KR20010035226A - Method for preparation of high diglyceride containing oil composition - Google Patents
Method for preparation of high diglyceride containing oil composition Download PDFInfo
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- KR20010035226A KR20010035226A KR1020010002974A KR20010002974A KR20010035226A KR 20010035226 A KR20010035226 A KR 20010035226A KR 1020010002974 A KR1020010002974 A KR 1020010002974A KR 20010002974 A KR20010002974 A KR 20010002974A KR 20010035226 A KR20010035226 A KR 20010035226A
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- Prior art keywords
- oil
- fat
- lipase
- composition
- diglyceride
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- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003921 oil Substances 0.000 claims abstract description 56
- 239000004367 Lipase Substances 0.000 claims abstract description 26
- 102000004882 Lipase Human genes 0.000 claims abstract description 26
- 108090001060 Lipase Proteins 0.000 claims abstract description 26
- 235000019421 lipase Nutrition 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 13
- 239000000194 fatty acid Substances 0.000 claims abstract description 13
- 229930195729 fatty acid Natural products 0.000 claims abstract description 13
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 12
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 3
- 239000003925 fat Substances 0.000 claims description 61
- 238000003756 stirring Methods 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000001877 deodorizing effect Effects 0.000 claims 1
- 235000019198 oils Nutrition 0.000 abstract description 50
- 235000012424 soybean oil Nutrition 0.000 abstract description 10
- 239000003549 soybean oil Substances 0.000 abstract description 10
- 239000008280 blood Substances 0.000 abstract description 4
- 210000004369 blood Anatomy 0.000 abstract description 4
- 240000008042 Zea mays Species 0.000 abstract 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract 1
- 239000000828 canola oil Substances 0.000 abstract 1
- 235000019519 canola oil Nutrition 0.000 abstract 1
- 235000005822 corn Nutrition 0.000 abstract 1
- 239000002075 main ingredient Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 5
- 238000000105 evaporative light scattering detection Methods 0.000 description 5
- 239000010977 jade Substances 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 Phosphorus monoglycerides Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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
- 239000008162 cooking oil Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 235000002316 solid fats Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000588881 Chromobacterium Species 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/18—Lipids
- A23V2250/182—Diglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2300/00—Processes
- A23V2300/28—Hydrolysis, degree of hydrolysis
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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
본 발명은 고함량의 디글리세라이드를 포함하는 유지 조성물의 제조 방법에 관한 것으로, 좀 더 자세하게는 유지에 물과 1,3 위치특이성 또는 비위치특이성 리파아제를 혼합한 후, 교반속도 200 ∼ 800 rpm, 온도 40 ∼ 70℃에서 30분 ∼ 30시간 동안 반응시켜서 고함량의 디글리세라이드를 포함하는 유지 조성물을 제조하는 것이다.The present invention relates to a method for producing a fat or oil composition comprising a high content of diglycerides, and more particularly, after mixing water and 1,3 position specific or non position specific lipase with fats and oils, the stirring speed is 200 to 800 rpm. It is made to react for 30 minutes-30 hours at the temperature of 40-70 degreeC, and to manufacture the oil-fat composition containing a high content of diglycerides.
최근 수년 동안 비만증 및 고지혈증에 대한 관심이 급증하면서 음식물에 함유된 트리글리세라이드 지방의 칼로리 및 체내 축적을 줄이기 위한 방법 및 대체 지방에 대한 요구가 증가되고 있는 실정이다. 이에 따라 트리글리세라이드 지방의 물리적 및 미각적인 특성을 가지거나 인체에 약간만 흡수되거나 전혀 흡수되지 않는 물질을 제공하는 것에 관한 기술들이 많이 개발되었는데, 이러한 물질은 무칼로리, 가성지방(pseudofat), 비소화성 지방 및 대체 지방으로서 다양하게 지칭되며, 매우 많은 종류들이 있다. 일예로 미국특허 제4,582,927호에서는 말론산의 지방 에스테르를 개시하고 있고, 미국특허 제4,582,715호는 알파아세틸화 트리글리세라이드, 미국 특허 제3,579,548호에서는 알파-분지쇄 카르복실산의 트리글리세라이드에 대하여 설명하고 있다. 미국 특허 제3,600,186호, 제4,368,213호 및 제4,461,782호에서는 다양한 식품 조성물에 비소화성 지방으로 슈크로즈 폴리에스테르(즉, 8개의 히드록실기중에 4개가 지방산으로 에스테르화된 슈크로즈)를 이용하는 방법에 관하여 기술하고 있는데, 이는 현재 상당히 관심을 받고 있는 화합물 중 하나이다.As the interest in obesity and hyperlipidemia has increased rapidly in recent years, there is an increasing demand for alternative fats and methods for reducing calories and body accumulation of triglyceride fats contained in food. As a result, many technologies have been developed to provide substances that have the physical and taste characteristics of triglyceride fats, or are only slightly absorbed or not absorbed by the human body. These substances are calorie-free, pseudofat and non-digestible fats. And variously referred to as replacement fats, and there are so many varieties. For example, US Pat. No. 4,582,927 discloses fatty esters of malonic acid, US Pat. No. 4,582,715 describes alphaacetylated triglycerides and US Pat. No. 3,579,548 describe triglycerides of alpha-branched chain carboxylic acids. have. U.S. Pat.Nos. 3,600,186, 4,368,213 and 4,461,782 describe methods of using sucrose polyesters (ie, sucrose esterified with four of eight hydroxyl groups out of eight hydroxyl groups) as non-digestible fats in various food compositions. It is one of the compounds of great interest.
최근 식용유 등의 유지 조성물 제품에 소량 함유된 디글리세라이드가 주성분인 트리글리세라이드와 그 대사 과정이 다르며, 혈중 지방치를 높이지 않고, 몸에 지방을 축적시키지 않는 생리효과를 가진다는 사실이 밝혀짐에 따라 디글리세라이드가 80%이상 함유된 식용유가 일본에서 출시되어 시장에서 호평을 받고 있다.Recently, it has been found that diglycerides contained in a small amount of oil or fat composition products, such as cooking oil, differ from the main components of triglycerides and their metabolic processes, and have a physiological effect that does not raise blood fat levels and does not accumulate fat in the body. Accordingly, cooking oils containing more than 80% of diglycerides have been released in Japan and are popular in the market.
디글리세라이드는 일반적으로 화장품, 의약품 등의 분야에서 다양한 용도의 기제로 이용되어 왔으며, 이의 제조를 위한 방법들이 몇가지 알려져 있다. 공지의 디글리세라이드 제조 방법으로는 유지와 글리세린을 혼합한 다음 리파아제를 이용하여 글리세롤리시스(Glycerolysis) 반응을 일으키는 방법과 지방산과 글리세린 원료에 1,3 위치특이성 리파아제를 사용하여 디글리세라이드를 합성하는 방법이 있다.Diglycerides have generally been used as a base for various uses in the fields of cosmetics, pharmaceuticals and the like, and several methods for their preparation are known. Known diglycerides are prepared by mixing fats and oils with glycerin and then causing glycerolsis reactions using lipases and synthesizing diglycerides using 1,3-position-specific lipases on fatty acids and glycerin raw materials. There is a way.
그러나 전자의 경우 액상 유지 상태로 디글리세라이드 함량을 높이는 데에는 한계가 있다. 일본 특개평 제6-343481호에는 상온에서 고체 유지의 형태를 갖는 원료를 사용하거나, 상온에서 디글리세라이드로 전환시 고체유지가 되는 성질의 것을 이용하여 디글리세라이드를 80%이상까지도 높였지만, 이는 상온에서 액상의 유지로 존재하지 않게 되는 단점을 갖고 있으며, 디글리세라이드 함량 60%이상의 액상유지는 만들 수 없다.However, in the former case, there is a limit in increasing the diglyceride content in a liquid holding state. In Japanese Patent Laid-Open No. 6-343481, diglycerides have been increased up to 80% or more by using raw materials having the form of solid fats and oils at room temperature, or those which become solid fats and oils when converted to diglycerides at room temperature. This has the disadvantage that it does not exist in the maintenance of the liquid phase at room temperature, and can not make the liquid retention of more than 60% diglyceride content.
후자의 경우 일본 특개평 제64-71495호 및 특개평 제11-123097호에 기술되어 있는데, 이 제조 방법은 유지를 1차 가수분해, 2차 합성하는 과정을 거쳐 고함량의 디글리세라이드를 함유한 유지 조성물을 제조하여야 하므로 제조 공정이 복잡하고 생산성 및 효소 원가측면에서 비효율적이고, 또한 식품 제조에 합성 공정이 포함된다는 부정적 이미지도 바람직하지 않다.The latter is described in Japanese Laid-Open Patent Publication Nos. Hei 64-71495 and Hei 11-123097, which contain a high content of diglycerides through the process of primary hydrolysis and secondary synthesis of fats and oils. The negative image that the manufacturing process is complex, inefficient in terms of productivity and enzyme cost, and that the synthetic process is involved in food production, is also undesirable because one fat or oil composition must be prepared.
이에 본 발명자들은 고함량의 디글리세라이드를 포함하는 유지 조성물을 제조하기 위해 기존의 가수분해 공정 및 에스테르합성 공정을 모두 거치는 대신 1,3위치 특이성 또는 비위치특이성 리파아제를 이용한 가수분해 공정만으로도 디글리세라이드 함량이 60%이상인 유지 조성물의 제조가 가능함을 확인하였으며, 본 발명은 이에 기초하여 완성되었다.Therefore, the inventors of the present invention, instead of going through the conventional hydrolysis process and ester synthesis process to prepare a fat or oil composition containing a high content of diglycerides, diglycerides only by hydrolysis process using 1,3-position-specific or non-position-specific lipase It was confirmed that the fat or oil composition having a ride content of 60% or more was possible, and the present invention was completed based on this.
따라서, 본 발명의 목적은 혈중 지방치를 높이지 않고, 몸에 지방을 축적시키지 않는 디글리세라이드의 함량이 높은 유지 조성물의 제조 방법을 제공하는 것이다.Accordingly, it is an object of the present invention to provide a method for producing a fat or oil composition having a high content of diglycerides that does not increase blood fat and does not accumulate fat in the body.
본 발명의 다른 목적은 기존의 가수분해 공정 및 에스테르 합성 공정을 모두 거치는 대신 제조 공정이 간단하고, 생산성이 높으며, 효소 원가측면에서 효율적인 고함량의 디글리세라이드를 포함하는 유지 조성물의 제조 방법을 제공하는 것이다.It is another object of the present invention to provide a method for preparing an oil-fat composition comprising a high content of diglyceride, which is simple in production, high in productivity, and efficient in terms of enzyme cost, instead of going through both the conventional hydrolysis and ester synthesis. It is.
본 발명의 또 다른 목적은 상기의 방법으로 제조된 유지 조성물을 제공하는 것이다.Another object of the present invention is to provide a fat or oil composition prepared by the above method.
상기 목적을 달성하기 위한 본 발명의 방법은 유지 100 중량부에 대하여 물 2 ∼ 15중량부, 및 1,3 위치특이성 리파아제 150 ∼ 500 유닛(unit)/유지 g, 또는 비위치특이성 리파아제 20 ∼ 300 유닛/유지 g을 혼합하는 단계; 및 상기의 혼합 원료를 교반속도 200 ∼ 800 rpm, 온도 40 ∼ 70℃에서 30분 ∼ 30시간 동안 반응시키는 단계로 이루어진다.The method of the present invention for achieving the above object is 2 to 15 parts by weight of water, and 1,3 regiospecific lipase 150 to 500 units / fats, or non-specific lipase 20 to 300 with respect to 100 parts by weight of fat or oil. Mixing unit / holding g; And reacting the mixed raw material for 30 minutes to 30 hours at a stirring speed of 200 to 800 rpm and a temperature of 40 to 70 ° C.
이하, 본 발명을 보다 구체적으로 설명하면 다음과 같다.Hereinafter, the present invention will be described in more detail.
본 발명에서는 우선, 유지에 물 및 리파아제를 첨가하여 혼합 원료를 준비한다.In the present invention, first, water and lipase are added to fats and oils to prepare a mixed raw material.
상기 유지는 탄소수 10∼22의 포화 또는 불포화 지방산을 주구성 지방산으로 하는 유지로부터 선택되어 사용될 수 있으며, 특히 대두유, 옥배유 및 채종유가 상업적인 원료확보 용이성의 이유로 바람직하다.The fats and oils may be selected and used from fats and oils having saturated or unsaturated fatty acids having 10 to 22 carbon atoms as the main fatty acid, and soybean oil, jade oil and rapeseed oil are preferable for reasons of commercial raw material availability.
상기 물은 상기 유지 100 중량부에 대하여 2∼15중량부로 첨가되며 2∼10중량부인 것이 바람직하다. 물의 함유량이 2중량부 미만일 경우에는 리파아제의 가수분해 활성이 나타나기 어렵고, 10중량부를 초과하면 과잉 반응으로 인하여 지방산 및 모노글리세라이드의 함량이 과다해진다.The water is added in 2 to 15 parts by weight with respect to 100 parts by weight of the fat and oil is preferably 2 to 10 parts by weight. If the water content is less than 2 parts by weight, the hydrolytic activity of the lipase is less likely to appear, and if it exceeds 10 parts by weight, the content of fatty acids and monoglycerides becomes excessive due to the excess reaction.
상기 리파아제는 1,3 위치특이성 리파아제와 비위치특이성 리파아제가 모두 사용될 수 있는데, 뮤코(Mucor)속, 아스퍼질러스(Aspergillus)속, 라이조푸스 (Rhizopus)속, 또는 크로모박테리움(Chromobacterium)속에서 유래된 1,3 위치특이성 리파아제는 상기 유지 g당 150 ∼ 500 유닛(unit), 바람직하게는 200 ∼ 400 유닛의 양이 사용된다. 칸디다 실린드라세아(Candida cylindracea) 유래의 비위치특이성 리파아제는 유지 g당 20 ∼ 300 유닛, 바람직하게는 50 ∼ 200 유닛의 양이 사용된다. 효소량이 상기 범위를 초과할 경우는 과잉 반응으로 인해 지방산 및 모노글리세라이드의 함량이 과다해지고, 반대로 상기 범위 미만일 경우는 활성의 저하로 인해 반응 효율이 현저히 떨어진다.The lipase can be used both 1,3 position-specific lipase and non-position-specific lipase, Muco genus, Aspergillus genus, Rhizopus genus or Chromobacterium genus The 1,3-position specific lipase derived from is used in an amount of 150 to 500 units, preferably 200 to 400 units per gram of the fat or oil. Non-specific lipases derived from Candida cylindracea are used in an amount of 20 to 300 units, preferably 50 to 200 units, per g fat. When the amount of the enzyme exceeds the above range, the content of fatty acids and monoglycerides becomes excessive due to the excess reaction, and on the contrary, when the amount of the enzyme exceeds the above range, the reaction efficiency is significantly lowered due to the decrease in activity.
상기의 방법으로 준비된 혼합 원료를 적절한 조건에서 효소반응을 통해 가수분해 시키는데 이때 교반 속도, 반응 온도 및 시간에 따라 반응 정도 및 효소 활성의 조절이 가능하다.The mixed raw material prepared by the above method is hydrolyzed through the enzyme reaction under appropriate conditions, whereby the degree of reaction and the enzyme activity can be controlled according to the stirring speed, reaction temperature and time.
상기 교반은 200rpm 이상의 속도로 수행할 수 있으며, 바람직하게는 200 ∼ 800rpm으로 수행한다. 이때 교반시 일반적으로 사용되는 프로펠라 타입 교반기가 사용될 수 있으나 이외에도 다양한 기기가 사용 가능하다.The stirring may be performed at a speed of 200 rpm or more, and preferably at 200 to 800 rpm. At this time, a propeller type stirrer which is generally used at the time of stirring may be used, but various apparatuses may be used.
본 발명의 가수분해 반응은 일반 가수분해 반응에 비해 적은 물과 효소를 사용하기 때문에 교반 속도 200rpm 미만에서는 해당 반응공정을 수행하기 어려운 상태가 된다.Since the hydrolysis reaction of the present invention uses less water and an enzyme than the general hydrolysis reaction, it becomes difficult to perform the reaction process at a stirring speed of less than 200 rpm.
반응 온도는 일반적인 가수분해 반응시 보다 높은데 이는 초기 활성을 높이고 역가를 실활시킴으로써 과도한 가수분해 진행을 억제하기 위한 것이다. 구체적으로는 40 ∼ 70℃의 일정한 온도를 유지하는데 40℃ 미만이면 효소의 지속적인 활성유지하여 지방산함량의 과다하게 되는 문제점이 있고, 70℃를 초과할 경우 급속한 효소저하로 반응 자체가 일어나기 어려운 문제점이 있다. 반응 시간은 30분 ∼ 30시간, 바람직하게는 30분 ∼ 10시간 반응하는데 30시간이 넘는 장시간 반응의 경우 디글리세라이드의 분해로 지방산 및 모노글리세라이드의 함량이 증가하는 단점이 있다.The reaction temperature is higher than in general hydrolysis reactions, in order to suppress excessive hydrolysis progression by increasing the initial activity and deactivating the titer. Specifically, if the temperature is lower than 40 ° C. to maintain a constant temperature of 40 ° C. to 70 ° C., there is a problem that the fatty acid content is excessive due to the sustained activity of the enzyme. have. The reaction time is 30 minutes to 30 hours, preferably 30 minutes to 10 hours in the case of a long reaction over 30 hours has the disadvantage of increasing the content of fatty acids and monoglycerides by decomposition of diglycerides.
가수분해 반응 만으로 디글리세라이드 함량이 높은 유지 조성물을 제조하는 본 발명의 방법은 유지의 기본 구조인 트리글리세라이드내 3개 지방산 중 1개의 지방산을 가수분해시키는 방법에 대한 효소반응 기술이며, 전술된 본 발명의 방법은 최소한의 효소와 물의 사용, 격렬한 교반 등을 통해 균일한 가수분해를 한다는 점에서 일반 가수분해 방법과 다르다.The method of the present invention for preparing a fat or oil composition having a high diglyceride content by only a hydrolysis reaction is an enzymatic reaction technique for hydrolyzing one of three fatty acids in triglyceride which is a basic structure of fats and oils. The method of the present invention differs from the general hydrolysis method in that uniform hydrolysis is achieved through the use of minimal enzyme and water, vigorous stirring, and the like.
글리세라이드류의 성분을 분석하는 방법으로는 TLC/FID(Thin Layer Chromatograph에 의해 분리하고, Flame Ionization Detector에 의해 검출)에 의한 분석이 가장 일반적이고, 여러 문헌에 보고되어 사용되고 있지만, 본 발명자는 신속하고 감도가 우수한 HPLC/ELSD(High Performance Liquid Chromatograph에 의해 분리하고, Evaporative Light Scattering Detector에 의해 검출)를 이용하여 유지조성물의 글리세라이드류 분석을 시도하였다. 상기 분석 방법에서 지방산 표준 물질 정량시 종류에 따라 차이(올레인산과 팔미틴산의 경우 2배의 차이를 확인했음)가 발생하므로 산가 측정법에 의해 지방산을 정량하고, 만들어진 지방산 염을 물로 분리해낸 뒤 나머지 유지 성분인 모노글리세라이드, 디글리세라이드, 및 트리글리세라이드를 HPLC/ELSD로 분석하였다.As a method of analyzing the components of the glycerides, the analysis by TLC / FID (separation by Thin Layer Chromatograph and detection by Flame Ionization Detector) is the most common and has been reported and used in various literatures. The glycerides of the oil-fat composition were attempted using HPLC / ELSD (high performance liquid chromatograph separated by sensitivity and detected by an evaporative light scattering detector) having excellent sensitivity. In the analytical method, there is a difference according to the type of fatty acid standard substance quantification (the difference between oleic acid and palmitic acid was confirmed by 2 times). Phosphorus monoglycerides, diglycerides, and triglycerides were analyzed by HPLC / ELSD.
상기의 방법에 따라 결과적으로 생성된 유지 조성물의 성분 분석 결과 디글리세라이드가 60%이상 포함되는 것이 확인되었는데, 부가적으로 결과적인 유지 조성물을 분자증류하여 모노글리세라이드와 지방산을 제거하거나, 탈산, 탈색, 탈취 및 윈트라이징 등 통상의 식용유지 정제 방법을 이용하여 정제를 할 경우 디글리세라이드를 80%이상 함유한 유지 조성물로 얻을 수 있다.As a result of component analysis of the resultant fat or oil composition according to the above method, it was found that 60% or more of diglyceride was contained. Additionally, the resulting fat or oil composition was molecularly distilled to remove monoglycerides and fatty acids, or deacidification, When purification is carried out using conventional edible oil and fat refining methods such as decolorization, deodorization, and wintrazing, a fat or oil composition containing 80% or more of diglyceride can be obtained.
이하, 실시예를 통하여 본 발명을 좀 더 구체적으로 살펴보지만, 하기 예에 본 발명의 범주가 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited to the following Examples.
실시예 1Example 1
프로펠라 타입 교반기가 설치된 1 ℓ용 사구 플라스크에 대두유 100 g, 물 3 g, 및 비위치특이성 리파아제 OF(메이토산교사; 360,000 unit/g) 30 mg을 넣은 후 플라스크를 항온 수조에 담가 60℃를 유지하면서 600rpm으로 4시간 동안 교반하여 결과물 유지를 얻었다. 얻어진 유지 조성물의 성분은 하기의 방법으로 분석하였다. 지방산은 산가 측정법으로 정량하고, 만들어진 지방산 염을 물로 분리해낸 뒤 나머지 유지성분인 모노글리세라이드, 디글리세라이드, 및 트리글리세라이드를 HPLC/ELSD로 분석하였다. 컬럼(Column)으로는 SUPELCOSIL LC-Si(SUPELCO사, 25*1/4″), 온도는 40℃, 용매 유속은 1.3 ㎖/min으로 하였다. 용매 A는 부피비로 벤젠 70 : 클로로포름 30 : 초산 2를 섞어 제조하였고, 용매 B는 이소프로파놀 100%로 준비하였다. 용매 A 100%를 주입후 3분간 통액시키고, 3∼4분 사이에 용매 A:용매 B를 95:5로 전환하여 8분까지 통액시키고, 8∼9분 사이에 용매 A 100%를 통액시켜 18분까지 전개시킨다. ELSD의 조건은 가스 유입율(GAS FLOW RATE) 2.2 ㎖/min, 드리프트 온도(Drift Temperature) 82℃로 조절하였다. 각 성분의 리텐션 시간(Retention Time)은 트리글리세라이드 2.3분, 1,3-디글리세라이드는 6.9분, 1,2-디글리세라이드는 9분, 1-모노글리세라이드는 13분, 2-모노글리세라이드는 15분 이었고, 분석 결과는 하기 표 1에 나타내었다.Into a 1 liter sand dune flask equipped with a propeller-type stirrer, 100 g of soybean oil, 3 g of water, and 30 mg of non-specific lipase OF (Meitosan, 360,000 unit / g) were added to the flask, and the flask was kept at 60 ° C. While stirring at 600 rpm for 4 hours to obtain the resulting oil. The component of the obtained oil-fat composition was analyzed by the following method. Fatty acids were quantified by acid value measurement, and the resulting fatty acid salts were separated with water and the remaining fats, monoglycerides, diglycerides, and triglycerides, were analyzed by HPLC / ELSD. As a column, SUPELCOSIL LC-Si (SUPELCO Co., 25 * 1/4 "), the temperature was 40 degreeC, and the solvent flow rate was 1.3 mL / min. Solvent A was prepared by mixing benzene 70: chloroform 30: acetic acid 2 in volume ratio, and solvent B was prepared with isopropanol 100%. 100% of solvent A was passed through for 3 minutes, and between 3-4 minutes, solvent A: solvent B was converted to 95: 5 and passed through for 8 minutes, and 100% of solvent A was passed between 8-9 minutes for 18 minutes. Deploy to minutes. The conditions of the ELSD were adjusted to a gas flow rate (GAS FLOW RATE) of 2.2 ml / min and a drift temperature of 82 ° C. Retention time of each component is 2.3 minutes for triglyceride, 6.9 minutes for 1,3-diglyceride, 9 minutes for 1,2-diglyceride, 13 minutes for 1-monoglyceride, 2-mono Glyceride was 15 minutes, the analysis results are shown in Table 1 below.
하기 표 1에 나타난 바와 같이, 본 실시예에서 제조된 유지 조성물 내 디글리세라이드의 함량은 61.8%임이 확인되었다.As shown in Table 1, it was confirmed that the content of diglyceride in the oil-fat composition prepared in this example was 61.8%.
실시예 2Example 2
프로펠라 타입 교반기가 설치된 1 ℓ용 사구 플라스크에 옥배유 100 g, 물 8 g, 및 1,3 위치특이성 리파아제인 리포라아제 100L(Lipolase 100L; 노보노르디스크사; 100,000 unit/g) 216 ㎎을 넣은 후 플라스크를 항온 수조에 담가 45℃를 유지하면서 500rpm으로 2시간 동안 교반하여 결과물 유지를 얻었다. 얻어진 유지의 성분은 실시예 1과 동일한 방법으로 확인하였고, 그 결과는 하기 표 1에 나타내었다.Into a 1 L four-necked flask equipped with a propeller-type stirrer, 100 g of jade oil, 8 g of water, and 216 mg of lipoase 100L (Lipolase 100L; Novo Nordisk; 100,000 unit / g), a 1,3 position-specific lipase, were placed in the flask. It was immersed in a constant temperature water bath and stirred at 500rpm for 2 hours while maintaining 45 ℃ to obtain the resulting oil. The obtained oil and fat components were confirmed in the same manner as in Example 1, and the results are shown in Table 1 below.
하기 표 1에 나타난 바와 같이, 본 실시예에서 제조된 유지 조성물 내 디글리세라이드의 함량은 63.0%임이 확인되었다.As shown in Table 1, it was confirmed that the content of diglyceride in the oil-fat composition prepared in this example was 63.0%.
실시예 3Example 3
프로펠라 타입 교반기가 설치된 1 ℓ사구 플라스크에 대두유 100 g, 물 3 g,및 비위치특이성 리파아제 OF(메이토산교사; 360,000 unit/g) 15 mg을 넣은 후 플라스크를 항온 수조에 담가 65℃를 유지하면서 300rpm으로 6시간 동안 교반하여 결과물 유지를 얻었다. 얻어진 유지의 성분은 실시예 1과 동일한 방법으로 확인하였고, 그 결과는 하기 표 1에 나타내었다.Into a 1 L four-necked flask equipped with a propeller-type stirrer, 100 g of soybean oil, 3 g of water, and 15 mg of non-specific lipase OF (Meitosan, 360,000 unit / g) were added to the flask, and the flask was kept at 65 ° C. Stirring at 300 rpm for 6 hours gave the resulting oil. The obtained oil and fat components were confirmed in the same manner as in Example 1, and the results are shown in Table 1 below.
하기 표 1에 나타난 바와 같이, 본 실시예에서 제조된 유지 조성물 내 디글리세라이드의 함량은 61.0%임이 확인되었다.As shown in Table 1 below, it was confirmed that the content of diglyceride in the oil-fat composition prepared in this example was 61.0%.
비교예 1Comparative Example 1
프로펠라 타입 교반기가 설치된 1 ℓ사구 플라스크에 대두유 100 g, 물 20 g, 및 비위치특이성 리파아제 OF(메이토산교사; 360,000 unit/g) 30 mg을 넣은 후 플라스크를 항온 수조에 담가 60℃를 유지하면서 600rpm으로 2시간 동안 교반하여 결과물 유지를 얻었다. 얻어진 유지의 성분은 실시예 1과 동일한 방법으로 확인하였고, 그 결과는 하기 표 1에 나타내었다.In a 1 L four-necked flask equipped with a propeller type stirrer, 100 g of soybean oil, 20 g of water, and 30 mg of non-specific lipase OF (Meitosan, 360,000 unit / g) were added to the flask, and the flask was kept at 60 ° C. Stirring at 600 rpm for 2 hours gave the resulting oil. The obtained oil and fat components were confirmed in the same manner as in Example 1, and the results are shown in Table 1 below.
하기 표 1에 나타난 바와 같이, 본 비교예에서 제조된 유지 조성물 내 디글리세라이드의 함량은 10.5%임이 확인되었다.As shown in Table 1, it was confirmed that the content of diglyceride in the oil-fat composition prepared in this comparative example is 10.5%.
비교예 2Comparative Example 2
프로펠라 타입 교반기가 설치된 1 ℓ사구플라스크에 옥배유 100 g, 물 20 g, 및 1,3 위치특이성 리포라아제 100L(노보노르디스크사; 100,000unit/g) 216 ㎎을 넣은 후 플라스크를 항온 수조에 담가 50℃를 유지하면서 100 rpm으로 6시간 동안 교반하여 결과물 유지를 얻었다. 얻어진 유지의 성분은 실시예 1과 동일한 방법으로 확인하였고, 그 결과는 하기 표 1에 나타내었다.Into a 1 L four-necked flask equipped with a propeller-type stirrer, 100 g of jade oil, 20 g of water, and 216 mg of 1,3 position-specific lipoase (Lonovo Nordisk; 100,000 units / g) were placed and the flask was immersed in a constant temperature water bath. The resultant oil was obtained by stirring at 100 rpm for 6 hours while maintaining the temperature. The obtained oil and fat components were confirmed in the same manner as in Example 1, and the results are shown in Table 1 below.
하기 표 1에 나타난 바와 같이, 본 비교예에서 제조된 유지 조성물 내 디글리세라이드의 함량은 35.2%임이 확인되었다.As shown in Table 1, it was confirmed that the content of diglyceride in the oil-fat composition prepared in this comparative example was 35.2%.
비교예 3Comparative Example 3
프로펠라 타입 교반기가 설치된 1 ℓ사구플라스크에 대두유 100 g, 물 3 g, 및 1,3 위치특이성 리포라아제 100L(노보노르디스크사; 100,000unit/g) 216 ㎎을 넣은 후 플라스크를 항온 수조에 담가 35℃를 유지하면서 400 rpm으로 10시간 동안 교반하여 결과물 유지를 얻었다. 얻어진 유지의 성분은 실시예 1과 동일한 방법으로 확인하였고, 그 결과는 하기 표 1에 나타내었다.Into a 1 liter sandblast flask equipped with a propeller-type stirrer, 100 g of soybean oil, 3 g of water, and 216 mg of 1,3 position-specific lipoase (L) (Novonordisk Inc .; 100,000 units / g) were placed and the flask was immersed in a constant temperature water bath. The resultant oil was obtained by stirring at 400 rpm for 10 hours while maintaining the temperature. The obtained oil and fat components were confirmed in the same manner as in Example 1, and the results are shown in Table 1 below.
하기 표 1에 나타난 바와 같이, 본 비교예에서 제조된 유지 조성물 내 디글리세라이드의 함량은 28.3%임이 확인되었다.As shown in Table 1 below, it was confirmed that the content of diglyceride in the oil-fat composition prepared in this comparative example was 28.3%.
상기 실시예에서 본 바와 같이, 본 발명의 방법은 리파아제를 이용한 가수분해 만으로 60%이상의 고함량의 디글리세라이드를 포함하는 유지 조성물을 얻을 수 있으므로, 제조 공정이 간단하고, 생산성이 높으며, 효소 원가측면에서 효율적일 뿐 아니라, 합성에 따른 식품의 부정적 이미지 문제도 해결하였다.As seen in the above embodiment, the method of the present invention can obtain a fat or oil composition containing a high content of diglyceride of 60% or more only by hydrolysis using lipase, so that the manufacturing process is simple, the productivity is high, and the enzyme cost In addition to being efficient in terms of aspects, it also solved the problem of negative image of food due to synthesis.
또한, 본 발명에 따른 유지 조성물은 혈중 지방치를 높이지 않고, 몸에 지방을 축적시키지 않으므로 매우 효과적이다.In addition, the fat or oil composition according to the present invention is very effective because it does not increase the fat level in the blood and does not accumulate fat in the body.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003064444A1 (en) * | 2002-01-31 | 2003-08-07 | Enzymotec Ltd. | Fractionation of phytosterol esters in oil |
| US8507466B2 (en) | 2003-02-10 | 2013-08-13 | Enzymotec Ltd. | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
| US8772270B2 (en) | 2004-08-10 | 2014-07-08 | Enzymotec Ltd. | Treatment methods requiring phyto-ingredients |
| CN117821533A (en) * | 2024-03-06 | 2024-04-05 | 长寿花食品股份有限公司 | Method for preparing 1, 3-diglyceride from corn crude oil |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100409053B1 (en) * | 2001-09-05 | 2003-12-11 | 주식회사 신동방 | Process for preparing high purity diglyceride lipid composition |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003064444A1 (en) * | 2002-01-31 | 2003-08-07 | Enzymotec Ltd. | Fractionation of phytosterol esters in oil |
| JP2005518421A (en) * | 2002-01-31 | 2005-06-23 | エンジィモテック リミテッド | Fractionation of phytosterol esters in oil |
| US8507466B2 (en) | 2003-02-10 | 2013-08-13 | Enzymotec Ltd. | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
| US8772270B2 (en) | 2004-08-10 | 2014-07-08 | Enzymotec Ltd. | Treatment methods requiring phyto-ingredients |
| CN117821533A (en) * | 2024-03-06 | 2024-04-05 | 长寿花食品股份有限公司 | Method for preparing 1, 3-diglyceride from corn crude oil |
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