil" should be understood to encompass solubility of the antioxidant that is higher than 0.1% by weight.
The term "relatively poor solubility in water" should be understood to encompass solubility of the antioxidant that is lower than 0.1% by weight.
In one embodiment of the subject invention, the at least one fat soluble antioxidant is present in the novel water-in-oil antioxidant composition at about 5-35% by weight. In a specific embodiment of the subject invention, the fat soluble antioxidants are tocopherols. In one specific embodiment of the subject invention, the tocopherols are Natural Mixed Tocopherols 50%. In a specific embodiment of the subject invention, Mixed Tocopherols 50% are present in the water-in-oil antioxidant composition of the invention at about 20 - 30 % by weight.
Another object of present invention is to provide a method of inhibiting oxidation of fats and oils, which comprises adding to said fats and oils an antioxidant effective amount of the water-in-oil antioxidant composition of the invention.
As used herein "inhibiting oxidation " also encompasses the consequences of such inhibition namely enhancement of the stability and quality of said fats and oils.
The water-in-oil antioxidant composition of the subject invention can be used in protecting any oils, fats, and fatty substances of plant, animal, mineral or synthetic origin. In one specific embodiment the oils are essential oils. In another specific embodiment the oils are cooking and frying oils.
By employment of the water-in-oil antioxidant composition the stability (usability) of a frying fat can be increased by a multiple (for example, extended at least by 1.5-fold as compared to the frying medium in the absence of the composition of the invention).
The term "antioxidant effective amount" refers to the amount of the composition which is sufficient to reduce the oxidation of a frying medium. The antioxidant effective amount may be determined using procedures well described in the art, for example, by the Oil Stability Index (OSI), an American Oil Chemists Society (AOCS) approved method Cd 12B-92. The OSI method determines the relative resistance of fat and oil samples to oxidation.
In practice, for stabilization of a frying medium, the quantity by weight of the water-in-oil antioxidant composition of the invention is added in amounts of 0.02% to 0.5% by weight of the frying medium.
The invention further provides a method of improving the quality of a fried product which comprises cooking the product in a frying medium that contains an antioxidant effective amount of the water-in-oil antioxidant composition of the invention.
The term "fried product" refers to fried food products such as for example fabricated crisps, tortillas, wheat thins, crackers, rice cakes, cereals, extruded snacks, potato chips, granola bars, etc. The fried food products may be sweet, salty, or savory. The invention further provides a method of improving the quality of a baked product which comprises baking the product using oil that contains an antioxidant effective amount of the water-in-oil antioxidant composition of the invention.
The term "baked product" refers to baked food products such as for example, crackers, waffles, pretzels, biscuits, cookies, Bars.
In another embodiment, the water-in-oil antioxidant composition of the invention can be used as an additive to fats, oils and fatty substances, to inhibit oxidation and enhance the stability and quality thereof.
The subject invention encompasses a use of a water-in-oil antioxidant composition of the invention as an additive to essential oils.
The subject invention also provides a use of a water-in-oil antioxidant composition of the invention as an additive to cooking and frying oils, such as for example deep-frying oils.
The water-in-oil antioxidant compositions of the invention are characterized by being an emulsion, having a shelf life of about one year, having an off white/beige to yellow/brown color, and a tea like oily taste.
EXAMPLES
EXAMPLE 1 - Preparation of water-in-oil antioxidant compositions of the invention
Origanox ™ WS-LB is a water-soluble powder of natural extract from lemon balm, an edible herb species belonging to the Labiatae family, available from RAD Natural Technologies Ltd. (Israel), and having the following specifications:
Appearance: Golden powder, Agglomerated
Aroma and flavor: Extra mild, tea like flavor
Antioxidant activity: > 90 units (Standardized by an in-house method)
Total Plate Count: < 5000 CFU/g
E. CoIi Absent / Ig Salmonella Absent / 25g Yeast and molds < 100 CFU/g
Solubility: Soluble in cold water Toxicity: Non toxic Shelf life 3 years when stored unopened according to specified conditions in original sealed packaging
The following formulations were prepared by mixing the aqueous phase (including water and water soluble components) with the oil phase, followed by homogenizing the mixture using a piston type homogenizer.
Formulation I:
Figure imgf000014_0001
Formulation II
Figure imgf000014_0002
Formulation III:
Figure imgf000015_0001
Formulation IV:
Figure imgf000015_0002
Formulation V:
Figure imgf000015_0003
Formulation VI:
Figure imgf000016_0001
In Formulations IV-VI, which include Tocopherols the Tocopherols were mixed with the Canola oil prior to mixing the oil component with the water and emulsifier.
EXAMPLE 2 - Antioxidant Activity of the Water-in-oil Compositions of the Invention
Antioxidant activity of Formulations I to VI was determined according to the Oil Stability Index (OSI), an American Oil Chemists Society (AOCS) approved method Cd 12B-92. The OSI method determines the relative resistance of fat and oil samples to oxidation.
OSI determinations were made in canola oil with Rancimat instrument at 12O0C and 20 liters/hours of air. The results are provided in Table 1.
Table 1
Figure imgf000017_0001
The results in Table 1 show that Formulations I- VI are effective in delaying oxidation. Natural antioxidants were employed for comparative purposes, i.e. Rosemary oil (4% carnosic acid) available from Kalsec (USA), under the trade name Herbalox™, and mixed Tocopherols.
The effect of Tocopherols was further investigated by adding Tocopherols to
Formulation I. As shown in Table 2 Formulation IV that contains tocopherols (in the oil before mixing with water and emulsifier) has a superior effect as compared to
Formulation I. Tocopherols has no effect when it is added separately to the Formulation
(Formulation I + tocopherols). Tocopherols alone (as well as Rosemary oil) have a lower activity than Formulation IV. These results suggest that mixing tocopherols in the oil component of the Formulation prior to mixing with the aqueous component affects the activity of the Formulation. Table 2
Figure imgf000018_0001
EXAMPLE 3 - Inhibition of oxidation by Origanox™ OS-MX in a baked product
Origanox™ OS-MX is an anti-oxidant composition comprising the following components: 15% Ascorbic acid 1% Origanox WS-LB
10% Mix tocopherols (soy oil)
24% Water
10% PGPR
40% oil (vegetable oil) Origanox™ OS-MX was added to the oil prior to mixing of the oil with water and flour. Two types of products, Crown waffles and crackers were then prepared according to conventional baking procedures.
The degree of oxidation in the baked products was determined by measuring the level of aldehydes that are generated upon decomposition of the oil and are thus used as an indication of the degree of the oxidation. Hexanal (an alkyl aldehyde) level was measured as shown in St. Angelo, et al (1980) Lipids 15, 45-49 using Headspace Gas chromatography (HS-GC). HS-GC is used for the analysis of volatiles and semi-volatile organics in solid, liquid, and gas samples. As shown in Figure 1, in both products Origanox™ OS-MX inhibits the formation of hexanal (Figure IA) and other aldehydes (off flavor, Figure IB) and therefore maintains the freshness longer.
EXAMPLE 4 - Use of Origanox™ OS-A in frying oil
Fried potato chips
Origanox™ OS-A is an anti-oxidant composition comprising the following components: 10% Ascorbic acid 5% Origanox WS- LB (Lemon balm extract) 20% water 15% PGPR 50% oil (Vegetable oil)
Origanox™ OS-A was added to oil used for frying potato chips. Origanox™ OS- A was used in the frying oil in order to increase shelf life and reduce rancidity of the fried potato chips.
Fried products may absorb around 30% of the frying oil, which is the main cause for rancidity development of the fried product.
As shown in Figure 2, addition of 0.1% or 0.2% of Origanox™ OS-A to the frying oil delayed oxidation of the potato chips (as measured by the Hexanal method) by 32% and 67% respectively. Fried peanuts
0.07% Origanox™ OS-A was dissolved in the frying oil used for flying peanuts.
The level of oxidation of the peanuts was measured by the Hexanal method using HS- GC. The test was carried out at accelerated conditions, namely the peanuts were stored at 6O0C for 30 days.
As shown in Figure 3, after 15 days, the oxidation level (as measured by the
Hexanal method) of a Control set (control=no anti oxidant added to the oil) and of the peanuts fried with 0.07% Origanox™ OS-A was similar. However, after 30 days the oxidation level of the peanuts fried with Origanox™ OS-A was about 40% that of the control.

Claims

1. A water-in-oil antioxidant composition comprising (i) water; (ii) at least one water-soluble antioxidant; (iii) at least one oil soluble and water insoluble emulsifier; and
(iv) oil.
2. A water-in-oil antioxidant composition according to claim 1 wherein said composition comprises at least 20% w/w water.
3. A water-in-oil antioxidant composition according to claim 2 wherein said composition comprises from about 20% to about 30% (w/w) water.
4. A water-in-oil antioxidant composition according to claim 1 wherein said at least one water soluble antioxidant is selected from the group consisting of ascorbic acid, citric acid, L-ascorbate (Vitamin C), erythrobic acid, lactic acid, ellagitannin, chlorogenic acid, anthocyanin, water soluble antioxidant herb or plant extract and combinations thereof.
5. A water-in-oil antioxidant composition according to claim 1 wherein said water- in-oil antioxidant composition comprises from about 5% to about 40% w/w water-soluble antioxidant.
6. A water-in-oil antioxidant composition according to claim 5 wherein said water- in-oil antioxidant composition comprises from about 5% to about 40% w/w water-soluble antioxidant.
7. A water-in-oil antioxidant composition according to claim 4 wherein said water soluble antioxidant is ascorbic acid.
8. A water-in-oil antioxidant composition according to claim 7 wherein said composition comprises from about 10% to about 30% w/w ascorbic acid.
9. A water-in-oil antioxidant composition according to claim 4 wherein said composition comprises a combination of ascorbic acid and a water soluble antioxidant herb extract.
10. A water-in-oil antioxidant composition according to claim 9 wherein said herb extract is selected from the group consisting of basil, lemon balm {Melissa officinalis), mint, rosemary, sage, savory, marjoram, oregano, thyme, lavender, and perilla extracts, and combinations thereof.
11. A water-in-oil antioxidant composition according to claim 10 wherein said water soluble antioxidant extract is a lemon balm (Melissa officinalis) extract.
12. A water-in-oil antioxidant composition according to any of claims 9-11 wherein said water soluble antioxidant herb extract is present at a concentration of from about 0.1 % to about 10% w/w.
13. A water-in-oil antioxidant composition according to claim 12 wherein said water soluble antioxidant herb extract is present at a concentration of from about 0.5% to about 5% w/w.
14. A water-in-oil antioxidant composition according to claim 13 wherein said water soluble antioxidant herb extract is present at a concentration of about 0.5% w/w.
15. A water-in-oil antioxidant composition according to claim 13 wherein said water soluble antioxidant herb extract is present at a concentration of about 5% w/w.
16. A water-in-oil antioxidant composition according to claim 1 wherein said composition comprises from about 0.5% to about 30% w/w oil soluble and water insoluble emulsifier.
17. A water-in-oil antioxidant composition according to claim 16 wherein said composition comprises from about 2% to about 20% w/w oil soluble and water insoluble emulsifier.
18. A water-in-oil antioxidant composition according to claim 1 wherein said at least one oil soluble and water insoluble emulsifier is selected from the group consisting of mono and di glycerides, glycerol, Tween® 40, Tween® 80, Span 80, Polyglycerol Polyricinoleate (PGPR), lecithin, propylene glycol, linoleic acid and combinations thereof.
19. A water-in-oil antioxidant composition according to claim 18 wherein said at least one oil soluble and water insoluble emulsifier is a mono or diglycerid.
20. A water-in-oil antioxidant composition according to claim 18 wherein said at least one oil soluble and water insoluble emulsifier is Polyglycerol Polyricinoleate (PGPR).
21. A water-in-oil antioxidant composition according to claim 20 wherein said composition comprises from about 2% to about 15% w/w PGPR.
22. A water-in-oil antioxidant composition according to claim 18 wherein said at least one oil soluble and water insoluble emulsifier is a combination of Polyglycerol Polyricinoleate (PGPR) and Span 80.
23. A water-in-oil antioxidant composition according to claim 22 wherein said composition comprises about 2% w/w PGPR and from about 0.1% to about 2% w/w Span
80.
24. A water-in-oil antioxidant composition according to claim 1 wherein said oil is selected from animal fat and plant oil.
25. A water-in-oil antioxidant composition according to claim 24 wherein said plant oil is selected from the group consisting of palm oil, olive oil, soybean oil, canola oil, pumpkin seed oil, corn oil, sunflower oil, safflower oil, peanut oil, grape seed oil, sesame oil, argan oil, rice bran oil, and combinations thereof.
26. A water-in-oil antioxidant composition according to any of claims 24 or 25 wherein said composition comprises from about 10% to about 60% (w/w) oil.
27. A water-in-oil antioxidant composition according to claim 25 wherein said oil is canola oil.
28. A water-in-oil antioxidant composition according to claim 27 wherein said composition comprises from about 15% to about 41% (w/w) canola oil.
29. A water-in-oil antioxidant composition according to any of claims 1-28 additionally comprising at least one fat soluble antioxidant.
30. A water-in-oil antioxidant composition according to claim 29 wherein said fat soluble antioxidant is selected from the group consisting of tocopherols, tocotrienols, retinol, rosemary oil, ascorbyl-palmitate and combinations thereof.
31. A water-in-oil antioxidant composition according to claim 29 wherein said composition comprises from about 5% to about 35% w/w fat-soluble antioxidant.
32. A water-in-oil antioxidant composition according to claim 30 wherein said fat soluble antioxidant are tocopherols.
33. A water-in-oil antioxidant composition according to claim 32 wherein said tocopherols are Natural Mixed Tocopherols 50% or 70%.
34. A water-in-oil antioxidant composition according to claim 33 wherein said composition comprises Natural Mixed Tocopherols 50% at a concentration of about 20% to about 30 % w/w.
35. A method of inhibiting oxidation of fats and oils comprising adding to said fats and oils an antioxidant effective amount of a water-in-oil antioxidant composition according to any of claims 1- 34.
36. Use of the water-in-oil antioxidant composition according to any of claims 1- 34 as an additive to fats and oils, for inhibiting oxidation thereof.
37. The method of claim 35 or use of claim 36 wherein the fats and oils are of plant or animal origin.
38. The method of claim 35 or use of claim 36 wherein the oils are essential oils.
39. The method of claim 35 or use of claim 36 wherein the fats and oils are cooking and frying oils.
40. Fried products, wherein said fried products were fried in oil comprising the water- in-oil antioxidant composition of claims 1-34.
41. Baked products, wherein said baked products were baked using oil comprising the water-in-oil antioxidant composition of claims 1-34.
PCT/IL2008/001037 2007-07-26 2008-07-27 Composition for protecting oils and fat WO2009013757A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US93511207P 2007-07-26 2007-07-26
US60/935,112 2007-07-26

Publications (1)

Publication Number Publication Date
WO2009013757A1 true WO2009013757A1 (en) 2009-01-29

Family

ID=39952325

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2008/001037 WO2009013757A1 (en) 2007-07-26 2008-07-27 Composition for protecting oils and fat

Country Status (1)

Country Link
WO (1) WO2009013757A1 (en)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101874531A (en) * 2010-04-10 2010-11-03 邯郸市天养生物科技有限公司 Grape seed oil added with tea polyphenol microemulsion and preparation method thereof
ES2385150A1 (en) * 2010-12-23 2012-07-19 Hojiblanca, S. Coop. And. Procedure for obtaining olive oil to fiber high stability. (Machine-translation by Google Translate, not legally binding)
WO2013184983A1 (en) * 2012-06-07 2013-12-12 Archer Daniels Midland Company Use of organic acids to improve lipid stability
WO2014081976A1 (en) * 2012-11-21 2014-05-30 Aviratek Biomedical Solutions, Llc Method and compositions for the use of botanical extracts in the treatment of viral infections, cancer, pain, itch, and inflammation
CN103891922A (en) * 2012-12-26 2014-07-02 丰益(上海)生物技术研发中心有限公司 Edible oil composition containing water soluble antioxidant and preparation method thereof
US20140242250A1 (en) * 2011-06-09 2014-08-28 Dupont Nutrition Biosciences Aps Low fat spread
CN105247029A (en) * 2013-05-20 2016-01-13 花王株式会社 Fat composition
WO2016159767A2 (en) 2015-03-30 2016-10-06 Bio-Based Product Ontwikkelings Cooperatie U.A. (Boc) Method for the preparation of a water-soluble extract of a vegetable biomass
CN106947594A (en) * 2017-05-10 2017-07-14 仲恺农业工程学院 A kind of microemulsion for delaying feeding oil to aoxidize and preparation method thereof
CN106967505A (en) * 2017-04-26 2017-07-21 东北农业大学 It is a kind of to add the method that complex natural antioxidant suppresses corn oil oxidation
CN107072227A (en) * 2014-10-31 2017-08-18 Cj第制糖株式会社 Extract oil emulsion containing antioxidant, kitchen oil containing it and preparation method thereof
CN108967558A (en) * 2018-07-20 2018-12-11 陈玉祥 A kind of oral edible oil and preparation method for toxin-expelling and face nourishing
CN108991134A (en) * 2018-02-06 2018-12-14 嘉吉公司 Emulsion including antioxidant
CN109321361A (en) * 2018-12-05 2019-02-12 天津南侨食品有限公司 It is a kind of it is water type bake grease anti-oxidant compositions and its application
JP2019024405A (en) * 2017-07-30 2019-02-21 株式会社Ｊ−オイルミルズ Oil absorption reducing agent, oil absorption reducing method and oil and fat composition for fried food
JP2019024404A (en) * 2017-07-30 2019-02-21 株式会社Ｊ−オイルミルズ Oil absorption reducing agent and oil absorption reducing method
IT201700103759A1 (en) * 2017-09-15 2019-03-15 Olitalia S R L COMPOSITION OF FOOD OIL, PARTICULARLY FOR USE IN FRYING AND COOKING FOOD
EP3425033A4 (en) * 2016-03-02 2019-10-23 Fuji Oil Holdings Inc. Fat or oil composition exhibiting anti-oxidation properties
CN111040875A (en) * 2020-01-06 2020-04-21 武汉轻工大学 Antioxidant and preparation method and application thereof
WO2021088210A1 (en) * 2019-11-06 2021-05-14 广州大正新材料科技有限公司 Haematococcus pluvialis powder composition having antioxidation effect, and preparation method therefor
RU2762034C1 (en) * 2020-10-01 2021-12-14 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный технологический университет" (ФГБОУ ВО "КубГТУ") Method for preparing a deep-frying composition
EP3777545A4 (en) * 2018-03-28 2021-12-22 Fuji Oil Holdings Inc. Fat composition
WO2023175391A1 (en) * 2022-03-16 2023-09-21 Alianza Team International S.A. Emulsions as oxidation protectants for conventional frying oils in food applications
US11957135B2 (en) 2016-03-02 2024-04-16 Fuji Oil Holdings Inc. Chocolate-like food containing polyunsaturated fatty acid

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5084289A (en) * 1989-02-01 1992-01-28 Korea Food Research Institute Method for the inhibition of oxidation of edible oils utilizing a fat soluble anti-oxidant and a water soluble anti-oxdant in a reverse micelle system
WO2000039248A1 (en) * 1998-12-24 2000-07-06 Rad Natural Technologies Ltd. Method for protecting a substance liable to oxidative deterioration
JP2002142673A (en) * 2000-11-17 2002-05-21 T Hasegawa Co Ltd Lipophilic antioxidant for oil and fat cooked food and method for producing the same
US20030026887A1 (en) * 2001-07-18 2003-02-06 Christian Gertz Use of water-in-oil emulsions for stabilization of oil of frying and boiling under frying conditions
WO2005011390A1 (en) * 2003-08-04 2005-02-10 Rad Natural Technologies Ltd. Compositions and methods for improving the efficiency of preservatives in foods
WO2005019397A1 (en) * 2003-08-22 2005-03-03 Oy Vegaoils Ltd Antioxidant and its use
JP2007185138A (en) * 2006-01-13 2007-07-26 Sanei Gen Ffi Inc Lipophilic antioxidant and method for producing the same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5084289A (en) * 1989-02-01 1992-01-28 Korea Food Research Institute Method for the inhibition of oxidation of edible oils utilizing a fat soluble anti-oxidant and a water soluble anti-oxdant in a reverse micelle system
WO2000039248A1 (en) * 1998-12-24 2000-07-06 Rad Natural Technologies Ltd. Method for protecting a substance liable to oxidative deterioration
JP2002142673A (en) * 2000-11-17 2002-05-21 T Hasegawa Co Ltd Lipophilic antioxidant for oil and fat cooked food and method for producing the same
US20030026887A1 (en) * 2001-07-18 2003-02-06 Christian Gertz Use of water-in-oil emulsions for stabilization of oil of frying and boiling under frying conditions
WO2005011390A1 (en) * 2003-08-04 2005-02-10 Rad Natural Technologies Ltd. Compositions and methods for improving the efficiency of preservatives in foods
WO2005019397A1 (en) * 2003-08-22 2005-03-03 Oy Vegaoils Ltd Antioxidant and its use
JP2007185138A (en) * 2006-01-13 2007-07-26 Sanei Gen Ffi Inc Lipophilic antioxidant and method for producing the same

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 200261, Derwent World Patents Index; AN 2002-569146, XP002504394 *
DATABASE WPI Week 200761, Derwent World Patents Index; AN 2007-644267, XP002504395 *
HERSCHOWITZ B., REZNIK R., IOUDKEVITCH C., SEGAL R.: "Synergetic Action of Herbal Extracts on Antioxidative Capacity of Lupine Protein Derivates", THE ANNALS OF THE UNIVERSITY DUNAREA DE JOS OF GALATI, 2003, Romania, pages 28 - 32, XP002504393, Retrieved from the Internet <URL:http://www.ann.ugal.ro/tpa/Annals%2003%20papers/08%20Full%20paper%20Herskowitz.pdf> [retrieved on 20081118] *
K. SCHWARZ, S.W. HUANG, J.B. GERMAN, B. TIERSCH, J. HARTMANN, E.N. FRANKEL: "Activities of Antioxidants are Affected by Colloidal Properties of Oil-in-Water and Water-in-Oil Emulsions and Bulk Oils", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 48, 2000, pages 4874 - 4882, XP002504392 *
P.D. DUH: "Antioxidant Activity of Water Extract of Four Harng Jyur (Chrysanthemum Morifolium Ramat) Varieties in Soybean Oil Emulsion", FOOD CHEMISTRY, vol. 66, 1999, pages 471 - 476, XP002504391 *

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101874531A (en) * 2010-04-10 2010-11-03 邯郸市天养生物科技有限公司 Grape seed oil added with tea polyphenol microemulsion and preparation method thereof
ES2385150A1 (en) * 2010-12-23 2012-07-19 Hojiblanca, S. Coop. And. Procedure for obtaining olive oil to fiber high stability. (Machine-translation by Google Translate, not legally binding)
US20140242250A1 (en) * 2011-06-09 2014-08-28 Dupont Nutrition Biosciences Aps Low fat spread
WO2013184983A1 (en) * 2012-06-07 2013-12-12 Archer Daniels Midland Company Use of organic acids to improve lipid stability
WO2014081976A1 (en) * 2012-11-21 2014-05-30 Aviratek Biomedical Solutions, Llc Method and compositions for the use of botanical extracts in the treatment of viral infections, cancer, pain, itch, and inflammation
US10842838B2 (en) 2012-11-21 2020-11-24 Aviratek Biomedical Solutions, Llc Method for the use of botanical extracts in the treatment of viral infections
CN103891922A (en) * 2012-12-26 2014-07-02 丰益(上海)生物技术研发中心有限公司 Edible oil composition containing water soluble antioxidant and preparation method thereof
CN105247029B (en) * 2013-05-20 2019-02-12 花王株式会社 Fat or oil composition
CN105247029A (en) * 2013-05-20 2016-01-13 花王株式会社 Fat composition
EP3000867A4 (en) * 2013-05-20 2017-01-11 Kao Corporation Fat composition
EP3213639A4 (en) * 2014-10-31 2018-04-04 Cj Cheiljedang Corporation Extract emulsified oil comprising antioxidant, edible oil containing same, and preparation method therefor
CN107072227A (en) * 2014-10-31 2017-08-18 Cj第制糖株式会社 Extract oil emulsion containing antioxidant, kitchen oil containing it and preparation method thereof
WO2016159767A2 (en) 2015-03-30 2016-10-06 Bio-Based Product Ontwikkelings Cooperatie U.A. (Boc) Method for the preparation of a water-soluble extract of a vegetable biomass
US11957135B2 (en) 2016-03-02 2024-04-16 Fuji Oil Holdings Inc. Chocolate-like food containing polyunsaturated fatty acid
EP3425033A4 (en) * 2016-03-02 2019-10-23 Fuji Oil Holdings Inc. Fat or oil composition exhibiting anti-oxidation properties
CN106967505A (en) * 2017-04-26 2017-07-21 东北农业大学 It is a kind of to add the method that complex natural antioxidant suppresses corn oil oxidation
CN106947594A (en) * 2017-05-10 2017-07-14 仲恺农业工程学院 A kind of microemulsion for delaying feeding oil to aoxidize and preparation method thereof
CN106947594B (en) * 2017-05-10 2020-12-08 仲恺农业工程学院 Microemulsion for delaying oxidation of feed oil and preparation method thereof
JP7102110B2 (en) 2017-07-30 2022-07-19 株式会社Ｊ－オイルミルズ Oil absorption reducing agent, oil absorption reducing method and fat composition for deep-fried foods
JP2019024405A (en) * 2017-07-30 2019-02-21 株式会社Ｊ−オイルミルズ Oil absorption reducing agent, oil absorption reducing method and oil and fat composition for fried food
JP2019024404A (en) * 2017-07-30 2019-02-21 株式会社Ｊ−オイルミルズ Oil absorption reducing agent and oil absorption reducing method
IT201700103759A1 (en) * 2017-09-15 2019-03-15 Olitalia S R L COMPOSITION OF FOOD OIL, PARTICULARLY FOR USE IN FRYING AND COOKING FOOD
CN108991134A (en) * 2018-02-06 2018-12-14 嘉吉公司 Emulsion including antioxidant
CN108991134B (en) * 2018-02-06 2023-05-02 嘉吉公司 Emulsions comprising antioxidants
EP3777545A4 (en) * 2018-03-28 2021-12-22 Fuji Oil Holdings Inc. Fat composition
CN108967558A (en) * 2018-07-20 2018-12-11 陈玉祥 A kind of oral edible oil and preparation method for toxin-expelling and face nourishing
CN109321361A (en) * 2018-12-05 2019-02-12 天津南侨食品有限公司 It is a kind of it is water type bake grease anti-oxidant compositions and its application
WO2021088210A1 (en) * 2019-11-06 2021-05-14 广州大正新材料科技有限公司 Haematococcus pluvialis powder composition having antioxidation effect, and preparation method therefor
CN111040875A (en) * 2020-01-06 2020-04-21 武汉轻工大学 Antioxidant and preparation method and application thereof
RU2762034C1 (en) * 2020-10-01 2021-12-14 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный технологический университет" (ФГБОУ ВО "КубГТУ") Method for preparing a deep-frying composition
WO2023175391A1 (en) * 2022-03-16 2023-09-21 Alianza Team International S.A. Emulsions as oxidation protectants for conventional frying oils in food applications

Similar Documents

Publication Publication Date Title
WO2009013757A1 (en) Composition for protecting oils and fat
JP7343105B2 (en) Oils containing oxidatively stable polyunsaturated fatty acids
AU2018202247B2 (en) Fat containing polyunsaturated fatty acid
EP2850949B1 (en) Edible fat or oil and process for producing same
AU2005254036B2 (en) Topical application of marine oils to foods
EP1186648A1 (en) Fat compositions
Boskou Non-nutrient antioxidants and stability of frying oils
CN109022148A (en) Quaternary built antioxidant, preparation method and the usage
WO2014027321A1 (en) A herbal extract composition and a process thereof
JP4516363B2 (en) Oil composition for cooking
Prabsangob et al. Effect of tea catechin derivatives on stability of soybean oil/tea seed oil blend and oxidative stability of fried fish crackers during storage
KR102379302B1 (en) Oil and fat composition for deep frying and method for manufacturing the same
US20160120200A1 (en) Fat and/or oil composition for heat cooking and method for manufacturing the fat and/or oil composition for heat cooking
Senanayake Enhancing oxidative stability and shelf life of frying oils with antioxidants
JP2015112024A (en) Edible oil and fat having rice flavor
JPH0783677B2 (en) Cooking oil for frying and cooking oil
JPS608076B2 (en) Antioxidant preparation
WO2009102019A1 (en) Antioxidative composition for feed raw material
Azizkhani et al. Effects of some natural antioxidant mixtures on margarine stability.
WO2019187242A1 (en) Fat composition
JP6774045B1 (en) Oil composition
KR101540854B1 (en) An oil for a seasoned laver which comtaining perilla oil and a seasoned laver comprising thereof
Deora et al. Natural Antioxidant During Frying: Food Industry Perspective
US20220295810A1 (en) Oil and fat composition
Azizkhani et al. Effect of natural antioxidant mixtures on margarine stability.

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08789713

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08789713

Country of ref document: EP

Kind code of ref document: A1