KR20030045038A - Fat compositions - Google Patents
Fat compositions Download PDFInfo
- Publication number
- KR20030045038A KR20030045038A KR10-2003-7002571A KR20037002571A KR20030045038A KR 20030045038 A KR20030045038 A KR 20030045038A KR 20037002571 A KR20037002571 A KR 20037002571A KR 20030045038 A KR20030045038 A KR 20030045038A
- Authority
- KR
- South Korea
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 167
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 71
- 239000000194 fatty acid Substances 0.000 claims abstract description 71
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- 150000004665 fatty acids Chemical class 0.000 claims abstract description 64
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 24
- 235000019197 fats Nutrition 0.000 claims description 71
- -1 sucrose fatty acid ester Chemical class 0.000 claims description 36
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 16
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 12
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 12
- 239000005720 sucrose Substances 0.000 claims description 12
- 239000003995 emulsifying agent Substances 0.000 claims description 11
- 150000004668 long chain fatty acids Chemical class 0.000 claims description 10
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 10
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 7
- 229920000223 polyglycerol Polymers 0.000 claims description 6
- 239000001384 succinic acid Substances 0.000 claims description 6
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- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 4
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- 230000037213 diet Effects 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 description 1
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- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- 229960002733 gamolenic acid Drugs 0.000 description 1
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- 125000005456 glyceride group Chemical group 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
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- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
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- 235000013555 soy sauce Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
Abstract
주로 트리글리세리드로 이루어지는 유지조성물로서, 유지조성물을 구성하는 전체 지방산에서 차지하는 중쇄 지방산의 비율이 5 ~ 23 질량% 이고, 또한 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 2 개 갖는 트리글리세리드의 비율이 1 ~ 20 질량% 인 것을 특징으로 하는 유지조성물.As a fat or oil composition mainly consisting of triglycerides, the ratio of the heavy chain fatty acid to the total fatty acids constituting the fat and fat composition is 5 to 23% by mass, and the ratio of the triglyceride having two heavy chain fatty acid residues in the molecule to the total triglyceride is 1 to 20. Oil composition, characterized in that the mass%.
본 유지조성물은 체지방 축적이 적고, 통상의 식용유와 동등한 조리적성을 갖고, 풍미가 양호하며 안정성이 높다.This oil-fat composition is low in body fat accumulation, has cookability equivalent to that of ordinary cooking oil, has good flavor and high stability.
Description
비만은 체지방이 과잉으로 축적된 상태이며, 당뇨병, 고지혈증 등의 대사이상이나 고혈압, 허혈성 심질환 등의 순환기 질환을 비롯하여 많은 질병을 동반하기 쉽다는 것은 잘 알려져 있다. 일본 후생성이 실시하고 있는 국민영양조사결과에 따르면, 성인 7 명당 1 명은 비만이라는 점에서, 비만은 구미뿐 아니라 일본에서도 긴밀한 문제이다. 식사 중에 함유되는 지방은 체지방의 축적과 가장 관계 깊은 영양소 중 하나로, 지나친 지방의 섭취는 비만을 가져올 가능성이 있다. 그러나, 지방에는 독특한 맛이 있어, 지나치게 지방을 줄인 식사는 만족도가 낮아지기 쉽다. 또, 튀김이나 볶음 요리를 조리할 때, 식용유는 열매체로서 필요 불가결하다.Obesity is a state in which excess body fat is accumulated, it is well known that it is easy to accompany many diseases, including metabolic abnormalities such as diabetes and hyperlipidemia, circulatory diseases such as hypertension and ischemic heart disease. According to the results of the National Nutrition Survey conducted by the Ministry of Health and Welfare, one in seven adults is obese, and obesity is a problem not only in Europe but also in Japan. Fats in your diet are one of the most important nutrients in your body fat accumulation, and excessive fat intake can lead to obesity. However, the fat has a unique taste, and the meal which reduced too much fat tends to lower satisfaction. Moreover, when cooking frying and stir-fry dishes, cooking oil is indispensable as a heat medium.
이러한 상황을 타개하기 위해, 소위 지방대체품이 개발되고 있다. 그러나, 이들 중에는 안전성, 물성, 조리적성, 풍미의 면에서 볼 때 충분히 만족시킬 수 있는 것은 없는 상황이다. 예컨대, 자당지방산에스테르는 소화관에서 흡수되지 않고 대변 중에 배설되기 때문에, 저칼로리유로서 사용할 수 있다는 취지가 개시되어 있다 (미국특허 제3600186호 명세서). 미국내에서는, 짠맛 스낵과자를 대상으로 사용이 허가되어 자당지방산에스테르를 사용한 포테이토칩이 이미 시판되고 있지만, 자당지방산에스테르를 사용한 상품에는, 「복부경련이나 변을 무르게 할 가능성이 있다는 것」, 「지용성 비타민의 흡수를 저해한다는 것」을 표시할 것이 의무화되고 있다. 단백질 및 탄수화물의 에너지 밀도는 지방의 절반 이하이다. 그래서, 단백질이나 탄수화물에 지방 유사 물성이나 풍미가 나도록 가공함으로써, 저칼로리 지방대체품을 제공할 수 있다는 것이 알려져 있다 (영양학 리뷰, 제 4 권, 제 4 호, 23 ~ 33 페이지, 1996). 이들 지방대체품을 이용함으로써, 저칼로리화된 아이스크림, 베이커리 제품, 케이크 등을 만들 수 있다. 그러나, 열에 대한 내성이 부족하여 튀김이나 볶음 요리의 열매체로서 사용할 수 없다는 등의 결점이 있다.To address this situation, so-called regional alternatives are being developed. However, none of these can be satisfactorily satisfied in view of safety, physical properties, cooking suitability, and flavor. For example, it is disclosed that sucrose fatty acid ester can be used as a low calorie oil because it is excreted in feces rather than absorbed in the digestive tract (US Patent No. 3600186). In the United States, it is licensed for salty snacks, and potato chips using sucrose fatty acid esters are already on the market, but for products using sucrose fatty acid esters, there is a possibility of softening abdominal cramps and stools. To inhibit the absorption of fat-soluble vitamins. ” The energy density of proteins and carbohydrates is less than half of fat. Therefore, it is known that low-calorie fat substitutes can be provided by processing proteins or carbohydrates to have fat-like properties or flavors (Nutritional Review, Vol. 4, No. 4, pages 23 to 33, 1996). By using these fatty substitutes, low-calorie ice cream, bakery products, cakes and the like can be made. However, there are drawbacks such as lack of heat resistance and the inability to be used as a heat medium for frying and stir-frying dishes.
일본 공표특허공보 평4-501812호에는, 장쇄 지방산과 단쇄 지방산으로 구성되는 트리글리세리드에 의해 저칼로리 유지를 제공할 수 있다는 것이 개시되어 있다. 그러나, 단쇄 지방산으로 이루어지는 트리글리세리드는 특유의 악취를 갖고 있기 때문에, 이용가능한 조리품이 한정되어 범용성있는 식용유로서 적합하지 않다. 또, 중쇄 지방산은 에너지화 되기 쉽기 때문에 체지방 축적이 적다는 것이 알려져 있다 (J. Lipid Res.37, 708-726 (1996)). 그러나, 중쇄 지방산으로 구성되는 트리글리세리드는 본래 안정성이 높지만, 한번에 다량으로 섭취한 경우, 설사, 구역질, 복통, 가슴앓이, 식욕부진 등의 증상을 일으킨다는 것이 보고되어 있다. 일본 공개특허공보 평4-300826호, 일본 공개특허공보 평8-60180호 및 일본 공개특허공보 평10-176181호에는, 디글리세리드를 유효 성분으로 하는 체지방 축적이 적은 유지조성물이 개시되어 있다. 그러나, 디글리세리드를 풍부하게 함유하는 유지조성물의 안전성은 완전하게 증명되어 있지 않다. 또, 고농도의 디글리세리드를 저비용으로 제조하기 어려워 경제적 견지에서 범용적으로 사용하기 어렵다는 결점이 있다. 또한, 일본 공개특허공보 평8-269478호에는, 디글리세리드 및 트리글리세리드로 이루어지는 유지조성물 성분 중, 분자내에 중쇄 지방산 잔기를 2 개 함유하는 트리글리세리드를 31 질량% 이상 함유하는 체지방 축적이 적은 유지조성물이 개시되어 있다. 이 발명 또한, 디글리세리드를 유효 성분으로 하기 위해, 상기 일본 공개특허공보 평4-300826호, 일본 공개특허공보 평8-60l80호 및 일본 공개특허공보 평10-176181호와 동일한 문제를 안고 있다. 또, 다량의 중쇄 지방산을 함유하기 때문에 발연점이 낮고, 거품 발생이 현저하여 튀김 조리에 적합하지 않다는 등의 결점이 있다.Japanese Laid-Open Patent Publication No. 4-501812 discloses that low calorie fats and oils can be provided by triglycerides composed of long chain fatty acids and short chain fatty acids. However, since triglycerides composed of short-chain fatty acids have peculiar odors, available cooking products are limited and are not suitable as general purpose cooking oils. In addition, heavy chain fatty acids are known to have low body fat accumulation because they are easily energized (J. Lipid Res. 37 , 708-726 (1996)). However, although triglycerides composed of medium-chain fatty acids are inherently high in stability, it has been reported that when ingested in large quantities at once, they cause diarrhea, nausea, abdominal pain, heartburn, anorexia and the like. Japanese Unexamined Patent Publication No. Hei 4-300826, Japanese Unexamined Patent Application Publication No. Hei 8-60180, and Japanese Patent Application Laid-Open No. Hei 10-176181 disclose a fat and oil composition having low body fat accumulation with diglyceride as an active ingredient. However, the safety of oil-fat compositions rich in diglycerides has not been fully demonstrated. In addition, there is a drawback that it is difficult to manufacture a high concentration of diglyceride at low cost and it is difficult to use it universally from an economic point of view. In addition, Japanese Patent Application Laid-Open No. 8-269478 discloses a fat or oil composition having a low body fat accumulation containing 31% by mass or more of triglycerides containing two heavy chain fatty acid residues in a molecule among fat or oil components consisting of diglycerides and triglycerides. It is. This invention also suffers from the same problems as those described in Japanese Patent Application Laid-Open No. Hei 4-300826, Japanese Patent Application Laid-Open No. Hei 8-60l80 and Japanese Patent Application Laid-open No. Hei 10-176181 in order to use diglyceride as an active ingredient. In addition, since it contains a large amount of heavy chain fatty acid, there are disadvantages such as low smoke point, foam generation is remarkable, and not suitable for frying cooking.
본 발명은 식용으로 이용되는 유지조성물에 관한 것이다. 더욱 상세하게는, 체지방 축적이 적고, 또한 식용유로서의 조리적성과 풍미가 우수한 유지조성물에 관한 것이다.The present invention relates to a fat and oil composition used for food. More specifically, the present invention relates to an oil-fat composition having low body fat accumulation and excellent cooking properties and flavor as cooking oil.
발명의 개시Disclosure of the Invention
본 발명의 목적은, 체지방 축적이 적고, 통상의 식용유와 동등한 조리적성을 가지며, 풍미가 양호하고 안정성이 높은 유지조성물을 제공하는 것이다.An object of the present invention is to provide a fat or oil composition which has a low body fat accumulation, has a cooking ability equivalent to that of ordinary cooking oil, and has a good flavor and high stability.
본 발명자들은 상기 과제를 해결하기 위해 예의 검토를 거듭한 결과, 전체 지방산 잔기에서 차지하는 중쇄 지방산 잔기의 비율, 및 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 2 개 갖는 트리글리세리드의 비율이 체지방축적정도와 밀접하게 관련된다는 것을 발견하고, 본 발명을 완성했다.MEANS TO SOLVE THE PROBLEM As a result of earnestly examining in order to solve the said subject, the ratio of the heavy chain fatty acid residue which occupies for a total fatty acid residue, and the ratio of the triglyceride which has two heavy chain fatty acid residue in a molecule in a molecule are closely related to the degree of body fat accumulation. The present invention has been completed, and the present invention has been completed.
즉, 본 발명은 주로 트리글리세리드로 이루어지는 유지조성물로서, 유지조성물을 구성하는 전체 지방산에서 차지하는 중쇄 지방산의 비율이 5 ~ 23 질량% 이며, 또한 전체 트리글리세리드에 차지하는 중쇄 지방산 잔기를 분자내에 2 개 갖는 트리글리세리드의 비율이 l ~ 20 질량% 인 것을 특징으로 하는 체지방 축적이 적은 유지조성물에 관한 것이다. 상기 중쇄 지방산은 탄소수 6 ~ 12 의 포화지방산인 것이 바람직하다. 또, 유지조성물을 구성하는 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 3 개 갖는 트리글리세리드의 비율이 3 질량% 이하인 것이 바람직하다. 또, 유지조성물을 구성하는 전체 장쇄 지방산에서 차지하는 장쇄 포화지방산의 비율이 20 질량% 이하인 것이 바람직하다.That is, the present invention is a fat or oil composition mainly composed of triglycerides, wherein the ratio of the heavy chain fatty acid to the total fatty acids constituting the oil and fat composition is 5 to 23% by mass, and also the triglyceride having two heavy chain fatty acid residues in the molecule. It relates to a maintenance composition with low body fat accumulation, characterized in that the ratio is l to 20% by mass. The medium chain fatty acid is preferably a saturated fatty acid having 6 to 12 carbon atoms. Moreover, it is preferable that the ratio of the triglyceride which has three heavy chain fatty acid residues in a molecule to all the triglycerides which comprise an oil-fat composition is 3 mass% or less. Moreover, it is preferable that the ratio of the long chain saturated fatty acid to all the long chain fatty acids which comprise an oil-fat composition is 20 mass% or less.
본 발명의 유지조성물에 유화제, 특히 특정 조합의 유화제를 함유시키는 경우에는, 튀김 적성, 특히 거품 발생 억제를 더욱 향상시킬 수 있다.When the oil-fat composition of this invention contains an emulsifier, especially the emulsifier of a specific combination, frying aptitude, especially suppression of foaming can be improved further.
또, 본 발명은 이러한 유지조성물을 함유하는 체지방 축적이 적고, 또한 통상의 식용유로 손색이 없는 조리적성 및 보존안정성을 갖는 조리용 유지조성물에 관한 것이다.The present invention also relates to a cooking fat composition having little body fat accumulation containing such a fat and oil composition, and having cooking suitability and storage stability which are comparable to ordinary cooking oil.
발명을 실시하기 위한 최선의 형태Best Mode for Carrying Out the Invention
이하에, 본 발명을 상세하게 설명한다.EMBODIMENT OF THE INVENTION Below, this invention is demonstrated in detail.
본 발명의 유지조성물은 주로 트리글리세리드로 이루어진다. 「주로」는, 유지조성물 중에 트리글리세리드가 85 질량% 이상, 바람직하게는 95 질량% 이상 함유되어 있는 것을 의미하는 것으로 한다.The oil-fat composition of this invention consists mainly of triglycerides. "Mainly" shall mean that the fat composition contains 85 mass% or more, preferably 95 mass% or more of triglycerides.
본 발명에서 중쇄 지방산이란, 탄소수가 6 ~ 12 인 지방산, 특히 포화지방산을 말하는 것으로 한다. 예로는, 카프로산, 카프릴산, 카프르산, 라우르산을 들 수 있고, 탄소수가 8 ~ 10 인 포화지방산, 특히 카프릴산 및 카프르산이 바람직하다. 본 발명에서 장쇄 지방산이란, 탄소수가 14 이상, 바람직하게는 14 ~ 22인 포화 및 불포화지방산을 나타낸다. 장쇄 지방산으로는, 탄소수가 14 이상, 바람직하게는 14 ~ 22 인 것, 예컨대 미리스트산, 팔미트산, 스테아르산, 아라키드산, 베헨산, 리그노세르산, 세로트산 등의 장쇄 포화지방산, 미리스톨레산, 펜타데센산, 팔미톨레산, 헥사데카트리엔산, 헵타데센산, 올레산, 리놀레산, α-리놀렌산, γ-리놀렌산, 옥타데카테트라엔산, 에이코센산, 에이코사디엔산, 에이코사트리엔산, 에이코사테트라엔산, 아라키돈산, 에이코사펜타엔산, 도코센산, 도코사디엔산, 도코사펜타엔산, 도코사헥사엔산 등의 장쇄 불포화지방산을 들 수 있다. 지방산 잔기는 지방산으로부터 카르복실기의 OH 를 제거한 기이다.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 and lauric acid, and saturated fatty acids having 8 to 10 carbon atoms, in particular caprylic acid and capric acid, are preferable. In the present invention, the long chain fatty acid refers to saturated and unsaturated fatty acids having 14 or more carbon atoms, preferably 14 to 22 carbon atoms. As long-chain fatty acid, carbon number 14 or more, Preferably it is 14-22, For example, Long-chain saturated fatty acids, such as myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoseric acid, a seric acid, etc. Myristoleic acid, pentadecenoic acid, palmitoleic acid, hexadecatenic acid, heptadenoic acid, oleic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, octadecatetraic acid, eicosane acid, eicosadienoic acid, eicosane And long chain unsaturated fatty acids such as satrienoic acid, eicosateraenoic acid, arachidonic acid, eicosapentaenoic acid, dococenic acid, docosadienoic acid, docosapentaic acid and docosahexaenoic acid. Fatty acid residue is the group which removed OH of carboxyl group from fatty acid.
본 발명의 유지조성물에 있어서는, 유지조성물을 구성하는 전체 지방산에서 차지하는 중쇄 지방산의 비율이 5 ~ 23 질량% 이며, 또한 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 2 개 갖는 트리글리세리드의 비율이 1 ~ 20 질량% 인 것이 필요하다. 이 범위 이외에서는 체지방 축적이 적다는 특징이 생기지 않는다. 상기 중쇄 지방산의 비율은 바람직하게는 6 ~ 23 질량% 이고, 상기트리글리세리드의 비율은 바람직하게는 3 ~ 20 질량% 이다.In the oil-fat composition of this invention, the ratio of the heavy chain fatty acid to the total fatty acid which comprises an oil-fat composition is 5-23 mass%, and also the ratio of the triglyceride which has two heavy chain fatty acid residues in a molecule in the molecule is 1-20. It is necessary to be mass%. Outside of this range, there is no characteristic that body fat accumulation is small. The proportion of the medium chain fatty acid is preferably 6 to 23% by mass, and the ratio of the triglyceride is preferably 3 to 20% by mass.
또, 유지조성물을 구성하는 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 3 개 갖는 트리글리세리드의 비율이 3 질량% 이하인 것이 바람직하고, 2 질량% 이하인 것이 더욱 바람직하며, 1 질량% 이하인 것이 더욱더 바람직하다. 이 비율이 3 질량% 를 초과하면, 조리시에 발연, 거품 발생이 증가하여 튀김용 유지로서 적합하지 않게 된다. 이 비율이 1 질량% 이하이면, 발연, 거품 발생에 현격한 개선이 보인다.Moreover, it is preferable that the ratio of the triglyceride which has three heavy chain fatty acid residues in a molecule | numerator among all the triglycerides which comprise an oil-fat composition is 3 mass% or less, It is more preferable that it is 2 mass% or less, It is further more preferable that it is 1 mass% or less. When this ratio exceeds 3 mass%, smoke and foaming at the time of cooking increase, and it is not suitable as a fats and oils for frying. If this ratio is 1 mass% or less, a marked improvement in smoke and bubble generation is seen.
또한, 유지조성물을 구성하는 전체 장쇄 지방산에서 차지하는 장쇄 포화지방산의 비율이 20 질량% 이하인 것이 바람직하고, 15 질량% 이하인 것이 더욱 바람직하며, 7 질량% 이하인 것이 더욱더 바람직하다. 이 비율이 20 질량% 를 초과하면, 저온에서의 안정성이 저하되고, 유지조성물에 유지의 결정화가 보이므로, 생식용에는 통상적으로 적합하지 않게 된다.Moreover, it is preferable that the ratio of the long chain saturated fatty acid to all the long chain fatty acids which comprise an oil-fat composition is 20 mass% or less, It is more preferable that it is 15 mass% or less, It is further more preferable that it is 7 mass% or less. If this ratio exceeds 20 mass%, stability at low temperature will fall, and since fats and oils crystallization will be seen in an oil-fat composition, it will not normally be suitable for reproduction.
본 발명의 체지방 축적이 적은 유지조성물은, 원료로서의 유지와 중쇄 지방산을 적절히 혼합한 후, 나트륨메틸레이트를 촉매로서 또는 지질분해효소의 존재하에 에스테르 교환반응을 실시하고, 이 때에, 유지조성물을 구성하는 전체 지방산에서 차지하는 중쇄 지방산의 비율 및 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 2 개 갖는 트리글리세리드의 비율이 상기 특정범위내에 들어가도록 에스테르 교환반응을 조정함으로써 얻을 수 있다.The fat or oil composition having low body fat accumulation according to the present invention is a mixture of fats and oils and heavy chain fatty acids as a raw material, and then transesterified in the presence of sodium methylate as a catalyst or in the presence of lipolytic enzymes. It can be obtained by adjusting the transesterification reaction so that the ratio of the heavy chain fatty acid to the total fatty acid and the ratio of the triglyceride having two heavy chain fatty acid residues to the total triglyceride in the molecule fall within the specific range.
상기 에스테르 교환반응시에 상기 조정에 추가하여, 유지조성물을 구성하는 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 3 개 갖는 트리글리세리드의 비율, 및/또는 유지조성물을 구성하는 전체 장쇄 지방산에서 차지하는 장쇄 포화지방산의 비율이 상기 특정범위내에 들어가도록 조정함으로써, 체지방 축적이 적으며, 튀김시의 발연, 거품 발생이 저감되고, 및/또는 저온안정성이 우수한유지조성물을 얻을 수 있다.In addition to the above adjustment in the transesterification reaction, the ratio of triglycerides having three heavy chain fatty acid residues in the molecule to the total triglycerides constituting the oil-fat composition, and / or the long chain saturated fatty acids to the total long-chain fatty acids constituting the oil-fat composition. By adjusting the ratio of to within the above-mentioned specific range, it is possible to obtain a maintenance composition having less body fat accumulation, less fuming and foaming during frying, and / or excellent low temperature stability.
원료유지로는, 통상의 식용유지, 예컨대 대두유, 채종유, 고올레산 채종유, 옥수수유, 참기름, 참깨샐러드유, 차조기유, 아마인유, 낙화생유, 홍화유, 고올레산 홍화유, 해바라기유, 고올레산 해바라기유, 면실유, 포도종유, 마카다미아넛츠유, 헤즐럿유, 호박종자유, 호두오일, 동백유, 다실유(茶室油), 들기름, 보라지유, 올리브유, 쌀겨유, 소맥배아유, 팜유, 팜핵유, 야자유, 카카오지, 우지, 라드, 닭기름, 유지 (乳脂), 어유(魚油), 해표유, 해초류유, 품질개량에 의해 저포화화된 이들 유지 및 이들의 수소첨가 유지, 분별 유지 등을 들 수 있다.As raw material fats and oils, edible oils, such as soybean oil, rapeseed oil, high oleic oil, corn oil, sesame oil, sesame salad oil, perilla oil, linseed oil, peanut oil, safflower oil, high oleic safflower oil, sunflower oil, and high oleic sunflower oil , Cottonseed oil, grape oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, walnut oil, camellia oil, green tea oil, perilla oil, borage oil, olive oil, rice bran oil, wheat germ oil, palm oil, palm kernel oil, palm oil, cacao Fats and oils, lard, lard, chicken oil, fats and oils, fish oil, seaweed oil, seaweed oil, these fats saturated with low quality, their hydrogenated fats and fractions, and the like.
중쇄 지방산에 대해서는 이미 기술했지만, 중쇄 지방산을 대신하여 또는 이것과 함께 중쇄 지방산 트리글리세리드를 사용할 수도 있다. 중쇄 지방산 트리글리세리드로는, 상기 중쇄 지방산과 글리세린을 통상적인 방법에 의해 에스테르화 반응으로 얻어지는 트리글리세리드를 사용할 수 있지만, 일반적으로 MCT (Medium Chain Triglycerides) 라고 일컬어지는 야자유 분해지방산 등의 탄소수가 8 ~ 10 인 포화지방산으로 구성되는 단산기(單酸基) 또는 혼산기(混酸基) 트리글리세리드, 예컨대 카프릴산/카프르산 = 60/40 ~ 75/25 (질량비) 의 트리글리세리드를 바람직하게 사용할 수 있다.Although medium chain fatty acids have already been described, medium chain fatty acid triglycerides may be used instead of or in combination with the medium chain fatty acids. As the medium-chain fatty acid triglycerides, triglycerides obtained by esterification of the medium-chain fatty acids and glycerin by a conventional method can be used, but generally have 8 to 10 carbon atoms such as palm oil-decomposed fatty acids called MCT (Medium Chain Triglycerides). Mono- or mixed-acid triglycerides composed of saturated fatty acids, such as triglycerides of caprylic / capric acid = 60/40 to 75/25 (mass ratio) can be preferably used.
유지조성물을 구성하는 전체 지방산에서 차지하는 중쇄 지방산의 비율 및 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 2 개 갖는 트리글리세리드의 비율, 필요한 경우의 유지조성물을 구성하는 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 3 개 갖는 트리글리세리드의 비율, 및 필요한경우의 유지조성물을 구성하는 전체 장쇄 지방산에서 차지하는 장쇄 포화지방산의 비율은, 원료유지 조성을 감안하고, 원료유지와 중쇄 지방산의 사용비율을 조정하여, 에스테르 교환반응 중 반응생성물의 트리글리세리드 조성을 측정함으로써 조정할 수 있다.The ratio of heavy chain fatty acids to total fatty acids constituting the oil-fat composition and the ratio of triglycerides having two heavy chain fatty acid residues to the total triglyceride in the molecule, and the heavy chain fatty acid residues to the total triglyceride constituting the oil-fat composition, if necessary The ratio of triglycerides in dogs and the proportion of long-chain saturated fatty acids in total long-chain fatty acids constituting the oil-and-fat composition, if necessary, are adjusted in the transesterification reaction by adjusting the use ratio of the raw material and medium-chain fatty acids in consideration of the raw material holding composition. It can adjust by measuring the triglyceride composition of a product.
나트륨메틸레이트를 촉매로 하는 에스테르 교환반응을 실시하는 경우, 원료유지와 중쇄 지방산 트리글리세리드를 전자/후자의 질량비 = 71/29 ~ 97/3 으로 혼합하고, 혼합물을 l00 ㎜Hg 이하의 감압하에서 80 ~ 120 ℃ 로 가열하여 원료혼합물에 함유된 기체성분 및 수분을 제거한다. 이것에 나트륨메틸레이트 O.02 ~ 0.5 질량% 를 첨가하고, 상압ㆍ질소기류하 또는 10 ㎜Hg 이하의 감압하에서 10 ~ 60 분 동안 80 ~ 120 ℃ 에서 교반함으로써 에스테르 교환반응을 실시한다. 반응의 완료는 가스크로마토그래피에 의해 반응생성물의 트리글리세리드 조성을 측정함으로써 확인한다. 반응의 정지는 반응생성물에 물을 첨가하거나 인산 등의 산을 첨가함으로써 실시한다. 그 후, 촉매 및 과잉의 산을 제거하기 위해 충분히 물로 세정하고 건조 후, 반응생성물을 통상적인 방법에 의해 탈색ㆍ탈취한다.In the case of performing the transesterification reaction using sodium methylate as a catalyst, the raw material oils and the medium-chain fatty acid triglycerides are mixed at the mass ratio of the former / the latter = 71/29 to 97/3, and the mixture is subjected to 80 to 80 under a reduced pressure of l00 mmHg or less. It is heated to 120 ℃ to remove the gas components and water contained in the raw material mixture. 0.02-0.5 mass% of sodium methylate is added to this, and a transesterification reaction is performed by stirring at 80-120 degreeC for 10 to 60 minutes under normal pressure, nitrogen stream, or the reduced pressure of 10 mmHg or less. 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. Thereafter, the mixture is washed with water sufficiently to remove the catalyst and excess acid, dried, and then the reaction product is decolorized and deodorized by a conventional method.
지질분해효소를 사용하여 에스테르 교환반응을 실시하는 경우, 원료유지와 중쇄 지방산 또는 중쇄 지방산 트리글리세리드를 전자/후자의 질량비 = 71/29 ~ 97/3 으로 혼합하고, 지질분해효소의 활성이 충분히 발휘되는 반응온도인 40 ~ 100 ℃ 의 범위로 온도를 조절한다. 이것에 지질분해효소를 원료혼합물에 대해 0.005 ~ 10 질량% 의 비율로 첨가하고, 2 ~ 48 시간의 범위에서 에스테르 교환반응을 실시한다. 이 반응은 상압하 질소기류중에서 실시하는 것이 바람직하다.반응의 완료는 가스크로마토그래피에 의해 반응생성물의 트리글리세리드 조성을 측정함으로써 확인한다. 반응의 정지는 효소를 여과에 의해 제거함으로써 실시한다. 반응 생성물은 물로 세정하고 건조 후, 통상적인 방법에 의해 탈색ㆍ탈취한다. 또한, 중쇄 지방산을 사용한 경우에는, 반응의 정지 후에 유리지방산을 박막식 증발기로 제거해 둔다.In the case of transesterification using lipolytic enzymes, the raw material oil and the medium or medium fatty acid triglycerides are mixed in the former / the latter mass ratio = 71/29 to 97/3, and the activity of the lipolytic enzyme is sufficiently exerted. Adjust the temperature in the range of 40 ~ 100 ℃ reaction temperature. Lipolytic enzyme is added to the mixture at a rate of 0.005 to 10% by mass, and transesterified in a range of 2 to 48 hours. The reaction is preferably carried out in a nitrogen stream at atmospheric 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 decolorized and deodorized by a conventional method. In the case of using a medium chain fatty acid, the free fatty acid is removed by a thin film type evaporator after the reaction is stopped.
지질분해효소를 사용한 에스테르 교환반응이 불충분하면, 중쇄 지방산 잔기를 분자내에 3 개 갖는 트리글리세리드의 비율이 많아진다. 중쇄 지방산 잔기를 분자내에 3 개 갖는 트리글리세리드의 비율이 많은 유지조성물은, 체지방 축적이 적다는 특징은 있지만, 연속된 튀김조리시에 발연, 거품 발생이 심하게 일어나 바람직하지 않다.If the transesterification reaction using lipolytic enzymes is insufficient, the proportion of triglycerides having three heavy chain fatty acid residues in the molecule increases. A fat or oil composition having a large proportion of triglycerides having three heavy chain fatty acid residues in its molecule is characterized by low accumulation of body fat, but it is not preferable because of fuming and foaming during continuous frying.
지질분해효소로는, 알칼리게네스속, 칸디다속, 라이조푸스속, 뮤코속 또는 슈도모나스속 유래의 리파아제나, 간장 유래의 포스폴리파아제 A 등을 들 수 있지만, 특히 칸디다속 또는 라이조푸스속 유래의 리파아제가 바람직하다.Examples of lipolytic enzymes include lipases derived from the genus Alkogen genes, Candida genus, Lyzopus genus, Muco genus or Pseudomonas, and phospholipase A derived from soy sauce, but are particularly derived from genus Candida or genus Lyzopus Lipase is preferred.
본 발명의 유지조성물은, 또한 유전자 재조합기술을 사용하여 본 발명의 유지조성물을 생산하도록 품종개량한 식물, 예컨대 대두, 채종, 옥수수, 야자, 팜, 올리브, 아마인, 해바라기, 홍화, 동백나무, 면실, 쿠페아(cuphea)로부터 추출에 의해 얻을 수도 있다.The oil-fat composition of the present invention is also a plant which has been cultivated to produce the oil-fat composition of the present invention using genetic recombination techniques such as soybean, rapeseed, corn, palm, palm, olive, flax seed, sunflower, safflower, camellia, It can also be obtained by extraction from cottonseed, cuphea.
본 발명의 유지조성물에 유화제를 함유시킴으로써, 튀김 적성, 특히 거품 발생 억제를 더욱 향상시킬 수 있다. 유화제로는, 자당지방산에스테르, 폴리글리세린지방산에스테르, 숙신산모노글리세리드, 모노글리세리드, 디글리세리드, 소르비톨지방산에스테르, 소르비탄지방산에스테르 등을 들 수 있다. 본 발명에서는 상기 유화제의 1 종 이상을 선택할 수 있고, 유지조성물로의 첨가량은 유화제 전체로서 0.1 ~ 6 질량% 가 바람직하고, 더욱 바람직하게는 0.3 ~ 5 질량% 이다.By containing an emulsifier in the oil-fat composition of this invention, frying aptitude, especially suppression of foam generation can be improved further. Examples of the emulsifier include sucrose fatty acid esters, polyglycerol fatty acid esters, succinic acid monoglycerides, monoglycerides, diglycerides, sorbitol fatty acid esters, and sorbitan fatty acid esters. In this invention, 1 or more types of the said emulsifier can be selected, The addition amount to a fats and oils composition is 0.1-6 mass% is preferable as the whole emulsifier, More preferably, it is 0.3-5 mass%.
자당지방산에스테르는 자당과 탄소수 6 ~ 22 의 포화 또는 불포화지방산과의 에스테르를 포함하지만, 전체 히드록시기의 평균치환도가 37.5 ~ 87.5 % 이고, 전체 자당지방산에스테르에서 차지하는 트리에스테르 이상의 폴리에스테르의 비율이 85 질량% 이상인 것이 바람직하다. 폴리글리세린지방산에스테르는 트리글리세린 이상에서 바람직하게는 데카글리세린까지의 폴리글리세린과 탄소수 6 ~ 22 의 포화 또는 불포화지방산과의 에스테르를 포함하지만, 전체 히드록시기의 평균치환도가 20 ~ 80 % 인 것이 바람직하다. 모노글리세리드, 디글리세리드는 글리세린 또는 디글리세린과 탄소수 6 ~ 22 의 포화 또는 불포화지방산과의 모노에스테르, 디에스테르를 각각 포함하지만, 모노글리세리드가 바람직하다. 숙신산모노글리세리드로는, 숙신산과 모노글리세리드 또는 디글리세리드를 3 : 1 ~ 0.1 : 1 로 에스테르화한 숙신산모노글리세리드가 바람직하다. 소르비톨지방산에스테르, 소르비탄지방산에스테르는, 소르비톨 또는 소르비탄과 탄소수 6 ~ 22 의 포화 또는 불포화지방산과의 모노 ~ 트리에스테르가 바람직하다. 상기에서 탄소수 6 ~ 22 의 포화 또는 불포화지방산의 예로는, 중쇄 지방산 및 장쇄 지방산의 예로서 든 것을 들 수 있다.Sucrose fatty acid esters include esters of sucrose with saturated or unsaturated fatty acids having 6 to 22 carbon atoms, but the average substitution degree of all hydroxy groups is 37.5 to 87.5%, and the proportion of polyesters of triesters or higher in the total sucrose fatty acid ester is 85 mass. It is preferable that it is% or more. The polyglycerol fatty acid ester includes esters of polyglycerol from triglycerine or higher, preferably decaglycerin, with saturated or unsaturated fatty acids having 6 to 22 carbon atoms, but the average substitution degree of all hydroxy groups is preferably 20 to 80%. Monoglycerides and diglycerides include monoesters and diesters of glycerin or diglycerin with saturated or unsaturated fatty acids having 6 to 22 carbon atoms, respectively, but monoglycerides are preferred. As succinic acid monoglyceride, succinic acid monoglyceride which esterified succinic acid, monoglyceride, or diglyceride to 3: 1 to 0.1: 1 is preferable. As for sorbitol fatty acid ester and sorbitan fatty acid ester, mono-triester of sorbitol or sorbitan and C6-C22 saturated or unsaturated fatty acid is preferable. Examples of the saturated or unsaturated fatty acid having 6 to 22 carbon atoms include those mentioned as examples of medium and long chain fatty acids.
유화제의 조합사용에 관해서는, 본 발명의 유지 조성물에 대해 자당지방산에스테르 및 폴리글리세린지방산에스테르에서 선택되는 1 종 이상을 0.1 ~ 3 질량%,숙신산모노글리세리드를 0.01 ~ 2 질량%, 및 모노글리세리드, 디글리세리드, 소르비톨지방산에스테르 및 소르비탄지방산에스테르에서 선택되는 1 종 이상을 0.1 ~ 3 질량%, 이 유화제의 총량이 0.3 ~ 5 질량% 가 되도록 첨가하여 함유시키는 것이 튀김 적성, 특히 거품 발생 억제를 한층 더 향상시키기 위해 가장 바람직하다.As for the combined use of the emulsifier, 0.1 to 3% by mass of the sucrose fatty acid ester and the polyglycerol fatty acid ester of the fat or oil composition of the present invention, 0.01 to 2% by mass of succinic acid monoglyceride, and monoglyceride, Adding at least one selected from diglycerides, sorbitol fatty acid esters, and sorbitan fatty acid esters so that the total amount of the emulsifier is 0.3 to 5% by mass is contained to further enhance frying ability, in particular, suppressing foaming. Most preferred for further improvement.
상기와 같이 하여 얻어지는 본 발명의 유지조성물은, 그대로 또는 조리용 유지조성물에 통상적으로 사용되는 첨가제를 배합하여 조리용 유지조성물로서 사용할 수 있다.The oil-fat composition of this invention obtained as mentioned above can be used as a cooking oil-fat composition as it is or mix | blends the additive normally used for a cooking fat composition.
이러한 첨가제로는, 보존안정성 향상, 산화안정성 향상, 열안정성 향상, 저온하에서의 결정화 억제 등을 목적으로 한 폴리글리세린지방산에스테스, 자당지방산에스테르, 소르비탄지방산에스테르, 비타민 E, 아스코르브산지방산에스테르, 리그난, 코엔자임 Q, 인지질, 올리자놀, 디글리세리드 등, 성인병 예방작용, 생활습관병 예방작용, 생체내 산화억제작용, 비만병 예방작용을 기대한 비타민 E, 아스코르브산지방산에스테르, 리그난, 코엔자임 Q, 인지질, 올리자놀 등을 들 수 있다.Such additives include polyglycerol fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, vitamin E, ascorbic acid fatty acid esters, lignans, for the purpose of improving storage stability, improving oxidation stability, improving thermal stability, suppressing crystallization at low temperatures, and the like. Coenzyme Q, Phospholipids, Oligool, Diglycerides, etc., Prevents adult diseases, prevents lifestyle diseases, inhibits oxidation in vivo, prevents obesity, vitamin E, ascorbic acid fatty acid esters, lignans, coenzyme Q, phospholipids, oligos Zanol and the like.
본 발명의 조리용 유지조성물은, 채종유, 옥수수유, 홍화유, 대두유와 같은 일반적으로 시판되고 있는 식용유와 동등 또는 그 이상의 풍미를 갖고, 볶음 요리, 튀김, 마리네이드 등의 조리에 사용할 수 있음은 물론, 유지를 함유하는 식품인 드레싱, 마요네즈, 마가린, 과자류, 케이크, 음료 등에도 사용할 수 있다. 조리품의 종류에 따라 풍미의 특성은 상이하지만, 소재의 맛을 살린 단백한 요리를 만들 수 있다. 또한, 튀김조리시에서의 기름의 튀는 정도는 통상의 식용유와 동등 또는 그 이하이다. 또, 본 발명의 조리용 유지조성물을 적량 계속적으로 섭취함으로써, 혈중지질농도가 저하되는 작용도 기대할 수 있다.The cooking oil composition of the present invention has the same or more flavor than commercially available cooking oils such as rapeseed oil, corn oil, safflower oil, and soybean oil, and can be used for cooking stir-fried dishes, fried foods, marinades and the like. It can also be used for dressings, mayonnaise, margarine, confectionary, cakes and drinks, which are foods containing oils and fats. The flavors vary depending on the type of food, but you can make a protein meal that uses the taste of the ingredients. In addition, the frying degree of the oil at the time of frying cooking is equal to or less than ordinary cooking oil. In addition, by continually ingesting the cooking fat and oil composition of the present invention, an effect of lowering blood lipid concentration can also be expected.
이하에, 실시예를 들어 본 발명을 보다 구체적으로 설명하지만, 본 발명은 이에 의해 한정되지 않는다.Although an Example is given to the following and this invention is demonstrated to it further more concretely, this invention is not limited by this.
실시예 1Example 1
채종 백교유 (닛신세이유 (주) 제조) 80 질량부와 구성지방산이 질량비로 카프릴산/카프르산 = 3/1 인 MCT 20 질량부를 혼합한 후, 감압하 120 ℃ 에서 교반하고, 탈기 및 탈수처리를 실시하였다. 이것에 촉매로서 나트륨메틸레이트 0.1 질량부를 첨가하고, 120 ℃ 에서 30 분 동안 랜덤 에스테르 교환반응을 실시하였다. 반응생성물을 통상적인 방법에 의해 물로 세정하고 건조 후, 탈색ㆍ탈취하여 유지조성물 1 을 얻었다. 또, 유지조성물 1 에 대해, 자당지방산에스테르 (미쯔비시가가꾸푸즈 (주) 제조, 상품명 료토 슈거 에스테르 O-170) 2.5 질량%, 숙신산모노글리세리드 (리껭비타민 (주) 제조, 상품명 포엠 B-10) 0.1 질량%, 소르비탄지방산에스테르 (리껭비타민 (주) 제조, 상품명 포엠 O-80) 1 질량% 를 첨가하여 유지조성물 2 를 얻었다. 유지조성물 1, 2 의 트리글리세리드 조성 및 지방산 조성을 각각 칼럼 GS-l 을 사용한 가스크로마토그래피 및「기준유지분석시험법 (1996)」에 준하여 측정하였다 (이하의 실시예 및 비교예에서도 동일). 결과를 표 1 에 나타낸다.80 parts by mass of Rapeseed White Bridge Oil (manufactured by Nisshinsei Oil Co., Ltd.) and 20 parts by mass of MCT with caprylic / capric acid = 3/1 in mass ratio are mixed, and then stirred at 120 ° C. under reduced pressure, and degassing. And dehydration treatment. 0.1 mass part of sodium methylate was added to this as a catalyst, and the random transesterification reaction was performed at 120 degreeC for 30 minutes. The reaction product was washed with water by a conventional method, dried, decolored and deodorized to obtain a fat or oil composition 1. Moreover, with respect to the oil-fat composition 1, 2.5 mass% of sucrose fatty acid ester (made by Mitsubishi Chemical Corporation, brand name Ryto sugar ester O-170), succinic acid monoglyceride (made by Ribitavitamin, brand name PEM B-10) 0.1 mass% and sorbitan fatty acid ester (The Ribvitamin Co., Ltd. make, brand name Poem O-80) were added, and the oil-fat composition 2 was obtained. The triglyceride composition and fatty acid composition of the oil-fat compositions 1 and 2 were measured according to gas chromatography using the column GS-1, and "standard maintenance analysis method (1996)" (the same is true for the following examples and comparative examples). The results are shown in Table 1.
실시예 2Example 2
대두 샐러드유 (닛신세이유 (주) 제조) 85 질량부와 구성지방산이 질량비로카프릴산/카프르산 = 3/1 인 MCT 15 질량부와의 혼합물에 리파아제 QL (메이또산교 (주) 제조) 0.1 질량부를 첨가하고, 교반하 60 ℃ 에서 l5 시간 동안 에스테르 교환반응을 실시하였다. 반응생성물로부터 효소를 여과 분리하고, 여과액을 물로 세정하고 건조 후, 탈색ㆍ탈취하여 유지조성물 3 을 얻었다. 유지조성물 3 의 트리글리세리드 조성 및 지방산 조성을 표 1 에 나타낸다.Soybean salad oil (manufactured by Nisshinsei Oil Co., Ltd.), lipase QL (made by Meito Sangyo Co., Ltd.) in a mixture of 85 parts by mass and 15 parts by mass of MCT having a constituent fatty acid ratio of caprylic acid / capric acid = 3/1. ) 0.1 parts by mass was added, and a transesterification reaction was carried out at 60 DEG C for l5 hours under stirring. The enzyme was separated from the reaction product by filtration, the filtrate was washed with water, dried, decolored and deodorized to obtain a fat or oil composition 3. The triglyceride composition and fatty acid composition of the oil-fat composition 3 are shown in Table 1.
실시예 3Example 3
팜유 (닛신세이유 (주) 제조) 77 질량부와 질량비로 카프릴산/카프르산 = 1/1 의 중쇄 지방산 혼합물 23 질량부를 혼합한 후, 혼합물에 리파아제 QL (메이또산교 (주) 제조) 0.1 질량부를 첨가하고, 교반하 60 ℃ 에서 15 시간 동안 에스테르 교환반응을 실시하였다. 반응 후 효소를 여과 분리하고, 여과액 중의 유리지방산을 박막식 증발기로 제거한 후, 탈색ㆍ탈취하여 유지조성물 4 를 얻었다. 유지조성물 4 의 트리글리세리드 조성 및 지방산 조성을 표 1 에 나타낸다.Palm oil (manufactured by Nisshinsei Oil Co., Ltd.) was mixed with 23 parts by mass of a heavy chain fatty acid mixture of caprylic / capric acid = 1/1 at 77 parts by mass and a mass ratio, and then the lipase QL (Meitosan Bridge Co., Ltd.) was manufactured. ) 0.1 parts by mass was added and transesterification was carried out at 60 ° C. for 15 hours under stirring. After the reaction, the enzyme was separated by filtration, and the free fatty acid in the filtrate was removed by a thin film evaporator, followed by decolorization and deodorization to obtain an oil-fat composition 4. The triglyceride composition and fatty acid composition of the oil-fat composition 4 are shown in Table 1.
실시예 4Example 4
옥수수유 (닛신세이유 (주) 제조) 77 질량부와 질량비로 카프릴산/카프르산 = 1/1 의 중쇄 지방산 혼합물 23 질량부를 혼합한 후, 혼합물에 리파아제 QL (메이또산교 (주) 제조) 0.1 질량부를 첨가하고, 교반하 60 ℃ 에서 15 시간 동안 에스테르 교환반응을 실시하였다. 반응 후 효소를 여과 분리하고, 여과액 중의 유리지방산을 박막식 증발기로 제거한 후, 탈색ㆍ탈취하여 유지조성물 5 를 얻었다. 유지조성물 5 의 트리글리세리드 조성 및 지방산 조성을 표 1 에 나타낸다.Corn oil (manufactured by Nisshinsei Oil Co., Ltd.) 77 parts by mass and 23 parts by mass of a heavy chain fatty acid mixture of caprylic acid / capric acid = 1/1 at a mass ratio, and then the lipase QL (Meitosan Bridge Co., Ltd.) Production) 0.1 parts by mass was added, and a transesterification reaction was carried out at 60 DEG C for 15 hours while stirring. After the reaction, the enzyme was separated by filtration, and the free fatty acid in the filtrate was removed by a thin film type evaporator, followed by decolorization and deodorization to obtain an oily composition 5. The triglyceride composition and fatty acid composition of the oil-fat composition 5 are shown in Table 1.
실시예 5Example 5
채종 백교유 (닛신세이유 (주) 제조) 93 질량부와 구성지방산이 질량비로 카프릴산/카프르산 = 3/1 인 MCT 7 질량부를 혼합한 후, 감압하 120 ℃ 에서 교반하고, 탈기 및 탈수처리를 실시하였다. 이것에 촉매로서 나트륨메틸레이트 0.1 질량부를 첨가하고, 120 ℃ 에서 30 분 동안 랜덤 에스테르 교환반응을 실시하였다. 반응생성물을 통상적인 방법에 의해 물로 세정하고 건조 후, 탈색ㆍ탈취하여 유지조성물 6 을 얻었다. 유지조성물 6 의 트리글리세리드 조성 및 지방산 조성을 표 2 에 나타낸다.Rapeseed white gyo oil (manufactured by Nisshinsei Oil Co., Ltd.) 93 parts by mass and constituent fatty acid were mixed in a mass ratio of 7 parts by mass of MCT having caprylic / capric acid = 3/1, and then stirred at 120 ° C under reduced pressure, and degassing. And dehydration treatment. 0.1 mass part of sodium methylate was added to this as a catalyst, and the random transesterification reaction was performed at 120 degreeC for 30 minutes. The reaction product was washed with water by a conventional method, dried, decolored and deodorized to obtain an oil-fat composition 6. The triglyceride composition and fatty acid composition of the oil-fat composition 6 are shown in Table 2.
실시예 6Example 6
채종 백교유 (닛신세이유 (주) 제조) 90 질량부와 구성지방산이 질량비로 카프릴산/카프르산 = 3/1 인 MCT l0 질량부를 혼합한 후, 감압하 120 ℃ 에서 교반하고, 탈기 및 탈수처리를 실시하였다. 이것에 촉매로서 나트륨메틸레이트 0.l 질량부를 첨가하고, 120 ℃ 에서 30 분 동안 랜덤 에스테르 교환반응을 실시하였다. 반응생성물을 통상적인 방법에 의해 물로 세정하고 건조 후, 탈색ㆍ탈취하여 유지조성물 7 을 얻었다. 유지조성물 7 의 트리글리세리드 조성 및 지방산 조성을 표 2 에 나타낸다.90 mass parts and constituent fatty acids of the cultivated Baekkyo oil (manufactured by Nisshinsei Oil Co., Ltd.) and MCT10 mass parts of caprylic / capric acid = 3/1 are mixed in a mass ratio, and then stirred at 120 ° C. under reduced pressure, and degassing. And dehydration treatment. 0.1 mass part of sodium methylate was added to this as a catalyst, and random transesterification was performed at 120 degreeC for 30 minutes. The reaction product was washed with water in a conventional manner, dried, decolored and deodorized to obtain an oily composition 7. The triglyceride composition and fatty acid composition of the oil-fat composition 7 are shown in Table 2.
실시예 7Example 7
실시예 2 와 동일한 혼합물에 리파아제 QL (메이또산교 (주) 제조) 0.1 질량부를 첨가하고, 교반하 60 ℃ 에서 3 시간 동안 에스테르 교환반응을 실시하였다. 반응생성물로부터 효소를 여과 분리하고, 여과액을 물로 세정하고 건조 후, 탈색ㆍ탈취하여 유지조성물 8 을 얻었다. 유지조성물 8 의 트리글리세리드 조성 및지방산 조성을 표 2 에 나타낸다.0.1 mass part of lipase QL (made by Meitosan Bridge Co., Ltd.) was added to the same mixture as Example 2, and the ester exchange reaction was performed at 60 degreeC for 3 hours, stirring. The enzyme was separated from the reaction product by filtration, the filtrate was washed with water, dried, decolored and deodorized to obtain an oily composition 8. The triglyceride composition and fatty acid composition of the oil-fat composition 8 are shown in Table 2.
비교예 1Comparative Example 1
채종 백교유 (닛신세이유 (주) 제조) 75 질량부와 구성지방산이 질량비로 카프릴산/카프르산 = 3/1 인 MCT 25 질량부를 혼합한 후, 감압하 120 ℃ 에서 교반하고, 탈기 및 탈수처리를 실시하였다. 이것에 촉매로서 나트륨메틸레이트 0.1 질량부를 첨가하고, 120 ℃ 에서 30 분 동안 랜덤 에스테르 교환반응을 실시하였다. 반응생성물을 통상적인 방법에 의해 물로 세정하고 건조 후, 탈색ㆍ탈취하여 유지조성물 9 를 얻었다. 유지조성물 9 의 트리글리세리드 조성 및 지방산 조성을 표 3 에 나타낸다.75 parts by mass of Rapeseed Baekkyo Oil (manufactured by Nisshinsei Oil Co., Ltd.) and 25 parts by mass of MCT having caprylic acid / capric acid = 3/1 in mass ratio are mixed, and then stirred at 120 ° C. under reduced pressure, and degassing. And dehydration treatment. 0.1 mass part of sodium methylate was added to this as a catalyst, and the random transesterification reaction was performed at 120 degreeC for 30 minutes. The reaction product was washed with water by a conventional method, dried, decolored and deodorized to obtain an oil-fat composition 9. The triglyceride composition and fatty acid composition of the oil-fat composition 9 are shown in Table 3.
비교예 2Comparative Example 2
채종 백교유 (닛신세이유 (주) 제조) 97 질량부와 구성지방산이 질량비로 카프릴산/카프르산 = 3/1 인 MCT 3 질량부를 혼합한 후, 감압하 120 ℃ 에서 교반하고, 탈기 및 탈수처리를 실시하였다. 이것에 촉매로서 나트륨메틸레이트 0.1 질량부를 첨가하고, 120 ℃ 에서 30 분 동안 랜덤 에스테르 교환반응을 실시하였다. 반응생성물을 통상적인 방법에 의해 물로 세정하고 건조 후, 탈색ㆍ탈취하여 유지조성물 1O 을 얻었다. 유지조성물 10 의 트리글리세리드 조성 및 지방산 조성을 표 3 에 나타낸다.97 parts by mass of rapeseed white gyo oil (manufactured by Nisshinsei Oil Co., Ltd.) and 3 parts by mass of MCT having caprylic / capric acid = 3/1 by mass ratio are mixed, and then stirred at 120 ° C. under reduced pressure, and degassing. And dehydration treatment. 0.1 mass part of sodium methylate was added to this as a catalyst, and the random transesterification reaction was performed at 120 degreeC for 30 minutes. The reaction product was washed with water by a conventional method, dried, decolored and deodorized to obtain an oil-containing composition 10. The triglyceride composition and fatty acid composition of the oil-fat composition 10 are shown in Table 3.
주) M ; 중쇄 지방산, L ; 장쇄 지방산, tr.-trace, 예컨대 C8 : 0 은 탄소수 8 이며 불포화 결합 (탄소-탄소 이중결합) 의 수가 0 인 것을 나타낸다(표 2, 3 및 4 에서도 동일).Note) M; Medium chain fatty acids, L; Long-chain fatty acids, tr.-trace, such as C8: 0, have 8 carbon atoms and indicate that the number of unsaturated bonds (carbon-carbon double bonds) is 0 (also in Tables 2, 3 and 4).
실시예 8Example 8
생후 4 주된 위스터계 수컷 랫트에 대두유 (닛신세이유 (주) 제조) (대조) (트리글리세리드 조성 및 지방산 조성을 표 4 에 나타냄) 또는 유지조성물 1, 6, 7, 9 또는 10 을 25 질량% 첨가한 사료를 8 주 동안 자유섭취시켰다. 사료의 조성을 표 5 에 나타낸다. 필수지방산 부족을 방지하기 위해, 모든 사료에 대해 대두유를 3 질량% 첨가하였다. 비타민 및 미네랄은 미국영양학회가 추천장려한 것을 사용하고, 사료에 대한 첨가량은 에너지 밀도에 따라 조정하였다. 실험식 투여 8 주 동안 후에 각 군 8 마리씩 해부하여 내장지방 질량을 측정하였다. 또, 피하지방량을 측정하기 위해, 시체를 동결건조하고 지방함량을 속슬렛을 사용하여 측정하였다. 8 주 동안 사육한 랫트의 결과를 표 6 에 나타낸다. 사료섭취량, 최종체중, 꼬리 길이는 모든 시험구에서 통계적으로 유의차는 보이지 않았다. 8 주 동안 사육한 랫트의 내장지방량 및 피하지방량은, 유지조성물 l, 6 및 7 군에서 통계적으로 유의하게 낮은 값을 나타냈다. 동물시험의 결과로부터, 유지조성물을 구성하는 전체 지방산에서 차지하는 중쇄 지방산의 비율, 및 전체 글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 2 개 갖는 트리글리세리드의 비율이 본 발명의 범위내에 들어오는 본 발명 유지조성물 1, 6, 7 을 사용한 경우에는, 대조 및 비교예 유지조성물 9, 10 을 사용한 경우에 비해 체지방 축적이 적다는 것이 판명되었다.25 mass% of soybean oil (manufactured by Nisshinsei Oil Co., Ltd.) (control) (triglyceride composition and fatty acid composition are shown in Table 4) or fat or oil composition 1, 6, 7, 9 or 10 was added to 4 week-old male rats. One feed was free intake for 8 weeks. The composition of the feed is shown in Table 5. To prevent essential fatty acid deficiency, soybean oil was added to all feeds by 3% by mass. Vitamins and minerals were recommended by the American Nutrition Society, and the amount of feed added was adjusted according to the energy density. Eight weeks after the experimental administration, each group was dissected to determine visceral fat mass. In addition, to measure the amount of subcutaneous fat, the body was lyophilized and fat content was measured using Soxhlet. The results of rats reared for 8 weeks are shown in Table 6. Feed intake, final weight, and tail length did not show statistically significant differences in all groups. The visceral fat mass and subcutaneous fat of rats reared for 8 weeks were statistically significantly lower in the oil compositions l, 6 and 7. From the results of the animal test, the oil-fat composition 1 of the present invention in which the ratio of the heavy chain fatty acid to the total fatty acids constituting the oil-fat composition and the ratio of the triglyceride having two heavy chain fatty acid residues in the whole glyceride in the molecule are within the scope of the present invention. When 6 and 7 were used, it was proved that body fat accumulation was smaller than that of the control and comparative example fat and oil compositions 9 and 10.
주) 데이터는, 평균치 ± 표준오차로 나타냈다Note) Data is expressed as mean ± standard error.
* 표시 ; 대조와 비교하여 위험률 5 % 이하에서 유의한 차이가 있음* Display ; Significant difference with a risk of less than 5% compared to the control
실시예 9Example 9
유지조성물을 사용하여 조리시험과 내한성 시험을 실시하였다. 조리시험에 대해서는, 발연, 거품 발생, 기름 튐, 조리품의 풍미를 검토하였다. 내한성 시험은 저온보관시의 외관을 관찰하였다. 유지조성물 샘플로는, 채종유 (닛신세이유 (주) 제조) (대조), 유지조성물 1, 유지조성물 2, 유지조성물 4, 유지조성물 6, 유지조성물 8 및 채종유와 구성지방산이 질량비로 카프릴산/카프르산 = 3/1 인 MCT 를 4 : 1 (질량비) 로 배합한 유지 (배합유) 의 7 종을 사용하였다. 채종유 및 배합유의 트리글리세리드 조성 및 지방산 조성을 표 4 에 나타낸다.Cooking and cold resistance tests were carried out using the oil and fat composition. For the cooking test, the smoke, foaming, grease, and flavor of the cooked food were examined. Cold resistance test observed the appearance at low temperature storage. Oil and fat composition samples include rapeseed oil (manufactured by Nisshinsei Oil Co., Ltd.) (control), oil and fat composition 1, oil and fat composition 2, oil and fat composition 4, oil and fat composition 6, oil and fat composition 8, and rapeseed oil and constituent fatty acids in mass ratio. Seven types of fats and oils (compounding oil) which mix | blended MCT of / capric acid = 3/1 by 4: 1 (mass ratio) were used. Table 4 shows the triglyceride composition and fatty acid composition of the rapeseed oil and the blended oil.
조리시험의 결과를 표 7 에 나타낸다. 조리시험의 결과로부터, 유지조성물을 구성하는 전체 지방산에서 차지하는 중쇄 지방산의 비율, 및 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 2 개 갖는 트리글리세리드의 비율이 본 발명의 범위내에 들어오는 본 발명의 유지조성물 l, 2, 4, 6, 8 은 통상의 식용유와 동등한 조리적성을 갖는다는 것이 판명되었다. 또한, 유지조성물을 구성하는 전체 트리글리세리드에서 차지하는 중쇄 지방산 잔기를 분자내에 3 개 갖는 트리글리세리드의 비율이 3 질량% 이하인 유지조성물 1, 2, 4, 6 은 튀김 조리시의 안정성이 높다는 것이 판명되었다. 특히, 유화제를 배합한 유지조성물 2 는, 거품 발생 억제효과가 우수하다는 것이 판명되었다. 또, 동일한 7 종의 샘플을 5 ℃ 에 48 시간 동안 정치하여 외관을 관찰하였다. 결과를 표 7 에 나타낸다. 그 결과, 유지조성물 4 에서는 결정의 석출이 보였지만, 다른 샘플은 외관이 투명했다.Table 7 shows the results of the cooking test. From the results of the cooking test, the oil-fat composition of the present invention in which the ratio of the heavy chain fatty acid to the total fatty acids constituting the oil-fat composition and the ratio of the triglyceride having two heavy chain fatty acid residues in the total triglycerides in the molecule are within the scope of the present invention. , 2, 4, 6, and 8 have been found to have cooking properties equivalent to those of ordinary cooking oil. In addition, it has been found that the oil-fat compositions 1, 2, 4, and 6 having 3 mass% or less of triglycerides having three heavy chain fatty acid residues in the molecule in the total triglycerides constituting the oil-fat composition have high stability at the time of frying cooking. In particular, the oil-fat composition 2 which mix | blended an emulsifier turned out to be excellent in the foam generation inhibitory effect. Moreover, the same 7 types of samples were left still at 5 degreeC for 48 hours, and external appearance was observed. The results are shown in Table 7. As a result, although the precipitation of the crystal | crystallization was seen in the oil-fat composition 4, the other sample was transparent in appearance.
주) 채종유를 대조 (10 점) 로 하여, 10 ~ 7 점 ; 사용 가능, 6 ~ 4 점Note) 10 to 7 points, with rapeseed oil as a control (10 points); Available, 6-4 points
; 사용에 약간 문제 있음, 3 ~ 1 점 ; 사용 불가능이라고 평가하였다.; Slightly trouble with use, 3 to 1 point; It was evaluated as unavailable.
발연 : 직경 24 ㎝ 이하인 테프론 가공 후라이팬를 미리 30 초 동안 가열하Fuming: A Teflon frying pan with a diameter of 24 cm or less is heated for 30 seconds in advance.
고, 샘플유를 15 g 넣어 다시 30 초 동안 가열하였다. 그 후, 야Then, 15 g of sample oil was added thereto and heated again for 30 seconds. After that, hey
채 볶음재료를 후라이팬에 넣고, 3 분 동안 가열한 시점에서 소금과Put the fried ingredients in a frying pan, and when salt is heated for 3 minutes
후추가루를 적량 첨가하였다. 볶음 조리시의 발연을 육안으로 관Black pepper was added in an appropriate amount. Visually observe fuming at the time of stir-fry cooking
찰하였다.It was cold.
거품 발생, 기름 튐, 풍미 : 가정용 전기 튀김기에 샘플유 600 g 을 넣고,Foaming, oil splatter, flavor: 600 g of sample oil in a household electric fryer,
180 ℃ 에서 새우튀김 4 마리를 투입하고, 1 분 후의 기름의 거품 발4 shrimp tempura at 180 ° C, and 1 minute after the foaming of oil
생, 기름 튐을 관찰하였다. 또, 조리한 새우튀김의 풍미를 평가하Raw and grease were observed. In addition, we evaluate flavor of cooked fried shrimp
였다.It was.
튀김 안정성: 가정용 전기 튀김기에 샘플유 600 g 을 넣고, 180 ℃ 에서 새Frying stability: add 600 g of sample oil to household electric fryer,
우튀김을 30 분 동안 튀긴 다음 고로케를 30 분 동안 튀기고, 마지막Fry the fried tempura for 30 minutes, then fry the croquettes for 30 minutes, and finally
에 닭튀김을 30 분 동안 튀겼다. 부글부글 거품이 발생하는 정도On fried chicken for 30 minutes. The degree to which bubbling bubbles occur
에 따라 튀김 조리에 대한 안정성을 평가하였다. 부글부글 거품To evaluate the stability of the frying cooking. Bubble bubble
의 발생이 튀김기 표면적의 100 % 가 된 시점에서 튀김을 중지하였다.The frying was stopped when the occurrence of became 100% of the fryer surface area.
내한성 : 저온보관시 (5 ℃ 에서 48 시간 정치) 의 외관을 관찰하였다.Cold resistance: The appearance of low temperature storage (fixed at 5 ° C for 48 hours) was observed.
본 발명의 유지조성물은, 체지방 축적이 적고, 통상의 식용유와 동등한 조리적성을 가지며, 풍미가 양호하고 안전성이 높다.The oil-fat composition of this invention has little body fat accumulation, has cooking property equivalent to normal cooking oil, good flavor, and high safety.
Claims (6)
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| Application Number | Priority Date | Filing Date | Title |
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| PCT/JP2000/005606 WO2002016534A1 (en) | 1998-11-13 | 2000-08-22 | Fat compositions |
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Cited By (1)
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| KR100903705B1 (en) * | 2008-12-17 | 2009-06-19 | 대한민국 | Continuous Enzymatic Transesterification in a Step-by-Step Temperature System to Develop Low Saturation, Trans Fat Free Fats and Oils |
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| CN102028045B (en) * | 2009-09-29 | 2014-06-25 | 日清奥利友集团株式会社 | Edible blend oil |
| CN101919450B (en) * | 2010-06-04 | 2012-12-12 | 山东三星玉米产业科技有限公司 | Corn oil containing medium chain fatty acid ester and preparation method thereof |
| JP5739180B2 (en) * | 2011-01-31 | 2015-06-24 | 日清オイリオグループ株式会社 | Oil composition for promoting insulin secretion |
| CN103380827B (en) * | 2012-05-02 | 2017-10-27 | 丰益(上海)生物技术研发中心有限公司 | It is a kind of to prevent fat or oil composition of obesity fatty liver and preparation method thereof |
| CN103891920B (en) * | 2012-12-25 | 2015-09-30 | 中粮营养健康研究院有限公司 | A kind of fat or oil composition containing middle Long carbon chain triglycerides and preparation method thereof |
| CN104247783A (en) * | 2013-06-27 | 2014-12-31 | 中粮营养健康研究院有限公司 | Grease composition for margarine and shortening and preparing method thereof |
| CN104413147A (en) * | 2013-09-11 | 2015-03-18 | 中粮营养健康研究院有限公司 | Grease composition for formula milk powder as well as preparation method and application of grease composition |
| CN104543045A (en) * | 2013-10-12 | 2015-04-29 | 中粮营养健康研究院有限公司 | Grease composition, preparation method and usage thereof |
| CN104642563B (en) * | 2013-11-19 | 2021-04-30 | 丰益(上海)生物技术研发中心有限公司 | Oil composition with stable flavor |
| CN103897811A (en) * | 2014-04-02 | 2014-07-02 | 河北康睿达脂质有限公司 | Production method for medium-chain and long-chain oil fatty acid |
| JP5881784B2 (en) * | 2014-07-17 | 2016-03-09 | 日清オイリオグループ株式会社 | Gel emulsion food |
| CN105638927B (en) * | 2014-11-13 | 2020-11-10 | 丰益(上海)生物技术研发中心有限公司 | Oil and fat composition and method for producing oil and fat composition |
| CN104689328B (en) * | 2015-03-23 | 2017-07-04 | 山东北大高科华泰制药有限公司 | Oryzanol composition |
| WO2016204089A1 (en) * | 2015-06-15 | 2016-12-22 | 日清オイリオグループ株式会社 | Plastic fat composition |
| WO2017073480A1 (en) * | 2015-10-26 | 2017-05-04 | 日清オイリオグループ株式会社 | Oily food |
| JP6925701B2 (en) * | 2017-01-04 | 2021-08-25 | 日清オイリオグループ株式会社 | Oil and fat composition for cooking rice, cooked rice, and method for manufacturing cooked rice |
| TWI776917B (en) * | 2017-09-01 | 2022-09-11 | 日商日清奧利友集團股份有限公司 | oil composition |
| CN112956543A (en) * | 2021-04-05 | 2021-06-15 | 江南大学 | Blending method of grease composition |
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| US5380544A (en) * | 1989-09-20 | 1995-01-10 | Nabisco, Inc. | Production of fat mixtures enriched with triglycerides bearing short, medium and long residues |
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- 2000-08-22 KR KR1020037002571A patent/KR100661780B1/en not_active Expired - Lifetime
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| KR100903705B1 (en) * | 2008-12-17 | 2009-06-19 | 대한민국 | Continuous Enzymatic Transesterification in a Step-by-Step Temperature System to Develop Low Saturation, Trans Fat Free Fats and Oils |
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| CN1293176C (en) | 2007-01-03 |
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| HK1059448A1 (en) | 2004-07-02 |
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