JP2000309794A - Fat and oil composition - Google Patents

Fat and oil composition

Info

Publication number
JP2000309794A
JP2000309794A JP11316243A JP31624399A JP2000309794A JP 2000309794 A JP2000309794 A JP 2000309794A JP 11316243 A JP11316243 A JP 11316243A JP 31624399 A JP31624399 A JP 31624399A JP 2000309794 A JP2000309794 A JP 2000309794A
Authority
JP
Japan
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.)
Granted
Application number
JP11316243A
Other languages
Japanese (ja)
Other versions
JP4733246B2 (en
Inventor
Hiroyuki Takeuchi
弘幸 竹内
Megumi Itakura
めぐみ 板倉
Fumie Kubota
文江 久保田
Nobuo Taguchi
信夫 田口
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 Oil Mills Ltd
Original Assignee
Nisshin Oil Mills Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nisshin Oil Mills Ltd filed Critical Nisshin Oil Mills Ltd
Priority to JP31624399A priority Critical patent/JP4733246B2/en
Priority to TW89116953A priority patent/TW589154B/en
Priority to PCT/JP2000/005606 priority patent/WO2002016534A1/en
Publication of JP2000309794A publication Critical patent/JP2000309794A/en
Application granted granted Critical
Publication of JP4733246B2 publication Critical patent/JP4733246B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, 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

Abstract

PROBLEM TO BE SOLVED: To provide a highly safe fat and oil composition which causes little accumulation of body fat, has usefulness in cooking equivalent to that of a common edible oil, and has a good flavor. SOLUTION: Provided is a fat and oil composition mainly consisting of triglycerides, wherein the rate of medium-chain fatty acids account for 5-23 mass % of all the fatty acids that constitute the composition, and the rate of triglycerides having two medium-chain fatty acid residues in the molecule is 1-20 mass %. It is desirable that the medium-chain fatty acids are 6-12C saturated fatty acids, and that the rate of triglycerides having three medium- chain fatty acid residues in the molecule is at most 3 mass %.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【発明の属する技術分野】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、
か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。TECHNICAL FIELD The present invention relates to an edible oil / fat composition. More specifically, body fat accumulation is low,
The present invention also relates to an oil and fat composition having excellent cooking suitability and flavor as an edible oil.

【０００２】[0002]

【従来の技術】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
であることから、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。2. Description of the Related Art Obesity is a condition in which body fat is excessively accumulated, and is liable to be accompanied by many diseases, including metabolic disorders such as diabetes and hyperlipidemia, circulatory diseases such as hypertension and ischemic heart disease. Is well known. According to the results of the National Nutrition Survey conducted by the Ministry of Health and Welfare, one in seven adults is obese, so obesity is a familiar problem not only in Europe and the United States but also in Japan. Fat in the diet is one of the nutrients most associated with the accumulation of body fat, and excessive fat intake can lead to obesity. However, fat has a unique taste, and a diet with extremely reduced fat tends to be less satisfactory. In addition, edible oil is indispensable as a heating medium when fry or stir-fry cooking.

【０００３】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***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３６００１８６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、低カロリー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巻、第
４号、２３〜３３頁、１９９６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クリ
ーム、ベーカリー製品、ケーキ等を作ることが可能であ
る。しかし、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。In order to overcome this situation, so-called fat substitutes have been developed. However, none of them is 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 snacks have been approved for use, and potato chips using sucrose fatty acid esters have already been marketed, but products using sucrose fatty acid esters include `` causing abdominal cramps and loose stools It is required to indicate "possible" and "inhibit the absorption of fat-soluble vitamins". The energy density of proteins and carbohydrates is less than half that of fat. Therefore,
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, 1996). By using these fat substitutes, it is possible to produce reduced-calorie ice cream, bakery products, cakes, and the like. However, it has a drawback that it has poor heat resistance and cannot be used as a heating medium for frying or stir-fry.

【０００４】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．Ｌｉｐｉｄ Ｒｅｓ．３
７、７０８−７２６（１９９６））。しかし、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８−６０１８０号公報および特開平１０−１７６１８
１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。しかし、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８−２
６９４７８号公報には、ジグリセリドおよびトリグリセ
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
公報および特開平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。[0004] 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, triglycerides composed of short-chain fatty acids have a peculiar smell, so that available cooked products are limited and are not suitable as versatile edible oils. In addition, it is known that medium-chain fatty acids are liable to be converted into energy, and thus have a low body fat accumulation (J. Lipid Res. 3) .
7 , 708-726 (1996)). However, although triglycerides composed of medium-chain fatty acids are inherently highly safe, they have been reported to cause symptoms such as diarrhea, nausea, abdominal pain, heartburn, and anorexia when taken in large quantities at once. . JP-A-4-300826, JP-A-8-60180 and JP-A-10-17618
No. 1 discloses an oil / fat composition containing diglyceride as an active ingredient and having low body fat accumulation. However, the safety of fats and oils compositions rich in diglycerides is not completely 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, JP-A-8-2
Japanese Patent Application Laid-Open No. 69478 discloses an oil / fat composition with a low body fat accumulation containing 31% by mass or more of a triglyceride containing two medium-chain fatty acid residues in a molecule in an oil / fat composition composed of diglyceride and triglyceride. . Since the present invention also uses diglyceride as an active ingredient, it has the same problems as those of JP-A-4-300826, JP-A-8-60180 and JP-A-10-176181. In addition, there are drawbacks such as low smoke point due to containing a large amount of medium-chain fatty acids and remarkable foaming, which is not suitable for frying.

【０００５】[0005]

【発明が解決しようとする課題】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。SUMMARY OF THE INVENTION An object of the present invention is to provide an oil / fat composition which has little body fat accumulation, has the same cooking aptitude as ordinary edible oil, and has a good flavor and high safety. .

【０００６】[0006]

【課題を解決するための手段】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。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５〜２３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１〜２０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６〜１２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２０質量％以下であることが好まし
い。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。また本発明は、
か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い調理適性および保存安定性
を有する調理用油脂組成物に関する。Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that the ratio of medium-chain fatty acid residues to all fatty acid residues and the ratio of medium-chain fatty acid residues to all triglycerides are small. The present inventors have found that the proportion of triglycerides having two chain fatty acid residues in the molecule is closely related to the degree of body fat accumulation, and completed the present invention. That is, the present invention relates to an oil / fat composition mainly comprising 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 the medium-chain fatty acid residues in the total triglycerides. Wherein the proportion of triglycerides having two in the molecule is 1 to 20% by mass,
The present invention relates to an oil / fat composition having a low body fat accumulation. The medium-chain fatty acid is preferably a saturated fatty acid having 6 to 12 carbon atoms. In addition, the proportion of triglycerides having three medium-chain fatty acid residues in the molecule in all triglycerides constituting the oil or fat composition is preferably 3% by weight or less. Further, it is preferable that the ratio of the long-chain saturated fatty acid to the full-length chain fatty acid constituting the fat and oil composition is 20% by mass or less. 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. The present invention also provides
The present invention relates to a cooking fat or oil composition containing such a fat or oil composition, which has little body fat accumulation and has cooking aptitude and storage stability comparable to that of ordinary cooking oil.

【０００７】[0007]

【発明の実施の形態】以下に本発明を詳しく説明する。
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８５質量％以上、好ましくは９５質量％以上含まれて
いることを意味するものとする。本発明で中鎖脂肪酸と
は炭素数が６〜１２の脂肪酸、特に飽和脂肪酸をいうも
のとする。例としては、カプロン酸、カプリル酸、カプ
リン酸、ラウリン酸が挙げられ、炭素数が８〜１０の飽
和脂肪酸、特にカプリル酸および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１４以上、好まし
くは１４〜２２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１４以上、好ましく
は１４〜２２のもの、例えばミリスチン酸、パルミチン
酸、ステアリン酸、アラキジン酸、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、ヘキサデカ
トリエン酸、ヘプタデセン酸、オレイン酸、リノール
酸、α−リノレン酸、γ−リノレン酸、オクタデカテト
ラエン酸、イコセン酸、イコサジエン酸、イコサトリエ
ン酸、イコサテトラエン酸、アラキドン酸、イコサペン
タエン酸、ドコセン酸、ドコサジエン酸、ドコサペンタ
エン酸、ドコサヘキサエ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Ｏ
Ｈを取った基である。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
The fat and oil composition of the present invention mainly comprises triglycerides. "Mainly" shall mean that the fat or oil composition contains 85% by mass or more, preferably 95% by mass or more of triglyceride. 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 caproic acid, caprylic acid, capric acid, lauric acid, with saturated fatty acids having 8 to 10 carbon atoms being preferred, especially caprylic acid and capric acid. In the present invention, long-chain fatty acids refer to saturated and unsaturated fatty acids having 14 or more carbon atoms, preferably 14 to 22 carbon atoms. As long-chain fatty acids, those having 14 or more carbon atoms, preferably 14 to 22 carbon atoms, such as long-chain saturated fatty acids such as myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, and cerotic acid, and myristoleic acid Pentadecenoic acid, palmitoleic acid, hexadecatrienoic acid, heptadecenoic acid, oleic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, octadecatetraenoic acid, icosenoic acid, icosadienoic acid, icosatrienoic acid, icosatetraenoic acid, arachidone Long-chain unsaturated fatty acids such as acid, icosapentaenoic acid, docosenoic acid, docosadienoic acid, docosapentaenoic acid, and docosahexaenoic acid. The fatty acid residue is obtained by converting the fatty acid to the carboxyl group O
It is the group that took H.

【０００８】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〜
２３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
１〜２０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６〜２３質量％であり、上記
トリグリセリドの割合は好ましくは３〜２０質量％であ
る。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。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２０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２０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。[0008] In the fat and oil composition of the present invention, the ratio of medium-chain fatty acids to the total fatty acids constituting the fat and oil composition is 5 to 5.
It is necessary that the proportion of triglycerides having two medium-chain fatty acid residues in the molecule is 23% by mass and 1 to 20% by mass of the total triglycerides. 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. Further, the proportion of triglycerides having three medium-chain fatty acid residues in the molecule in all triglycerides constituting the oil or fat composition is preferably 3% by mass or less, more preferably 2% by mass or less, It is even more preferred that the content be 1% by mass or less. If this proportion exceeds 3% by mass, smoke and foaming increase during cooking, making it unsuitable for frying fats and oils. When the proportion is 1% by mass or less, remarkable improvement in smoking and foaming can be seen. Further, the proportion of long-chain saturated fatty acids in the full-length chain fatty acids constituting the oil / fat composition is preferably 20% by mass or less, and preferably 1% by mass or less.
The content is more preferably 5% by mass or less, and even more preferably 7% by mass or less. When this proportion exceeds 20% by mass, stability at low temperatures is reduced, and crystallization of fats and oils is observed in the fats and oils composition.

【０００９】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、ナトリウ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。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／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／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。The fat and oil composition of the present invention having a low body fat accumulation is prepared by appropriately mixing a fat and oil as a raw material and a medium-chain fatty acid, and subjecting the mixture to a transesterification reaction using sodium methylate as a catalyst or in the presence of a lipolytic enzyme. In this case, the ratio of the medium-chain fatty acids in the total fatty acids constituting the oil and fat composition, and the ratio of the triglycerides having two medium-chain fatty acid residues in the molecule in the total triglycerides are within the specific range. By adjusting the transesterification reaction. In the transesterification reaction,
In addition to the above adjustments, the proportion of triglycerides having three medium-chain fatty acid residues in the molecule in the total triglycerides constituting the fat / oil composition, and / or the long-chain saturated fatty acids in the full-length chain fatty acids constituting the fat / oil composition By adjusting the ratio to fall within the above-mentioned specific range, it is possible to obtain an oil / fat composition having less body fat accumulation, reduced smoke and frothing during frying, and / or excellent in low-temperature stability.

【００１０】原料油脂としては、通常の食用油脂、例え
ば大豆油、菜種油、高オレイン酸菜種油、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、高オレイン酸紅花油、ひまわり油、高オレイン酸
ひまわり油、綿実油、ブドウ種油、マカデミアナッツ
油、ヘーゼルナッツ油、カボチャ種子油、クルミ油、椿
油、茶実油、エゴマ油、ボラージ油、オリーブ油、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、アザラシ油、
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、分別油脂等が挙げられ
る。As raw material fats and oils, common 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, high oleic safflower oil, Sunflower oil, high oleic sunflower oil, cottonseed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, walnut 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, tallow, lard, chicken fat, milk fat, fish oil, seal oil,
Algae oils, these fats and oils which have been made less saturated by quality improvement, hydrogenated fats and oils, and fractionated fats and oils are exemplified.

【００１１】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
よりエステル化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（ＭｅｄｉｕｍＣ
ｈａｉｎ Ｔｒｉｇｌｙｃｅｒｉｄｅｓ）と称せられ
る、ヤシ油分解脂肪酸等の炭素数が８〜１０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、例えばカプリル酸／カプリン酸＝６０／４０〜７５
／２５（質量比）のトリグリセリドが好適に使用でき
る。Although the 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 esterification reaction by a conventional method can be used, and generally, MCT (Medium C)
triglycerides, which are composed of saturated fatty acids having 8 to 10 carbon atoms such as coconut oil-decomposed fatty acids, such as caprylic acid / capric acid = 60 / 40-75.
/ 25 (mass ratio) triglyceride can be suitably used.

【００１２】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 fat and oil composition, the proportion of triglycerides having two medium-chain fatty acid residues in the molecule in all of the triglycerides, and, if necessary, the composition of the fat and oil. The proportion of triglycerides having three medium-chain fatty acid residues in the molecule in all the constituent triglycerides and, if necessary, the proportion of long-chain saturated fatty acids in the full-length chain fatty acids in the fat and oil composition, The ratio can be adjusted by adjusting the use ratio between the raw oil and fat and the medium-chain fatty acid in consideration of the oil and fat composition, and measuring the triglyceride composition of the reaction product during the transesterification reaction.

【００１３】ナトリウ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／後者の質量比＝７１／２９〜９７／３
で混合し、混合物を１００ｍｍＨｇ以下の減圧下で８０
〜１２０℃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。これにナトリウムメチラート０．
０２〜０．５質量％を添加し、常圧・窒素気流下あるい
は１０ｍｍＨｇ以下の減圧下で１０〜６０分間、８０〜
１２０℃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 is carried out using sodium methylate as a catalyst, the mass ratio of the raw material fats and oils to the medium-chain fatty acid triglycerides is 71/29 to 97/3.
At 80 ° C. under a reduced pressure of 100 mmHg or less.
Heat to ~ 120 ° C to remove gaseous components and moisture contained in the raw material mixture. Add sodium methylate to this.
And then added under normal pressure and nitrogen flow or under reduced pressure of 10 mmHg or less for 10 to 60 minutes.
The transesterification reaction is performed by stirring at 120 ° C. The 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, perform sufficient washing with water to remove the catalyst and excess acid, and after drying,
The reaction product is decolorized and deodorized by a conventional method.

【００１４】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／後者の質量比＝７１／２９〜９
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４０〜１００℃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０．００５〜１
０質量％の割合で添加し、２〜４８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
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。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、キャンデイダ属、リゾプス属、ムコール
属またはシュードモナス属由来のリパーゼや、肝臓由来
のホスホリパーゼＡ等が挙げられるが、特にキャンデイ
ダ属またはリゾプス属由来のリパーゼが好ましい。When a transesterification reaction is carried out using a lipolytic enzyme, the raw material fat and the medium-chain fatty acid or medium-chain fatty acid triglyceride are prepared in the former / latter mass ratio = 71 / 29-9.
The mixture is mixed at 7/3, and the temperature is adjusted to the range of 40 to 100 ° C., which is the reaction temperature at which the activity of the lipolytic enzyme is sufficiently exhibited. The lipolytic enzyme is added to the raw material mixture in an amount of 0.005 to 1
It is added at a ratio of 0% by mass, and the transesterification reaction is performed within a range of 2 to 48 hours. This reaction is desirably carried out in a nitrogen stream at normal pressure. The 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 a medium-chain fatty acid is used, free fatty acids are removed by a thin-film evaporator after the reaction is stopped. If the transesterification reaction using the lipolytic enzyme is insufficient, medium-chain fatty acid
The proportion of triglycerides that are present. 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 undesirably causes a large amount of smoke and foaming during continuous frying. Examples of the lipolytic enzyme include lipases derived from the genera Alcaligenes, Candida, Rhizopus, Mucor and Pseudomonas, and phospholipase A derived from the liver, and lipases derived from the genus Candida or Rhizopus are particularly preferred.

【００１５】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、オリーブ、亜麻仁、ひまわり、紅花、つば
き、綿実、クヘアから抽出によって得ることも可能であ
る。[0015] The oil / fat composition of the present invention may also be a plant breeded to produce the oil / fat composition of the present invention using a genetic recombination technique, for example, soybean, rapeseed, corn, palm, palm, olive. , Flax seeds, sunflowers, safflowers, camellia, cottonseed, and khair can be obtained by extraction.

【００１６】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。ショ糖脂肪酸エステルはショ糖と炭素数６
〜２２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３７．５〜８７．５％
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８５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６〜２２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２０
〜８０％であることが好ましい。モノグリセリド、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
〜２２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でエステル化したコハク酸モノグリセリドが好ま
しい。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
６〜２２の飽和もしくは不飽和脂肪酸とのモノ〜トリエ
ステルが好ましい。上記で炭素数６〜２２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。By including an emulsifier in 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 or oil composition is 0.1% as a whole.
To 6% by mass, more preferably 0.3 to 5% by mass. Sucrose fatty acid ester is sucrose and carbon number 6
To 22 saturated or unsaturated fatty acids, but the average degree of substitution of all hydroxyl groups is 37.5 to 87.5%.
It is preferred that the proportion of polyesters equal to or higher than triesters in all sucrose fatty acid esters 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.
It is preferably about 80%. Monoglyceride and diglyceride are glycerin or diglycerin and carbon number 6
Monoesters with ~ 22 saturated or unsaturated fatty acids;
Each includes diesters, but monoglycerides are preferred. As the succinic monoglyceride, succinic acid and monoglyceride or diglyceride are used in a ratio of 3: 1 to 0.
Succinic monoglycerides esterified 1: 1 are preferred. The sorbitol fatty acid ester and the sorbitan fatty acid ester are preferably mono- to tri-esters of sorbitol or sorbitan and a saturated or unsaturated fatty acid having 6 to 22 carbon atoms. Examples of the saturated or unsaturated fatty acids having 6 to 22 carbon atoms described above include those exemplified as the medium-chain fatty acids and the long-chain fatty acids.

【００１７】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％、コハク酸モノグリセリドを
０．０１〜２質量％、およびモノグリセリド、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。With respect to the combined use of emulsifiers, 0.1 to 3% by mass of at least one selected from sucrose fatty acid esters and polyglycerin fatty acid esters and 0.1% by mass of succinic acid monoglyceride are used in the oil and fat composition of the present invention. 0.1 to 2% by mass, and 0.1 to 3% of at least one selected from monoglyceride, diglyceride, sorbitol fatty acid ester and sorbitan fatty acid ester.
It is most preferable to add and contain the emulsifier so that the total amount of the emulsifier is 0.3 to 5% by mass in order to further improve the suitability for frying, especially the suppression of foaming.

【００１８】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。か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、アスコルビン酸脂肪酸エステル、リグ
ナン、コエンザイム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、アスコルビン酸脂肪酸エステル、リグナン、コエン
ザイムＱ、リン脂質、オリザノール等が挙げられる。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 cooking oil / fat compositions. Examples of such additives include polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, vitamin E, vitamin E, and the like for the purpose of improving storage stability, improving oxidative stability, improving thermal stability, suppressing crystallization at low temperatures, and the like. Ascorbic acid fatty acid ester, lignan, coenzyme Q, phospholipid, oryzanol, diglyceride, etc., vitamin E, ascorbic acid fatty acid ester, which are expected to prevent adult diseases, prevent lifestyle-related diseases, suppress in vivo oxidation, and prevent obesity. Lignan, coenzyme Q, phospholipids, oryzanol and the like.

【００１９】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。The cooking oil and fat composition of the present invention has a flavor equal to or higher than that of generally available edible oils such as rapeseed oil, corn oil, safflower oil, and soybean oil.
It can be used not only for cooking fried foods and marinades, but also for dressings, mayonnaise, margarine, confectioneries, cakes, beverages, etc., which are foods containing fats and oils. The flavor characteristics vary depending on the type of cooked product, but it is possible to make a refreshing dish that takes advantage of the taste of the ingredients. In addition, the degree of splash of the oil during frying is equal to or less than that of ordinary edible 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.

【００２０】[0020]

【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って限定されるもので
はない。 実施例１ 菜種白絞油（日清製油（株）製）８０質量部と構成脂肪
酸が質量比でカプリル酸／カプリン酸＝３／１であるＭ
ＣＴ２０質量部とを混合後、減圧下１２０℃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℃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、商品名リョートーシ
ュガーエステルＯ−１７０）２．５質量％、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％、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よび脂肪酸組成をそれぞれカラムＧ
Ｓ−１を用いたガスクロマトグラフィーおよび「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。EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto. Example 1 M in which rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) is 80 parts by mass and the constituent fatty acids are caprylic acid / capric acid = 3/1 by mass ratio.
After mixing with 20 parts by mass of CT, the mixture was stirred at 120 ° C. under reduced pressure,
Degassing and dehydration 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 is washed with water, dried and then decolorized and deodorized by a conventional method to obtain an oil / fat composition 1
I got Further, 2.5% by mass of sucrose fatty acid ester (manufactured by Mitsubishi Chemical Foods, Inc., trade name: Ryoto Sugar Ester O-170) 2.5% by mass, and succinic acid monoglyceride (manufactured by RIKEN Vitamin Co., Ltd.) Product name Poem B
-10) 0.1% by mass, sorbitan fatty acid ester (Poem O-80, manufactured by Riken Vitamin Co., Ltd.) 1% by mass
Was added to obtain an oil / fat composition 2. The column G
The measurement was carried out according to gas chromatography using S-1 and "Standard Fatty Acid Analysis Test Method (1996)" (the same applies to the following Examples and Comparative Examples). Table 1 shows the results.

【００２１】実施例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／カプリン酸＝３／１である
ＭＣＴ１５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℃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。Example 2 Lipase QL (name sugar) was added to a mixture of 85 parts by mass of soybean salad oil (manufactured by Nisshin Oil Co., Ltd.) and 15 parts by mass of MCT in which the constituent fatty acids were in a mass ratio of caprylic acid / capric acid = 3/1. 0.1 part by mass (manufactured by Sangyo Co., Ltd.)
The transesterification was performed for hours. The enzyme was filtered off from the reaction product, 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.

【００２２】実施例３ パーム油（日清製油（株）製）７７質量部と質量比でカ
プリル酸／カプリン酸＝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ＱＬ（名糖産業
（株）製）０．１質量部を添加し、攪拌下６０℃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。Example 3 Medium-chain fatty acid mixture 23 of caprylic acid / capric acid = 1/1 by mass ratio of 77 parts by mass of palm oil (manufactured by Nisshin Oil Co., Ltd.)
After mixing, 0.1 part by mass of Lipase QL (manufactured by Meito Sangyo Co., Ltd.) was added to the mixture, and the mixture was stirred at 60 ° C. for 15 minutes.
The transesterification was performed for hours. 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 an oil / fat composition 4. Oil composition 4
Table 1 shows the triglyceride composition and fatty acid composition of.

【００２３】実施例４ コーン油（日清製油（株）製）７７質量部と質量比でカ
プリル酸／カプリン酸＝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ＱＬ（名糖産業
（株）製）０．１質量部を添加し、攪拌下６０℃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び脂肪酸組成を表１に示す。Example 4 Medium-chain fatty acid mixture 23 of caprylic acid / capric acid = 1/1 by mass ratio to 77 parts by mass of corn oil (manufactured by Nisshin Oil Co., Ltd.)
After mixing, 0.1 part by mass of Lipase QL (manufactured by Meito Sangyo Co., Ltd.) was added to the mixture, and the mixture was stirred at 60 ° C. for 15 minutes.
The transesterification was performed for hours. 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 an oil / fat composition 5. Oil composition 5
Table 1 shows the triglyceride composition and fatty acid composition of.

【００２４】実施例５ 菜種白絞油（日清製油（株）製）９３質量部と構成脂肪
酸が質量比でカプリル酸／カプリン酸＝３／１であるＭ
ＣＴ７質量部とを混合後、減圧下１２０℃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℃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び脂肪
酸組成を表２に示す。EXAMPLE 5 93 parts by mass of rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) and capric acid / capric acid = 3/1 by mass ratio of the constituent fatty acids M
After mixing with 7 parts by mass of CT, the mixture was stirred at 120 ° C. under reduced pressure to perform deaeration and 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 is washed with water, dried and then decolorized and deodorized by a conventional method to obtain an oil / fat composition 6
I got Table 2 shows the triglyceride composition and fatty acid composition of Fat / Oil Composition 6.

【００２５】実施例６ 菜種白絞油（日清製油（株）製）９０質量部と構成脂肪
酸が質量比でカプリル酸／カプリン酸＝３／１であるＭ
ＣＴ１０質量部とを混合後、減圧下１２０℃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℃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
７を得た。油脂組成物７のトリグリセリド組成および脂
肪酸組成を表２に示す。Example 6 M in which rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) is 90 parts by mass and the constituent fatty acids are caprylic acid / capric acid = 3/1 by mass ratio.
After mixing with 10 parts by mass of CT, the mixture was stirred at 120 ° C. under reduced pressure,
Degassing and dehydration were performed. To this, 0.1 part by mass of sodium methylate was added as a catalyst.
A random transesterification reaction was performed for minutes. The reaction product was washed with water, dried, decolorized and deodorized by a conventional method to obtain an oil / fat composition 7. Table 2 shows the triglyceride composition and the fatty acid composition of the fat and oil composition 7.

【００２６】実施例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℃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。Example 7 Lipase QL (Meito Sangyo Co., Ltd.) was added to the same mixture as in Example 2.
0.1 parts by mass) and a transesterification reaction was performed at 60 ° C. for 3 hours with stirring. The enzyme is separated from the reaction product by filtration, and the filtrate is washed with water, dried, decolorized and deodorized to obtain the oil / fat composition 8
I got Table 2 shows the triglyceride composition and the fatty acid composition of the fat and oil composition 8.

【００２７】比較例１ 菜種白絞油（日清製油（株）製）７５質量部と構成脂肪
酸が質量比でカプリル酸／カプリン酸＝３／１であるＭ
ＣＴ２５質量部とを混合後、減圧下１２０℃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℃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９
を得た。油脂組成物９のトリグリセリド組成および脂肪
酸組成を表３に示す。Comparative Example 1 M in which rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) is 75 parts by mass and the constituent fatty acids are caprylic acid / capric acid = 3/1 by mass ratio.
After mixing with 25 parts by mass of CT, the mixture was stirred at 120 ° C. under reduced pressure,
Degassing and dehydration 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 is washed with water, dried and then decolorized and deodorized by a conventional method to obtain a fat and oil composition 9
I got Table 3 shows the triglyceride composition and fatty acid composition of the oil composition 9.

【００２８】比較例２ 菜種白絞油（日清製油（株）製）９７質量部と構成脂肪
酸が質量比でカプリル酸／カプリン酸＝３／１であるＭ
ＣＴ３質量部とを混合後、減圧下１２０℃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℃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
０を得た。油脂組成物１０のトリグリセリド組成および
脂肪酸組成を表３に示す。Comparative Example 2 M in which rapeseed white squeezed oil (manufactured by Nisshin Oil Co., Ltd.) is 97 parts by mass and the constituent fatty acids are caprylic acid / capric acid = 3/1 by mass ratio.
After mixing with 3 parts by mass of CT, the mixture was stirred at 120 ° C. under reduced pressure to perform deaeration and dehydration. 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 is washed with water, dried and then decolorized and deodorized by a conventional method to obtain an oil / fat composition 1
0 was obtained. Table 3 shows the triglyceride composition and the fatty acid composition of the fat and oil composition 10.

【００２９】[0029]

【表１】 [Table 1]

【００３０】[0030]

【表２】 [Table 2]

【００３１】[0031]

【表３】 [Table 3]

【００３２】[0032]

【表４】 [Table 4]

【００３３】実施例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）（対照）（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１０を２５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、アメリカ栄養学会が
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、１０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。Example 8 Four-week-old male Wistar rats were soybean oil (manufactured by Nisshin Oil Co., Ltd.) (control) (triglyceride composition and fatty acid composition are shown in Table 4) or oil / fat compositions 1, 6, The feed to which 7, 9, or 10 was added in an amount of 25% by mass was freely taken for 8 weeks. Table 5 shows the composition of the feed. To prevent the deficiency of essential fatty acids, 3% by weight of soybean oil was added to all feeds. The vitamins and minerals used were those recommended by the American Nutrition Society, and the amount added to the feed was adjusted according to the energy density. Eight weeks after the 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 bred for 8 weeks.
Shown in There was no statistically significant difference in feed intake, final body weight, and tail length in all test groups. The visceral fat amount and subcutaneous fat amount of the rats bred for 8 weeks showed statistically significantly lower values in the oil composition 1, 6, and 7 groups. From the results of animal tests, 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 are within the scope of the present invention. The present fat and oil composition 1 of the present invention,
It was found that the body fat accumulation was smaller when using Nos. 6 and 7 than when using the control and comparative fat and oil compositions 9 and 10.

【００３４】[0034]

【表５】 [Table 5]

【００３５】[0035]

【表６】 [Table 6]

【００３６】実施例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）（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カプリル酸／カプリン酸
＝３／１であるＭＣＴ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。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、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、
乳化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℃に４８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。Example 9 A cooking test and a cold resistance test were performed using the oil / fat composition. Regarding the cooking test, smoke emission, foaming, flying splash of oil, and flavor of the cooked product were examined. In the cold resistance test, the appearance during low-temperature storage was observed. The oil / fat composition samples include rapeseed oil (manufactured by Nisshin Oil Co., Ltd.) (control), oil / fat composition 1, oil / fat composition 2, oil / fat composition 4, oil / fat composition 6, oil / fat composition 8, rapeseed oil and constituent fatty acids Were mixed with MCT having a mass ratio of caprylic acid / capric acid = 3/1 at a ratio of 4: 1 (mass ratio). Table 4 shows the triglyceride composition and fatty acid composition of the rapeseed oil and the blended oil. Table 7 shows the results of the cooking test. From the results of the cooking test, the proportion of medium-chain fatty acids in the total fatty acids constituting the fat composition,
And the ratio of the triglyceride having two medium-chain fatty acid residues in the molecule to the total triglyceride is within the scope of the present invention. It was found to have comparable cookability. Furthermore, occupy in all the triglycerides constituting the oil and fat composition,
Fat compositions 1, 2, 4, 6 wherein the proportion of triglycerides having three medium-chain fatty acid residues in the molecule is 3% by mass or less.
Was found to have high stability during fried food cooking. In particular,
It was found that the oil and fat composition 2 containing the emulsifier had an excellent foaming suppressing effect. Also, the same seven samples
It was left 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 oil / fat composition 4, but the other samples had a transparent appearance.

【００３７】[0037]

【表７】 [Table 7]

【００３８】発煙：直径２４ｃｍのテフロン加工フライ
パンを予め３０秒加熱し、サンプル油を１５ｇ入れ、さ
らに３０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
量添加した。炒め調理時の発煙を、肉眼で観察した。 泡立ち、油ハネ、風味：家庭用電気フライヤーにサンプ
ル油６００ｇを入れ、１８０℃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、調理した海老の天ぷらの風味を評価した。 揚げ物安定性：家庭用電気フライヤーにサンプル油６０
０ｇを入れ、１８０℃で、海老の天ぷらを３０分間揚
げ、ついでコロッケを３０分間揚げ、最後に鳥の唐揚を
３０分間揚げた。カニ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。カニ泡の発生が、フライ
ヤー表面積の１００％となった時点で揚げ物を中止し
た。 耐寒性：低温保管時（５℃で４８時間静置）の外観を観
察した。Smoke: A Teflon-coated frying pan having a diameter of 24 cm was heated in advance for 30 seconds, 15 g of a sample oil was added, and further heated for 30 seconds. Then, the stir-fry tool was put into a frying pan, and when heated for 3 minutes, appropriate amounts of salt and pepper were added. Smoke emission during stir-fry cooking was visually observed. Foaming, oil splash, flavor: 600 g of the sample oil was placed in a household electric fryer, and four shrimp tempuras were added at 180 ° C., and after 1 minute, oil foaming and oil splash were observed. The flavor of the cooked shrimp tempura was also evaluated. Frying stability: 60 sample oils on a home electric fryer
After adding 0 g, the shrimp tempura was fried for 30 minutes at 180 ° C., then the croquettes were fried for 30 minutes, and finally the fried chicken was fried for 30 minutes. The stability to fried food cooking was evaluated based on the degree of crab foam generation. The frying was stopped when the generation of crab foam reached 100% of the fryer surface area. Cold resistance: The external appearance was observed during low-temperature storage (left at 48C for 5 hours).

【００３９】[0039]

【発明の効果】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。Industrial Applicability The oil / fat composition of the present invention has a low body fat accumulation, has cooking aptitude equivalent to that of ordinary edible oil, and has good flavor and high safety.

───────────────────────────────────────────────────── フロントページの続き (72)発明者 田口 信夫 神奈川県横須賀市浦賀町５−42−172 Ｆターム(参考） 4B026 DC07 DK01 DK03 DK04 4H059 BA26 BA30 BA33 BA35 BB02 BB03 BB15 BB22 BB44 BB45 BC03 BC13 CA37 CA51 DA09 EA01 EA11 EA40  ────────────────────────────────────────────────── ─── Continuing on the front page (72) Nobuo Taguchi 5-42-172 Uraga-cho, Yokosuka-shi, Kanagawa F-term (reference) 4B026 DC07 DK01 DK03 DK04 4H059 BA26 BA30 BA33 BA35 BB02 BB03 BB15 BB22 BB44 BB45 BC03 BC13 CA37 CA51 DA09 EA01 EA11 EA40

Claims (6)

【特許請求の範囲】[Claims] 【請求項１】 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５〜２３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１〜２０質量％であることを特
徴とする油脂組成物。An oil / fat composition mainly comprising 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 the medium-chain fatty acid residues in the total triglycerides. The ratio of the triglyceride which has two in a molecule | numerator is 1-20 mass%, The fats-and-oils composition characterized by the above-mentioned. 【請求項２】 中鎖脂肪酸が炭素数６〜１２の飽和脂肪
酸である請求項１記載の油脂組成物。2. The fat or oil composition according to claim 1, wherein the medium-chain fatty acid is a saturated fatty acid having 6 to 12 carbon atoms. 【請求項３】 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％以下である請求項１または２
記載の油脂組成物。3. The ratio of triglycerides having three medium-chain fatty acid residues in the molecule to all triglycerides constituting the oil or fat composition is 3% by mass or less.
The fat and oil composition as described in the above. 【請求項４】 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２０質量％以下である請求
項１〜３のいずれかに記載の油脂組成物。4. The fat or oil composition according to claim 1, wherein the proportion of the long-chain saturated fatty acid in the full-length fatty acid constituting the fat or oil composition is 20% by mass or less. 【請求項５】 該油脂組成物に対して、いずれも乳化剤
として、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％、コハク酸モノグリセリドを０．０１〜２質量
％、およびモノグリセリド、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、含有させた請
求項１〜４のいずれかに記載の油脂組成物。5. The oil / fat composition according to claim 1, wherein at least one selected from sucrose fatty acid esters and polyglycerin fatty acid esters is used as an emulsifier in an amount of from 0.1 to 3%.
% By mass, 0.01 to 2% by mass of succinic monoglyceride, 0.1 to 3% by mass of at least one selected from monoglyceride, diglyceride, sorbitol fatty acid ester and sorbitan fatty acid ester, and the total amount of the emulsifier is 0.3 The fat or oil composition according to any one of claims 1 to 4, wherein the fat or oil composition is contained so as to be 5 to 5% by mass. 【請求項６】 請求項１〜５のいずれかに記載の油脂組
成物を含有する調理用油脂組成物。6. An oil / fat composition for cooking comprising the oil / fat composition according to any one of claims 1 to 5.
JP31624399A 1998-11-13 1999-11-08 Oil composition Expired - Lifetime JP4733246B2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP31624399A JP4733246B2 (en) 1998-11-13 1999-11-08 Oil composition
TW89116953A TW589154B (en) 1998-11-13 2000-08-21 Oil composition
PCT/JP2000/005606 WO2002016534A1 (en) 1998-11-13 2000-08-22 Fat compositions

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP1998323665 1998-11-13
JP10-323665 1998-11-13
JP32366598 1998-11-13
JP1999049300 1999-02-26
JP4930099 1999-02-26
JP11-49300 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

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2010171346A Division JP2010279381A (en) 1998-11-13 2010-07-30 Oil or fat composition and method for producing oil or fat composition

Publications (2)

Publication Number Publication Date
JP2000309794A true JP2000309794A (en) 2000-11-07
JP4733246B2 JP4733246B2 (en) 2011-07-27

Family

ID=27455287

Family Applications (1)

Application Number Title Priority Date Filing Date
JP31624399A Expired - Lifetime JP4733246B2 (en) 1998-11-13 1999-11-08 Oil composition

Country Status (2)

Country Link
JP (1) JP4733246B2 (en)
WO (1) WO2002016534A1 (en)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001226693A (en) * 2000-02-18 2001-08-21 Nisshin Oil Mills Ltd:The Oils-and-fats composition
WO2002016534A1 (en) * 1998-11-13 2002-02-28 The Nisshin Oillio, Ltd. Fat compositions
WO2002018524A1 (en) * 2000-08-28 2002-03-07 The Nisshin Oillio,Ltd. Fat and oil composition having a foam-controlling effect
WO2003007932A1 (en) * 2001-07-16 2003-01-30 The Nisshin Oillio, Ltd. Body fat level controllers
JP2003210968A (en) * 2002-01-18 2003-07-29 Taiyo Kagaku Co Ltd Oil-in-water type emulsion oil composition
JP2003265104A (en) * 2002-03-18 2003-09-24 Honen Corp Oil-and-fat composition
JP2004075653A (en) * 2002-06-19 2004-03-11 Nisshin Oillio Ltd Adipose decomposition accelerator and food or beverage
US6827963B2 (en) 2001-12-28 2004-12-07 The Nisshin Oillio, Ltd. Fats and oils composition for reducing lipids in blood
JP2005105248A (en) * 2003-09-10 2005-04-21 Nisshin Oillio Group Ltd Oil and fat composition, food using the composition and process for refining oil and fat
JPWO2003062182A1 (en) * 2002-01-18 2005-05-19 株式会社カネカ Method and composition for stabilizing reduced coenzyme Q bottom 10
JP2005171237A (en) * 2003-11-18 2005-06-30 Kao Corp Oil or fat composition
JP2005218380A (en) * 2004-02-06 2005-08-18 Nisshin Oillio Group Ltd Oil and fat composition
JP2006117557A (en) * 2004-10-20 2006-05-11 Nisshin Oillio Group Ltd Blood adiponectin level increasing agent
JPWO2004080209A1 (en) * 2003-03-13 2006-06-08 日清オイリオグループ株式会社 Serum remnant-like lipoprotein concentration regulator
WO2012105130A1 (en) * 2011-01-31 2012-08-09 日清オイリオグループ株式会社 Fat and oil composition for promoting insulin secretion
JP2013135629A (en) * 2011-12-28 2013-07-11 Riken Vitamin Co Ltd Creaming property improver for oil and fat, and oil and fat composition containing the same
JP2014189628A (en) * 2013-03-27 2014-10-06 Kao Corp Method for producing refined oils and fats
WO2015040839A1 (en) * 2013-09-19 2015-03-26 日清オイリオグループ株式会社 Interesterified oil or fat, and oily food using said interesterified oil or fat
WO2016010101A1 (en) * 2014-07-17 2016-01-21 日清オイリオグループ株式会社 Gel-form emulsified food
JP2017104133A (en) * 2015-10-26 2017-06-15 日清オイリオグループ株式会社 Oil-based food
CN109497169A (en) * 2017-09-15 2019-03-22 日清奥利友集团株式会社 Heating cooking fat or oil composition and its manufacturing method
JP2019050801A (en) * 2017-09-01 2019-04-04 日清オイリオグループ株式会社 Oil and fat composition
JP2019118306A (en) * 2018-01-05 2019-07-22 日清オイリオグループ株式会社 Edible oil
JP2020022425A (en) * 2017-09-15 2020-02-13 日清オイリオグループ株式会社 Oil and fat composition for cooking and manufacturing method therefor
WO2022230679A1 (en) * 2021-04-28 2022-11-03 日清オイリオグループ株式会社 Flavor-imparting agent and method for producing same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8158184B2 (en) 2004-03-08 2012-04-17 Bunge Oils, Inc. Structured lipid containing compositions and methods with health and nutrition promoting characteristics

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5026804A (en) * 1973-03-26 1975-03-19
JPS5431407A (en) * 1977-08-15 1979-03-08 Asahi Denka Kogyo Kk Fat composition
JPS61173743A (en) * 1985-01-29 1986-08-05 Nippon Oil & Fats Co Ltd Liquid oil having high stability
JPH021799A (en) * 1987-12-15 1990-01-08 Procter & Gamble Co:The Low caloric fat produced from triglycelide containing medium-chain fatty acid and long-chain fatty acid
JPH0614710A (en) * 1992-06-29 1994-01-25 Fuji Oil Co Ltd Freeze-resistant oil and fat, its production and frozen food containing oil and fat
JPH0716052A (en) * 1993-06-30 1995-01-20 Kao Corp Oil and fat composition for preparation of fried food
JPH07179882A (en) * 1993-12-22 1995-07-18 Nisshin Oil Mills Ltd:The Antifreezing oil or fat and its production
JPH08214891A (en) * 1995-02-17 1996-08-27 Osaka City Production of oil and fat containing highly unsaturated fatty acid-containing triglyceride
JPH08269478A (en) * 1995-03-29 1996-10-15 Kao Corp Oil or fat composition and food containing the same
JPH09154474A (en) * 1995-12-12 1997-06-17 Kao Corp Fried breads
JPH09165595A (en) * 1995-12-14 1997-06-24 Asahi Denka Kogyo Kk Oil-and-fat composition and its production and baked confectionery produced by using the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5380544A (en) * 1989-09-20 1995-01-10 Nabisco, Inc. Production of fat mixtures enriched with triglycerides bearing short, medium and long residues
JP4733246B2 (en) * 1998-11-13 2011-07-27 日清オイリオグループ株式会社 Oil composition

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5026804A (en) * 1973-03-26 1975-03-19
JPS5431407A (en) * 1977-08-15 1979-03-08 Asahi Denka Kogyo Kk Fat composition
JPS61173743A (en) * 1985-01-29 1986-08-05 Nippon Oil & Fats Co Ltd Liquid oil having high stability
JPH021799A (en) * 1987-12-15 1990-01-08 Procter & Gamble Co:The Low caloric fat produced from triglycelide containing medium-chain fatty acid and long-chain fatty acid
JPH0614710A (en) * 1992-06-29 1994-01-25 Fuji Oil Co Ltd Freeze-resistant oil and fat, its production and frozen food containing oil and fat
JPH0716052A (en) * 1993-06-30 1995-01-20 Kao Corp Oil and fat composition for preparation of fried food
JPH07179882A (en) * 1993-12-22 1995-07-18 Nisshin Oil Mills Ltd:The Antifreezing oil or fat and its production
JPH08214891A (en) * 1995-02-17 1996-08-27 Osaka City Production of oil and fat containing highly unsaturated fatty acid-containing triglyceride
JPH08269478A (en) * 1995-03-29 1996-10-15 Kao Corp Oil or fat composition and food containing the same
JPH09154474A (en) * 1995-12-12 1997-06-17 Kao Corp Fried breads
JPH09165595A (en) * 1995-12-14 1997-06-24 Asahi Denka Kogyo Kk Oil-and-fat composition and its production and baked confectionery produced by using the same

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002016534A1 (en) * 1998-11-13 2002-02-28 The Nisshin Oillio, Ltd. Fat compositions
JP2001226693A (en) * 2000-02-18 2001-08-21 Nisshin Oil Mills Ltd:The Oils-and-fats composition
WO2002018524A1 (en) * 2000-08-28 2002-03-07 The Nisshin Oillio,Ltd. Fat and oil composition having a foam-controlling effect
US7037549B2 (en) 2000-08-28 2006-05-02 The Nisshin Oillio Group, Ltd. Oil and fat compositions having antifoaming effect
JPWO2003007932A1 (en) * 2001-07-16 2004-11-04 日清オイリオ株式会社 Body fat mass regulator
WO2003007932A1 (en) * 2001-07-16 2003-01-30 The Nisshin Oillio, Ltd. Body fat level controllers
KR100950638B1 (en) 2001-07-16 2010-04-01 닛신 오일리오그룹 가부시키가이샤 Body fat level controllers
JPWO2003056928A1 (en) * 2001-12-28 2005-05-12 日清オイリオグループ株式会社 Oil composition for lowering blood lipid
US6827963B2 (en) 2001-12-28 2004-12-07 The Nisshin Oillio, Ltd. Fats and oils composition for reducing lipids in blood
JP2003210968A (en) * 2002-01-18 2003-07-29 Taiyo Kagaku Co Ltd Oil-in-water type emulsion oil composition
US8562975B2 (en) 2002-01-18 2013-10-22 Kaneka Corporation Method for stabilizing reduced coenzyme Q10 and composition therefor
JPWO2003062182A1 (en) * 2002-01-18 2005-05-19 株式会社カネカ Method and composition for stabilizing reduced coenzyme Q bottom 10
JP4572073B2 (en) * 2002-01-18 2010-10-27 株式会社カネカ Method and composition for stabilizing reduced coenzyme Q10
JP2010189437A (en) * 2002-01-18 2010-09-02 Kaneka Corp Method for stabilizing reduced coenzyme q10 and composition
JP2003265104A (en) * 2002-03-18 2003-09-24 Honen Corp Oil-and-fat composition
JP2004075653A (en) * 2002-06-19 2004-03-11 Nisshin Oillio Ltd Adipose decomposition accelerator and food or beverage
JPWO2004080209A1 (en) * 2003-03-13 2006-06-08 日清オイリオグループ株式会社 Serum remnant-like lipoprotein concentration regulator
JP2005105248A (en) * 2003-09-10 2005-04-21 Nisshin Oillio Group Ltd Oil and fat composition, food using the composition and process for refining oil and fat
JP2005171237A (en) * 2003-11-18 2005-06-30 Kao Corp Oil or fat composition
JP4568585B2 (en) * 2003-11-18 2010-10-27 花王株式会社 Oil composition
WO2005074697A1 (en) * 2004-02-06 2005-08-18 The Nisshin Oillio Group, Ltd. Fat composition
JP2005218380A (en) * 2004-02-06 2005-08-18 Nisshin Oillio Group Ltd Oil and fat composition
JP2006117557A (en) * 2004-10-20 2006-05-11 Nisshin Oillio Group Ltd Blood adiponectin level increasing agent
WO2012105130A1 (en) * 2011-01-31 2012-08-09 日清オイリオグループ株式会社 Fat and oil composition for promoting insulin secretion
JP2012158544A (en) * 2011-01-31 2012-08-23 Nisshin Oillio Group Ltd Oil-and-fat composition for promoting insulin secretion
JP2013135629A (en) * 2011-12-28 2013-07-11 Riken Vitamin Co Ltd Creaming property improver for oil and fat, and oil and fat composition containing the same
JP2014189628A (en) * 2013-03-27 2014-10-06 Kao Corp Method for producing refined oils and fats
CN105530819B (en) * 2013-09-19 2020-09-04 日清奥利友集团株式会社 Transesterified fat and oily food using the same
WO2015040839A1 (en) * 2013-09-19 2015-03-26 日清オイリオグループ株式会社 Interesterified oil or fat, and oily food using said interesterified oil or fat
CN105530819A (en) * 2013-09-19 2016-04-27 日清奥利友集团株式会社 Interesterified oil or fat, and oily food using said interesterified oil or fat
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
JP2015082999A (en) * 2013-09-19 2015-04-30 日清オイリオグループ株式会社 Transesterification fat and oily foods using the transesterification fat
WO2016010101A1 (en) * 2014-07-17 2016-01-21 日清オイリオグループ株式会社 Gel-form emulsified food
JP2016021889A (en) * 2014-07-17 2016-02-08 日清オイリオグループ株式会社 Gel-like emulsified food
KR20170031151A (en) * 2014-07-17 2017-03-20 닛신 오일리오그룹 가부시키가이샤 Gel-form emulsified food
KR102472964B1 (en) 2014-07-17 2022-12-01 닛신 오일리오그룹 가부시키가이샤 Gel-form emulsified food
JP2017104133A (en) * 2015-10-26 2017-06-15 日清オイリオグループ株式会社 Oil-based food
JP2019050801A (en) * 2017-09-01 2019-04-04 日清オイリオグループ株式会社 Oil and fat composition
JP7237415B2 (en) 2017-09-01 2023-03-13 日清オイリオグループ株式会社 fat composition
JP2020022425A (en) * 2017-09-15 2020-02-13 日清オイリオグループ株式会社 Oil and fat composition for cooking and manufacturing method therefor
TWI751356B (en) * 2017-09-15 2022-01-01 日商日清奧利友集團股份有限公司 Grease composition for heating conditioning and its manufacturing method
JP7076912B2 (en) 2017-09-15 2022-05-30 日清オイリオグループ株式会社 Oil and fat composition for cooking and its manufacturing method
CN109497169A (en) * 2017-09-15 2019-03-22 日清奥利友集团株式会社 Heating cooking fat or oil composition and its manufacturing method
JP2019118306A (en) * 2018-01-05 2019-07-22 日清オイリオグループ株式会社 Edible oil
JP7127991B2 (en) 2018-01-05 2022-08-30 日清オイリオグループ株式会社 Cooking oil
WO2022230679A1 (en) * 2021-04-28 2022-11-03 日清オイリオグループ株式会社 Flavor-imparting agent and method for producing same

Also Published As

Publication number Publication date
JP4733246B2 (en) 2011-07-27
WO2002016534A1 (en) 2002-02-28

Similar Documents

Publication Publication Date Title
JP4733246B2 (en) Oil composition
JP2010279381A (en) Oil or fat composition and method for producing oil or fat composition
US6004611A (en) General-purpose oils composition
JP3569116B2 (en) Liquid general-purpose fat composition
KR101108796B1 (en) Fat or oil composition
US20100280112A1 (en) Composition Enriched in Diglyceride with Conjugated Linoleic Acid
KR100661780B1 (en) Fat compositions
JPH0738771B2 (en) Liquid edible oil composition
JP3997043B2 (en) Oil composition and processed oil product
JP4098927B2 (en) Oil composition
JPH06503230A (en) Low calorie fat substitute and its production method
TW200529763A (en) Fat composition
JP2001161265A (en) Oil and fat composition
JP4046438B2 (en) Oil composition
JPWO2003056928A1 (en) Oil composition for lowering blood lipid
JP2004156046A (en) Oil or fat composition and food containing the same
JP4410872B2 (en) Oil composition
JP4046437B2 (en) Oil composition
JP4242972B2 (en) Low calorie liquid oil
JP3082280B2 (en) How to reduce calories in food
JP2000290681A (en) Oil and fat composition
JP2003265104A (en) Oil-and-fat composition
JP2005065645A (en) Edible oil and fat composition
WO2003092396A1 (en) Fat compositions for reducing body fat and foods containing the same
JP2003253293A (en) Low-caloric substitute composition for fat and food containing the composition

Legal Events

Date Code Title Description
A711 Notification of change in applicant

Free format text: JAPANESE INTERMEDIATE CODE: A712

Effective date: 20040701

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20060831

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20091217

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20100105

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100302

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20100601

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100730

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A821

Effective date: 20100730

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20101221

A521 Written amendment

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20110318

A911 Transfer to examiner for re-examination before appeal (zenchi)

Free format text: JAPANESE INTERMEDIATE CODE: A911

Effective date: 20110328

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20110419

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20110422

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20140428

Year of fee payment: 3

R150 Certificate of patent or registration of utility model

Ref document number: 4733246

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

RD04 Notification of resignation of power of attorney

Free format text: JAPANESE INTERMEDIATE CODE: R3D04

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

EXPY Cancellation because of completion of term