WO2002016534A1 - Fat compositions - Google Patents
Fat compositions Download PDFInfo
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- 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
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- WIPO (PCT)
- Prior art keywords
- oil
- fat
- fatty acid
- mass
- composition
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Classifications
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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 OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
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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
- C11C3/04—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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Abstract
Description
明 細 書 油脂組成物 Description Oil and fat composition
技術分野 Technical field
本発明は食用に供される油脂組成物に関する。 さらに詳しくは体脂肪蓄積が少 なく、 力つ食用油としての調理適性と風味に優れた油脂組成物に関する。 背景技術 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
肥満は体脂肪が過剰に蓄積した状態であり、 糖尿病、 高脂血症などの代謝異常 や高血圧、 虚血性心疾患など循環器疾患を始めとして、 多くの疾病を伴いやすい ことはよく知られている。 厚生省が行っている国民栄養調査の結果によれば、 成 人の 7人に 1人は肥満者であること力 ら、 肥満は欧米だけでなく我が国において も身近な問題である。 食事中に含まれる脂肪は、 体脂肪の蓄積と最も関係の深い 栄養素の 1つであり、 過剰な脂肪の摂取は肥満をもたらす可能性がある。 しかし 、 脂肪には独特の旨味があり、 極端に脂肪を減らした食事は満足度の低いものと なりやすい。 また、 揚げ物や炒め物調理を行う際、 食用油は熱媒体として必要不 可欠である。 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.
このような状況を打開するため、 いわゆる脂肪代替品が開発されている。 しか し、 これらの中には、 安全性、 物性、 調理適性、 風味の点から見て十分満足でき るものはない状況である。 例えば、 ショ糖脂肪酸エステルは消化管で吸収されず 糞便中に排泄されることから、 低カロリー油として使用できる旨が開示されてい る (米国特許第 3 6 0 0 1 8 6号明細書) 。 米国内においては、 塩味スナック菓 子を対象に使用が許可され、 ショ糖脂肪酸エステルを使用したポテトチップがす でに市販されているが、 ショ糖脂肪酸エステルを使用した商品には、 「腹部痙攣 や軟便を引き起こす可能性があること」 、 「脂溶性ビタミンの吸収を阻害するこ と」 を表示することが義務付けられている。 蛋白質および炭水化物のエネルギー 密度は、 脂肪の半分以下である。 そこで、 蛋白質や炭水化物に脂肪様の物性や風 味が出るように加工することによって、 低カロリ一の脂肪代替品を提供し得るこ とが知られている (栄養学レビュー、 第 4卷、 第 4号、 2 3〜3 3頁、 1 9 9 6 年) 。 これらの脂肪代替品を利用することにより、 低カロリー化したアイスタリ ーム、 ベーカリー製品、 ケーキ等を作ることが可能である。 し力 し、 熱に対する 耐性が乏しくフライや炒め物の熱媒体として使用することはできないなどの欠点 がある。 To overcome this situation, so-called fat substitutes are being developed. However, none of them are sufficiently satisfactory in terms of safety, physical properties, cooking suitability, and flavor. For example, it is disclosed that 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). 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. Thus, it is known that 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) . By using these fat substitutes, it is possible to make low-calorie ice cream, bakery products and cakes. However, it has poor resistance to heat and cannot be used as a heating medium for frying or stir-fry.
特表平 4 -501812号公報には、 長鎖脂肪酸と短鎖脂肪酸から構成される トリグリセリドにより、 低カロリー油脂が提供でき得ることが開示されている。 しかし、 短鎖脂肪酸からなるトリグリセリドは特有の臭いを有していることから 、 利用可能な調理品が限られ汎用性のある食用油として適さない。 また、 中鎖脂 肪酸はエネルギー化されやすいことから体脂肪蓄積が少ないことが知られている ( J. L i i d Re s. 37、 708- 726 (1996) ) 。 し力 し、 中 鎖脂肪酸から構成されるトリグリセリドは本来安全性の高いものであるが、 一度 に多量に摂取した場合、 下痢、 吐き気、 腹痛、 胸焼け、 食欲不振などの症状を起 こすことが報告されている。 特開平 4— 300826号公報、 特開平 8— 601 80号公報および特開平 10—176181号公報には、 ジグリセリドを有効成 分とする体脂肪蓄積が少ない油脂組成物が開示されている。 し力 し、 ジグリセリ ドを豊富に含む油脂組成物の安全性は、 完全に証明されているわけではない。 ま た、 高濃度のジグリセリ ドを低コストで製造することは難しく、 経済的見地から 汎用的に使用しにくい欠点がある。 さらに特開平 8— 269478号公報には、 ジグリセリ ドおよぴトリグリセリドからなる油脂組成物成分中、 分子内に中鎖脂 肪酸残基を 2つ含有するトリグリセリ ドを 31質量%以上含む体脂肪蓄積の少な い油脂組成物が開示されている。 この発明もまたジグリセリドを有効成分とする ため、 前記特開平 4 -300826号公報、 特開平 8 _ 60180号公報おょぴ 特開平 10— 176181号公報と同様の問題を抱えている。 また、 多量の中鎖 脂肪酸を含むため発煙点が低く、 泡立ちが著しいことからフライ調理に適さない などの欠点がある。 発明の開示 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. However, since triglycerides composed of short-chain fatty acids have a peculiar odor, available cooked products are limited and are not suitable as versatile edible oils. It is also known that medium-chain fatty acids are less susceptible to energy conversion and thus have less body fat accumulation (J. Lid Res. 37, 708-726 (1996)). Although 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. However, the safety of fat compositions rich in diglycerides has not been fully proven. In addition, 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. Further, 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
本発明の目的は、 体脂肪蓄積が少なく、'通常の食用油と同等の調理適性を持ち 、 さらに風味良好で安全性の高い油脂組成物を提供することである。 本発明者らは上記課題を解決するために、 鋭意検討を重ねた結果、 全脂肪酸残 基に占める中鎖脂肪酸残基の割合、 およぴ全トリグリセリドに占める、 中鎖脂肪 酸残基を分子内に 2つ有するトリグリセリドの割合が体脂肪蓄積の度合いと密接 に関連することを見出し、 本発明を完成した。 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.
すなわち本発明は、 主としてトリグリセリドからなる油脂組成物であって、 油 脂組成物を構成する全脂肪酸に占める中鎖脂肪酸の割合が 5〜2 3質量%で、 か っ全トリグリセリ ドに占める、 中鎖脂肪酸残基を分子内に 2つ有するトリグリセ リドの割合が 1〜2 0質量%であることを特徴とする、 体脂肪蓄積の少ない油脂 組成物に関する。 上記中鎖脂肪酸は炭素数 6〜1 2の飽和脂肪酸であることが好 ましい。 また、 油脂組成物を構成する全トリグリセリドに占める、 中鎖脂肪酸残 基を分子内に 3つ有するトリグリセリドの割合が 3重量%以下であることが好ま しい。 また、 油脂糸且成物を構成する全長鎖脂肪酸に占める長鎖飽和脂肪酸の割合 が 2 0質量%以下であることが好ましい。 That is, 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. Further, it is preferable that 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.
本発明の油脂組成物に乳化剤、 特に特定の組合せの乳化剤を含有させる場合に は、 フライ適性、 特に泡立ち抑制をさらに向上させることができる。 When 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.
また本発明は、 力かる油脂組成物を含有する、 体脂肪蓄積の少なく、 かつ通常 の食用油と遜色のなレヽ調理適性およぴ保存安定性を有する調理用油脂組成物に関 する。 発明を実施するための最良の形態 In addition, 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. BEST MODE FOR CARRYING OUT THE INVENTION
以下に本発明を詳しく説明する。 Hereinafter, the present invention will be described in detail.
本発明の油脂組成物は主としてトリグリセリ ドからなる。 「主として」 は、 油 脂組成物中に、 トリグリセリドが 8 5質量%以上、 好ましくは 9 5質量。 /0以上含 まれていることを意味するものとする。 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.
本発明で中鎖脂肪酸とは炭素数が 6〜 1 2の脂肪酸、 特に飽和脂肪酸をいうも のとする。 例としては、 カブロン酸、 力プリル酸、 力プリン酸、 ラウリン酸が拳 げられ、 炭素数が 8〜1 0の飽和脂肪酸、 特に力プリル酸おょぴカプリン酸が好 ましい。 本発明で長鎖脂肪酸とは炭素数が 1 4以上、 好ましくは 1 4〜2 2の飽 和および不飽和脂肪酸をいうものとする。 長鎖脂肪酸としては炭素数が 1 4以上 、 好ましくは 1 4〜 2 2のもの、 例えばミリスチン酸、 パルミチン酸、 ステアリ ン酸、 ァラキジン酸、 ベヘン酸、 リグノセリン酸、 セロチン酸等の長鎖飽和脂肪 酸、 ミリストレイン酸、 ペンタデセン酸、 パルミトレイン酸、 へキサデ力トリエ ン酸、 ヘプタデセン酸、 ォレイン酸、 リノール酸、 α—リノレン酸、 γ—リノレ ン酸、 ォクタデカテトラェン酸、 ィコセン酸、 ィコサジェン酸、 ィコサトリェン 酸、 ィコサテトラェン酸、 ァラキドン酸、 ィコサペンタエン酸、 ドコセン酸、 ド コサジェン酸、 ドコサペンタエン酸、 ドコサへキサェン酸等の長鎖不飽和脂肪酸 が挙げられる。 脂肪酸残基は脂肪酸からカルボキシル基の Ο Ηを取った基である 本発明の油脂組成物においては、 油脂組成物を構成する全脂肪酸に占める中鎖 脂肪酸の割合が 5〜 2 3質量%で、 かつ全トリグリセリドに占める、 中鎖脂肪酸 残基を分子内に 2つ有するトリグリセリドの割合が 1〜 2 0質量%であることが 必要である。 この範囲外では体脂肪蓄積が少ないという特長が生じない。 上記中 鎖脂肪酸の割合は好ましくは 6〜 2 3質量%であり、 上記トリグリセリ ドの割合 は好ましくは 3〜 2 0質量%である。 In the present invention, 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. In the present invention, 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, α-linolenic acid, γ-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 docosahexaenoic acid. The fatty acid residue is a group obtained by removing the carboxyl group from the fatty acid. In the oil / fat composition of the present invention, the ratio of the medium-chain fatty acid to the total fatty acids constituting the oil / fat composition is 5 to 23% by mass, In addition, 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.
また、 油脂組成物を構成する全トリグリセリドに占める、 中鎖脂肪酸残基を分 子内に 3つ有するトリグリセリドの割合が 3質量%以下であることが好ましく、 2質量%以下であることがさらに好ましく、 1質量%以下であることがさらに一 層好ましい。 この割合が 3質量%を越えると、 調理時に発煙、 泡立ちが増加し、 フライ用の油脂として適さなくなる。 該割合が 1質量%以下であると、 発煙、 泡 立ちに格段の改善が見られる。 Further, 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.
さらに、 油脂組成物を構成する全長鎖脂肪酸に占める、 長鎖飽和脂肪酸の割合 が 2 0質量%以下であることが好ましく、 1 5質量%以下であることがさらに好 ましく、 7質量%以下であることがさらに一層好ましい。 この割合が 2 0質量% を越えると低温での安定性が低下し、 油脂組成物に油脂の結晶化が見られるよう になるので、 生食用には通常適さなくなる。 Further, 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.
本発明の体脂肪蓄積が少ない油脂組成物は、 原料としての油脂と中鎖脂肪酸と を適宜混合した後、 ナトリゥムメチラートを触媒としてまたは脂質分解酵素の存 在下にエステル交換反応を行い、 この際に、 油脂組成物を構成する全脂肪酸に占 める中鎖脂肪酸の割合、 およぴ全トリグリセリドに占める、 中鎖脂肪酸残基を分 子内に 2つ有するトリグリセリドの割合が前記特定範囲内に入るようにエステル 交換反応を調整することにより得ることができる。 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. By adjusting 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.
上記エステル交換反応に際し、 上記調整に加え、 油脂組成物を構成する全トリ グリセリドに占める、 中鎖脂肪酸残基を分子内に 3つ有するトリグリセリドの割 合、 および Zまたは油脂組成物を構成する全長鎖脂肪酸に占める長鎖飽和脂肪酸 の割合が前記特定範囲内に入るように調整することにより、 体脂肪蓄積が少なく 、 かつフライ時の発煙、 泡立ちが低減され、 および Zまたは低温安定性に優れる 油脂組成物を得ることができる。 In the above transesterification reaction, in addition to the above adjustments, 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.
原料油脂としては、 通常の食用油脂、 例えば大豆油、 菜種油、 高ォレイン酸菜 種油、 コーン油、 ゴマ油、 ゴマサラダ油、 シソ油、 亜麻仁油、 落花生油、 紅花油 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
、 高ォレイン酸紅花油、 ひまわり油、 高ォレイン酸ひまわり油、 綿実油、 プドウ 種油、 マカデミアナッツ油、 ヘーゼルナッツ油、 カポチヤ種子油、 タルミ油、 椿 油、 茶実油、 エゴマ油、 ボラージ油、 ォリーブ油、 米糠油、 小麦胚芽油、 パーム 油、 パーム核油、 ヤシ油、 カカオ脂、 牛脂、 ラード、 鶏脂、 乳脂、 魚油、 ァザラ シ油、 藻類油、 品質改良によって低飽和化されたこれらの油脂およびこれらの水 素添加油脂、 分別油脂等が拳げられる。 , High oleic safflower oil, sunflower oil, high oleic sunflower oil, cottonseed oil, podo seed oil, macadamia nut oil, hazelnut oil, capochia seed oil, tallumi oil, camellia oil, teaseed oil, perilla oil, borage oil, olive oil , Rice bran oil, wheat germ oil, palm oil, palm kernel oil, coconut oil, cocoa butter, beef tallow, lard, chicken fat, milk fat, fish oil, seal oil, algae oil, these oils that have been reduced in quality by improving quality And these hydrogenated fats and oils and fractionated fats and oils are fisted.
中鎖脂肪酸についてはすでに記述したが、 中鎖脂肪酸に代えてまたはこれと共 に中鎖脂肪酸トリグリセリドを用いることもできる。 中鎖脂肪酸トリグリセリ ド としては、 前記中鎖脂肪酸とグリセリンとを常法によりエステクレイ匕反応に付して 得られるトリグリセリドを用いることができるが、 一般に MCT (Me d i um Ch a i n Tr i g l y c e r i d e s) と称せられる、 ヤシ油分解脂肪酸 等の炭素数が 8〜: L 0の飽和脂肪酸から構成される単酸基もしくは混酸基トリグ リセリド、 例えば力プリル酸/力プリン酸 = 60Z40〜 75/25 (質量比) のトリグリセリ ドが好適に使用できる。 Although 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. As 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. with 8 or more carbon atoms: mono- or mixed-acid triglycerides composed of saturated fatty acids with L0, for example, pyrrolic acid / pyric acid = 60Z40-75 / 25 (mass ratio) Triglycerides can be suitably used.
油脂組成物を構成する全脂肪酸に占める中鎖脂肪酸の割合、 および全トリグリ セリドに占める、 中鎖脂肪酸残基を分子内に 2つ有するトリグリセリドの割合、 必要な場合の、 油脂組成物を構成する全トリグリセリドに占める、 中鎖脂肪酸残 基を分子内に 3つ有するトリグリセリドの割合、 および、 必要な場合の、 油脂組 成物を構成する全長鎖脂肪酸に占める長鎖飽和脂肪酸の割合は、 原料油脂組成を 勘案し、 原料油脂と中鎖脂肪酸との使用比率を調整し、 エステル交換反応中の反 応生成物のトリグリセリド組成を測定することによって調整できる。 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.
ナトリゥムメチラートを触媒とするエステル交換反応を行う場合、 原料油脂と 中鎖脂肪酸トリグリセリドとを前者 Z後者の質量比 = 7 1 / 2 9〜 9 7 Z 3で混 合し、 混合物を 1 0 O mmH g以下の減圧下で 8 0〜1 2 0 °Cに加熱し、 原料混 合物に含まれる気体成分および水分を除去する。 これにナトリゥムメチラ一ト 0 . 0 2〜0 . 5質量%を添加し、 常圧 '窒素気流下あるいは 1 O mmH g以下の 減圧下で 1 0〜 6 0分間、 8 0〜: 1 2 0 °Cで攪拌することによりエステル交換反 応を行う。 反応の完了はガスクロマトグラフィーにより反応生成物のトリグリセ リド組成を測定することにより確認する。 反応の停止は反応生成物に水を添加す るかリン酸などの酸を添加することにより行う。 その後、 触媒および過剰の酸を 除去するために十分な水洗を行い、 乾燥後、 反応生成物を常法により脱色、 脱臭 する。 When a transesterification reaction using sodium methylate as a catalyst is carried out, the raw material fat and the medium-chain fatty acid triglyceride are mixed at the former Z latter mass ratio = 7 1/2 9 to 97 Z 3 and the mixture is mixed at 1 Heat to 80 to 120 ° C under reduced pressure of 0 O mmHg or less to remove gaseous components and water contained in the raw material mixture. 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. Completion of the reaction is confirmed by measuring the triglyceride composition of the reaction product by gas chromatography. The reaction is stopped by adding water or an acid such as phosphoric acid to the reaction product. After that, it is washed sufficiently with water to remove the catalyst and excess acid, and after drying, the reaction product is decolorized and deodorized by a conventional method.
脂質分解酵素を用いてエステル交換反応を行う場合、 原料油脂と中鎖脂肪酸も しくは中鎖脂肪酸トリグリセリドとを前者 Z後者の質量比 = 7 1 Z 2 9〜9 7 / 3で混合し、 脂質分解酵素の活性が十分に発揮される反応温度である 4 0〜1 0 0 °Cの範囲に調温する。 これに脂質分解酵素を原料混合物に対して 0. 0 0 5〜 1 0質量%の割合で添カ卩し、 2〜4 8時間の範囲でエステル交換反応を行う。 こ の反応は常圧下で窒素気流中で行うことが望ましい。 反応の完了はガスクロマト グラフィ一により反応生成物のトリグリセリド組成を測定することにより確認す る。 反応の停止は酵素を濾過により除去することにより行う。 反応生成物は水洗 、 乾燥の後、 常法により脱色、 脱臭する。 なお、 中鎖脂肪酸を使用した場合は、 反応の停止後に遊離脂肪酸を薄膜式エバポレーターで除去しておく。 When a transesterification reaction is carried out using a lipolytic enzyme, the raw fat and oil and medium-chain fatty acid or medium-chain fatty acid triglyceride are mixed in the former Z latter mass ratio = 71 1 Z 29-97/3, and the lipid is mixed. 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. Then, 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. When medium-chain fatty acids are used, free fatty acids are removed with a thin-film evaporator after the reaction is stopped.
脂質分解酵素を用いたエステル交換反応が不十分であると、 中鎖脂肪酸残基を 分子内に 3つ有するトリグリセリドの割合が多くなる。 中鎖脂肪酸残基を分子内 に 3つ有するトリグリセリドの割合が多い油脂組成物は、 体脂肪蓄積が少ないと いう特長はあるものの、 連続したフライ調理時において発煙、 泡立ちが激しく起 こり好ましくない。 脂質分解酵素としては、 アルカリゲネス属、 キャンディダ属、 リゾプス属、 ム コール属またはシユードモナス属由来のリパーゼゃ、 肝臓由来のホスホリパーゼ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. Examples of lipolytic enzymes include lipases derived from Alcaligenes, Candida, Rhizopus, Mucor or Pseudomonas, and liver lipase.
A等が挙げられるが、 特にキャンディダ属またはリゾプス属由来のリパーゼが好 ' ましい。 A, etc., and a lipase derived from the genus Candida or Rhizopus is particularly preferred.
本発明の油脂組成物は、 また、 遺伝子組換えの技術を用いて、 本発明の油脂組 成物を生産するように品種改良した植物、 例えば大豆、 菜種、 コーン、 ヤシ、 パ ーム、 ォリーブ、 亜麻仁、 ひまわり、 紅花、 つばき、 綿実、 クヘアから抽出によ つて得ることも可能である。 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.
本発明の油脂組成物に乳化剤を含有させることでフライ適性、 特に泡立ち抑制 をさらに向上させることができる。 乳化剤としては、 ショ糖脂肪酸エステル、 ポ リグリセリン脂肪酸エステル、 コハク酸モノグリセリ ド、 モノグリセリ ド、 ジグ リセリ ド、 ソルビトール脂肪酸エステル、 ソルビタン脂肪酸エステル等が挙げら れる。 本発明では上記乳化剤の少なくとも 1種が選択でき、 油脂組成物への添加 量は、 乳化剤全体として 0. 1〜 6質量%が好ましく、 さらに好ましくは 0. 3 〜 5質量%である。 By adding an emulsifier to the oil or fat composition of the present invention, the suitability for frying, particularly the suppression of foaming, can be further improved. Examples of 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. In the present invention, 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.
ショ糖脂肪酸エステルはショ糖と炭素数 6〜 2 2の飽和もしくは不飽和脂肪酸 とのエステルを包含するが、 全水酸基の平均置換度が 3 7 . 5〜 8 7. 5 %であ り、 全ショ糖脂肪酸エステルに占めるトリエステル以上のポリエステルの割合が 8 5質量%以上であることが好ましい。 ポリグリセリン脂肪酸エステルはトリグ リセリン以上で好ましくはデカグリセリンまでのポリグリセリンと炭素数 6〜 2 2の飽和もしくは不飽和脂肪酸とのエステルを包含するが、 全水酸基の平均置換 度が 2 0〜 8 0 %であることが好ましい。 モノダリセリド、 ジグリセリドはグリ セリンもしくはジグリセリンと炭素数 6〜 2 2の飽和もしくは不飽和脂肪酸との モノエステル、 ジエステルをそれぞれ包含するが、 モノグリセリ ドが好ましい。 コハク酸モノグリセリ ドとしては、 コハク酸とモノグリセリドもしくはジグリセ リ ドとを 3 : 1 〜 0 . 1 : 1でエステルイ匕したコハク酸モノグリセリドが好まし レ、。 ソルビトール脂肪酸エステル、 ソルビタン脂肪酸エステルは、 ソルビトール もしくはソルビタンと炭素数 6〜 2 2の飽和もしくは不飽和脂肪酸とのモノ〜ト リエステルが好ましレ、。 上記で炭素数 6〜 2 2の飽和もしくは不飽和脂肪酸の例 としては、 中鎖脂肪酸および長鎖脂肪酸の例として挙げたものが挙げられる。 乳化剤の組み合わせ使用については、 本発明の油脂組成物に対して、 ショ糖脂 肪酸エステルおよびポリグリセリン脂肪酸エステルから選ばれる少なくとも 1種 を 0 . 1〜3質量0 /。、 コハク酸モノグリセリドを 0 . 0 1〜2質量0 /0、 およぴモ ノグリセリ ド、 ジグリセリ ド、 ソルビトール脂肪酸ェステルおよびソルビタン脂 肪酸エステルから選ばれる少なくとも 1種を 0 . 1〜3質量%、 該乳化剤の総量 が 0 . 3〜 5質量%となるように、 添加、 含有させるのが、 フライ適性、 特に泡 立ち抑制のさらなる向上のため、 もっとも好ましい。 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. As the 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. Examples of 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. The combined use of 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%, It is most preferable to add or contain the emulsifier so that the total amount of the emulsifier is 0.3 to 5% by mass, for further improving the suitability for frying, especially the suppression of foaming.
上記のようにして得られる本発明の油脂組成物は、 そのままでもしくは調理用 油脂組成物に通常用いられる添加剤を配合して、 調理用油脂組成物として使用す ることができる。 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.
カゝかる添加剤としては、 保存安定性向上、 酸化安定'性向上、 熱安定性向上、 低 温下での結晶化抑制等を目的としたポリグリセリン脂肪酸エステル、 ショ糖脂肪 酸エステル、 ソルビタン脂肪酸エステル、 ビタミン E、 ァスコルビン酸脂肪酸ェ ステル、 リグナン、 コェンザィム Q、 リン脂質、 オリザノール、 ジグリセリド等 、 成人病予防作用、 生活習慣病予防作用、 生体内酸化抑制作用、 肥満症予防作用 を期待したビタミン E、 ァスコルビン酸脂肪酸エステル、 リグナン、 コェンザィ ム Q、 リン脂質、 オリザノール等が挙げられる。 Examples of the additive 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.
本発明の調理用油脂組成物は、 菜種油、 コーン油、 紅花油、 大豆油といった一 般に市販されている食用油と同等あるいはそれ以上の風味を持ち、 炒め物、 揚げ 物、 マリネなどの調理に使用することができることはもちろんのこと、.油脂を含 有する食品であるドレッシング、 マヨネーズ、 マーガリン、 菓子類、 ケーキ、 飲 料等にも使用可能である。 調理品の種類によって風味の特性は異なるが、 素材の 味を生かしたさっぱりとした料理を作ることが可能である。 また、 フライ調理時 における油のハネ度合いは、 通常の食用油と同等あるいはそれ以下である。 また 、 本発明の調理用油脂組成物を適量継続的に摂取することにより、 血中脂質濃度 が低下する作用も期待できる。 実施例 以下に実施例を挙げて本発明をより具体的に説明するが、 本発明はそれらによ つて限定されるものではない。 実施例 1 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. In addition, the degree of oil splash during frying is equal to or less than that of ordinary cooking oil. In addition, 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 Hereinafter, the present invention will be described more specifically with reference to Examples, but the present invention is not limited thereto. Example 1
菜種白絞油 (日清製油 (株) 製) 80質量部と構成脂肪酸が質量比で力プリル 酸/力プリン酸 =3Zlである MCT20質量部とを混合後、 減圧下 120°Cで 攪拌し、 脱気おょぴ脱水処理を行った。 これに触媒としてナトリウムメチラート 0. 1質量部を加え、 120°Cで 30分間、 ランダムエステル交換反応を行った 。 反応生成物を常法により水洗、 乾燥後、 脱色、 脱臭して油脂組成物 1を得た。 また、 油脂組成物 1に対して、 ショ糖脂肪酸エステル (三菱化学フーズ (株) 製 、 商品名リヨ一トーシュガーエステル O_ 170) 2. 5質量。 /0、 コハク酸モノ グリセリド (理研ビタミン (株) 製、 商品名ポエム B— 10) 0. 1質量0 /0、 ソ ルビタン脂肪酸エステル (理研ビタミン (株) 製、 商品名ポエム O— 80) 1質 量%を添加して油脂組成物 2を得た。 油脂組成物 1、 2のトリグリセリ ド組成お ょぴ脂肪酸組成をそれぞれカラム GS— 1を用いたガスクロマトグラフィーおよ ぴ 「基準油脂分析試験法 (1996) 」 に準じて測定した (以下の実施例および 比較例でも同様) 。 結果を表 1に示す。 実施例 2 Rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) 80 parts by mass and 20 parts by mass of MCT, in which the constituent fatty acids are in the weight ratio of prylic acid / potassic acid = 3Zl, 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 performed 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 a fat and oil composition 1. In addition, 2.5 mass of sucrose fatty acid ester (manufactured by Mitsubishi Chemical Foods Co., Ltd., trade name: Lyotosugar Ester O_170) was 2.5 mass with respect to the oil / fat composition 1. / 0, 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 By adding% by mass, 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
大豆サラダ油 (日清製油 (株) 製) 85質量部と構成脂肪酸が質量比でカプリ ル酸 Z力プリン酸 =3ノ 1である MCT 15質量部との混合物にリパーゼ QL ( 名糖産業 (株) 製) 0. 1質量部を添加し、 攪拌下 60°Cで 15時間、 エステル 交換反応を行った。 反応生成物から酵素を濾別し、 濾液を水洗、 乾燥後、 脱色、 脱臭して油脂組成物 3を得た。 油脂組成物 3のトリグリセリド組成および脂肪酸 組成を表 1に示す。 実施例 3 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. Example 3
パーム油 (日清製油 (株) 製) 77質量部と質量比で力プリル酸/力プリン酸 = 1 / 1の中鎖脂肪酸混合物 23質量部とを混合後、 混合物にリパーゼ Q L (名 糖産業 (株) 製) 0. 1質量部を添加し、 攪拌下 60°Cで 15時間、 エステル交 換反応を行った。 反応後酵素を濾別し、 濾液中の遊離脂肪酸を薄膜式エバポレー ターで除去後、 脱色、 脱臭して油脂組成物 4を得た。 油脂組成物 4のトリグリセ リド組成および脂肪酸組成を表 1に示す。 実施例 4 After mixing 77 parts by mass of palm oil (manufactured by Nisshin Oil Co., Ltd.) and 23 parts by mass of a medium-chain fatty acid mixture of force prillic acid / force pric acid = 1/1 by mass ratio, Lipase QL (name 0.1 part by mass was added, and the ester exchange reaction was carried out at 60 ° C for 15 hours with stirring. After the reaction, the enzyme was filtered off, and the free fatty acid in the filtrate was removed with a thin film evaporator, followed by decolorization and deodorization to obtain a fat / oil composition 4. Table 1 shows the triglyceride composition and fatty acid composition of Fat and Oil Composition 4. Example 4
コーン油 (日清製油 (株) 製) 77質量部と質量比で力プリル酸 Z力プリン酸 = 1/1の中鎖脂肪酸混合物 23質量部とを混合後、 混合物にリパーゼ Q L (名 糖産業 (株) 製) 0. 1質量部を添加し、 攪拌下 60°Cで 15時間、 エステル交 換反応を行った。 反応後酵素を濾別し、 濾液中の遊離脂肪酸を薄膜式エバポレー ターで除去後、 脱色、 脱臭して油脂組成物 5を得た。 油脂組成物 5のトリグリセ リド組成およぴ脂肪酸組成を表 1に示す。 実施例 5 Corn oil (manufactured by Nisshin Oil Co., Ltd.) After mixing 77 parts by mass and 23 parts by mass of a medium-chain fatty acid mixture of force prillic acid Z force pric acid = 1/1 by mass ratio, Lipase QL (name sugar industry) is added to the mixture. 0.1 part by mass was added, and the ester exchange reaction was carried out at 60 ° C for 15 hours with stirring. After the reaction, the enzyme was separated by filtration, the free fatty acids in the filtrate were removed by a thin-film evaporator, and then the mixture was decolorized and deodorized to obtain a fat / oil composition 5. Table 1 shows the triglyceride composition and fatty acid composition of the fat composition 5. Example 5
菜種白絞油 (日清製油 (株) 製) 93質量部と構成脂肪酸が質量比で力プリル 酸/力プリン酸 =3//1である MCT7質量部とを混合後、 減圧下 120°Cで攪 拌し、 脱気および脱水処理を行った。 これに触媒としてナトリウムメチラート 0 . 1質量部を加え、 120。Cにて 30分間、 ランダムエステル交換反応を行った 。 反応生成物を常法により水洗、 乾燥後、 脱色、 脱臭して油脂組成物 6を得た。 油脂組成物 6のトリグリセリド組成およぴ脂肪酸組成を表 2に示す。 実施例 6 Rapeseed White refined oil (The Nisshin Oil Mills Co., Ltd.) were mixed and MCT7 parts by the force prill acid / force purine acid = 3 / / 1 93 parts by mass constituent fatty acids in a weight ratio, under reduced pressure 120 ° C And degassed and dehydrated. To this, 0.1 part by mass of sodium methylate was added as a catalyst, and 120. C. A random transesterification reaction was performed 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 6. Table 2 shows the triglyceride composition and fatty acid composition of Fat Composition 6. Example 6
菜種白絞油 (日清製油 (株) 製) 90質量部と構成脂肪酸が質量比で力プリル 酸 /カブリン酸 =3Zlである MCT10質量部とを混合後、 減圧下 1 20°Cで 攪拌し、 脱気おょぴ脱水処理を行った。 これに触媒としてナトリウムメチラート 0. 1質量部を加え、 120°Cにて 30分間、 ランダムエステル交換反応を行つ た。 反応生成物を常法により水洗、 乾燥後、 脱色、 脱臭して油脂組成物 7を得た 。 油脂組成物 7のトリグリセリド組成およぴ脂肪酸組成を表 2に示す。 実施例 7 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 7
実施例 2と同じ混合物にリパーゼ QL (名糖産業 (株) 製) 0. 1質量部を添 加し、 攪拌下 60°Cで 3時間、 エステル交換反応を行った。 反応生成物から酵素 を濾別し、 濾液を水洗、 乾燥後、 脱色、 脱臭して油脂組成物 8を得た。 油脂組成 物 8のトリグリセリド組成および脂肪酸組成を表 2に示す。 比較例 1 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
菜種白絞油 (日清製油 (株) 製) 75質量部と構成脂肪酸が質量比で力プリル 酸/力プリン酸 =3/1である MCT 25質量部とを混合後、 減圧下 120°Cで 攪拌し、 脱気および脱水処理を行った。 これに触媒としてナトリウムメチラート 0. 1質量部を加え、 120 °Cで 30分間、 ランダムエステル交換反応を行つた 。 反応生成物を常法により水洗、 乾燥後、 脱色、 脱臭して油脂組成物 9を得た。 油脂組成物 9のトリグリセリド組成およぴ脂肪酸組成を表 3に示す。 比較例 2 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
菜種白絞油 (日清製油 (株) 製) 97質量部と構成脂肪酸が質量比で力プリル 酸/力プリン酸 =3Zlである MCT3質量部とを混合後、 減圧下 120°Cで攪 拌し、 脱気および脱水処理を行った。 これに触媒としてナトリウムメチラート 0 . 1質量部を加え、 120°Cで 30分間、 ランダムエステル交換反応を行った。 反応生成物を常法により水洗、 乾燥後、 脱色、 脱臭して油脂組成物 10を得た。 油脂組成物 10のトリグリセリド組成およぴ脂肪酸組成を表 3に示す。 Rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) 97 parts by mass and 3 parts by mass of MCT in which the constituent fatty acids are by weight ratio of prylic acid / potassic acid = 3Zl, and then stirred at 120 ° C under reduced pressure Then, degassing and dehydration treatments were performed. To this was added 0.1 parts by mass of sodium methylate as a catalyst, and a random transesterification reaction was performed 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 a fat and oil composition 10. Table 3 shows the triglyceride composition and fatty acid composition of the fat composition 10.
表 1 油脂組成物の分析値 (質暈%) Table 1 Analytical values of oil and fat composition (quality halo%)
«例 «Example
油脂組成物 1油脂組成物 2油脂繊物 3 油脂組成物 5 トリグリセリド組成 Fat composition 1 Fat composition 2 Fat fiber 3 Fat composition 5 Triglyceride composition
3M0 L 1. 5 1. 5 t Γ. 2. 0 1. Θ 3M0 L 1. 5 1.5 t Γ. 2. 1. 1.
2M1 L 15. 9 15. 9 10. 2 19. 1 18. 52M1 L 15.9 15.9 10.2 19.1 18.5
1 2 L 44. 2 44. 2 41. 1 45. 4 45. 51 2 L 44.2 44.2 41.1 45.4 45.5
0M3L 38. 4 38. 4 48. 7 33. 5 34. 1 脂肪酸組成 0M3L 38.4 38.4 48.7 33.5 34.1 Fatty acid composition
C 8 : 0 1 . 4 1 . 3 10. 5 10. 8 11. 0 C 8: 0 1 .4 1 .3 10.5 10.8 11.0
C 10: 0 4. 8 4. 6 3. 4 11. 1 11. 2C 10: 0 4. 8 4. 6 3. 4 11. 1 11.2
C 12: 0 0. 0 0. 0 0. 0 1. 0 0. 0C 12: 0 0. 0 0. 0 0. 0 1. 0 0. 0
C 1 : 0 0. 0 0. 0 0. 0 0. 8 0. 0C1: 0 0. 0 0. 0 0. 0 0. 8 0. 0
C 16: 0 3. 2 3. 1 8. 6 33. 3 10. 2C 16: 0 3.2 3. 1 8. 6 33. 3 10. 2
C 18: 0 1. 6 2. 0 3. 3 3. 3 1. 6C 18: 0 1. 6 2. 0 3. 3 3. 3 1. 6
C 18: 1 49. 2 49. 4 20. 7 31. 6 23. 3C 18: 1 49. 2 49. 4 20. 7 31. 6 23.3
C 18: 2 17. Θ 17. 9 46. 2 7. Θ 42. 7C 18: 2 17. Θ 17. 9 46. 2 7. Θ 42. 7
C 18: 3 8. 9 8. 7 7. 1 0. 0 0. 0 others 0. 0 0. 0 0. 2 0. 2 0. 0 注) M;中麵腿、 L; SSS tr.= tracer 例えば C8: 0は^ S8で不辦 Π*½ 體—織二離合)の!^ 0であることを示す。 (表 2、 3および 4でも同様) 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 Π * 體 body-weave union! Indicates that it is ^ 0. (Same for Tables 2, 3 and 4)
表 2 油脂誠物の分析値 (ΜΜ%) Table 2 Analytical values of oils and fats (ΜΜ%)
実施例 Example
油脂組成物 6 油脂繊物 7 油脂組成物 8 トリグリセリド組成 Fat composition 6 Fat composition 7 Fat composition 8 Triglyceride composition
3Μ0 L 0. 1 t r. 4. 8 3Μ0 L 0.1 t r. 4.8
2M1 L 3. 4 5. 1 6. 12M1 L 3.4 5.1 6.1
1M2L 25. 6 31. 9 35. 11M2L 25. 6 31. 9 35. 1
0Μ3 L 70. 9 63. 0 54. 0 脂肪酸組成 0Μ3 L 70.9 63.0 54.0 Fatty acid composition
C 8: 0 5. 0 7. 2 10. 9 C 8: 0 5.0 7. 2 10. 9
C 10: 0 1. 8 2. 4 3. 0C 10: 0 1. 8 2. 4 3.0
C 12: 0 0. 0 0. 0 0. 0C 12: 0 0. 0 0. 0 0. 0
C 1 : 0 0. 0 0. 0 0. 0C1: 0 0. 0 0. 0 0. 0
C 16: 0 3. 5 3. 6 8. 1C 16: 0 3.5 3. 6 8. 1
C 18: 0 2. 1 1. δ 3. 8C 18: 0 2.1 1.δ 3.8
C 18: 1 56. 2 55. 1 20. 0C 18: 1 56. 2 55. 1 20.0
C 18: 2 20. 9 19. 8 46r 9C 18: 2 20. 9 19. 8. 46r 9
C 18: 3 10. 2 10, 1 7. 2 others 0. 3 0. 0 0. 1 C18: 3 10. 2 10, 1 7.2 others 0.3 0. 0 0.1
表 3 油脂 物の分析値 %) (Table 3 Analysis value of fats and oils%)
比較例 Comparative example
油脂組成物 9 油脂雌物 10 トリグリセリド組成 Oil composition 9 Oil composition 10 Triglyceride composition
3M0L 2. 8 t r. 3M0L 2.8 t r.
2M1 L 21. 0 0. 52M1 L 21. 0 0.5
1M2 L 45. 5 11. 71M2 L 45.5 11.7
0M3L 30. 7 87. 8 脂肪酸組成 0M3L 30.7 87.8 Fatty acid composition
C 8 : 0 18. 5 2. 1 C 8: 0 18.5 2.1
C 10: 0 5. 9 1. 0C 10: 0 5.9.10
C 12: 0 0. 0 0. 0C 12: 0 0. 0 0. 0
C 14: 0 0. 0 0. 0C 14: 0 0. 0 0. 0
C 16: 0 3. 1 3. 7C 16: 0 3.1 3.7
C 18: 0 1. 5 2. 1C 18: 0 1.5 2. 1
C 18: 1 45. 9 58. 5C 18: 1 45. 9 58. 5
C 18: 2 16. 7 21. 7C 18: 2 16. 7 21. 7
C 18: 3 8. 4 10. 6 others 0. 0 0. 3 C 18: 3 8. 4 10. 6 others 0. 0 0.3
表 4 油脂組成物の分析値 %) (Table 4 Analytical value of fat composition)
対照 Contrast
油 BE合油 Oil BE oil
トリグリセリド組成 Triglyceride composition
3M0 L 0 0 2 0. 0 3M0 L 0 0 2 0. 0
2M 1 L 0 0 - 2M 1 L 0 0-
1 M2 L 0 0 一 1 M2 L 0 0 1
0M3 L 1 0 0 1 0 0 8 0. 0 0M3 L 1 0 0 1 0 0 8 0. 0
脂肪酸組成 Fatty acid composition
C 8 : 0 0. 0 0. 0 1 5. 1 C 8: 0 0. 0 0. 0 1 5.1
C 1 0: 0 0. 0 0. 0 4. 9 C 1 0: 0 0 .0 0 .0 4.9
C 1 2: 0 0. 0 0. 0 0. 0 C 1 2: 0 0. 0 0. 0 0. 0
C 1 : 0 0. 0 0. 0 0. 0 C1: 0 0. 0 0. 0 0. 0
C 1 6: 0 1 0. 5 3. 8 3. 1 C 16: 0 1 0.5 0.5 3.8 3.1
C 1 8: 0 3. 8 2. 2 1 . 8 C 18: 0 3.8.2 2.1.8
C 1 8: 1 2 3. 6 6 0. 3 4 8. 0 C 18: 1 2 3. 6 6 0.3 4 8.0
C 1 8: 2 5 4. 2 2 2. 4 1 7. 9 C 1 8: 2 5 4. 2 2 2. 4 1 7. 9
C 1 8: 3 7. 6 1 0. 9 8. 9 C 18: 3 7. 6 1 0.9. 9
others 0. 3 0. 4 0. 3 others 0. 3 0. 4 0. 3
実施例 8 Example 8
4週齢のウィスター系雄性ラットに、 大豆油 (日清製油 (株) 製) (对照) ( トリグリセリド組成および脂肪酸組成を表 4に示す) または油脂組成物 1、 6、 7、 9もしくは 1 0を 2 5質量%添加した飼料を 8週間自由摂取させた。 飼料の 組成を表 5に示す。 必須脂肪酸不足を防ぐために、 すべての飼料に対して大豆油 を 3質量%添加した。 ビタミンおよびミネラルは、 ァメリ力栄養学会が推奨した ものを用い、 飼料への添加量はエネルギー密度により調整した。 実験食投与 8週 間後に各群 8匹ずつ解剖し、 内臓脂肪質量を測定した。 また、 皮下脂肪量を測定 するため、 屍体を凍結乾燥し脂肪含量をソックスレーを用いて測定した。 8週間 飼育したラットの結果を表 6に示す。 飼料摂取量、 終体重、 尾長は、 すべての試 験区で統計的に有意な差は見られなかった。 8週間飼育したラットの内臓脂肪量 および皮下脂肪量は、 油脂組成物 1、 6および 7群で統計的に有意に低い値を示 した。 動物試験の結果から、 油脂組成物を構成する全脂肪酸に占める中鎖脂肪酸 の割合、 および全トリグリセリドに占める、 中鎖脂肪酸残基を分子内に 2つ有す るトリグリセリ ドの割合が本発明の範囲内に入る本発明油脂組成物 1、 6、 7を 使用した場合には、 対照および比較例油脂組成物 9、 1 0を使用した場合に比し 、 体脂肪蓄積が少ないことが判明した。 表 5 飼料繊 Four-week-old male Wistar rats were treated with soybean oil (manufactured by Nisshin Oil Co., Ltd.) (对照) (triglyceride composition and fatty acid composition are shown in Table 4) or oil composition 1, 6, 7, 9 or 10 Was fed freely for 8 weeks. Table 5 shows the composition of the feed. To prevent the deficiency of essential fatty acids, 3% by mass of soybean oil was added to all feeds. The vitamins and minerals used were those recommended by the Ameri Society for Nutrition and the amount added to the feed was adjusted according to the energy density. Eight weeks after administration of the experimental diet, 8 animals were dissected in each group, and the visceral fat mass was measured. In order to measure the amount of subcutaneous fat, the cadaver was freeze-dried, and the fat content was measured using a Soxhlet. Table 6 shows the results of rats reared for 8 weeks. There was no statistically significant difference in feed intake, final body weight, or tail length in any of the test groups. The visceral fat amount and subcutaneous fat amount of the rats reared for 8 weeks showed statistically significantly lower values in the oil composition 1, 6 and 7 groups. Based on the results of animal tests, the ratio of medium-chain fatty acids in the total fatty acids constituting the oil and fat composition, and two medium-chain fatty acid residues in the total triglycerides in the molecule When the fats and oils compositions 1, 6 and 7 of the present invention whose triglyceride ratio falls within the range of the present invention are used, the body weight is higher than when the fat and oil compositions 9 and 10 of the control and comparative examples are used. Fat accumulation was found to be low. Table 5 Forage fiber
表 6 動«験の結果 (8週間飼育) Table 6 Test results (bred for 8 weeks)
注) データは、 平均値土標準誤差で表した。 Note) Data is shown as the average soil standard error.
*印;対照と比べて危険率 5%以下で有意な差あり, *: Significant difference at risk ratio 5% or less compared to control,
実施例 9 Example 9
油脂組成物を用いて調理試験と耐寒性試験を行った。 調理試験については、 発 煙、 泡立ち、 油の飛びハネ、 調理品の風味を検討した。 耐寒性試験は低温保管時 の外観を観察した。 油脂組成物サンプルとしては、 菜種油 (日清製油 (株) 製)A cooking test and a cold resistance test were performed using the oil / fat composition. In the cooking test, smoke emission, foaming, splashing of oil, and flavor of the cooked food were examined. Cold resistance test at low temperature storage Was observed. Rapeseed oil (manufactured by Nisshin Oil Co., Ltd.)
(対照) 、 油脂組成物 1、 油脂組成物 2、 油脂組成物 4、 油脂組成物 6、 油脂組 成物 8および菜種油と構成脂肪酸が質量比で力プリル酸/力プリン酸 = 3 / 1で ある MC Tとを 4 : 1 (質量比) で配合した油脂 (配合油) の 7種を用いた。 菜 種油および配合油のトリグリセリド組成および脂肪酸組成を表 4に示す。 (Control), fat composition 1, fat composition 2, fat composition 4, fat composition 6, fat composition 8, fat and oil composition and rapeseed oil and constituent fatty acids in a weight ratio of prillic acid / pyric acid = 3/1 Seven types of fats and oils (blended oils) were used in which a certain MCT was blended at a ratio of 4: 1 (mass ratio). Table 4 shows the triglyceride composition and fatty acid composition of rapeseed oil and blended oil.
調理試験の結果を表 7に示す。 調理試験の結果より、 油脂組成物を構成する全 脂肪酸に占める中鎖脂肪酸の割合、 およぴ全トリグリセリドに占める、 中鎖脂肪 酸残基を分子内に 2つ有するトリグリセリドの割合が本発明の範囲内に入る本発 明油脂組成物 1、 2、 4、 6、 8は、 通常の食用油と同等の調理適性を有するこ とが分った。 さらに、 油脂組成物を構成する全トリグリセリ ドに占める、 中鎖脂 肪酸残基を分子内に 3つ有するトリグリセリドの割合が 3質量%以下である油脂 組成物 1、 2、 4、 6は、 揚げ物調理時の安定性が高いことが分った。 特に、 乳 ィ匕剤を配合した油脂組成物 2は、 泡立ち抑制効果に優れていることが分った。 ま た、 同じ 7種のサンプルを、 5 °Cに 4 8時間静置し外観を観察した。 結果を表 7 に示す。 その結果、 油脂組成物 4では結晶の析出が見られたが、 他のサンプルは 透明な外観であった。 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. In particular, it was found that the oil / fat composition 2 containing the milky lantern had an excellent foaming suppressing effect. In addition, 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.
表 7 調理試験おょぴ耐寒性試験の結果 Table 7 Results of cooking test cold resistance test
3 1点;使用不可と評価した。 3 1 point; evaluated as unusable.
発煙:直径 2 4 c mのテフロン加工フライパンを予め 3 0秒加熱し、 サンプル油 を 1 5 g入れ、 さらに 3 0秒間加熱した。 その後、 野菜炒めの具をフライ パンに投入し、 3分間加熱した時点で塩とコショウを適量添カ卩した。 炒め 調理時の発煙を、 肉眼で観察した。 Smoke emission: A 24 cm diameter Teflon-coated frying pan was heated in advance for 30 seconds, 15 g of sample oil was added, and further heated for 30 seconds. After that, the stir-fry ingredients were put into a frying pan, and heated for 3 minutes. Stirring The smoke generated during cooking was visually observed.
泡立ち、 油ハネ、 風味:家庭用電気フライヤ一にサンプル油 6 0 0 gを入れ、Foaming, oil splash, flavor: 600 g of sample oil in a household electric fryer,
1 8 0 °Cで、 海老の天ぷら 4匹を投入し、 1分後の油の泡立ち、 油ハネを 観察した。 また、 調理した海老の天ぶらの風味を評価した。 At 180 ° C, four shrimp tempuras were introduced, and one minute later, oil foaming and oil splash were observed. In addition, the flavor of the cooked shrimp tempura was evaluated.
揚げ物安定性:家庭用電気フライヤ一にサンプル油 6 0 0 gを入れ、 1 8 0 °C で、 海老の天ぶらを 3 0分間揚げ、 ついでコロッケを 3 0分間揚げ、 最後 に鳥の唐揚を 3 0分間揚げた。 力二泡の発生度合いにより、 揚げ物調理に 対する安定性を評価した。 力二泡の発生が、 フライヤ 表面積の 1 0 0 % となった時点で揚げ物を中止した。 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.
耐寒性:低温保管時 (5 で4 8時間静置) の外観を観察した。 本発明の油脂組成物は、 体脂肪蓄積が少なく、 通常の食用油と同等の調理適性 を持ち、 さらに風味良好で安全性が高い。 Cold resistance: The appearance during cold storage (5 to 48 hours standing) was observed. 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.
Claims
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31624399A JP4733246B2 (en) | 1998-11-13 | 1999-11-08 | Oil composition |
| CNB008198403A CN1293176C (en) | 2000-08-22 | 2000-08-22 | Fat compositions |
| KR1020037002571A KR100661780B1 (en) | 2000-08-22 | 2000-08-22 | Fat and oil composition |
| PCT/JP2000/005606 WO2002016534A1 (en) | 1998-11-13 | 2000-08-22 | Fat compositions |
| HK04102416.8A HK1059448B (en) | 2000-08-22 | Fat compositions |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32366598 | 1998-11-13 | ||
| JP4930099 | 1999-02-26 | ||
| JP31624399A JP4733246B2 (en) | 1998-11-13 | 1999-11-08 | Oil composition |
| PCT/JP2000/005606 WO2002016534A1 (en) | 1998-11-13 | 2000-08-22 | Fat compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2002016534A1 true WO2002016534A1 (en) | 2002-02-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/JP2000/005606 Ceased WO2002016534A1 (en) | 1998-11-13 | 2000-08-22 | Fat compositions |
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| Country | Link |
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| JP (1) | JP4733246B2 (en) |
| WO (1) | WO2002016534A1 (en) |
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| JP2000309794A (en) | 2000-11-07 |
| JP4733246B2 (en) | 2011-07-27 |
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