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WO2002016534A1 - Composition de graisses - Google Patents

Composition de graisses Download PDF

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Publication number
WO2002016534A1
WO2002016534A1 PCT/JP2000/005606 JP0005606W WO0216534A1 WO 2002016534 A1 WO2002016534 A1 WO 2002016534A1 JP 0005606 W JP0005606 W JP 0005606W WO 0216534 A1 WO0216534 A1 WO 0216534A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
fat
fatty acid
mass
composition
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2000/005606
Other languages
English (en)
Japanese (ja)
Inventor
Hiroyuki Takeuchi
Megumi Itakura
Fumie Kubota
Nobuo Taguchi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nisshin Oillio Group Ltd
Original Assignee
Nisshin Oil Mills Ltd
Nisshin Oillio 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
Priority to JP31624399A priority Critical patent/JP4733246B2/ja
Application filed by Nisshin Oil Mills Ltd, Nisshin Oillio Ltd filed Critical Nisshin Oil Mills Ltd
Priority to CNB008198403A priority patent/CN1293176C/zh
Priority to KR1020037002571A priority patent/KR100661780B1/ko
Priority to PCT/JP2000/005606 priority patent/WO2002016534A1/fr
Priority to HK04102416.8A priority patent/HK1059448B/xx
Publication of WO2002016534A1 publication Critical patent/WO2002016534A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • 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
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange

Definitions

  • the present invention relates to an edible oil / fat composition. More specifically, the present invention relates to an oil / fat composition that has a low body fat accumulation and is excellent in cooking suitability and flavor as a power cooking oil. Background art
  • Obesity is a condition in which body fat is accumulated excessively, and it is well known that obesity is likely to accompany many diseases, including metabolic disorders such as diabetes and hyperlipidemia, and cardiovascular diseases such as hypertension and ischemic heart disease. I have. According to the results of the Ministry of Health and Welfare's National Nutrition Survey, obesity is a familiar problem not only in Europe and the United States but also in Japan, as one in seven adults is obese. Dietary fat is one of the nutrients most associated with body fat accumulation, and excessive fat intake can lead to obesity. However, fat has a unique taste, and extremely low-fat diets tend to be less satisfactory. When cooking fried or stir-fried food, edible oil is an essential heat medium.
  • sucrose fatty acid esters can be used as low-calorie oils because they are excreted in feces without being absorbed in the digestive tract (US Pat. No. 3,600,186).
  • sucrose fatty acid esters In the United States, salted snack confectionery is permitted to be used, and potato chips using sucrose fatty acid esters are already on the market.However, products using sucrose fatty acid esters include "abdominal cramps” And may cause loose stool "and” inhibit the absorption of fat-soluble vitamins ". The energy density of proteins and carbohydrates is less than half that of fat.
  • low-calorie fat substitutes can be provided by processing proteins and carbohydrates to give them fat-like physical properties and flavors (Nutrition Review, Vol. 4, No. 4, 23-33, 1 9 9 6 Year) .
  • these fat substitutes it is possible to make low-calorie ice cream, bakery products and cakes.
  • it has poor resistance to heat and cannot be used as a heating medium for frying or stir-fry.
  • Japanese Patent Publication No. 4-501812 discloses that a triglyceride composed of a long-chain fatty acid and a short-chain fatty acid can provide a low-calorie oil and fat.
  • triglycerides composed of short-chain fatty acids have a peculiar odor, available cooked products are limited and are not suitable as versatile edible oils.
  • medium-chain fatty acids are less susceptible to energy conversion and thus have less body fat accumulation (J. Lid Res. 37, 708-726 (1996)).
  • triglycerides composed of medium-chain fatty acids are naturally safe, they are reported to cause symptoms such as diarrhea, nausea, abdominal pain, heartburn, and anorexia when taken in large quantities at once. Have been.
  • JP-A-4-300826, JP-A-8-60180 and JP-A-10-176181 disclose an oil / fat composition containing diglyceride as an effective component and having a small body fat accumulation.
  • the safety of fat compositions rich in diglycerides has not been fully proven.
  • it is difficult to produce high-concentration diglycerides at low cost and there is a disadvantage that it is difficult to use for general purposes from an economic viewpoint.
  • Japanese Patent Application Laid-Open No. 8-269478 discloses a body fat containing at least 31% by mass of a triglyceride containing two medium-chain fatty acid residues in a molecule in an oil / fat composition comprising diglyceride and triglyceride.
  • Fat compositions with low accumulation are disclosed. Since this invention also uses diglyceride as an active ingredient, it has the same problems as those described in JP-A-4-300826, JP-A-8-60180, and JP-A-10-176181. In addition, it contains a large amount of medium-chain fatty acids, has a low smoke point, and has significant drawbacks, making it unsuitable for frying. Disclosure of the invention
  • An object of the present invention is to provide an oil / fat composition which has less body fat accumulation, has cooking suitability equivalent to that of a normal edible oil, has a good flavor, and is highly safe.
  • the present inventors have conducted intensive studies in order to solve the above-described problems, and as a result, have determined that the ratio of medium-chain fatty acid residues in the total fatty acid residues and the medium-chain fatty acid residues in the total triglycerides are molecular.
  • the present inventors have found that the proportion of triglycerides having two of them is closely related to the degree of body fat accumulation, and completed the present invention.
  • the present invention relates to an oil / fat composition mainly composed of triglycerides, wherein the proportion of medium-chain fatty acids in the total fatty acids constituting the oil / fat composition is 5 to 23% by mass, and thus accounts for the total triglycerides.
  • the present invention relates to an oil / fat composition with a low accumulation of body fat, characterized in that the proportion of triglycerides having two chain fatty acid residues in the molecule is 1 to 20% by mass.
  • the medium-chain fatty acid is preferably a saturated fatty acid having 6 to 12 carbon atoms.
  • the proportion of triglycerides having three medium-chain fatty acid residues in the molecule to all triglycerides constituting the oil / fat composition is 3% by weight or less. Further, it is preferable that the ratio of the long-chain saturated fatty acid to the full-length fatty acid constituting the fat and oil thread is 20% by mass or less.
  • the oil or fat composition of the present invention contains an emulsifier, particularly a specific combination of emulsifiers, the suitability for frying, particularly the suppression of foaming, can be further improved.
  • the present invention relates to a cooking fat or oil composition containing a powerful fat or oil composition, having low body fat accumulation, and having the same reparing suitability and storage stability as ordinary cooking oil.
  • the oil / fat composition of the present invention mainly comprises triglycerides. “Mainly” means that the oil composition contains 85% by mass or more of triglyceride, and preferably 95% by mass. / 0 or more is included.
  • the medium-chain fatty acid refers to a fatty acid having 6 to 12 carbon atoms, particularly a saturated fatty acid.
  • examples include cabronic acid, caprylic acid, capric acid, lauric acid, and saturated fatty acids having 8 to 10 carbon atoms, especially caprylic acid and capric acid.
  • a long-chain fatty acid refers to a saturated or unsaturated fatty acid having 14 or more carbon atoms, preferably 14 to 22 carbon atoms.
  • Long chain fatty acids have 14 or more carbon atoms And preferably those of 14 to 22; for example, long-chain saturated fatty acids such as myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, and cerotic acid, myristoleic acid, pentadecenoic acid, and palmitoleic acid Hexadenic trienoic acid, heptadecenoic acid, oleic acid, linoleic acid, ⁇ -linolenic acid, ⁇ -linolenic acid, octadecatetraenoic acid, icosenoic acid, icosageneic acid, icosatrienoic acid, icosatetraenoic acid, arachidonic acid And long-chain unsaturated fatty acids such as icosapentaenoic acid, docosenoic acid, docosagenic acid, docosapentaenoic acid, and
  • the fatty acid residue is a group obtained by removing the carboxyl group from the fatty acid.
  • the ratio of the medium-chain fatty acid to the total fatty acids constituting the oil / fat composition is 5 to 23% by mass
  • the proportion of triglycerides having two medium-chain fatty acid residues in the molecule in the total triglycerides needs to be 1 to 20% by mass. Outside this range, the feature of low body fat accumulation does not occur.
  • the proportion of the medium-chain fatty acids is preferably 6 to 23% by mass, and the proportion of the triglycerides is preferably 3 to 20% by mass.
  • the proportion of triglycerides having three medium-chain fatty acid residues in the molecule in the total triglycerides constituting the oil / fat composition is preferably 3% by mass or less, more preferably 2% by mass or less. And more preferably 1% by mass or less. If this proportion exceeds 3% by mass, smoke and foaming increase during cooking, making it unsuitable for frying fats. When the proportion is 1% by mass or less, remarkable improvement in smoking and foaming can be seen.
  • the proportion of the long-chain saturated fatty acid in the full-length fatty acid constituting the fat or oil composition is preferably 20% by mass or less, more preferably 15% by mass or less, and still more preferably 7% by mass or less. Is even more preferred. If this proportion exceeds 20% by mass, the stability at low temperatures is reduced, and the fat and oil composition becomes crystallized in the fat and oil composition.
  • the fat / oil composition of the present invention having a low body fat accumulation is prepared by appropriately mixing a fat / oil as a raw material with a medium-chain fatty acid, and then performing a transesterification reaction using sodium methylate as a catalyst or in the presence of a lipolytic enzyme. At this time, all fatty acids constituting the fat composition are occupied.
  • the transesterification reaction so that the ratio of the medium-chain fatty acid and the ratio of the triglyceride having two medium-chain fatty acid residues in the molecule to the total triglyceride fall within the above-mentioned specific range. be able to.
  • the proportion of triglycerides having three medium-chain fatty acid residues in the molecule to the total triglycerides constituting the oil / fat composition, and Z or the total length constituting the oil / fat composition By adjusting the proportion of long-chain saturated fatty acids in the chain fatty acids so as to fall within the above-mentioned specific range, fats and oils that reduce body fat accumulation, reduce smoke and frothing during frying, and are excellent in Z or low-temperature stability A composition can be obtained.
  • Raw fats and oils include ordinary edible fats and oils, such as soybean oil, rapeseed oil, high oleic rapeseed oil, corn oil, sesame oil, sesame salad oil, perilla oil, linseed oil, peanut oil, safflower oil
  • medium-chain fatty acids have already been described, medium-chain fatty acid triglycerides can be used instead of or together with medium-chain fatty acids.
  • the medium-chain fatty acid triglyceride triglyceride obtained by subjecting the above-mentioned medium-chain fatty acid and glycerin to an estracray reaction by an ordinary method can be used, and is generally referred to as MCT (Medium Chryin Triglycerides). Coconut oil-decomposed fatty acid, etc.
  • the proportion of medium-chain fatty acids in the total fatty acids constituting the oil and fat composition, and the proportion of triglycerides having two medium-chain fatty acid residues in the molecule in the total triglycerides, and when necessary, constitute the fat and oil composition Percentage of triglycerides having three medium-chain fatty acid residues in the molecule to all triglycerides, and if necessary, oils and fats
  • the proportion of long-chain saturated fatty acids in the full-length fatty acids constituting the product is adjusted by taking into account the composition of the raw fats and oils, adjusting the ratio of the raw fats and oils to the medium-chain fatty acids, and the triglycerides of the reaction products during the transesterification reaction. It can be adjusted by measuring the composition.
  • To this is added 0.22 to 0.5% by mass of sodium methylate, and the mixture is added at normal pressure under a nitrogen stream or under a reduced pressure of 1 OmmHg for 10 to 60 minutes, 80 to: 120 °.
  • the transesterification reaction is performed by stirring at C.
  • reaction product is decolorized and deodorized by a conventional method.
  • the temperature is adjusted within the range of 40 to 100 ° C., which is the reaction temperature at which the activity of the degrading enzyme is sufficiently exhibited.
  • the lipolytic enzyme is added to the raw material mixture at a ratio of 0.05 to 10% by mass, and transesterification is performed for a period of 2 to 48 hours. This reaction is preferably carried out in a nitrogen stream at normal pressure.
  • Completion of the reaction is confirmed by measuring the triglyceride composition of the reaction product by gas chromatography.
  • the reaction is stopped by removing the enzyme by filtration.
  • the reaction product is washed with water, dried, and then decolorized and deodorized by a conventional method.
  • free fatty acids are removed with a thin-film evaporator after the reaction is stopped.
  • Insufficient transesterification using lipolytic enzymes increases the proportion of triglycerides having three medium-chain fatty acid residues in the molecule.
  • An oil / fat composition having a high proportion of triglycerides having three medium-chain fatty acid residues in the molecule has a feature that the accumulation of body fat is small, but unfavorably causes a large amount of smoke and foaming during continuous frying.
  • lipolytic enzymes include lipases derived from Alcaligenes, Candida, Rhizopus, Mucor or Pseudomonas, and liver lipase.
  • a lipase derived from the genus Candida or Rhizopus is particularly preferred.
  • the oil / fat composition of the present invention also includes plants breeded to produce the oil / fat composition of the present invention using genetic engineering techniques, for example, soybeans, rapeseed, corn, palm, palm, olive, and the like. It can also be obtained by extraction from linseed, sunflower, sunflower, safflower, tsubaki, cottonseed, and khair.
  • the suitability for frying, particularly the suppression of foaming can be further improved.
  • the emulsifier include sucrose fatty acid ester, polyglycerin fatty acid ester, succinic acid monoglyceride, monoglyceride, diglyceride, sorbitol fatty acid ester, sorbitan fatty acid ester and the like.
  • at least one of the above emulsifiers can be selected, and the amount of the emulsifier added to the fat composition is preferably from 0.1 to 6% by mass, more preferably from 0.3 to 5% by mass.
  • Sucrose fatty acid esters include esters of sucrose with saturated or unsaturated fatty acids having 6 to 22 carbon atoms, but the average degree of substitution of all hydroxyl groups is 37.5 to 87.5%. It is preferable that the proportion of polyesters equal to or higher than triesters in the sucrose fatty acid ester is 85% by mass or more.
  • the polyglycerin fatty acid ester includes esters of polyglycerin having triglycerin or more, preferably up to decaglycerin, and a saturated or unsaturated fatty acid having 6 to 22 carbon atoms, but having an average degree of substitution of all hydroxyl groups of 20 to 80. %.
  • Monodaliceride and diglyceride include monoesters and diesters of glycerin or diglycerin and a saturated or unsaturated fatty acid having 6 to 22 carbon atoms, respectively. Monoglycerides are preferred.
  • succinic acid monoglyceride succinic acid monoglyceride obtained by esterifying succinic acid and monoglyceride or diglyceride in a ratio of 3: 1 to 0.1: 1 is preferable.
  • the sorbitol fatty acid ester and sorbitan fatty acid ester are preferably sorbitol or a mono-triester of sorbitan and a saturated or unsaturated fatty acid having 6 to 22 carbon atoms.
  • saturated or unsaturated fatty acids having 6 to 22 carbon atoms above Examples include those mentioned as examples of medium-chain fatty acids and long-chain fatty acids.
  • an emulsifier, relative to oil and fat composition of the present invention at least one selected from sucrose fatty acid esters and polyglycerol fatty acid ester 0.1 to 3 weight 0 /.
  • Succinic acid monoglyceride 0.0 1-2 mass 0/0
  • Oyopimo Noguriseri de Jiguriseri de, at least one selected from sorbitol fatty Esuteru and sorbitan fatty acid ester 0.1 to 3 wt%
  • the oil / fat composition of the present invention obtained as described above can be used as a cooking oil / fat composition as it is or by mixing additives usually used in the cooking oil / fat composition.
  • the additive examples include polyglycerin fatty acid ester, sucrose fatty acid ester, and sorbitan fatty acid for the purpose of improving storage stability, improving oxidative stability, improving thermal stability, and suppressing crystallization at low temperatures.
  • Ester Vitamin E, Ascorbic acid fatty acid ester, Lignan, Koenzim Q, Phospholipid, Oryzanol, Diglyceride, etc.Vitamin E expected to prevent adult diseases, prevent lifestyle-related diseases, suppress in vivo oxidation, and prevent obesity , Ascorbic acid fatty acid ester, lignan, coenzyme Q, phospholipid, oryzanol and the like.
  • the cooking oil / fat composition of the present invention has a flavor equal to or higher than that of commonly available edible oils such as rapeseed oil, corn oil, safflower oil, and soybean oil, and is used for cooking stir-fry, fried food, marinade, etc. It can be used for foods containing oils and fats, such as dressings, mayonnaise, margarine, confectioneries, cakes, and drinks.
  • the flavor characteristics vary depending on the type of food, but it is possible to make a refreshing dish that takes advantage of the taste of the ingredients.
  • the degree of oil splash during frying is equal to or less than that of ordinary cooking oil.
  • Example 1 An effect of lowering the blood lipid concentration can be expected by continuously ingesting an appropriate amount of the cooking fat or oil composition of the present invention.
  • Example 1 the present invention will be described more specifically with reference to Examples, but the present invention is not limited thereto.
  • sucrose fatty acid ester manufactured by Mitsubishi Chemical Foods Co., Ltd., trade name: Lyotosugar Ester O_170
  • sucrose fatty acid ester was 2.5 mass with respect to the oil / fat composition 1.
  • succinic acid mono glyceride (Riken Vitamin Co., Ltd., trade name Poem B- 10) 0. 1 mass 0/0
  • Seo Rubitan fatty acid ester (manufactured by Riken Vitamin Co., Ltd., trade name POEM O-80) 1
  • a fat composition 2 was obtained.
  • the triglyceride composition and fatty acid composition of the fats and oils compositions 1 and 2 were measured by gas chromatography using a column GS-1 and according to the “Standard Fatty Acid Analysis Test Method (1996)” (the following examples). And the same for the comparative example). Table 1 shows the results.
  • Example 2
  • Soybean salad oil (manufactured by Nisshin Oil Co., Ltd.) Lipase QL (Meito Sangyo Co., Ltd.) 0.1 part by mass was added, and a transesterification reaction was carried out at 60 ° C. for 15 hours with stirring.
  • the enzyme was separated from the reaction product by filtration, and the filtrate was washed with water, dried, decolorized and deodorized to obtain an oil / fat composition 3.
  • Table 1 shows the triglyceride composition and fatty acid composition of Oil Composition 3.
  • Rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) 90 parts by mass and 10 parts by mass of MCT, in which the constituent fatty acids are 3% by weight of prillic acid / cabric acid, are mixed, and then stirred at 120 ° C under reduced pressure. Degassing was performed for dehydration. To this, 0.1 part by mass of sodium methylate was added as a catalyst, and a random transesterification reaction was carried out at 120 ° C for 30 minutes. The reaction product was washed with water, dried and then decolorized and deodorized by a conventional method to obtain an oil / fat composition 7. Table 2 shows the triglyceride composition and fatty acid composition of Fat and Oil Composition 7.
  • Example 2 To the same mixture as in Example 2, 0.1 part by mass of Lipase QL (manufactured by Meito Sangyo Co., Ltd.) was added, and transesterification was carried out at 60 ° C. for 3 hours with stirring. The enzyme was separated from the reaction product by filtration, and the filtrate was washed with water, dried, decolorized and deodorized to obtain an oil / fat composition 8.
  • Table 2 shows the triglyceride composition and fatty acid composition of Fat and Oil Composition 8. Comparative Example 1
  • Rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) After mixing 75 parts by mass and 25 parts by mass of MCT in which the constituent fatty acids are 3/1 by weight of prillic acid / potassic acid, and then reduced to 120 ° C under reduced pressure And degassed and dehydrated. To this was added 0.1 part by mass of sodium methylate as a catalyst, and a random transesterification reaction was carried out at 120 ° C for 30 minutes. The reaction product was washed with water, dried and then decolorized and deodorized by a conventional method to obtain an oil / fat composition 9. Table 3 shows the triglyceride composition and fatty acid composition of Fat Composition 9. Comparative Example 2
  • Table 3 shows the triglyceride composition and fatty acid composition of the fat composition 10.
  • C 18: 3 8. 9 8. 7 7. 1 0. 0 0. 0 others 0. 0 0. 0 0. 2 0. 2 0. 0 Note) M; middle thigh, L; SSS tr. Tracer For example, C8: 0 is ⁇ S8, which is not ⁇ * ⁇ body-weave union! Indicates that it is ⁇ 0. (Same for Tables 2, 3 and 4)
  • Oil composition 9 Oil composition 10 Triglyceride composition
  • Table 7 shows the results of the cooking test. According to the results of the cooking test, the proportion of medium-chain fatty acids in the total fatty acids constituting the oil and fat composition and the proportion of triglycerides having two medium-chain fatty acid residues in the molecule in all triglycerides of the present invention were The inventive oil and fat compositions 1, 2, 4, 6, and 8 falling within the range were found to have cooking aptitude equivalent to that of ordinary edible oil. Furthermore, fats and oils compositions 1, 2, 4, and 6, in which the proportion of triglycerides having three medium-chain fatty acid residues in the molecule in all triglycerides constituting the fats and oils composition is 3% by mass or less, It was found that the stability during fried food cooking was high.
  • the oil / fat composition 2 containing the milky lantern had an excellent foaming suppressing effect.
  • the same seven kinds of samples were allowed to stand at 5 ° C for 48 hours, and the appearance was observed. Table 7 shows the results. As a result, precipitation of crystals was observed in the fat / oil composition 4, but the other samples had a transparent appearance.
  • Frying stability Put 600 g of sample oil in a household electric fryer, fry the shrimp tempura for 30 minutes at 180 ° C, fry the croquettes for 30 minutes, and finally fry the birds. Was fried for 30 minutes. The stability of fried food was evaluated based on the degree of generation of force bubbles. Frying was stopped when the generation of force bubbles reached 100% of the surface area of the fryer.
  • the oil / fat composition of the present invention has little body fat accumulation, has cooking suitability equivalent to that of ordinary edible oil, and has good flavor and high safety.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Edible Oils And Fats (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'invention porte sur des compositions principalement à base de triglycérides dans lesquelles le rapport massique entre les acides gras de la chaîne centrale et la totalité des acides gras est compris entre 5 et 23 %, et le rapport massique entre les triglycérides présentant deux résidus d'acides gras de chaîne centrale par molécule, et la totalité des triglycérides est compris entre 1 et 20 %. Ces compositions de graisses ne s'accumulant que peu sous forme de graisses corporelles ont les même avantages culinaires que les huiles comestibles usuelles, ont un goût agréable, et ne présentent aucun danger.
PCT/JP2000/005606 1998-11-13 2000-08-22 Composition de graisses Ceased WO2002016534A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP31624399A JP4733246B2 (ja) 1998-11-13 1999-11-08 油脂組成物
CNB008198403A CN1293176C (zh) 2000-08-22 2000-08-22 油脂组合物
KR1020037002571A KR100661780B1 (ko) 2000-08-22 2000-08-22 유지 조성물
PCT/JP2000/005606 WO2002016534A1 (fr) 1998-11-13 2000-08-22 Composition de graisses
HK04102416.8A HK1059448B (en) 2000-08-22 Fat compositions

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP32366598 1998-11-13
JP4930099 1999-02-26
JP31624399A JP4733246B2 (ja) 1998-11-13 1999-11-08 油脂組成物
PCT/JP2000/005606 WO2002016534A1 (fr) 1998-11-13 2000-08-22 Composition de graisses

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WO2002016534A1 true WO2002016534A1 (fr) 2002-02-28

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WO (1) WO2002016534A1 (fr)

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US8158184B2 (en) 2004-03-08 2012-04-17 Bunge Oils, Inc. Structured lipid containing compositions and methods with health and nutrition promoting characteristics

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JP4463586B2 (ja) * 2003-09-10 2010-05-19 日清オイリオグループ株式会社 大豆油の精製方法
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JP2006117557A (ja) * 2004-10-20 2006-05-11 Nisshin Oillio Group Ltd 血中アディポネクチン濃度増加剤
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JP6150582B2 (ja) * 2013-03-27 2017-06-21 花王株式会社 精製油脂の製造方法
AU2014322531B2 (en) * 2013-09-19 2017-11-02 The Nisshin Oillio Group, Ltd. Interesterified oils and fats, and oil based food including the interesterified oils and fats
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JPWO2024090546A1 (fr) * 2022-10-27 2024-05-02
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