KR102583074B1 - Water-soluble emulsion composition comprising natural polyphenolic compound - Google Patents
Water-soluble emulsion composition comprising natural polyphenolic compound Download PDFInfo
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- KR102583074B1 KR102583074B1 KR1020210010126A KR20210010126A KR102583074B1 KR 102583074 B1 KR102583074 B1 KR 102583074B1 KR 1020210010126 A KR1020210010126 A KR 1020210010126A KR 20210010126 A KR20210010126 A KR 20210010126A KR 102583074 B1 KR102583074 B1 KR 102583074B1
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- 239000000839 emulsion Substances 0.000 title claims abstract description 170
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 150000008442 polyphenolic compounds Chemical class 0.000 title description 2
- -1 polyphenol compound Chemical class 0.000 claims abstract description 106
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 83
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 76
- 235000013824 polyphenols Nutrition 0.000 claims abstract description 52
- 235000006708 antioxidants Nutrition 0.000 claims description 74
- 239000004094 surface-active agent Substances 0.000 claims description 72
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 53
- 229930195729 fatty acid Natural products 0.000 claims description 53
- 239000000194 fatty acid Substances 0.000 claims description 53
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 36
- 235000011187 glycerol Nutrition 0.000 claims description 32
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 23
- 235000005487 catechin Nutrition 0.000 claims description 20
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims description 20
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 19
- 229950001002 cianidanol Drugs 0.000 claims description 19
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 18
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 17
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 15
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims description 14
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 claims description 14
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- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 2
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 2
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 2
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 2
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 2
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 2
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- OEIJRRGCTVHYTH-UHFFFAOYSA-N Favan-3-ol Chemical compound OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 OEIJRRGCTVHYTH-UHFFFAOYSA-N 0.000 description 1
- 238000001159 Fisher's combined probability test Methods 0.000 description 1
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000001765 catechin Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 1
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011987 flavanols Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000010428 oil painting Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000004792 oxidative damage Effects 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/15—Vitamins
-
- 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
- A23V2200/00—Function of food ingredients
- A23V2200/20—Ingredients acting on or related to the structure
- A23V2200/222—Emulsifier
-
- 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
- A23V2250/20—Natural extracts
- A23V2250/21—Plant extracts
- A23V2250/2112—Curcumin, turmeric
-
- 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
- A23V2250/20—Natural extracts
- A23V2250/21—Plant extracts
- A23V2250/2116—Flavonoids, isoflavones
- A23V2250/21168—Quercetin
-
- 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
- A23V2250/20—Natural extracts
- A23V2250/21—Plant extracts
- A23V2250/2132—Other phenolic compounds, polyphenols
-
- 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
- A23V2250/70—Vitamins
- A23V2250/712—Vitamin E
Abstract
본 발명은 수용성 항산화제 유화물을 함유하는 천연 폴리페놀 화합물 함유 수용성 유화 조성물에 관한 것이다.
본 발명의 일 구현예에 따른 천연 폴리페놀 화합물 함유 수용성 유화 조성물은 기능성 수난용 물질을 수용화 시킴으로써 물질의 흡수율과 효능을 증대시킬 수 있어, 물질이 갖는 기능성을 다양한 분야에 활용될 수 있도록 한다.
또한, 수용성 항산화제 유화물을 함유하여, 수용액 상에서 산소에 의한 산화를 예방할 수 있는 산화 안정성이 우수하다. The present invention relates to a water-soluble emulsion composition containing a natural polyphenol compound containing a water-soluble antioxidant emulsion.
A water-soluble emulsion composition containing a natural polyphenol compound according to an embodiment of the present invention can increase the absorption rate and efficacy of a functional water-resistant material by water-solubilizing it, allowing the material's functionality to be utilized in various fields.
In addition, it contains a water-soluble antioxidant emulsion and has excellent oxidation stability to prevent oxidation by oxygen in an aqueous solution.
Description
본 발명은 수용성 항산화제 유화물을 함유하는 천연 폴리페놀 화합물 함유 수용성 유화 조성물에 관한 것이다. The present invention relates to a water-soluble emulsion composition containing a natural polyphenol compound containing a water-soluble antioxidant emulsion.
천연 폴리페놀 화합물은 식물계와 일부 미생물들에 다양하게 존재하는 이차 대사 물질로, 대표적인 기능으로는 크게 항산화 작용과 호르몬적 활성으로 나눌 수 있다. 현재 상업적으로 이용되고 있는 대표적인 천연 폴리페놀 화합물은 녹차에거 유래한 카테킨류가 있으며, 레스베라트롤, 퀘세틴 등이 항산화 작용이 있는 것으로 알려져 있다. 또한 플리보놀 계열 화합물의 하나인 쿼세틴은 항산화 효과 외에도 항암, 항염증, 및 당뇨 예방 기능이 있다고 보고되었다. Natural polyphenol compounds are secondary metabolites that exist in various ways in the plant world and some microorganisms, and their representative functions can be broadly divided into antioxidant activity and hormonal activity. Representative natural polyphenol compounds currently used commercially include catechins derived from green tea, and resveratrol and quercetin are known to have antioxidant properties. In addition, quercetin, one of the flavanol-based compounds, has been reported to have anti-cancer, anti-inflammatory, and anti-diabetic functions in addition to antioxidant effects.
이와 같은 천연 폴리페놀 화합물을 비롯한 기능성 천연물들은 대부분 수난용성이며 체내흡수성이 매우 낮아 생체 이용률이 떨어지는 문제점이 있다. 따라서 이들이 갖는 생리활성물질을 활용한 식품, 의약품, 사료 등의 적용에 제한점이 있다. 또한 기존의 수용화된 기능성 유화물들은 O/W형의 유화물로 수상인 물과 물에 함유되어 산소에 의해서 산화되어 항산화 효능을 소실하거나 산패되는 문제점을 가지고 있다. Most functional natural products, including such natural polyphenol compounds, are poorly soluble in water and have very low body absorption, resulting in low bioavailability. Therefore, there are limitations in the application of these bioactive substances to food, medicine, feed, etc. In addition, existing water-soluble functional emulsions are O/W type emulsions and have the problem of losing their antioxidant efficacy or becoming rancid due to oxidation by oxygen when contained in the water phase and water.
한편, α-Tocopherol은 대표적인 천연 항산화제로써 종자유(Seed oil)나 곡류 그리고 녹색 잎을 갖는 야채에 많이 분포되어 있으며, 비타민 E로써 세포막에 존재하는 주요한 지용성의 항산화제이며, 지방의 산화를 막아준다. 비타민 E는 퍼옥시 라디칼(ROO·), CCl3, HO· 포함하는 다양한 산소 라디칼뿐만 아니라 수퍼옥사이드 라디칼(O2·)과 직접 반응할 수 있다. 항산화력은 δ > γ > β> α 순으로 높다. 작용기작으로 세포막을 구성하는 다가불포화지방산은 세포에서 만들어진 자유라디칼에 의해 쉽게 산화되는데, 토코페롤은 이러한 산화과정을 중단시키고 자유라디칼을 제거해 세포막을 산화적 손상으로부터 보호해준다. Meanwhile, α-Tocopherol is a representative natural antioxidant and is widely distributed in seed oil, grains, and vegetables with green leaves. As vitamin E, it is a major fat-soluble antioxidant present in cell membranes and prevents fat oxidation. . Vitamin E can react directly with superoxide radicals (O 2 ·) as well as various oxygen radicals, including peroxy radicals (ROO·), CCl 3 , and HO·. Antioxidant power is high in the order δ > γ > β > α. As a mechanism of action, polyunsaturated fatty acids that make up cell membranes are easily oxidized by free radicals created in cells. Tocopherol stops this oxidation process and removes free radicals to protect cell membranes from oxidative damage.
본 발명의 과제는 기능성 난용성 물질을 수용화 시켜 물질의 흡수율과 효능을 증대시킬 수 있을 뿐만 아니라 수용액 상에서 산화 안정성이 우수한 천연 폴리페놀 화합물 함유 수용성 유화 조성물을 제공하는 것이다. The object of the present invention is to provide a water-soluble emulsion composition containing a natural polyphenol compound that can not only increase the absorption rate and efficacy of a functional poorly soluble material by water-solubilizing it, but also has excellent oxidation stability in aqueous solution.
상기한 과제를 달성하기 위해 본 발명은 In order to achieve the above task, the present invention
(1) 전체 100 중량%를 만족하도록 하기 성분을 포함하는 수용성 항산화제 유화물: (1) Water-soluble antioxidant emulsion containing the following ingredients to satisfy a total of 100% by weight:
토코페롤 1 내지 40 중량%,1 to 40% by weight of tocopherol,
카테킨 1 내지 40 중량%,1 to 40% by weight of catechin,
HLB 3 내지 HLB 7의 제1 계면활성제 1 내지 30 중량%,1 to 30% by weight of a first surfactant of HLB 3 to HLB 7,
HLB 10 내지 HLB 14의 제2 계면활성제 10 내지 80 중량%;10 to 80% by weight of a second surfactant of HLB 10 to HLB 14;
공계면활성제 10 내지 45 중량%, 및10 to 45% by weight of cosurfactant, and
식용 유지 1 내지 35 중량%,1 to 35% by weight of edible oil,
(2) 전체 100 중량%를 만족하도록 하기 성분을 포함하는 천연 폴리페놀 화합물 유화물:(2) Natural polyphenol compound emulsion containing the following components to satisfy 100% by weight of the total:
천연 폴리페놀 화합물 1 내지 30 중량%,1 to 30% by weight of natural polyphenol compounds,
HLB 3 내지 HLB 7의 제1 계면활성제 1 내지 10 중량%,1 to 10% by weight of a first surfactant of HLB 3 to HLB 7,
HLB 10 내지 HLB 14의 제2 계면활성제 1 내지 20 중량%, 및1 to 20% by weight of a second surfactant from HLB 10 to HLB 14, and
공계면활성제 40 내지 97 중량%, 40 to 97% by weight of cosurfactant,
를 포함하는, 수용성 항산화제 유화물을 함유하는 천연 폴리페놀 화합물 함유 수용성 유화 조성물을 제공한다. It provides a water-soluble emulsion composition containing a natural polyphenol compound containing a water-soluble antioxidant emulsion.
본 발명의 일 구현예에 따른 천연 폴리페놀 화합물 함유 수용성 유화 조성물은 기능성 수난용 물질을 수용화 시킴으로써 물질의 흡수율과 효능을 증대시킬 수 있어, 물질이 갖는 기능성을 다양한 분야에 활용될 수 있도록 한다.The water-soluble emulsion composition containing a natural polyphenol compound according to an embodiment of the present invention can increase the absorption rate and efficacy of the functional water-resistant material by water-solubilizing it, allowing the material's functionality to be utilized in various fields.
또한, 수용성 항산화제 유화물을 함유하여, 수용액 상에서 산소에 의한 산화를 예방할 수 있는 산화 안정성이 우수하다. In addition, because it contains a water-soluble antioxidant emulsion, it has excellent oxidation stability to prevent oxidation by oxygen in an aqueous solution.
도 1은 비교예 33의 천연 폴리페놀 화합물 함유 수용성 유화 조성물의 유화 입자를 광학현미경으로 관찰한 사진이다.
도 2는 실시예 1의 천연 폴리페놀 화합물 함유 수용성 유화 조성물의 유화 입자를 광학현미경으로 관찰한 사진이다. Figure 1 is a photograph of emulsified particles of a water-soluble emulsion composition containing a natural polyphenol compound of Comparative Example 33 observed with an optical microscope.
Figure 2 is a photograph of emulsified particles of the water-soluble emulsion composition containing natural polyphenol compounds of Example 1 observed with an optical microscope.
이하 본 발명의 일 구현예에 따른 수용성 항산화 유화물과 천연 폴리페놀 화합물 유화물을 상세히 설명한다. Hereinafter, a water-soluble antioxidant emulsion and a natural polyphenol compound emulsion according to an embodiment of the present invention will be described in detail.
본 발명의 일 구현예에 따른 천연 폴리페놀 화합물 함유 수용성 유화 조성물은 수용성 항산화 유화물과 천연 폴리페놀 화합물 유화물을 포함한다. A water-soluble emulsion composition containing a natural polyphenol compound according to an embodiment of the present invention includes a water-soluble antioxidant emulsion and a natural polyphenol compound emulsion.
상기 수용성 항산화제 유화물은 전체 100 중량%를 만족하도록, 토코페롤 1 내지 40 중량%, 카테킨 1 내지 40 중량%, HLB 3 내지 HLB 7의 제1 계면활성제 1 내지 30 중량%, HLB 10 내지 HLB 14의 제2 계면활성제 10 내지 80 중량%, 공계면활성제 10 내지 45 중량%, 및 식용 유지 1 내지 35 중량%를 포함한다. The water-soluble antioxidant emulsion contains 1 to 40% by weight of tocopherol, 1 to 40% by weight of catechin, 1 to 30% by weight of the first surfactant of HLB 3 to HLB 7, and HLB 10 to HLB 14 to satisfy a total of 100% by weight. It includes 10 to 80% by weight of a second surfactant, 10 to 45% by weight of a cosurfactant, and 1 to 35% by weight of edible oil.
상기 토코페롤과 카테킨은 각각 지용성, 수용성 항산화제로서 유화물 내에 포함된다. 이때 토코페롤과 카테킨의 함량이 상기 범위 미만이면 첨가에 따른 항산화 효과가 미미하고, 이와 반대로 상기 범위를 초과하면 유화물의 유화 안정성이 현저히 저하되는 문제점이 있다. The tocopherol and catechin are included in the emulsion as fat-soluble and water-soluble antioxidants, respectively. At this time, if the content of tocopherol and catechin is less than the above range, the antioxidant effect due to addition is minimal, and on the contrary, if it exceeds the above range, there is a problem in that the emulsion stability of the emulsion is significantly reduced.
상기 HLB(Hydrophile-Lipophile Balance)는 계면활성제가 물과 기름에 대한 친화성 정도를 나타내는 값이며, HLB는 그 값이 작을수록 분자 전체로서 친유성이 강하고, 그 값이 커질수록 친수성이 강한 것을 나타낸다. The HLB (Hydrophile-Lipophile Balance) is a value that indicates the affinity of the surfactant for water and oil. The smaller the HLB value, the stronger the lipophilicity of the molecule as a whole, and the larger the value, the stronger the hydrophilicity. .
상기 수용성 항산화 유화물과 천연 폴리페놀 화합물 유화물은 각 유화물의 유화 안정성을 확보하고, 친수성 공계면활성제 내에 잘 녹으면서 계면활성 효과를 나타내기 위한 측면에서 HLB(Hydrophile-Lipophile Balance)가 상이한 2종의 계면활성제를 포함한다. The water-soluble antioxidant emulsion and the natural polyphenol compound emulsion are two types of interfaces with different HLB (Hydrophile-Lipophile Balance) in order to ensure the emulsion stability of each emulsion and to exhibit a surfactant effect while dissolving well in the hydrophilic cosurfactant. Contains activators.
상기 제1 계면활성제는 HLB가 3 내지 7인 것을 사용하고, 제2 계면활성제는 HLB가 10 내지 14인 것을 사용하는 것이 유화 입자 간 응집을 방지하고, 친수성 공계면활성제와 식용 유지 내에서 항산화제인 토코페롤과 카테킨이 각각의 항산화력을 유지하기 위한 측면에서 더욱 효과적이다. 상기 제1 계면활성제의 HLB가 3 미만인 경우 에멀젼이 잘 형성되지 않으며, HLB가 7을 초과하는 경우 입자 간 응집이 발생하여 유화 안정성이 저하된다. 상기 제2 계면활성제의 HLB가 10 미만인 경우 유화가 어렵고, 반대로 HLB 14를 초과하는 경우 유화 안정성이 떨어진다. The first surfactant has an HLB of 3 to 7, and the second surfactant has an HLB of 10 to 14 to prevent agglomeration between emulsified particles and to be an antioxidant in the hydrophilic co-surfactant and edible oil. Tocopherol and catechin are more effective in maintaining their respective antioxidant power. If the HLB of the first surfactant is less than 3, the emulsion is not formed well, and if the HLB is more than 7, agglomeration occurs between particles and the emulsion stability is reduced. If the HLB of the second surfactant is less than 10, emulsification is difficult, and conversely, if the HLB of the second surfactant exceeds 14, emulsion stability is poor.
상기 HLB 3 내지 HLB 7의 제1 계면활성제는 공지된 것이라면 제한 없이 사용할 수 있으며, 예컨대 글리세린 지방산 에스테르, 폴리글리세린 지방산 에스테르, 솔비탄 지방 에스테르, 레시틴, 프로필렌글리콜 지방산 에스테르 및 이들의 혼합물로 이루어진 군에서 선택된 1종이 가능하다. 이때 제1 계면활성제의 함량은 수용성 항산화제 유화물 전체 중량에 대해 1 내지 30 중량%이다. 제1 계면활성제의 함량이 상기 범위 미만이면 식용 유지의 유화 입자에 대한 유화 작용이 약화되어 에멀젼 형성이 어렵고, 상기 범위를 초과하면 유화 안정성이 떨어지는 문제점이 있다. The first surfactant of HLB 3 to HLB 7 can be used without limitation as long as it is known, for example, from the group consisting of glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, lecithin, propylene glycol fatty acid ester, and mixtures thereof. One selected type is available. At this time, the content of the first surfactant is 1 to 30% by weight based on the total weight of the water-soluble antioxidant emulsion. If the content of the first surfactant is less than the above range, the emulsifying effect on the emulsified particles of the edible oil is weakened, making it difficult to form an emulsion, and if it exceeds the above range, the emulsion stability is poor.
상기 HLB 10 내지 HLB 14의 제2 계면활성제는 폴리글리세린 지방산 에스테르, 폴리옥시에틸렌 솔비탄 지방산 에스테르, 자당 지방산 에스테르, 효소분해 레시틴 및 이들의 혼합물로 이루어진 군에서 선택된 1종이 가능하나, 이에 한정되는 것은 아니다. 상기 제2 계면활성제의 함량이 상기 수치 범위를 만족하는 경우, 토코페롤과 카테킨의 항산화능을 해하지 않으면서, 수용성 항산화제 유화물 내에 토코페롤과 카테킨이 안정적으로 분산될 수 있도록 한다. The second surfactant of HLB 10 to HLB 14 may be one selected from the group consisting of polyglycerol fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, enzymatically degraded lecithin, and mixtures thereof, but is limited thereto. no. When the content of the second surfactant satisfies the above numerical range, tocopherol and catechin can be stably dispersed in the water-soluble antioxidant emulsion without harming the antioxidant ability of tocopherol and catechin.
상기 공계면활성제는 유화에 보조적인 역할을 할 뿐만 아니라 용해제로 사용된다. 상기 공계면활성제는 글리세린, 솔비톨, 폴리에틸렌글리콜, 프로필렌글리콜, 트리아세틴 및 이들의 혼합물로 이루어진 군에서 선택된 1종이 가능하나, 이에 한정되는 것은 아니다. 이러한 공계면활성제의 함량은 수용성 항산화제 유화물 총 중량 대비 10 내지 45 중량%인 것이 바람직하다. 공계면활성제 함량이 10 중량% 미만이면 카테킨을 용해시키는 것이 용이하지 않으며, 45 중량%를 초과하여 사용하면 유화 입자가 잘 형성되지 않고 유화 안정성이 저하되는 문제가 있다. The co-surfactant not only plays an auxiliary role in emulsification but is also used as a solubilizing agent. The cosurfactant may be one selected from the group consisting of glycerin, sorbitol, polyethylene glycol, propylene glycol, triacetin, and mixtures thereof, but is not limited thereto. The content of this co-surfactant is preferably 10 to 45% by weight based on the total weight of the water-soluble antioxidant emulsion. If the cosurfactant content is less than 10% by weight, it is not easy to dissolve catechin, and if it is used in excess of 45% by weight, emulsified particles are not formed well and emulsion stability is reduced.
상기 식용 유지는 식물 또는 동물로부터 얻은 원유나 이를 원료로 하여 제조, 가공한 것이라면 제한 없이 사용 가능하다. 예컨대, 대두유, 옥수수유, 채종유, 고올레산 채종유, 홍화유, 미강유, 팜유, 올리브유, 해바라기유, 야자유, 소맥 배아유, 중쇄중성지방유(MCT Oil)에서 선택된 1종 이상의 유지가 가능하다. 이러한 식용 유지의 함량은 조성물 총 중량에 대해 1 내지 35 중량%일 수 있다. 1 중량% 미만에서는 오일의 양이 너무 적어 토코페롤의 용해가 어렵고, 35 중량%를 초과하면 에멀젼의 경시 안정성이 불량하다. The edible oil can be used without limitation as long as it is crude oil obtained from plants or animals, or manufactured and processed using it as a raw material. For example, one or more oils selected from soybean oil, corn oil, rapeseed oil, high oleic acid rapeseed oil, safflower oil, rice bran oil, palm oil, olive oil, sunflower oil, palm oil, wheat germ oil, and medium chain triglyceride oil (MCT Oil) are available. The content of this edible oil may be 1 to 35% by weight based on the total weight of the composition. If it is less than 1% by weight, the amount of oil is too small and it is difficult to dissolve the tocopherol, and if it exceeds 35% by weight, the stability of the emulsion over time is poor.
상기 천연 폴리페놀 화합물 유화물은 전체 100 중량%를 만족하도록, 천연 폴리페놀 화합물 1 내지 30 중량%, HLB 3 내지 HLB 7의 유중 수적형 계면활성제 1 내지 10 중량%, HLB 10 내지 HLB 14의 수중 유적형 계면활성제 1 내지 20 중량%, 및 공계면활성제 40 내지 97 중량%를 포함한다. The natural polyphenol compound emulsion contains 1 to 30% by weight of a natural polyphenol compound, 1 to 10% by weight of a water-in-oil surfactant of HLB 3 to HLB 7, and oil in water of HLB 10 to HLB 14 to satisfy a total of 100% by weight. It contains 1 to 20% by weight of a surfactant and 40 to 97% by weight of a cosurfactant.
상기 천연 폴리페놀 화합물은 경구 투여시 포유동물에서 생물학적인 영향을 미치는 것은 제한 없이 사용할 수 있으며, 배당체 뿐만 아니라 비배당체도 가능하다. 일 예로, 실리마린(Silymarin), 커큐민(Curcumin), 카테킨(Catechin), 캠퍼롤(kaempferol), 레스베라트롤(Resveratrol), 루테올린(Luteolin), 퀘르세틴(Quercetin), 루틴(Rutin), 갈산(Gallic acid), 탄닌(Tannin), 헤스페레틴(Hesperetin), 헤스페리딘(Hesperidin), 안토시아니딘(Anthocyanidin), 안토시아닌(Anthocyanin), 나린제닌(Naringenin), 나린진(Naringin), 바이칼레인(Baicalein), 바이칼린(Baicalin)이다. The natural polyphenol compounds can be used without limitation as long as they have a biological effect on mammals when administered orally, and can be glycosides as well as non-glycosides. For example, Silymarin, Curcumin, Catechin, kaempferol, Resveratrol, Luteolin, Quercetin, Rutin, Gallic acid , Tannin, Hesperetin, Hesperidin, Anthocyanidin, Anthocyanin, Naringenin, Naringin, Baicalein, Baicalin (Baicalin).
이러한 천연 폴리페놀 화합물은 천연 폴리페놀 화합물 유화물 전체 중량에 대해 1 내지 30 중량%로 포함된다. 만약 천연 폴리페놀 화합물의 함량이 상기 범위 미만이면 첨가에 따른 효과가 미미하고, 30 중량%를 초과하면 유화 입자 형성이 어려운 문제점이 있다. These natural polyphenol compounds are contained in an amount of 1 to 30% by weight based on the total weight of the natural polyphenol compound emulsion. If the content of the natural polyphenol compound is less than the above range, the effect of addition is minimal, and if it exceeds 30% by weight, there is a problem in that it is difficult to form emulsified particles.
천연 폴리페놀 화합물 유화물은 친수성 공계면활성제 내에 잘 녹으면서 계면활성 효과를 나타내어 유화 조성물의 유화 안정성을 유지하기 위해 상기한 HLB 값을 갖는 제1 계면활성제와 제2 계면활성제를 포함한다.The natural polyphenol compound emulsion contains a first surfactant and a second surfactant having the above-mentioned HLB value in order to maintain the emulsion stability of the emulsion composition by dissolving well in the hydrophilic co-surfactant and exhibiting a surfactant effect.
HLB가 3 내지 7인 제1 계면활성제는 천연 폴리페놀 화합물 유화물 전체 중량에 대해 1 내지 10 중량%로 포함된다. 제1 계면활성제의 함량이 1 중량% 미만이면 천연 폴리페놀 화합물 유화 입자에 대한 유화 작용이 약화되어 에멀젼 형성이 어려운 문제점이 있고, 10 중량%를 초과하면 유화 안정성이 저하되는 문제점이 있다. The first surfactant having an HLB of 3 to 7 is included in an amount of 1 to 10% by weight based on the total weight of the natural polyphenol compound emulsion. If the content of the first surfactant is less than 1% by weight, the emulsifying effect on the emulsified particles of the natural polyphenol compound is weakened, making it difficult to form an emulsion, and if it exceeds 10% by weight, the emulsion stability is reduced.
HLB가 10 내지 14인 제2 계면활성제는 천연 폴리페놀 화합물 유화물 전체 중량에 대해 1 내지 20 중량%로 함유된다. 이때 제2 계면활성제의 함량이 1 중량% 미만이면 친수성 공계면활성제에 대한 유화 작용이 약화되어 유화가 어렵고, 20 중량%를 초과하면 유화 안정성을 유지가 어려운 문제점이 있다. The second surfactant having an HLB of 10 to 14 is contained in an amount of 1 to 20% by weight based on the total weight of the natural polyphenol compound emulsion. At this time, if the content of the second surfactant is less than 1% by weight, the emulsifying effect on the hydrophilic co-surfactant is weakened, making emulsification difficult, and if it exceeds 20% by weight, it is difficult to maintain emulsion stability.
제1 계면활성제와 제2 계면활성제의 구체적인 종류는 상기에서 언급한 바를 따른다. The specific types of the first and second surfactants are as mentioned above.
상기 공계면활성제는 천연 폴리페놀 화합물을 분산, 용해시키고, 유화에 보조적인 역할을 하기 위해 첨가되는 것으로, 천연 폴리페놀 화합물 유화물 중 그 함량은 40 내지 97 중량%이다. 40 중량% 미만에서는 유화 안정성 유지가 어렵고, 97 중량%를 초과하면 천연 폴리페놀 화합물의 안정적인 분산이 어렵다. The cosurfactant is added to disperse and dissolve the natural polyphenol compound and play an auxiliary role in emulsification, and its content in the natural polyphenol compound emulsion is 40 to 97% by weight. If it is less than 40% by weight, it is difficult to maintain emulsion stability, and if it exceeds 97% by weight, it is difficult to stably disperse the natural polyphenol compound.
상기 천연 폴리페놀 화합물 함유 수용성 유화 조성물은 상기 수용성 항산화제 유화물 0.1 내지 20 중량%; 및 상기 천연 폴리페놀 화합물 유화물 80 내지 99.9 중량%를 포함한다. The water-soluble emulsion composition containing a natural polyphenol compound includes 0.1 to 20% by weight of the water-soluble antioxidant emulsion; and 80 to 99.9% by weight of the natural polyphenol compound emulsion.
본 발명의 천연 폴리페놀 화합물 함유 수용성 유화 조성물은 기능성 수난용 물질인 천연 폴리페놀 화합물을 수용화 시킴으로써 물질의 흡수율과 효능을 증대시킬 수 있어, 물질이 갖는 기능성을 다양한 분야에 활용될 수 있도록 한다. 또한, 수용성 항산화제 유화물을 함유하여, 수용액 상에서 산소에 의한 산화를 예방할 수 있는 산화 안정성이 우수하다. The water-soluble emulsion composition containing a natural polyphenol compound of the present invention can increase the absorption rate and efficacy of the material by water-solubilizing the natural polyphenol compound, which is a functional water-resistant material, allowing the material's functionality to be utilized in various fields. In addition, because it contains a water-soluble antioxidant emulsion, it has excellent oxidation stability to prevent oxidation by oxygen in an aqueous solution.
이하 본 발명을 실시예를 통해 상세히 설명한다. 그러나 이러한 실시예들로 본 발명의 범위를 한정하는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, these examples do not limit the scope of the present invention.
실시예Example
하기 표 1 내지 표 13의 조성으로 각각 수용성 항산화제 유화물과 천연 폴리페놀 화합물 유화물을 제조한 후 최종 천연 폴리페놀 화합물 함유 수용성 유화 조성물을 제조하였다. A water-soluble antioxidant emulsion and a natural polyphenol compound emulsion were prepared using the compositions shown in Tables 1 to 13 below, respectively, and then a final water-soluble emulsion composition containing a natural polyphenol compound was prepared.
(HLB: 4)Glycerin fatty acid esters
(HLB: 4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB:12)Polyglycerin fatty acid esters
(HLB:12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
제1계면활성제, 제2계면활성제를 호모 믹서에 투입한 후, 온도를 50 ℃ 이상으로 유지하면서 500 rpm 이하로 교반하였다. 이후 카테킨, 대두유, 토코페롤을 순차적으로 투입하여 원료 1을 제조하였다. After adding the first surfactant and the second surfactant to the homomixer, the mixture was stirred at 500 rpm or less while maintaining the temperature at 50°C or higher. Afterwards, raw material 1 was prepared by sequentially adding catechin, soybean oil, and tocopherol.
이와는 별도로 글리세린에 제2계면활성제를 투입하여 원료 2를 제조하였다.Separately, raw material 2 was prepared by adding a second surfactant to glycerin.
이때 제2계면활성제는 원료 1과 원료 2에 총 사용량 중 30 중량%와 70 중량%를 각각 사용하였다. At this time, 30% by weight and 70% by weight of the total amount of the second surfactant were used in raw material 1 and raw material 2, respectively.
원료 2에 원료 1을 혼합하면서 호모믹서로 5,000 rpm 이상으로 유화 분산을 진행하여 수용성 항산화제 유화물을 제조하였다. A water-soluble antioxidant emulsion was prepared by mixing raw material 1 with raw material 2 and performing emulsification and dispersion using a homomixer at more than 5,000 rpm.
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
(HLB:4)Glycerin fatty acid esters
(HLB:4)
(HLB: 2)Sucrose fatty acid ester
(HLB: 2)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 12)Polyglycerin fatty acid esters
(HLB: 12)
(HLB: 8)Polyglyceryl-6 diisostearate
(HLB: 8)
(HLB: 18)PEG-18 stearate
(HLB: 18)
제1계면활성제, 제2계면활성제를 호모 믹서에 투입한 후, 온도를 50도 이상으로 유지하면서 500 rpm 이하로 교반하였다. 이후 엑다이손 원료를 투입하고 엑타이손이 유화물에 습윤되기 시작하면, 호모믹서의 교반을 시작하여 서서히 rpm을 올리면서 5,000 rpm 이상에서 유화 분산을 진행하였다. 유화가 완료되면 글리세린을 투입한 후 500 rpm 이하에서 교반하여 엑다이손 유화물을 제조하였다.After adding the first surfactant and the second surfactant to the homomixer, the mixture was stirred at 500 rpm or less while maintaining the temperature at 50 degrees or higher. Afterwards, when the ecdysone raw material was added and the ecdysone began to be wetted in the emulsion, stirring of the homomixer was started and the rpm was gradually increased to carry out emulsion dispersion at over 5,000 rpm. When emulsification was completed, glycerin was added and stirred at 500 rpm or less to prepare an ecdysone emulsion.
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상기 표 14 내지 표 25에 기재된 조성에 따라 이렇게 얻은 천연 폴리페놀 화합물 유화물에 상기에서 제조된 수용성 항산화제 유화물을 투입한 후 유화액의 성상을 확인하면서 500 rpm 이하에서 혼합 분산 작업을 진행하여 수용성 항산화제 유화물을 함유하는 천연 폴리페놀 화합물 함유 수용성 유화 조성물을 제조하였다. After adding the water-soluble antioxidant emulsion prepared above to the natural polyphenol compound emulsion thus obtained according to the composition shown in Tables 14 to 25, mixing and dispersion was performed at 500 rpm or less while checking the properties of the emulsion to dissolve the water-soluble antioxidant. A water-soluble emulsion composition containing a natural polyphenol compound containing an emulsion was prepared.
실험예 1: 항산화 효과 측정 Experimental Example 1: Measurement of antioxidant effect
DPPH 측정법을 이용하여 수용성 항산화제 유화물을 포함하는 천연 폴리페놀 화합물 함유 수용성 유화 조성물의 항산화 효과를 측정하였다. The antioxidant effect of a water-soluble emulsion composition containing natural polyphenol compounds, including a water-soluble antioxidant emulsion, was measured using the DPPH measurement method.
DPPH 라디칼 소거 활성 측정은 항산화능을 측정하는데 가장 보편적으로 사용되는 방법으로 색상 변화로 항산화능을 평가하는 방법으로, 항산화능이 뛰어난 시료를 처리하면 색의 변화가 뚜렷하고 효과가 떨어지는 시료를 처리하면 보라색에서 많은 변화가 일어나지 않아서 이러한 변화 정도를 spectrophotometer(517nm)로 흡광도를 측정하여 항산화능을 비교하며, 값이 높을수록 항산화 효과도 높다고 평가한다. 실험조건(가혹조건 시험: 40℃에서 1주일간 방치하여 산화 유도)은 아래와 같다. DPPH radical scavenging activity measurement is the most commonly used method to measure antioxidant capacity. It evaluates antioxidant capacity through color change. When samples with excellent antioxidant capacity are treated, the color change is clear, and when samples with poor antioxidant capacity are treated, the color changes from purple to purple. Since not much change occurs, the degree of this change is measured by absorbance using a spectrophotometer (517 nm) to compare the antioxidant capacity. The higher the value, the higher the antioxidant effect. The experimental conditions (harsh conditions test: oxidation induced by leaving at 40℃ for 1 week) are as follows.
① 용매 - 에탄올① Solvent – Ethanol
② 함량 - 0.01 wt% 분산액, 0.1 wt% 분산액② Content - 0.01 wt% dispersion, 0.1 wt% dispersion
③ 방법 - shaking waterbath 사용. 30℃, 2hr③ Method - Use a shaking waterbath. 30℃, 2hrs
④ 필터 - No.5 여과지 사용 자연여과후 0.45μm 카트리지 필터 사용④ Filter - Use No.5 filter paper and use 0.45μm cartridge filter after natural filtration.
실험 결과는 아래 표 18 내지 표 25에 나타내었다. The experimental results are shown in Tables 18 to 25 below.
상기 표 26 내지 표 37에 나타낸 바와 같이, 수용성 항산화 유화물에 카테킨이나 토코페롤을 포함하지 않은 제조예 3, 제조예 4의 수용성 항산화 유화물을 사용하는 경우 천연 폴리페놀 화합물 함유 수용성 유화 조성물의 항산화 효과가 낮은 것을 확인할 수 있었다. As shown in Tables 26 to 37, when the water-soluble antioxidant emulsion of Preparation Example 3 and Preparation Example 4, which does not contain catechin or tocopherol, is used, the antioxidant effect of the water-soluble emulsion composition containing natural polyphenol compounds is low. could be confirmed.
실험예 2: 수용해도 확인 Experimental Example 2: Confirmation of acceptability
상기 표 38 내지 표 61에 기재된 조성에 따라 엑다이손 유화물에 수용성 항산화제 유화물을 투입한 후 유화액의 성상을 확인하면서 500 rpm 이하에서 혼합 분산 작업을 진행하여 수용성 항산화제 유화물을 함유하는 천연 폴리페놀 화합물 함유 수용성 유화 조성물을 제조하였다. After adding the water-soluble antioxidant emulsion to the ecdysone emulsion according to the composition shown in Tables 38 to 61, mixing and dispersion was performed at 500 rpm or less while checking the properties of the emulsion to obtain natural polyphenol containing the water-soluble antioxidant emulsion. A water-soluble emulsion composition containing the compound was prepared.
제조된 천연 폴리페놀 화합물 함유 수용성 유화 조성물의 수용해도를 아래와 같이 확인하였다. 증류수 50 ml를 항온수조에서 수온 38 ℃를 유지하고, 100 rpm 속도를 유지하면서 실시예와 비교예의 유화 조성물을 1g을 투입하였다. 1시간 후 원심분리 후 여과한 다음 Karl Fisher method 로 수분함량 측정하여 유기물 함량 정량하였다. The water solubility of the prepared water-soluble emulsion composition containing natural polyphenol compounds was confirmed as follows. 50 ml of distilled water was maintained at a water temperature of 38°C in a constant temperature water bath, and 1 g of the emulsion composition of the examples and comparative examples was added while maintaining a speed of 100 rpm. After 1 hour, it was centrifuged and filtered, and the moisture content was measured using the Karl Fisher method to quantify the organic matter content.
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division
카테킨General powder type
catechin
캠페롤General powder type
kaempferol
레스베라트롤General powder type
Resveratrol
루테올린General powder type
luteolin
퀘르세틴 General powder type
Quercetin
탄닌General powder type
tannin
헤스페리딘General powder type
hesperidin
안토시아니딘 General powder type
Anthocyanidin
나린제닌General powder type
naringenin
바이칼레인General powder type
baicalein
division
3Example
3
43Comparative example
43
44Comparative example
44
45Comparative example
45
division
5Example
5
103Comparative example
103
104Comparative example
104
105Comparative example
105
division
7Example
7
63Comparative example
63
64Comparative example
64
65Comparative example
65
division
9Example
9
73Comparative example
73
74Comparative example
74
75Comparative example
75
division
11Example
11
83Comparative example
83
84Comparative example
84
85Comparative example
85
division
13Example
13
93Comparative example
93
94Comparative example
94
95Comparative example
95
division
15Example
15
103Comparative example
103
104Comparative example
104
105Comparative example
105
division
17Example
17
113Comparative example
113
114Comparative example
114
115Comparative example
115
division
19Example
19
123Comparative example
123
124Comparative example
124
125Comparative example
125
division
21Example
21
133Comparative example
133
134Comparative example
134
135Comparative example
135
division
23Example
23
143Comparative example
143
144Comparative example
144
145Comparative example
145
상기 표 62 내지 표 74에 나타낸 바와 같이, HLB(Hydrophile-Lipophile Balance)가 상이한 2종의 계면활성제를 포함하는 수용성 항산화 유화물과 천연 폴리페놀 화합물 유화물을 사용한 실시예 1 내지 15의 조성물은 비교예의 유화물과 비교하여 수용해도가 매우 높은 것으로 나타났다. As shown in Tables 62 to 74, the compositions of Examples 1 to 15 using a water-soluble antioxidant emulsion containing two types of surfactants with different Hydrophile-Lipophile Balance (HLB) and a natural polyphenol compound emulsion were compared to the emulsion of Comparative Example. Compared to , the acceptance solubility was found to be very high.
실험예 3: 수분산 유화 입자 확인Experimental Example 3: Confirmation of water-dispersed emulsified particles
상기 표 38 내지 표 61에 따라 제조된 천연 폴리페놀 화합물 함유 수용성 유화 조성물의 유화 압자 크기를 아래와 같이 확인하였다. 증류수 50 ml를 항온수조에서 수온 38 ℃를 유지하고, 100 rpm 속도를 유지하면서 실시예와 비교예의 유화 조성물을 1g을 투입하였다. 1시간 후 광학현미경으로 유화 입자를 관찰하고 그 결과를 도 1 및 도 2에 나타내었다. The emulsion indenter size of the water-soluble emulsion composition containing natural polyphenol compounds prepared according to Tables 38 to 61 was confirmed as follows. 50 ml of distilled water was maintained at a water temperature of 38°C in a constant temperature water bath, and 1 g of the emulsion composition of the examples and comparative examples was added while maintaining a speed of 100 rpm. After 1 hour, the emulsified particles were observed with an optical microscope, and the results are shown in Figures 1 and 2.
Zetasizer Nano ZS(Malvern Instrument, U.K.)를 사용하여 상기 증류수 중 유화입자의 크기를 측정하였다. 이때 시료에 대하여 3회 반복 측정하였고, 그 평균값을 하기 표 75에 나타내었다. The size of emulsified particles in the distilled water was measured using Zetasizer Nano ZS (Malvern Instrument, U.K.). At this time, the sample was repeatedly measured three times, and the average values are shown in Table 75 below.
division
1Example
One
3Example
3
5Example
5
7Example
7
9Example
9
(μm)Oil painting particle size
(μm)
상기 표 75, 도 1 및 도 2를 참조하면, 본 발명의 일 실시예에 해당하는 천연 폴리페놀 화합물 함유 수용성 유화 조성물은 평균 1.0 내지 2.5 μm의 유화 입자를 형성하는 반면, 비교예 33 내지 152의 천연 폴리페놀 화합물 함유 수용성 유화 조성물은 유화 입자가 잘 형성되지 않는 것을 볼 수 있었다. 이로부터 본 발명에 따른 천연 폴리페놀 화합물 함유 수용성 유화 조성물은 생체에서 흡수되어 높은 생체이용률을 나타낼 수 있을 것으로 예상할 수 있다. Referring to Table 75 and Figures 1 and 2, the water-soluble emulsion composition containing a natural polyphenol compound corresponding to an example of the present invention forms emulsion particles with an average of 1.0 to 2.5 μm, while the emulsion particles of Comparative Examples 33 to 152 It was found that water-soluble emulsion compositions containing natural polyphenol compounds did not form emulsified particles well. From this, it can be expected that the water-soluble emulsion composition containing natural polyphenol compounds according to the present invention will be absorbed in the living body and exhibit high bioavailability.
Claims (7)
토코페롤 1 내지 10 중량%,
카테킨 1 내지 5 중량%,
HLB 3 내지 HLB 7의 제1 계면활성제 1 내지 15 중량%,
HLB 10 내지 HLB 14의 제2 계면활성제 10 내지 50 중량%;
공계면활성제 15 내지 45 중량%, 및
식용 유지 5 내지 35 중량%,
(2) 전체 100 중량%를 만족하도록 하기 성분을 포함하는 천연 폴리페놀 화합물 유화물:
천연 폴리페놀 화합물 1 내지 20 중량%,
HLB 3 내지 HLB 7의 제1 계면활성제 1 내지 10 중량%,
HLB 10 내지 HLB 14의 제2 계면활성제 1 내지 20 중량%, 및
공계면활성제 50 내지 97 중량%를 포함하고,
상기 천연 폴리페놀 화합물은
실리마린(Silymarin), 커큐민(Curcumin), 카테킨(Catechin), 캠퍼롤 (kaempferol), 레스베라트롤(Resveratrol), 루테올린(Luteolin), 퀘르세틴 (Quercetin), 루틴(Rutin), 갈산(Gallic acid), 탄닌(Tannin), 헤스페레틴 (Hesperetin), 헤스페리딘(Hesperidin), 안토시아니딘(Anthocyanidin), 안토시아닌 (Anthocyanin), 나린제닌(Naringenin), 나린진(Naringin), 바이칼레인(Baicalein), 바이칼린(Baicalin) 및 이들의 혼합물로 이루어진 군에서 선택된 1종이고,
상기 제1 계면활성제는
글리세린 지방산 에스테르, 폴리글리세린 지방산 에스테르, 솔비탄 지방 에스테르, 레시틴, 프로필렌글리콜 지방산 에스테르 및 이들의 혼합물로 이루어진 군에서 선택된 1종이고,
상기 제2 계면활성제는
폴리글리세린 지방산 에스테르, 폴리옥시에틸렌 솔비탄 지방산 에스테르, 자당 지방산 에스테르, 효소분해 레시틴 및 이들의 혼합물로 이루어진 군에서 선택된 1종이고,
상기 공계면활성제는
글리세린, 솔비톨, 폴리에틸렌글리콜, 프로필렌글리콜, 트리아세틴 및 이들의 혼합물로 이루어진 군에서 선택된 1종이고,
상기 식용 유지는
두유, 옥수수유, 채종유, 고올레산 채종유, 홍화유, 미강유, 팜유, 올리브유, 해바라기유, 야자유, 소맥 배아유, 및 중쇄중성지방유(MCT Oil)으로 이루어진 군에서 선택된 1종 이상의 식용 유지이고,
상기 수용성 항산화제 유화물 1 내지 10 중량%; 및
상기 천연 폴리페놀 화합물 유화물 90 내지 99 중량%를 포함하는 것인,
수용성 항산화제 유화물을 함유하는 천연 폴리페놀 화합물 함유 수용성 유화 조성물.
(1) Water-soluble antioxidant emulsion containing the following ingredients to satisfy a total of 100% by weight:
1 to 10% by weight of tocopherol,
1 to 5% by weight of catechin,
1 to 15% by weight of a first surfactant of HLB 3 to HLB 7,
10 to 50% by weight of a second surfactant of HLB 10 to HLB 14;
15 to 45% by weight of cosurfactant, and
5 to 35% by weight of edible oil,
(2) Natural polyphenol compound emulsion containing the following components to satisfy 100% by weight of the total:
1 to 20% by weight of natural polyphenol compounds,
1 to 10% by weight of a first surfactant of HLB 3 to HLB 7,
1 to 20% by weight of a second surfactant from HLB 10 to HLB 14, and
Contains 50 to 97% by weight of a cosurfactant,
The natural polyphenol compounds are
Silymarin, Curcumin, Catechin, kaempferol, Resveratrol, Luteolin, Quercetin, Rutin, Gallic acid, Tannin ( Tannin, Hesperetin, Hesperidin, Anthocyanidin, Anthocyanin, Naringenin, Naringin, Baicalein, Baicalin and one selected from the group consisting of mixtures thereof,
The first surfactant is
One selected from the group consisting of glycerin fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, lecithin, propylene glycol fatty acid esters, and mixtures thereof,
The second surfactant is
It is one selected from the group consisting of polyglycerol fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, enzymatically degraded lecithin, and mixtures thereof,
The cosurfactant is
It is one selected from the group consisting of glycerin, sorbitol, polyethylene glycol, propylene glycol, triacetin, and mixtures thereof,
The edible oil is
It is one or more edible oils selected from the group consisting of soy milk, corn oil, rapeseed oil, high oleic acid rapeseed oil, safflower oil, rice bran oil, palm oil, olive oil, sunflower oil, palm oil, wheat germ oil, and medium chain triglyceride oil (MCT Oil),
1 to 10% by weight of the water-soluble antioxidant emulsion; and
Containing 90 to 99% by weight of the natural polyphenol compound emulsion,
A water-soluble emulsion composition containing a natural polyphenol compound containing a water-soluble antioxidant emulsion.
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