WO2020090609A1 - パーム系油脂の酸化処理物、酸化処理物の製造方法、食品の甘味増強方法、及び食品の甘味増強用組成物 - Google Patents
パーム系油脂の酸化処理物、酸化処理物の製造方法、食品の甘味増強方法、及び食品の甘味増強用組成物 Download PDFInfo
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- WO2020090609A1 WO2020090609A1 PCT/JP2019/041660 JP2019041660W WO2020090609A1 WO 2020090609 A1 WO2020090609 A1 WO 2020090609A1 JP 2019041660 W JP2019041660 W JP 2019041660W WO 2020090609 A1 WO2020090609 A1 WO 2020090609A1
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- 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
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
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- 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
- A23L27/88—Taste or flavour enhancing agents
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- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
- A21D2/165—Triglycerides
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- 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
-
- 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
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
- A23D9/05—Forming free-flowing pieces
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
- A23G1/36—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the fats used
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
- A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
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- 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
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2028—Carboxy compounds
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- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/10—General methods of cooking foods, e.g. by roasting or frying
- A23L5/11—General methods of cooking foods, e.g. by roasting or frying using oil
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- 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
- A23L9/00—Puddings; Cream substitutes; Preparation or treatment thereof
- A23L9/20—Cream substitutes
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
- A23C9/123—Fermented milk preparations; Treatment using microorganisms or enzymes using only microorganisms of the genus lactobacteriaceae; Yoghurt
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
- A23F5/24—Extraction of coffee; Coffee extracts; Making instant coffee
- A23F5/36—Further treatment of dried coffee extract; Preparations produced thereby, e.g. instant coffee
- A23F5/40—Further treatment of dried coffee extract; Preparations produced thereby, e.g. instant coffee using organic additives, e.g. milk, sugar
Definitions
- the present invention relates to an oxidation-treated product of palm-based fats and oils, which has an excellent effect of enhancing sweetness, and its use.
- Patent Document 1 discloses a method for enhancing the sweetness of foods by using a long-chain highly unsaturated fatty acid and / or an ester thereof.
- Patent Document 2 discloses a sweetness enhancer containing an oxidized partially hydrogenated oil or fat having a peroxide value of 25 to 300 as an active ingredient.
- Patent Document 3 discloses a sweetness enhancer containing a oxidized oil and fat having a peroxide value of 15 to 180 and containing 10 to 100% by mass of milk and fat as an active ingredient.
- an object of the present invention is to provide an edible material having an excellent sweetening effect.
- the present invention in its first aspect, is A palm-based oil and fat oxidation product
- the palm-based oil and fat has a total content of ⁇ -carotene and ⁇ -carotene of 50 mass ppm or more and 2000 mass ppm or less
- the oxidation treated product has a peroxide value of 3 or more and 250 or less.
- the present invention provides an oil and fat composition containing the above-mentioned oxidized product.
- the above oil / fat composition is preferably for cooking with heat.
- the palm-based fat having a total content of ⁇ -carotene and ⁇ -carotene of 50 mass ppm or more and 2000 mass ppm or less has a peroxide value of 3 or more and 250 or less.
- the present invention provides a method for producing an oxidation-treated product, which comprises a step of performing the oxidation treatment.
- the oxidation treatment step is performed at a heating temperature of 50 ° C. or higher and 220 ° C. or lower and a heating time of 0.1 hour or longer and 240 hours or shorter.
- the oxidation treatment step is performed by supplying oxygen to the palm-based oil and fat.
- the present invention provides a method for enhancing the sweetness of a food, which comprises incorporating the above-mentioned oxidized product or the above oil / fat composition into the food.
- the present invention provides a composition for enhancing sweetness of foods, which comprises an oxidation-treated palm oil or fat.
- composition for enhancing sweetness of foods described above preferably contains the oxidation-treated product in an amount of 1 ⁇ 10 ⁇ 8 % by mass or more and 100% by mass or less.
- the present invention provides a food product containing the above-mentioned oxidized product.
- an edible material that is derived from palm oil and fat and has an excellent sweetening effect.
- the present invention provides an oxidative product of palm oil and fat as an edible material having an excellent sweetening effect.
- the palm-based oil and fat used in the present invention may be any palm-based oil or fat obtained from the fruits of oil palm, and may be subjected to treatments such as molecular distillation, fractionation, degumming, deoxidation, decolorization and deodorization. Good.
- the method of each treatment is not particularly limited, and a method generally used for processing and refining oils and fats can be adopted.
- the fractionation can be performed by solvent fractionation or low temperature filtration.
- the total content of ⁇ -carotene and ⁇ -carotene is 50 mass ppm or more and 2000 mass ppm or less, preferably 50 mass ppm or more and 1500 mass ppm or less, and 50 mass ppm or more and 1000 mass ppm or less.
- the palm-based fats and oils may have a total content of ⁇ -carotene and ⁇ -carotene within the above range, and one kind may be used alone, or two or more kinds may be used in combination so as to be within the above range. Good.
- the above palm-based fats and oils are oxidized to obtain an oxidized product.
- the peroxide value (hereinafter, also referred to as “POV”) of the oxidized product is 3 or more and 250 or less, preferably 3 or more and 220 or less, more preferably 3 or more and 180 or less, and 3 or more and 150 or less. The following is more preferable.
- the POV can be measured in accordance with "Standard Oil and Fat Analysis Test Method 2.5.2 Peroxide Value" (Japan Oil Chemists' Society). By oxidizing the POV so that the POV falls within the above-mentioned predetermined range, it is possible to obtain an edible material having an excellent sweetening effect.
- the method for oxidizing the palm-based fats and oils is not particularly limited as long as it can be a POV in the above-mentioned predetermined range, but is preferably heat treatment, and from the viewpoint of production on an industrial scale, such as a tank. It is preferable that the heating is carried out in an appropriate container and then equipped with a heating means such as an electric heating type, an open flame burner type, a microwave type, a steam type, or a hot air type provided in the container.
- the conditions of the heat treatment are not unconditional, but typically, for example, the heating temperature is 50 ° C. or higher and 220 ° C. or lower, and the heating time is 0.1 hour or longer and 240 hours or shorter. More typically, for example, The heating temperature is 60 ° C.
- the condition of the cumulative amount of heating temperature (° C.) ⁇ heating time (hour) is, for example, that the heat treatment is performed at a cumulative amount of 200 or more and 20000 or less, and more typically 220 or more and 18000, for example.
- the heat treatment is performed in the following integrated amount, and more typically, the heat treatment is performed in the integrated amount of 240 to 15000, for example.
- the integrated amount of the heating temperature (° C) ⁇ the heating time (hour) is the heating temperature (° C) before the temperature is changed ⁇ the heating time (hour) before the temperature is changed + It can be calculated as the heating temperature (° C.) after changing the temperature ⁇ the heating time (hour) after changing the temperature, or an integrated value of the heating temperature (° C.) over the heating time (hour).
- oxygen air
- the oxygen source may be air or the like. This accelerates the oxidation of the palm-based oil and fat.
- the supply amount of oxygen be 0.001 to 2 L / min per 1 kg of the raw material oil and fat.
- air it is preferably 0.005 to 10 L / min, and more preferably 0.01 to 5 L / min, per 1 kg of raw material oil and fat.
- the palm-based oil and fat oxidation-treated product obtained as described above is added to any other appropriate edible oil / fat, as long as it does not impair the desired sweetness-enhancing functionality, and contains the oxidation-treated product. It may be a fat composition.
- Other edible oils and fats include vegetable oils such as soybean oil, rapeseed oil (canola oil), palm oil, corn oil, olive oil, sesame oil, safflower oil, sunflower oil, cottonseed oil, rice oil, peanut oil, palm kernel oil, and palm oil.
- Animal fats and oils such as beef tallow, lard, pork fat, chicken fat, fish oil and milk fat, medium chain fatty acid triglycerides, and processed fats and oils obtained by subjecting these fats and oils to fractionation, hydrogenation, transesterification and the like.
- These edible oils and fats may be used alone or as a mixture of two or more kinds.
- the mixing ratio is not particularly limited, but from the viewpoint of not impairing the desired functionality of enhancing sweetness, the content of the palm oil-based fat oxidation product relative to the total mass of the palm oil-based fat oxidation product and other edible fats and oils Is preferably 1 ⁇ 10 ⁇ 8 mass% or more and less than 100 mass%, more preferably 1 ⁇ 10 ⁇ 7 mass% or more and less than 100 mass%, more preferably 1 ⁇ 10 ⁇ 6 mass% or more and 100 mass%. It is more preferably less than 100% by mass, more preferably 1 ⁇ 10 ⁇ 5 % by mass or more and less than 100% by mass.
- the said oil-fat composition may be made to contain one kind of oxidation-treated thing in another edible oil-and-fat individually, or may use two or more kinds of oxidation-treated things together.
- the above content is the total content of the two or more types.
- an appropriate additive material is appropriately blended.
- an appropriate additive material is appropriately blended.
- Oxidized palm-based fats and oils obtained as described above, and fats and oils compositions containing it are not particularly limited in form, and examples thereof include margarine, shortening, fat spread, powdered fats and oils. May be Further, the oxidation-treated product and the oil / fat composition can be used for various foods, and particularly for the purpose of enhancing sweetness. That is, in cooking, processing, or manufacturing of various foods, cooking oil such as loosening oil, cooking oil, cooking oil such as frying oil and stir-frying oil, kneading oil, injection oil, seasoning oil, etc.
- the present invention By using as an oil or the like, or after cooking, processing, or manufacturing of various foods, by adding, mixing, coating, dissolving, dispersing, emulsifying, etc., and incorporating it into the food, it is derived from the above oxidation-treated product. Ingredients can be added to the food to enhance the sweetness of the food.
- the food to which the present invention can be applied is not particularly limited, but examples thereof include bakery foods such as cakes and breads; Western confectionery such as whipped cream, pancakes, madeleines, chocolates, cookies; yogurt, almond tofu, pudding.
- Frozen desserts such as jelly; ice desserts such as ice cream, ice milk, lacto ice; soups such as corn soup and consomme soup; stews such as beef stew and cream stew; beverages such as coffee drinks and milk drinks; baked pork; Processed meat products such as char siu; beef cutlet, pork cutlet, chicken cutlet, fried chicken, fried Tatsuta, donuts, etc .; fried foods such as scrambled eggs, fried eggs; seafood processed foods such as kamaboko, fish sausage, and the like. , Western confectionery, frozen desserts, frozen desserts, soups, beverages, fried foods It is preferable to apply to.
- the amount to be mixed into food there is no particular limitation on the amount to be mixed into food, the content of the palm-based oil and fat oxidation product, relative to the total mass of the food to which it is added, the content of the palm-based oil and fat oxidation product, It is preferable to add the above-mentioned palm oil and fat oxidation-treated product to foods so that the amount is 1 ⁇ 10 ⁇ 8 % by mass or more and 10% by mass or less, and the amount is 1 ⁇ 10 ⁇ 7 % by mass or more and 10% by mass or less. It is more preferable that the content be 1 ⁇ 10 ⁇ 6 % by mass or more and 10% by mass or less, further preferably 1 ⁇ 10 ⁇ 5 % by mass or more and 10% by mass or less. It is even more preferable.
- the palm oil or fat oxidation-treated product obtained as described above may be used in the form of a sweetness-enhancing composition of a food containing the same.
- the oxidation-treated product is contained, and it may be in a good dispersed state, or in a form that can be stably maintained, and a form that can be used by adding it to a food product,
- the pharmaceutical form There is no particular limitation on the pharmaceutical form.
- it may be prepared into a liquid oil / fat mainly comprising an oil / fat component, margarine, shortening, fat spread, powdered oil / fat, etc.
- the palm-based oil and fat oxidation product and the oil and fat composition containing the same may be used as they are as one form of a composition for enhancing sweetness of foods.
- the content of the oxidation-treated product in the sweetness-enhancing composition of the food may be determined from the viewpoint of a suitable amount desired when applied to the food, or from the viewpoint of ease of handling.
- a suitable amount desired when applied to the food or from the viewpoint of ease of handling.
- it is preferably 1 ⁇ 10 ⁇ 8 mass% or more and 100 mass% or less, more preferably 1 ⁇ 10 ⁇ 7 mass% or more and 100 mass% or less, and 1 ⁇ 10 ⁇ 6 mass% or more. It is more preferably 100% by mass or less, further preferably 1 ⁇ 10 ⁇ 5 % by mass or more and 100% by mass or less.
- the content of the above-mentioned oxidized product is Is preferably prepared in the following ranges.
- Fats and oils for chocolate 1 ⁇ 10 ⁇ 6 % by mass or more and 70% by mass or less
- Powdered fats and oils 3 ⁇ 10 ⁇ 6 % by mass or more and 100% by mass or less
- Margarine 2 ⁇ 10 ⁇ 6 % by mass or more and 95% by mass or less 1 ⁇ 10 ⁇ 6 mass% or more and 10 mass% or less
- the above composition for enhancing sweetness of food may contain one kind of oxidation-treated product as a single product, or may use two or more kinds of oxidation-treated products together.
- the above content is the total content of the two or more types.
- the mode of use of the composition for enhancing sweetness of the above food is the same as the above-described palm oil and fat oxidized product or the oil and fat composition containing the same, and if desired, if used so as to be included in the food. Good.
- the content of the above-mentioned oxidized product is 1 ⁇ 10 ⁇ 8 % by mass or more based on the total mass of the composition for enhancing sweetness of the above food and the food to which it is added.
- the composition for enhancing sweetness of the food is contained in the food so as to be 10% by mass or less, more preferably 1 ⁇ 10 ⁇ 7 % by mass or more and 10% by mass or less,
- the content is more preferably 1 ⁇ 10 ⁇ 6 mass% or more and 10 mass% or less, still more preferably 1 ⁇ 10 ⁇ 5 mass% or more and 10 mass% or less.
- -Red palm oil (unrefined, low-temperature filtered): Total content of ⁇ -carotene and ⁇ -carotene 341 mass ppm, EV REDPALM OIL, manufactured by Rain Forest Herb Co.-Red palm oil (molecular distillation, 2 fractionation): ⁇ -Total content of carotene and ⁇ -carotene 411 mass ppm, Carocino Premium, Carocino Red Palm Oil (molecular distillation, fractionated once): Total content of ⁇ -carotene and ⁇ -carotene 373, 470, 444, 457 mass ppm, carocino pure olein, manufactured by Carocino Co., Ltd./prepared red palm oil (molecular distillation, single fractionation): Red
- the calibration curve was analyzed by HPLC using ⁇ -carotene (model number 035-17981) and ⁇ -carotene (model number 035-05531) reagents (manufactured by Wako Pure Chemical Industries, Ltd.) as a quantitative standard for each predetermined concentration. It was created from the peak area of the sample.
- the main analysis conditions are shown below.
- Table 2 shows the used red palm oil, the total content of ⁇ -carotene and ⁇ -carotene in the red palm oil, the heat treatment conditions, the total residual amount of ⁇ -carotene and ⁇ -carotene after the heat treatment, and the heating.
- the values of the peroxide value (POV) measured before and after the treatment are shown respectively.
- Example 21 The total residual amount of ⁇ -carotene and ⁇ -carotene in Example 21 (heating temperature: 103 ° C., heating time: 32 hr, air blowing amount: 0.1 L / min) was 103 mass ppm, and air blowing was performed. Promoted the decomposition of ⁇ -carotene and ⁇ -carotene. However, as seen in Example 18, all of ⁇ -carotene and ⁇ -carotene in red palm oil could be decomposed by the heat treatment without blowing air.
- the raw material red palm oil that was not heat-treated was added to the corn soup, and the sweetness of the five-step evaluation rank of the sweetness was E-judgment when it was eaten. Also, the contents and the aftertaste were judged to be D, and the result was poor in the effect of enhancing the sweetness of corn soup.
- the oxidization-treated product obtained by subjecting the corn soup to a certain degree of sweetness has sweetness in all of the first taste, the middle content, and the aftertaste when the corn soup is eaten.
- the five-rank evaluation rank is either A judgment, B judgment, or C judgment, and depending on the type of palm oil and fat used and the degree of heat treatment, a better B judgment or a further better A judgment result. was also obtained, and an excellent sweetness enhancing effect was recognized.
- the sensory evaluation was carried out by three people using the evaluation sheet in which the scores of -3, -2, -1, 0, 1, 2, 3 shown on the following criteria were drawn on the line segment of 6 cm at intervals of 1 cm. It was done by a specialized panel. Specifically, the evaluation of the specialized panel is arbitrarily plotted on the line segment, the length from the score 0 is measured in 0.1 cm units, and the length is used as the evaluation value of each specialized panel. did.
- the rapeseed oil-based oil and fat composition containing 1% by mass of the above-mentioned oxidized product can enhance the sweetness of yogurt in a dose-dependent manner.
- the sensory evaluation was carried out by three people using the evaluation sheet in which the scores of -3, -2, -1, 0, 1, 2, 3 shown on the following criteria were drawn on the line segment of 6 cm at intervals of 1 cm. It was done by a specialized panel. Specifically, the evaluation of the specialized panel is arbitrarily plotted on the line segment, the length from the score 0 is measured in 0.1 cm units, and the length is used as the evaluation value of each specialized panel. did.
- the sensory evaluation was carried out by three people using the evaluation sheet in which the scores of -3, -2, -1, 0, 1, 2, 3 shown on the following criteria were drawn on the line segment of 6 cm at intervals of 1 cm. It was done by a specialized panel. Specifically, the evaluation of the specialized panel is arbitrarily plotted on the line segment, the length from the score 0 is measured in 0.1 cm units, and the length is used as the evaluation value of each specialized panel. did.
- Powdered coffee (blendy, manufactured by Ajinomoto AGF Co., Ltd.) 0.6% by mass, granulated sugar 2.6% by mass, powdered fats and oils (plain) 2.9% by mass, hot water 93.9% by mass and a coffee beverage having a compounding ratio.
- powdered fats and oils prepared as described above in Table 7, referred to as “powdered fats and oils (containing 1% by mass of“ oxidized product of Example 26 ”)” and powdered fats and oils (plain) in the formulation shown in Table 7. was further added to the coffee beverage to prepare a coffee beverage, and the obtained coffee beverage was subjected to sensory evaluation.
- the strength of sweetness when eating a coffee beverage is described as the powdered fat and oil prepared above (in Table 7, "powdered fat and oil (containing 1% by mass of" oxidized product of Example 26 ”)"). It was evaluated by relative comparison with the case of not adding.
- the sensory evaluation was carried out by three people using the evaluation sheet in which the scores of -3, -2, -1, 0, 1, 2, 3 shown on the following criteria were drawn on the line segment of 6 cm at intervals of 1 cm. It was done by a specialized panel. Specifically, the evaluation of the specialized panel is arbitrarily plotted on the line segment, the length from the score 0 is measured in 0.1 cm units, and the length is used as the evaluation value of each specialized panel. did.
- Powdered fats and oils prepared in Test Example 5 (indicated as "powdered fats and oils (containing 1% by mass of" oxidized product of Example 26 “in 1 mass%)") in the formulation shown in Table 9 and powdered fats and oils (plain) ) was used to prepare the Madeleine.
- Powdered fats and oils prepared in Test Example 5 (indicated as "powdered fats and oils (containing 1% by mass of" oxidized product of Example 26 "in 1 mass%)) in the formulation shown in Table 9 and powdered fats and oils (plain) )
- Table 9 powdered fats and oils (plain)
- the sensory evaluation was carried out by three people using the evaluation sheet in which the scores of -3, -2, -1, 0, 1, 2, 3 shown on the following criteria were drawn on the line segment of 6 cm at intervals of 1 cm. It was done by a specialized panel. Specifically, the evaluation of the specialized panel is arbitrarily plotted on the line segment, the length from the score 0 is measured in 0.1 cm units, and the length is used as the evaluation value of each specialized panel. did.
- the yogurt was prepared by adding the oxidation-treated product (Example 27) prepared above or rapeseed oil to a yogurt (Meiji Bulgaria yogurt LB81 low sugar, manufactured by Meiji Co., Ltd.) in a formulation shown in Table 10 to obtain a yogurt.
- a sensory evaluation of sweetness of yogurt was performed by the Time Intensity method.
- the evaluator operates the evaluation scale bar connected to the personal computer to continuously evaluate the sweetness felt during the measurement and measure the change in sweetness intensity over time.
- yogurt was put into the mouth 5 seconds after the start of measurement, chewed at a rate of 2 times per second for 15 seconds from the start of measurement, and then swallowed, and measurement was further continued until 25 seconds after the start of measurement. And finished.
- Figure 1 shows the results of sensory evaluation by the Time Intensity method.
- chocolate was put into the mouth 5 seconds after the start of the measurement, and chewed at a pace of 2 times per second from the start of the measurement until 15 seconds, and then swallowed, and further measured until the start of the measurement 60 seconds. And then finished.
- Figure 2 shows the results of sensory evaluation by the Time Intensity method.
- Example 10 (Evaluation with donuts) ⁇ Preparation of fats and oils for cooking>
- the oxidation treatment product of Example 27 was added to frying oil (J Flyup 500, manufactured by J-Oil Mills Co., Ltd.) so that the amount thereof would be 10000 mass ppm to obtain a fat for heating and cooking.
Abstract
Description
パーム系油脂の酸化処理物であって、
前記パーム系油脂は、α-カロテン及びβ-カロテンの合計含有量が50質量ppm以上2000質量ppm以下であり、
前記酸化処理物の過酸化物価が3以上250以下である、該酸化処理物を提供するものである。
チョコレート用油脂:1×10-6質量%以上70質量%以下
粉末油脂:3×10-6質量%以上100質量%以下
マーガリン:2×10-6質量%以上95%質量%以下
加熱調理用油脂:1×10-6質量%以上10質量%以下
〔パーム系油脂〕
・レッドパーム油(精製無し、低温濾過):α-カロテン及びβ-カロテンの合計含有量341質量ppm、EV REDPALM OIL、レインフォレストハーブ社製
・レッドパーム油(分子蒸留、2回分別):α-カロテン及びβ-カロテンの合計含有量411質量ppm、カロチーノ プレミアム、カロチーノ社製
・レッドパーム油(分子蒸留、1回分別):α-カロテン及びβ-カロテンの合計含有量373、470、444、457質量ppm、カロチーノ ピュアオレイン、カロチーノ社製
・調合レッドパーム油(分子蒸留、1回分別):上記レッドパーム油(分子蒸留、1回分別)とパームオレイン(株式会社J-オイルミルズ製、社内調製品)を1:2の割合で調合したもの。α-カロテン及びβ-カロテンの合計含有量114質量ppm
α-カロテン及びβ-カロテンの定量は、高速液体クロマトグラフィーによる分析(HPLC分析)にて行った。具体的には、パーム系油脂、又は酸化処理物を0.5g秤量し、アセトン:テトラヒドロフラン=1:1で10mLにそれぞれメスアップし、HPLC分析に供し、検量線からα-カロテン及びβ-カロテンの含有量を定量した。なお、検量線は定量標品としてα-カロテン(型番035-17981)及びβ-カロテン(型番035-05531)の試薬(和光純薬工業株式会社製)を使用して、所定濃度ごとにHPLC分析に供したときのピーク面積から作成した。以下にはおもな分析条件を示す。
・検出器:フォトダイオドアレイ検出器「2996 PHOTODIODE ARRAY DETECTOR」(Waters社)、300~600nmで検出
・カラム:Shim-pack VP-ODS, 4.6mmID×250mm, 4.6μm(株式会社島津製作所)
・カラム温度:50℃
・注入量:5uL
・流速:1.2mL/min
・移動相A:アセトニトリル
・移動相B:エタノール
・移動相C:アセトン
・グラジエント条件:表1に示す
「基準油脂分析試験法 2.5.2 過酸化物価」(日本油化学会)に則って測定した。
表2に示す各種のパーム系油脂を使用し、その酸化処理物を調製した。具体的には、α-カロテン及びβ-カロテンを所定含有量(質量ppm)で含有するレッドパーム油を準備し、これを撹拌しながら表2に示される各加熱処理条件で加熱処理して、実施例1~25の酸化処理物を得た。なお、実施例18以外は空気を所定量(0.01L/分、0.1L/分、又は0.2L/分)で吹き込みながら加熱処理した。また、加熱処理を行わない原料レッドパーム油の1つを、対照として比較例1とした。
比較例1、実施例1~25の酸化処理物について、官能評価を行った。具体的には、酸化処理物をコーンスープ(クノール カップスープ コーンクリーム、味の素株式会社製、粉末コーンスープ17.6gに対して、お湯150mLを加えてコーンスープを得た)に添加し、食したときの先味、中味、及び後味のそれぞれにおける甘味の強さを、酸化処理物を添加しない場合との相対比較で評価した。官能評価は4名もしくは5名の専門パネルで行い、以下の基準で点数付けをして中央値を求めた。また、得られた中央値の結果について、以下の5段階評価でランク付けした。
3 かなり強い
2 強い
1 やや強い
0 同等
-1 やや弱い
-2 弱い
-3 かなり弱い
A 2≦中央値
B 1<中央値<2
C 0.75≦中央値≦1
D 0<中央値<0.75
E -3≦中央値≦0
(ヨーグルトでの評価)
<実施例26の酸化処理物の調製>
本試験例にて用いた酸化処理物(実施例26)の調製方法を説明する。α-カロテン及びβ-カロテンの合計含有量が300質量ppmのレッドパーム油を撹拌しながら、空気吹き込み無し、140℃にて11時間加熱処理して酸化処理物を得た。このとき酸化処理物のカロテン残存量は0質量ppm、過酸化物価(POV)41.9であった。
菜種油に上記で調製した酸化処理物を1質量%含有させて、α-カロテン及びβ-カロテンの合計含有量が加熱処理前の該α-カロテン及びβ-カロテンの合計含有量に換算した量として3質量ppmの含有量で含有する油脂組成物を調製した。
表4に示す配合で、上記で調製した油脂組成物(表4中、「菜種油(「実施例26の酸化処理物」を1質量%含有)」と表記した。)をヨーグルト(明治ブルガリアヨーグルトLB81低糖、株式会社明治社製)に含有せしめてヨーグルトを調製し、得られたヨーグルトについて官能評価を行った。具体的にはヨーグルトを食したときの甘味の強さを、上記で調製した油脂組成物(表4中、「菜種油(「実施例26の酸化処理物」を1質量%含有)」と表記した。)を添加しない場合との相対比較で評価した。官能評価は、以下の基準で示す-3、-2、-1、0、1、2、3の評点が1cm間隔で6cmの線分上に描かれた評価用紙を使用して、3名の専門パネルで行なった。具体的には、専門パネルの評価を任意にその線分上にプロットしてもらい、評点0からの長さを0.1cm単位で計測して、その長さを、各専門パネルの評価値とした。
3 かなり強い
2 強い
1 やや強い
0 同等
-1 やや弱い
-2 弱い
-3 かなり弱い
(ラクトアイスでの評価)
<ラクトアイスの調製と評価>
表5に示す配合で、試験例2で調製した油脂組成物(表5中、「菜種油(「実施例26の酸化処理物」を1質量%含有)」と表記した。)をラクトアイス(明治エッセルスーパーカップ、株式会社明治社製)に含有せしめてラクトアイスを調製し、得られたラクトアイスについて官能評価を行った。具体的にはラクトアイスを食したときの甘味の強さを、試験例2で調製した油脂組成物(表5中、「菜種油(「実施例26の酸化処理物」を1質量%含有)」と表記した。)を添加しない場合との相対比較で評価した。官能評価は、以下の基準で示す-3、-2、-1、0、1、2、3の評点が1cm間隔で6cmの線分上に描かれた評価用紙を使用して、3名の専門パネルで行なった。具体的には、専門パネルの評価を任意にその線分上にプロットしてもらい、評点0からの長さを0.1cm単位で計測して、その長さを、各専門パネルの評価値とした。
3 かなり強い
2 強い
1 やや強い
0 同等
-1 やや弱い
-2 弱い
-3 かなり弱い
(ホイップクリームでの評価)
<ホイップクリームの調製と評価>
表6に示す配合で、試験例2で調製した油脂組成物(表6中、「菜種油(「実施例26の酸化処理物」を1質量%含有)」と表記した。)を植物性クリーム(ホイップ植物性脂肪、雪印メグミルク株式会社製)に含有せしめて泡立てて、ホイップクリームを調製し、得られたホイップクリームについて、官能評価を行った。具体的にはホイップクリームを食したときの甘味の強さを、試験例2で調製した油脂組成物(表6中、「菜種油(「実施例26の酸化処理物」を1質量%含有)」と表記した。)を添加しない場合との相対比較で評価した。官能評価は、以下の基準で示す-3、-2、-1、0、1、2、3の評点が1cm間隔で6cmの線分上に描かれた評価用紙を使用して、3名の専門パネルで行なった。具体的には、専門パネルの評価を任意にその線分上にプロットしてもらい、評点0からの長さを0.1cm単位で計測して、その長さを、各専門パネルの評価値とした。
3 かなり強い
2 強い
1 やや強い
0 同等
-1 やや弱い
-2 弱い
-3 かなり弱い
(コーヒー飲料での評価)
<粉末油脂の調製>
粉末油脂に実施例26の酸化処理物を1質量%含有させて、α-カロテン及びβ-カロテンの合計含有量が加熱処理前の該α-カロテン及びβ-カロテンの合計含有量に換算した量として3質量ppmの含有量で含有する粉末油脂を調製した。前記粉末油脂は、特開2017-63784の段落0046の方法により、前記酸化処理物を1質量%含有させて調製した。また、同じ方法にて油脂組成物を含有しない粉末油脂(プレーン)を調製した。
粉末コーヒー(ブレンディ、味の素AGF株式会社製)0.6質量%、グラニュー糖2.6質量%、粉末油脂(プレーン)2.9質量%、お湯93.9質量%の配合比としたコーヒー飲料を調製した。さらに表7に示す配合で、上記で調製した粉末油脂(表7中、「粉末油脂(「実施例26の酸化処理物」を1質量%含有)」と表記した。)および粉末油脂(プレーン)を前記コーヒー飲料にさらに含有せしめてコーヒー飲料を調製し、得られたコーヒー飲料について官能評価を行った。具体的にはコーヒー飲料を食したときの甘味の強さを、上記で調製した粉末油脂(表7中、「粉末油脂(「実施例26の酸化処理物」を1質量%含有)」と表記した。)を添加しない場合との相対比較で評価した。官能評価は、以下の基準で示す-3、-2、-1、0、1、2、3の評点が1cm間隔で6cmの線分上に描かれた評価用紙を使用して、3名の専門パネルで行なった。具体的には、専門パネルの評価を任意にその線分上にプロットしてもらい、評点0からの長さを0.1cm単位で計測して、その長さを、各専門パネルの評価値とした。
3 かなり強い
2 強い
1 やや強い
0 同等
-1 やや弱い
-2 弱い
-3 かなり弱い
(マドレーヌでの評価)
<マドレーヌ生地の調製>
表8に示す配合で、マドレーヌ生地を調製した。
表9に示す配合で、試験例5で調製した粉末油脂(表9中、「粉末油脂(「実施例26の酸化処理物」を1質量%含有)」と表記した。)および粉末油脂(プレーン)を使用してマドレーヌを調製した。具体的には、上記で調製した生地を45gずつに分け、粉末油脂および粉末油脂(プレーン)と混ぜ合わせて、型に6~7分目の量になるように生地を入れ、生地が平らになるように型を軽くたたいてならし、温めておいたオーブンに入れて170℃で15分間焼成してマドレーヌを得た。
3 かなり強い
2 強い
1 やや強い
0 同等
-1 やや弱い
-2 弱い
-3 かなり弱い
(Time Intensity法によるヨーグルトの甘味の官能評価)
<実施例27の酸化処理物の調製>
α-カロテン及びβ-カロテンの合計含有量が373質量ppmのレッドパーム油(分子蒸留、1回分別)を撹拌しながら、空気吹込み量0.2L/min、103℃にて40時間加熱処理して酸化処理物を得た。このとき酸化処理物のカロテン残存量は2質量ppm、過酸化物価(POV)56であった。
表10に示す配合で、上記で調製した酸化処理物(実施例27)又は比較として菜種油をヨーグルト(明治ブルガリアヨーグルトLB81低糖、株式会社明治社製)に含有せしめてヨーグルトを調製し、得られたヨーグルトについて、Time Intensity法によるヨーグルトの甘味の官能評価を行った。
(Time Intensity法によるチョコレートの甘味の官能評価)
<チョコレートの調製と評価>
表11に示す配合でチョコレートを調製し、官能評価を行った。具体的には、市販のチョコレート(明治ブラックチョコレート、株式会社明治社製)を湯煎で溶かし、試験例7で調製した酸化処理物(実施例27)又は比較として菜種油を0.2質量%の含有量となるよう添加して、型に入れ、冷蔵庫で固めてチョコレートを調製した。得られたチョコレートについて、試験例7と同様にして、Time Intensity法によるチョコレートの甘味の官能評価を行った。なお、本試験例では、測定開始から5秒後にチョコレートを口の中へ入れ、測定開始から15秒まで1秒当たり2回のペースで咀嚼し、その後嚥下して、測定開始60秒まで更に測定を続けて、終了した。
(甘味料としてステビアを配合したヨーグルトでの評価)
<ヨーグルトの調製と評価>
表12に示す配合で、ヨーグルト(明治ブルガリアヨーグルトLB81低糖、株式会社明治社製)に甘味料としてステビア(ステビアRA7J、池田糖化工業株式会社製)を配合したうえ、試験例7で調製した酸化処理物(実施例27)を0.001質量%又は0.01質量%の含有量となるよう添加して、ヨーグルトを調製し、得られたヨーグルトについて官能評価を行った。具体的にはヨーグルトを食したときの甘味の強さを(先味、中味、後味として)、試験例1において比較のため使用した比較例1のレッドパーム油(非加熱処理)を添加した場合との相対比較で評価した。官能評価は、以下の基準で示す-3、-2、-1、0、1、2、3の評点が1cm間隔で6cmの線分上に描かれた評価用紙を使用して、3名の専門パネルで行なった。具体的には、専門パネルの評価を任意にその線分上にプロットしてもらい、評点0からの長さを0.1cm単位で計測して、その長さを、各専門パネルの評価値とした。
3 かなり強い
2 強い
1 やや強い
0 同等
-1 やや弱い
-2 弱い
-3 かなり弱い
(ドーナッツでの評価)
<加熱調理用油脂の調製>
フライ油(J フライアップ500、株式会社J-オイルミルズ製)に実施例27の酸化処理物を10000質量ppmとなるように添加し、加熱調理用油脂を得た。
上記で調製した加熱料理用油脂を180℃に加熱し、ドーナツ生地(ドーナツミックス、株式会社プティパ社製)を50秒揚げ、ひっくり返して、更に80秒揚げ、ドーナッツ1を得た。比較対照として、実施例27の酸化処理物を添加しないフライ油を用いたこと以外は同じ方法で、ドーナッツ2を作製した。ドーナッツを食して比較したところ、ドーナッツ1はドーナッツ2よりも甘味が強かった。
Claims (11)
- パーム系油脂の酸化処理物であって、
前記パーム系油脂は、α-カロテン及びβ-カロテンの合計含有量が50質量ppm以上2000質量ppm以下であり、
前記酸化処理物の過酸化物価が3以上250以下である、該酸化処理物。 - 請求項1に記載の酸化処理物を含む、油脂組成物。
- 加熱調理用である、請求項2に記載の油脂組成物。
- α-カロテン及びβ-カロテンの合計含有量が50質量ppm以上2000質量ppm以下であるパーム系油脂を過酸化物価が3以上250以下となるように酸化処理する工程を含む、酸化処理物の製造方法。
- 前記酸化処理する工程は、加熱温度が50℃以上220℃以下、加熱時間が0.1時間以上240時間以下で行う、請求項4に記載の製造方法。
- 前記酸化処理する工程は、前記パーム系油脂に酸素を供給して行う、請求項4又は5に記載の製造方法。
- 請求項1に記載の酸化処理物又は請求項2に記載の油脂組成物を食品に含有せしめる、食品の甘味増強方法。
- 前記食品に対し前記酸化処理物を1×10-8質量%以上10質量%以下含有せしめる、請求項7に記載の方法。
- パーム系油脂の酸化処理物を含む、食品の甘味増強用組成物。
- 前記酸化処理物を1×10-8質量%以上100質量%以下含有する、請求項9に記載の組成物。
- 請求項1に記載の酸化処理物を含む、食品。
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US17/287,192 US20210352928A1 (en) | 2018-10-31 | 2019-10-24 | Oxidized product of palm-based oil and fat, method for producing oxidized product, method for enhancing food sweetness, and composition for enhancing food sweetness |
JP2020553830A JP7454501B2 (ja) | 2018-10-31 | 2019-10-24 | パーム系油脂の酸化処理物、酸化処理物の製造方法、食品の甘味増強方法、及び食品の甘味増強用組成物 |
SG11202104013WA SG11202104013WA (en) | 2018-10-31 | 2019-10-24 | Oxidized product of palm-based oil and fat, method for producing oxidized product, method for enhancing food sweetness, and composition for enhancing food sweetness |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021079693A1 (ja) * | 2019-10-24 | 2021-04-29 | 株式会社J-オイルミルズ | カロテノイド分解物を有効成分とする高甘味度甘味料の呈味改善剤 |
WO2021153309A1 (ja) * | 2020-01-31 | 2021-08-05 | 株式会社J-オイルミルズ | カロテノイド分解物を有効成分とする苦味抑制剤 |
WO2021153311A1 (ja) * | 2020-01-31 | 2021-08-05 | 株式会社J-オイルミルズ | カロテノイド分解物を有効成分とする酸味抑制剤 |
WO2021153310A1 (ja) * | 2020-01-31 | 2021-08-05 | 株式会社J-オイルミルズ | カロテノイド分解物を有効成分とする塩味増強剤 |
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JPS5271509A (en) * | 1975-12-11 | 1977-06-15 | Asahi Denka Kogyo Kk | Purification of palm oil |
JP2002511108A (ja) * | 1996-10-31 | 2002-04-09 | グローバル パーム プロダクツ エスディーエヌ ビーエイチディー | 天然カロチンおよびビタミンeに富んだ食用油の精製 |
JP2012514470A (ja) * | 2009-01-08 | 2012-06-28 | サイム ダービー リサーチ スンディリアン ブルハド | 食用油の精製 |
WO2014077019A1 (ja) * | 2012-11-14 | 2014-05-22 | 株式会社J-オイルミルズ | 甘味及び/又は乳風味増強剤 |
WO2018037926A1 (ja) * | 2016-08-22 | 2018-03-01 | 株式会社J-オイルミルズ | 甘味及び/または塩味の増強剤 |
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2019
- 2019-10-24 US US17/287,192 patent/US20210352928A1/en active Pending
- 2019-10-24 WO PCT/JP2019/041660 patent/WO2020090609A1/ja active Application Filing
- 2019-10-24 JP JP2020553830A patent/JP7454501B2/ja active Active
- 2019-10-24 SG SG11202104013WA patent/SG11202104013WA/en unknown
- 2019-10-24 CA CA3116992A patent/CA3116992A1/en not_active Abandoned
- 2019-10-28 TW TW108138845A patent/TW202027609A/zh unknown
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JPS5271509A (en) * | 1975-12-11 | 1977-06-15 | Asahi Denka Kogyo Kk | Purification of palm oil |
JP2002511108A (ja) * | 1996-10-31 | 2002-04-09 | グローバル パーム プロダクツ エスディーエヌ ビーエイチディー | 天然カロチンおよびビタミンeに富んだ食用油の精製 |
JP2012514470A (ja) * | 2009-01-08 | 2012-06-28 | サイム ダービー リサーチ スンディリアン ブルハド | 食用油の精製 |
WO2014077019A1 (ja) * | 2012-11-14 | 2014-05-22 | 株式会社J-オイルミルズ | 甘味及び/又は乳風味増強剤 |
WO2018037926A1 (ja) * | 2016-08-22 | 2018-03-01 | 株式会社J-オイルミルズ | 甘味及び/または塩味の増強剤 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021079693A1 (ja) * | 2019-10-24 | 2021-04-29 | 株式会社J-オイルミルズ | カロテノイド分解物を有効成分とする高甘味度甘味料の呈味改善剤 |
WO2021153309A1 (ja) * | 2020-01-31 | 2021-08-05 | 株式会社J-オイルミルズ | カロテノイド分解物を有効成分とする苦味抑制剤 |
WO2021153311A1 (ja) * | 2020-01-31 | 2021-08-05 | 株式会社J-オイルミルズ | カロテノイド分解物を有効成分とする酸味抑制剤 |
WO2021153310A1 (ja) * | 2020-01-31 | 2021-08-05 | 株式会社J-オイルミルズ | カロテノイド分解物を有効成分とする塩味増強剤 |
Also Published As
Publication number | Publication date |
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JPWO2020090609A1 (ja) | 2021-09-24 |
US20210352928A1 (en) | 2021-11-18 |
CA3116992A1 (en) | 2020-05-07 |
JP7454501B2 (ja) | 2024-03-22 |
TW202027609A (zh) | 2020-08-01 |
SG11202104013WA (en) | 2021-05-28 |
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