KR20230092767A - Polyphenol tromethamine salt containing carboxyl group and use therof - Google Patents
Polyphenol tromethamine salt containing carboxyl group and use therof Download PDFInfo
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- KR20230092767A KR20230092767A KR1020220172710A KR20220172710A KR20230092767A KR 20230092767 A KR20230092767 A KR 20230092767A KR 1020220172710 A KR1020220172710 A KR 1020220172710A KR 20220172710 A KR20220172710 A KR 20220172710A KR 20230092767 A KR20230092767 A KR 20230092767A
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- South Korea
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- acid
- tromethamine salt
- polyphenol
- tromethamine
- weight
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- -1 Polyphenol tromethamine salt Chemical class 0.000 title claims abstract description 62
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 40
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
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- C07C215/18—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with hydroxy groups and at least two amino groups bound to the carbon skeleton
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- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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Abstract
Description
본 발명은 카복실기를 포함하는 폴리페놀 트로메타민염 및 이의 용도에 관한 것이다.The present invention relates to polyphenol tromethamine salts containing carboxyl groups and uses thereof.
폴리 페놀은 과일, 채소, 곡물 및 음료에서 주로 발견되는 자연 발생 화합물이다. 포도, 사과, 배, 체리 및 딸기와 같은 과일에는 신선한 무게 100g 당 최대 200 - 300 mg 폴리 페놀이 들어있다. 일반적으로 레드 와인, 차 또는 커피 한 잔에는 약 100mg의 폴리 페놀이 들어있다. 곡물, 마른 콩과 식물 및 초콜릿에도 폴리페놀이 다량 함유되어 있는 것으로 알려져 있다. 폴리 페놀은 식물의 2 차 대사 산물이며 일반적으로 자외선 또는 병원체에 의한 침략에 대한 방어에 관여한다. Polyphenols are naturally occurring compounds found primarily in fruits, vegetables, grains, and beverages. Fruits such as grapes, apples, pears, cherries and strawberries contain up to 200 - 300 mg polyphenols per 100 g of fresh weight. A typical cup of red wine, tea or coffee contains about 100 mg of polyphenols. Grains, dried legumes and chocolate are also known to contain high levels of polyphenols. Polyphenols are secondary metabolites of plants and are usually involved in defense against invasion by UV light or pathogens.
폴리페놀은 항염증, 면역증진 등 인체에 생리적으로 도움이 되는 활성을 나타내는 것으로 알려져 있어 다양하게 활용되고 있다. Polyphenols are known to exhibit physiologically beneficial activities in the human body, such as anti-inflammation and immunity enhancement, and are therefore used in various ways.
그러나 폴리페놀은 물에 대한 용해도가 낮은 한계가 있다. 종래에는 이러한 한계를 극복하기 위하여 가용화제나 계면활성제 등 첨가제를 이용하였는데, 이는 일정량을 초과할 경우 독성물질로서 인체에 해가 될 수 있는 문제가 있다.However, polyphenols have a limited solubility in water. Conventionally, in order to overcome these limitations, additives such as solubilizers and surfactants have been used, which have a problem of being harmful to the human body as toxic substances when a certain amount is exceeded.
본 발명은 위와 같은 문제를 해결하기 위하여 안출된 것으로 본 발명에서 해결하고자 하는 과제는 폴리페놀의 낮은 용해도가 개선된 화합물을 제공하는데 있다.The present invention has been made to solve the above problems, and the problem to be solved in the present invention is to provide a compound with improved low solubility of polyphenols.
또한, 본 발명에서 해결하고자 하는 과제는 항산화 효과를 갖는 식품 조성물을 제공하는데 있다.In addition, the problem to be solved in the present invention is to provide a food composition having an antioxidant effect.
또한, 본 발명에서 해결하고자 하는 과제는 항산화 효과를 갖는 화장료 조성물을 제공하는데 있다.In addition, the problem to be solved in the present invention is to provide a cosmetic composition having an antioxidant effect.
위와 같은 과제를 해결하기 위한 본 발명은 카복실기를 포함하는 폴리페놀 트로메타민염 화합물에 기술적 특징이 있다. The present invention for solving the above problems has a technical feature in a polyphenol tromethamine salt compound containing a carboxyl group.
또한, 위와 같은 과제를 해결하기 위한 본 발명의 상기 폴리페놀은 카페산, 페룰산 및 갈산으로부터 선택되는 어느 하나인 것을 기술적 특징으로 한다. In addition, the polyphenol of the present invention for solving the above problems is characterized in that it is any one selected from caffeic acid, ferulic acid and gallic acid.
또한, 위와 같은 과제를 해결하기 위한 본 발명의 상기 폴리페놀 트로메타민염은 용해도가 증가된 것을 기술적 특징으로 한다.In addition, the polyphenol tromethamine salt of the present invention for solving the above problems is characterized by increased solubility.
또한, 위와 같은 과제를 해결하기 위한 본 발명의 항산화용 식품 조성물은 카복실기를 포함하는 폴리페놀 트로메타민염을 유효성분으로 함유하는 것을 기술적 특징으로 한다. In addition, the antioxidant food composition of the present invention for solving the above problems is characterized by containing a polyphenol tromethamine salt containing a carboxyl group as an active ingredient.
또한, 위와 같은 과제를 해결하기 위한 본 발명의 상기 폴리페놀은 카페산, 페룰산 및 갈산으로 이루어진 군에서 선택되는 적어도 어느 하나인 것을 기술적 특징으로 한다. In addition, the polyphenol of the present invention for solving the above problems is characterized in that it is at least one selected from the group consisting of caffeic acid, ferulic acid and gallic acid.
또한, 위와 같은 과제를 해결하기 위한 본 발명의 상기 식품 조성물은, 카페산 트로메타민염, 페룰산 트로메타민염 및 갈산의 트로메타민염이 중량비 기준으로 1:1:1의 비율로 혼합되는 것을 기술적 특징으로 한다.In addition, the food composition of the present invention for solving the above problems is technical in that caffeic acid tromethamine salt, ferulic acid tromethamine salt and gallic acid tromethamine salt are mixed in a ratio of 1: 1: 1 based on weight ratio to be characterized
또한, 위와 같은 과제를 해결하기 위한 본 발명의 상기 폴리페놀 트로메타민염은 DPPH(2,2-diphenyl-1-picrylhydrazyl) 라디칼 소거 활성을 갖는 것을 기술적 특징으로 한다.In addition, the polyphenol tromethamine salt of the present invention for solving the above problems is characterized by having DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity.
또한, 위와 같은 과제를 해결하기 위한 본 발명의 상기 폴리페놀 트로메타민염은 용해도가 증가된 것을 기술적 특징으로 한다.In addition, the polyphenol tromethamine salt of the present invention for solving the above problems is characterized by increased solubility.
또한, 위와 같은 과제를 해결하기 위한 본 발명의 항산화용 화장료 조성물은 카복실기를 포함하는 폴리페놀 트로메타민염을 유효성분으로 함유하는 것을 기술적 특징으로 한다. In addition, the cosmetic composition for antioxidation of the present invention for solving the above problems is characterized in that it contains a polyphenol tromethamine salt containing a carboxyl group as an active ingredient.
본 발명은 수용액 상태의 액상제품에 표준적으로 사용되고 있는 아스코르빈산에 비하여 안정성이 우수하고 pH에 대한 영향이 적어 수용액 상태의 액상 제품에 아스코르빈산의 대체품으로 사용될 수 있다.The present invention has excellent stability and less influence on pH compared to ascorbic acid, which is standardly used for liquid products in aqueous solution, and can be used as a substitute for ascorbic acid in liquid products in aqueous solution.
또한, 카페산，페룰산갈산의 트로메타민염은 본래 화합물에 비하여 용해도가 크게 향상되어 항산화, 항염증, 면역증강 효능에 유용한 식품 조성물의 유효성분으로 사용될 수 있다. 본 발명의 화합물은 용해도가 우수하기 때문에 다양한 형태의 제품에 적용할 수 있다.In addition, tromethamine salts of caffeic acid and gallic acid ferulic acid have greatly improved solubility compared to the original compounds, and thus can be used as active ingredients of food compositions useful for antioxidant, anti-inflammatory, and immune enhancing effects. Since the compound of the present invention has excellent solubility, it can be applied to various types of products.
또한, 본 발명의 화합물은 항산화 능력이 크게 향상되어 장기보존이 필요한 제품에 보존제와 함께 첨가제로 사용될 수 있다.In addition, the compound of the present invention can be used as an additive together with a preservative in products requiring long-term storage because its antioxidant ability is greatly improved.
도 1은 카페산 트로메타민염의 박층크로마토그램 결과이다. (tris: 트로메타민, CA: 카페산, CA·tris: 카페산 트로메타민염)
도 2는 페룰산 트로메타민염의 박층크로마토그램 결과이다. (tris: 트로메타민, FA: 페룰산, FA·tris: 페룰산 트로메타민염)
도 3은 갈산 트로메타민염의 박층크로마토그램 결과이다. (tris: 트로메타민, GA: 갈산, GA·tris: 갈산 트로메타민염)1 is a result of a thin layer chromatogram of caffeic acid tromethamine salt. (tris: tromethamine, CA: caffeic acid, CA tris: caffeic acid tromethamine salt)
2 is a thin layer chromatogram result of tromethamine salt of ferulic acid. (tris: tromethamine, FA: ferulic acid, FA tris: ferulic acid tromethamine salt)
3 is a result of a thin layer chromatogram of gallic acid tromethamine salt. (tris: tromethamine, GA: gallic acid, GA tris: gallic acid tromethamine salt)
이하, 첨부한 도면을 참조하여 본 발명에 대해 상세히 설명한다. 본 발명은 다양한 변경을 가할 수 있고 여러 가지 형태를 가질 수 있는 바, 특정 실시예들을 도면에 예시하고 본문에 상세하게 설명하고자 한다. 그러나 이는 본 발명을 특정한 개시 형태에 대해 한정하려는 것이 아니며, 본 발명의 사상 및 기술 범위에 포함되는 모든 변경, 균등물 내지 대체물을 포함하는 것으로 이해되어야 한다.Hereinafter, the present invention will be described in detail with reference to the accompanying drawings. Since the present invention may have various changes and various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to a specific form disclosed, and should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.
본 명세서에서 사용한 용어는 단지 특정한 실시예를 설명하기 위해 사용된 것으로서 본 발명을 한정하려는 의도가 아니다. 단수의 표현은 문맥상 명백하게 다르게 뜻하지 않는 한, 복수의 표현을 포함한다. 본 출원에서, "포함하다" 또는 "가지다" 등의 용어는 명세서 상에 기재된 특징, 단계, 구성요소 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 단계, 구성요소 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다.Terms used in this specification are used only to describe specific embodiments and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this application, terms such as "comprise" or "having" are intended to designate that the features, steps, components, or combinations thereof described in the specification exist, but that one or more other features, steps, components, or It should be understood that it does not preclude the possibility of existence or addition of combinations thereof.
다르게 정의되지 않는 한, 기술적이거나 과학적인 용어를 포함해서 여기서 사용되는 모든 용어들은 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자에 의해 일반적으로 이해되는 것과 동일한 의미를 가지고 있다. 일반적으로 사용되는 사전에 정의되어 있는 것과 같은 용어들은 관련 기술의 문맥 상 가지는 의미와 일치하는 의미를 가지는 것으로 해석되어야 하며, 본 출원에서 명백하게 정의하지 않는 한, 이상적이거나 과도하게 형식적인 의미로 해석되지 않는다.Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. Terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with the meaning in the context of the related art, and unless explicitly defined in the present application, they should not be interpreted in an ideal or excessively formal meaning. don't
본 명세서의 "카페산(caffeic acid, C9H8O4)"은 화학식 1의 물질을 기본 단위로 하는 유기화합물로서 페놀 및 아크릴 작용기를 포함한다. 카페산은 식물 바이오매스와 그 잔류물의 주성분 중 하나인 리그닌 생합성의 중간체이기 때문에 모든 식물에서 발견된다.The term "caffeic acid (C 9 H 8 O 4 )" in the present specification is an organic compound having a substance represented by Chemical Formula 1 as a basic unit, and includes phenol and acryl functional groups. Caffeic acid is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the main components of plant biomass and its residues.
[화학식 1][Formula 1]
본 명세서의 "페룰산(ferulic acid, C10H10O4)"은 화학식 2의 물질을 기본 단위로 하는 유기화합물로서 펙틴 및 리그닌과 같은 리그노셀룰로오스의 구성 요소이므로 여러 식물성 공급원을 포함하여 식물계 어디에나 존재한다.As used herein, "ferulic acid (C 10 H 10 O 4 )" is an organic compound having a substance of Formula 2 as a basic unit, and is a component of lignocellulose such as pectin and lignin, so it can be used in plants, including various vegetable sources. It exists everywhere.
[화학식 2][Formula 2]
본 명세서의 "갈산(gallic acid, C7H6O5)"화학식 3의 물질을 기본 단위로 하는 유기화합물로서 오배자, 옻나무, 찻잎, 참나무 껍질 및 기타 식물에서 발견된다. "Gallic acid (gallic acid, C 7 H 6 O 5 )" of the present specification is an organic compound based on a substance represented by Chemical Formula 3 and is found in gall nut, sumac, tea leaves, oak bark and other plants.
[화학식 3][Formula 3]
본 명세서의 "트로메타민(tromethamine, C4H11NO3)"은 화학식 4에 기재된 바와 같이 1차 아민 및 하이드록시기를 포함하고 있는 유기화합물이다.As used herein, "tromethamine (C 4 H 11 NO 3 )" is an organic compound containing a primary amine and a hydroxyl group as described in Chemical Formula 4.
[화학식 4][Formula 4]
본 발명은 폴리페놀 트로메타민염 화합물을 제공하는데 그 목적이 있다. 구체적으로 폴리페놀은 카복실기를 포함하는 것으로 일 실시예로 카페산, 페룰산 및 갈산이 해당된다. 카페산 트로메타민염, 페룰산 트로메타민염 및 갈산 트로메타민염은 이하의 화학식 5 내지 7에 기재되어 있다.An object of the present invention is to provide a polyphenol tromethamine salt compound. Specifically, polyphenols include carboxyl groups, and examples include caffeic acid, ferulic acid, and gallic acid. Caffeic acid tromethamine salt, ferulic acid tromethamine salt and gallic acid tromethamine salt are described in Formulas 5 to 7 below.
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
이하에서는 본 발명의 실시 형태에 대하여 설명한다. EMBODIMENT OF THE INVENTION Below, embodiment of this invention is described.
본 발명의 일 실시예에 따른 식품 조성물은 항산화 기능을 갖는다. 본 발명의 식품 조성물은 식품 제조 시에 통상적으로 첨가되는 성분을 포함하며, 예를 들어, 단백질, 탄수화물, 지방, 영양소 및 조미제를 포함한다. 예컨대, 드링크제로 제조되는 경우에는 유효성분 이외에 향미제 또는 천연 탄수화물을 추가 성분으로서 포함시킬 수 있다. 예를 들어, 천연 탄수화물은 모노사카라이드(예컨대, 글루코오스, 프럭토오스 등); 디사카라이드(예컨대, 말토스, 수크로오스 등); 올리고당; 폴리사카라이드(예컨대, 덱스트린, 시클로덱스트린 등); 및 당알코올(예컨대, 자일리톨, 소르비톨, 에리쓰리톨 등)을 포함할 수 있다.A food composition according to an embodiment of the present invention has an antioxidant function. The food composition of the present invention includes components commonly added during food preparation, and includes, for example, proteins, carbohydrates, fats, nutrients, and seasonings. For example, when prepared as a drink, a flavoring agent or natural carbohydrate may be included as an additional ingredient in addition to the active ingredient. For example, natural carbohydrates include monosaccharides (eg, glucose, fructose, etc.); disaccharides (eg, maltose, sucrose, etc.); oligosaccharide; polysaccharides (eg, dextrins, cyclodextrins, etc.); and sugar alcohols (eg, xylitol, sorbitol, erythritol, etc.).
향미제로서 천연 향미제(예컨대, 타우마틴, 스테비아 추출물 등) 및 합성 향미제(예컨대, 사카린, 아스파르탐 등)을 이용할 수 있다.As the flavoring agent, natural flavoring agents (eg, thaumatin, stevia extract, etc.) and synthetic flavoring agents (eg, saccharin, aspartame, etc.) may be used.
본 발명의 일 실시예에 따른 화장료 조성물은 항산화 효과를 통해 피부 상태 개선에 효과가 있다. 상기 "피부 상태 개선"은 주름의 발생 억제, 피부 노화 억제, 피부 탄력 개선, 피부 재생, 상처 또는 창상 회복(wound healing), 각막 재생, 피부 자극 완화 및 이의 조합으로 이루어진 군에서 선택되는, 피부 세포의 기능 저하 또는 손실로부터 피부를 보호 또는 피부 상태를 개선하거나, 또는 피부 질환을 예방 또는 개선하는 것을 의미한다. 상기 피부 질환은 아토피성 피부염, 알레르기, 피부 습진, 여드름, 건선, 가려움증 및 이의 조합으로 이루어진 군에서 선택되는 것일 수 있다.The cosmetic composition according to an embodiment of the present invention is effective in improving skin condition through an antioxidant effect. The "improvement of skin condition" is a skin cell selected from the group consisting of inhibition of wrinkles, inhibition of skin aging, improvement of skin elasticity, skin regeneration, wound or wound healing, corneal regeneration, skin irritation relief, and combinations thereof. It means to protect the skin or improve skin conditions from functional degradation or loss, or to prevent or improve skin diseases. The skin disease may be selected from the group consisting of atopic dermatitis, allergy, skin eczema, acne, psoriasis, itching, and combinations thereof.
본 발명에 따른 화장료 조성물은 피부 상태의 개선을 위한 화장료 제조에 사용될 수 있다.The cosmetic composition according to the present invention can be used to prepare cosmetics for improving skin conditions.
상기 화장료 조성물은 당업계에서 통상적으로 제조되는 화장료 제형으로 제제화될 수 있다. 상기 화장료 조성물은 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클렌징, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화될 수 있으나, 본 발명이 이에 한정되는 것은 아니다. 보다 상세하게는, 유연 화장수, 영양 화장수, 영양 크림, 마사지 크림, 에센스, 아이 크림, 클렌징 크림, 클렌징폼, 클렌징 워터, 팩, 스프레이 또는 파우더의 제형으로 제제화될 수 있다.The cosmetic composition may be formulated into a cosmetic formulation commonly prepared in the art. The cosmetic composition is formulated into, for example, a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation and spray, etc. However, the present invention is not limited thereto. More specifically, it may be formulated into a formulation of softening lotion, nutrient lotion, nutrient cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.
본 발명에 따른 화장료 조성물의 제형이 페이스트, 크림 또는 겔인 경우에는 동물성유, 식물성유, 왁스, 파라핀, 전분, 트라가칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크, 산화아연 및 이의 혼합물로 이루어진 군에서 선택되는 담체 성분을 포함할 수 있다.When the formulation of the cosmetic composition according to the present invention is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tragacanth, cellulose derivatives, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide and their A carrier component selected from the group consisting of mixtures may be included.
본 발명에 따른 화장료 조성물의 제형이 용액 또는 유탁액인 용매, 용매화제, 유탁화제 및 이의 혼합물로 이루어진 군에서 선택되는 담체 성분을 포함할 수 있다. 이의 예로는, 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알코올, 벤질 벤조에이트, 프로필렌 글리콜, 1,3-부틸글리콜 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜, 소르비탄 지방산 에스테르, 및 이의 혼합물 등을 들 수 있다.The formulation of the cosmetic composition according to the present invention may include a carrier component selected from the group consisting of a solution or emulsion solvent, a solvating agent, an emulsifying agent, and mixtures thereof. Examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butyl glycol oil, glycerol aliphatic esters, polyethylene glycol, sorbitan fatty acid esters, and mixtures thereof. can be heard
본 발명에 따른 화장료 조성물의 제형이 현탁액인 경우에는 물, 에탄올 또는 프로필렌 글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미세결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가, 트라가칸트 및 이의 혼합물로 이루어진 군에서 선택되는 담체 성분을 포함할 수 있다.When the formulation of the cosmetic composition according to the present invention is a suspension, a liquid diluent such as water, ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, fine and a carrier component selected from the group consisting of crystalline cellulose, aluminum metahydroxide, bentonite, agar, tragacanth, and mixtures thereof.
본 발명은 상기 화장료 조성물을 이용하여 피부 상태를 개선시키는 방법을 제공한다.The present invention provides a method for improving skin condition using the cosmetic composition.
상기 피부 상태를 개선시키는 방법은 본 발명에 따른 화장료 조성물을 이를 필요로 하는 대상의 피부에 도포하는 단계를 포함할 수 있다. 상기 대상은 포유동물일 수 있고, 구체적으로는 인간일 수 있다.The method of improving the skin condition may include applying the cosmetic composition according to the present invention to the skin of a subject in need thereof. The target may be a mammal, specifically a human.
피부에 도포하는 단계는 본 발명에 따른 화장료 조성물을 그 형태에 따라 피부에 직접 도포하거나, 분무하는 것을 포함할 수 있다. 이때, 상기 화장료 조성물의 도포량 및 하루 사용 횟수는, 사용자의 연령, 성별, 용도, 증상의 정도 등에 따라 적절하게 설정될 수 있고, 예를 들면, 상기 화장료 조성물의 적당량을 하루 1 내지 6회의 빈도로 피부에 도포할 수 있다.The step of applying to the skin may include directly applying or spraying the cosmetic composition according to the present invention to the skin according to its form. At this time, the amount of application of the cosmetic composition and the number of times of use per day may be appropriately set according to the user's age, gender, use, degree of symptoms, etc., for example, an appropriate amount of the cosmetic composition at a frequency of 1 to 6 times a day. It can be applied to the skin.
이하에서는 실시예를 통해 본 발명에 따른 화합물의 제조 및 그 효과에 대하여 상세히 설명한다.Hereinafter, the preparation of the compound according to the present invention and its effect will be described in detail through examples.
실시예 1. 카페산 트로메타민염의 제조Example 1. Preparation of caffeic acid tromethamine salt
카페산을 메탄올에 용해시켜 용액을 제조하고，여기에 카페산과 1：1 당량의 몰비로 트로메타민을 적가한 후 6O℃에서 1시간 동안 교반하였다. 이후 40℃에서 회전감암증발기로 메탄올을 농축하고 농축물에 아세톤을 천천히 적가한 후 상온에서 2시간 동안 교반한 후 여과하였다. 여과물을 아세톤으로 세척한 후 얻어진 고체를 40℃에서 진공건조하여 카페산 트로메타민염을 얻었다(순도 98.3 %, 수득율 92.4 %).A solution was prepared by dissolving caffeic acid in methanol, and caffeic acid and tromethamine were added dropwise thereto in a molar ratio of 1:1 equivalent, followed by stirring at 60° C. for 1 hour. Thereafter, methanol was concentrated with a rotary evaporator at 40° C., and acetone was slowly added dropwise to the concentrate, followed by stirring at room temperature for 2 hours and filtering. After washing the filtrate with acetone, the obtained solid was vacuum-dried at 40° C. to obtain tromethamine salt of caffeic acid (purity: 98.3%, yield: 92.4%).
실시예 2. 페룰산 트로메타민염의 제조Example 2. Preparation of ferulic acid tromethamine salt
페룰산을 메탄올에 용해시켜 용액을 제조하고, 여기에 페룰산과 1：1 당량의 몰비로 트로메타민을 적가한 후 60℃에서 1시간 동안 교반하였다. 이후 40℃에서 회전감암증발기로 메탄올을 농축하고 농축물에 아세톤을 천천히 적가한 후 상온에서 2시간 동안 교반한 후 여과하였다. 여과물을 아세톤으로 세척한 후 얻어진 고체를 40℃에서 진공건조하여 페룰산 트로메타민염을 얻었다(순도 95.7 %, 수득을 96.3 %).A solution was prepared by dissolving ferulic acid in methanol, to which ferulic acid and tromethamine were added dropwise in a molar ratio of 1:1, followed by stirring at 60° C. for 1 hour. Thereafter, methanol was concentrated with a rotary evaporator at 40° C., and acetone was slowly added dropwise to the concentrate, followed by stirring at room temperature for 2 hours and filtering. After washing the filtrate with acetone, the obtained solid was vacuum-dried at 40° C. to obtain tromethamine salt of ferulic acid (95.7% purity, 96.3% yield).
실시예 3. 갈산 트로메타민염의 제조Example 3. Preparation of gallic acid tromethamine salt
갈산을 메탄올에 용해시켜 용액을 제조하고, 여기에 갈산과 1:1 당량의 몰비로 트로메타민을 적가한 후 60℃에서 1시간 동안 교반하였다. 이후 40℃에서 회전감암증발기로 메탄올을 농축하고 농축물에 아세톤을 천천히 적가한 다음 상온에서 2시간 동안 교반한 후 여과하였다. 여과물을 아세톤으로 세척한 후 얻어진 고체를 40℃에서 진공건조하여 갈산 트로메타민염을 얻었다(순도 95.4 %, 수득을: 85.8 %).A solution was prepared by dissolving gallic acid in methanol, and gallic acid and tromethamine were added dropwise thereto in a molar ratio of 1:1 equivalent, followed by stirring at 60° C. for 1 hour. Thereafter, methanol was concentrated with a rotary evaporator at 40° C., and acetone was slowly added dropwise to the concentrate, followed by stirring at room temperature for 2 hours and filtering. After washing the filtrate with acetone, the obtained solid was vacuum-dried at 40° C. to obtain tromethamine gallic acid salt (purity: 95.4%, yield: 85.8%).
실시예 4. 핵자기공명 스펙트럼 분석Example 4. Nuclear Magnetic Resonance Spectral Analysis
실시예 1 내지 3에 따른 카페산, 페룰산 및 갈산에 대하여 brunker advance Ⅱ 500 (500 MHz)을 이용하여 1H-핵자기공명(nuclear magnetic resonance, NMR) 분석을 수행하였다. 각 트로메타민염의 결과는 다음의 표 1과 같고, 이를 통해 각 폴리페놀 트로메타민염이 제조된 것을 확인하였다.Caffeic acid, ferulic acid and gallic acid according to Examples 1 to 3 were subjected to 1H-nuclear magnetic resonance (NMR) analysis using a Brunker Advance II 500 (500 MHz). The results of each tromethamine salt are shown in Table 1 below, and through this, it was confirmed that each polyphenol tromethamine salt was prepared.
실시예 5. 박층크로마토그램Example 5. Thin Layer Chromatogram
실시예 1 내지 3에 따른 카페산 트로메타민염，페룰산 트로메타민염 및 갈산 트로메타민염에 대하여 실리카겔 TLC plate를 사용하여 박층크로마토그래피 분석을 수행하였다. 전개액은 디클로르메탄:메탄올:증류수를 50：50 으로 혼합한 용액으로 하였으며，발색은 요오드 증기에 접촉시킨 다음 닌히드린(ninhydrin) 시액을 스프레이하여 트로메타민，본래 화합물 및 염의 형태로 된 화합물을 확인하였다. Thin layer chromatography analysis was performed on the tromethamine salt of caffeic acid, tromethamine salt of ferulic acid and tromethamine gallic acid according to Examples 1 to 3 using a silica gel TLC plate. The developing solution was a 50:50 mixture of dichloromethane: methanol: distilled water, and the color was contacted with iodine vapor and then sprayed with ninhydrin solution to obtain tromethamine, the original compound, and a compound in the form of a salt. confirmed.
도 1은 카페산 트로메타민염의 박층크로마토그램 결과 (tris: 트로메타민, CA: 카페산, CA·tris: 카페산 트로메타민염), 도 2는 페룰산 트로메타민염의 박층크로마토그램 결과 (tris: 트로메타민, FA: 페룰산, FA·tris: 페룰산 트로메타민염) 및 도 3은 갈산 트로메타민염의 박층크로마토그램 결과 (tris: 트로메타민, GA: 갈산, GA·tris: 갈산 트로메타민염)이다. Figure 1 is a thin layer chromatogram result of caffeic acid tromethamine salt (tris: tromethamine, CA: caffeic acid, CA tris: caffeic acid tromethamine salt), Figure 2 is a thin layer chromatogram result of ferulic acid tromethamine salt ( tris: tromethamine, FA: ferulic acid, FA tris: ferulic acid tromethamine salt) and FIG. 3 is a thin layer chromatogram of gallic acid tromethamine salt (tris: tromethamine, GA: gallic acid, GA tris: gallic acid tromethamine salt).
각 결과의 Rf값은 표 2에 기재되어 있다.The Rf values of each result are listed in Table 2.
실시예 6. 용해도 측정Example 6. Solubility measurement
실시예 1 내지 3에 따른 카페산 트로메타민염，페룰산 트로메타민염 및 갈산 트로메타민염의 물에 대한 용해도를 하기와 같은 방법으로 측정하였다.The solubility of tromethamine caffeic acid, tromethamine salt of ferulic acid and tromethamine gallic acid according to Examples 1 to 3 in water was measured by the following method.
과량의 카페산 또는 카페산 트로메타민염을 증류수에 현탁시킨 용액을 0.45 //m 시린지 필터로 여과하여 여액 중 카페산 트로메타민염의 농도를 HPLC로 측정하였다. HPLC 분석 컬럼은 Inertsil C18(4.6 x 150 mm, 5 ㎛)을，검출기는 자외선흡광도계를 사용하였다. 이때，시료는 30 ㎕를 주입하였고，유속은 1.0 ㎖/min으로 하였다. 또한，이동상으로 아세토니트릴 및 1% 인산(phosphoric acid) 수용액을 50:50(v/v)으로 혼합하여 사용하였다.A solution in which an excess of caffeic acid or caffeic acid tromethamine salt was suspended in distilled water was filtered through a 0.45 //m syringe filter, and the concentration of caffeic acid tromethamine salt in the filtrate was measured by HPLC. The HPLC analysis column was Inertsil C18 (4.6 x 150 mm, 5 μm), and an ultraviolet absorbance detector was used. At this time, 30 μl of the sample was injected, and the flow rate was 1.0 ml/min. In addition, as a mobile phase, a mixture of acetonitrile and 1% phosphoric acid aqueous solution at a ratio of 50:50 (v/v) was used.
페룰산 또는 갈산을 트로메타민염으로 제조한 화합물에 대해서도 상기 카페산-트로메타민염의 경우와 동일한 방법으로 자외선흡광도계를 이용하여 물에 대한 용해도를 측정하였다. 위와 같이 실시하여 측정한 카페 익애씨드，페룰산 및 갈산의 트로메타민염에 대한 용해도 측정 결과는 아래의 표 3에 나타내었다.The solubility in water of the compounds prepared as tromethamine salts of ferulic acid or gallic acid was measured using an ultraviolet absorbance spectrophotometer in the same manner as in the case of the caffeic acid-tromethamine salts. The results of measuring the solubility of tromethamine salts of caffeic acid, ferulic acid and gallic acid measured by the above method are shown in Table 3 below.
(㎍/㎖)raw material solubility
(μg/ml)
(㎍/㎖)tromethamine salt solubility
(μg/ml)
실시예 7. 항산화력 측정Example 7. Antioxidant activity measurement
실시예 1 내지 3에 따른 카페산 트로메타민염，페룰산 트로메타민염 및 갈산 트로메타민염의 항산화력은 DPPH (1,1-diphenyl-2-picrylhydrazyl)에 대한 수소공여 효과로 측정하였다. The antioxidant capacity of tromethamine caffeic acid, tromethamine salt of ferulic acid and tromethamine gallic acid according to Examples 1 to 3 was measured by the hydrogen donor effect on DPPH (1,1-diphenyl-2-picrylhydrazyl).
구체적으로， 0.2 mM DPPH 용액 (에탄올에 용해됨) 400 ㎕에 여러 농도의 시료 100 ㎕를 가하고 약 10초간 볼텍싱(vortexing)한 다음 어두운 곳에서 30 분간 반응시킨 뒤 517 nm의 파장으로 흡광도를 측정하였다. 각 시료의 항산화력은 흡수분광광도계를 사용하여 시료 첨가 전 및 후의 흡광도를 아래의 식으로 계산하였다. 이 식에서 Abs of control은 상기 0.2 mM DPPH 용액 400 ㎕와 95 % 에탄올 100 ㎕을 혼합한 다음 약 10 초간 볼텍싱하고 어두운 곳에서 30분간 반응시킨 다음 517 nm의 파장으로 측정한 흡광도를 말한다. 결과는 표 4에 기재되어 있다.Specifically, 100 μl of samples of various concentrations were added to 400 μl of 0.2 mM DPPH solution (dissolved in ethanol), vortexed for about 10 seconds, reacted for 30 minutes in the dark, and then measured absorbance at a wavelength of 517 nm did The antioxidant capacity of each sample was calculated by the following formula using the absorbance before and after addition of the sample using an absorption spectrophotometer. Abs of control in this formula refers to the absorbance measured at a wavelength of 517 nm after mixing 400 μl of the 0.2 mM DPPH solution and 100 μl of 95% ethanol, vortexing for about 10 seconds, reacting for 30 minutes in a dark place. The results are listed in Table 4.
항산화력(%) = 100x(Abs of control- Abs of sample/Abs of control)Antioxidant power (%) = 100x (Abs of control- Abs of sample/Abs of control)
실시예 1 내지 3에 따른 카페산 트로메타민염，페룰산 트로메타민염 및 갈산 트로메타민염에 대하여 항산화력을 측정한 결과, 본래의 화합물에 비해 항산화력이 유의미하게 향상되는 것을 확인하였다.As a result of measuring the antioxidant activity of the tromethamine salt of caffeic acid, tromethamine salt of ferulic acid and tromethamine gallic acid according to Examples 1 to 3, it was confirmed that the antioxidant activity was significantly improved compared to the original compound.
제조예manufacturing example
카페산, 페룰산 및 갈산으로 이루어진 군으로부터 선택되는 적어도 어느 하나로 이루어지는 폴리페놀 화합물의 트로메타민염을 이용하여 식품 제제를 제조하였다.A food preparation was prepared using a tromethamine salt of a polyphenol compound consisting of at least one selected from the group consisting of caffeic acid, ferulic acid and gallic acid.
제조예 1. 선식Production Example 1. Wire
현미, 보리, 찹쌀, 율무를 공지의 방법으로 알파화시켜 건조시킨 것을 배전한 후 분쇄기로 입도 60 메쉬의 분말로 만들었다. 검정콩, 검정깨, 들깨도 공지의 방법으로 쪄서 건조시킨 것을 배전한 후 분쇄기로 입도 60 메쉬의 분말로 만들었다. Brown rice, barley, glutinous rice, and adlay were alphanized and dried by a known method, and after roasting, they were made into powder with a particle size of 60 mesh using a grinder. Black beans, black sesame seeds, and perilla seeds were also steamed and dried by a known method, roasted, and then made into powder with a particle size of 60 mesh by a grinder.
상기에서 제조한 곡물류, 종실류 및 폴리페놀 트로메타민염을 다음의 비율로 배합하여 과립을 만들었다.Granules were prepared by mixing the grains, seeds, and polyphenol tromethamine salts prepared above in the following ratio.
곡물류 : 현미 30 중량%, 율무 15 중량%, 보리 20 중량%, 찹쌀 9 중량%,Cereals: brown rice 30% by weight, adlay 15% by weight, barley 20% by weight, glutinous rice 9% by weight,
종실류 : 들깨 7 중량%, 검정콩 8 중량%, 검정깨 7 중량%,Seeds: Perilla 7% by weight, black soybean 8% by weight, black sesame 7% by weight,
폴리페놀 트로메타민염 분말 3 중량%, 영지 0.5 중량%, 지황 0.5 중량%3% by weight of polyphenol tromethamine salt powder, 0.5% by weight of ganoderma lucidum, 0.5% by weight of Rehmannia Root
제조예 2. 츄잉껌Production Example 2. Chewing Gum
껌 베이스 20 중량%, 설탕 76.9 중량%, 향료 1 중량% 및 물 2 중량%와 본 발명의 폴리페놀 트로메타민염 0.1 중량%를 배합하여 통상의 방법으로 츄잉껌을 제조하였다.Chewing gum was prepared by a conventional method by mixing 20% by weight of gum base, 76.9% by weight of sugar, 1% by weight of flavoring agent and 2% by weight of water, and 0.1% by weight of the polyphenol tromethamine salt of the present invention.
제조예 3. 캔디Production Example 3. Candy
설탕 60 중량%, 물엿 39.8 중량% 및 향료 0.1 중량%와 본 발명의 폴리페놀 트로메타민염 분말 0.1 중량%를 배합하여 통상의 방법으로 캔디를 제조하였다.60% by weight of sugar, 39.8% by weight of starch syrup, 0.1% by weight of flavoring, and 0.1% by weight of the polyphenol tromethamine salt powder of the present invention were blended to prepare candy in a conventional manner.
제조예 4. 비스켓Production Example 4. Biscuits
박력 1급 25.59 중량%, 중력 1급 22.22 중량%, 정백당 4.80 중량%, 식염 0.73 중량%, 포도당 0.78 중량%, 팜쇼트닝 11.78 중량%, 암모늄 1.54 중량%, 중조 0.17 중량%, 중아황산나트륨 0.16 중량%, 쌀가루 1.45 중량%, 비타민 B1.0001 중량%, 비타민 B2.0001 중량%, 밀크향 0.04 중량%, 물 20.6998 중량%, 전지분유 1.16 중량%,대용분유 0.29 중량%, 제1인산칼슘 0.03 중량%, 살포염 0.29 중량% 및 분무유 7.27 중량%와 본 발명의 폴리페놀 트로메타민염 1 중량%를 배합하여 통상의 방법으로 비스켓을 제조하였다.Strength 1st grade 25.59% by weight, gravity 1st grade 22.22% by weight, white sugar 4.80% by weight, table salt 0.73% by weight, glucose 0.78% by weight, palm shortening 11.78% by weight, ammonium 1.54% by weight, sodium bicarbonate 0.17% by weight, sodium bisulfite 0.16% by weight , Rice flour 1.45% by weight, vitamin B1.0001% by weight, vitamin B2.0001% by weight, milk flavor 0.04% by weight, water 20.6998% by weight, whole milk powder 1.16% by weight, substitute milk powder 0.29% by weight, monobasic calcium phosphate 0.03% by weight , 0.29% by weight of spreading salt and 7.27% by weight of spraying oil were mixed with 1% by weight of the polyphenol tromethamine salt of the present invention to prepare a biscuit in a conventional manner.
제조예 5. 건강 음료Preparation Example 5. Health drink
꿀 0.26 중량%, 치옥토산아미드 0.0002 중량%, 니코틴산아미드 0.0004 중량%, 염산리보플라빈나트륨 0.0001 중량%, 염산피리독신 0.0001 중량%, 이노시톨 0.001 중량%, 오르트산 0.002 중량% 및 물 98.7362 중량%와 본 발명의 폴리페놀 트로메타민염 1 중량%를 배합하여 통상의 방법으로 건강 음료를 제조하였다.0.26% by weight of honey, 0.0002% by weight of thioctic acid amide, 0.0004% by weight of nicotinic acid amide, 0.0001% by weight of sodium riboflavin hydrochloride, 0.0001% by weight of pyridoxine hydrochloride, 0.001% by weight of inositol, 0.002% by weight of orthic acid and 98.7362% by weight of water and the present invention A health drink was prepared by a conventional method by blending 1% by weight of polyphenol tromethamine salt.
제조예 6. 건강보조식품Manufacturing Example 6. Health Supplements
스피루리나 55 중량%, 구아검효소 분해물 10 중량%, 비타민 B1 염산염 0.01중량%, 비타민 B6 염산염 0.01 중량%, DL-메티오닌 0.23 중량%, 스테아린산 마그네슘 0.7 중량%, 유당 22.2 중량% 및 옥수수전분 1.85 중량%와 폴리페놀 트로메타민염 0 중량%를 배합하여 통상의 방법으로 정제형 건강보조식품을 제조하였다.Spirulina 55% by weight, guar gum enzyme hydrolyzate 10% by weight, vitamin B1 hydrochloride 0.01% by weight, vitamin B6 hydrochloride 0.01% by weight, DL-methionine 0.23% by weight, magnesium stearate 0.7% by weight, lactose 22.2% by weight and corn starch 1.85% by weight and 0% by weight of polyphenol tromethamine salt were blended to prepare a tablet-type health supplement in a conventional manner.
Claims (11)
상기 폴리페놀은 카페산, 페룰산 및 갈산으로부터 선택되는 어느 하나인 것을 특징으로 하는 화합물.According to claim 1,
The polyphenol is a compound, characterized in that any one selected from caffeic acid, ferulic acid and gallic acid.
DPPH(2,2-diphenyl-1-picrylhydrazyl) 라디칼 소거 활성을 갖는 것을 특징으로 하는 폴리페놀 트로메타민염 화합물.According to claim 1,
A polyphenol tromethamine salt compound characterized by having DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity.
상기 폴리페놀은 카페산, 페룰산 및 갈산으로부터 선택되는 적어도 어느 하나인 것을 특징으로 하는 식품 조성물.According to claim 4,
The polyphenol is a food composition, characterized in that at least one selected from caffeic acid, ferulic acid and gallic acid.
상기 식품 조성물은, 카페산 트로메타민염, 페룰산 트로메타민염 및 갈산의 트로메타민염이 중량비 기준으로 1:1:1의 비율로 혼합되는 것을 특징으로 하는 식품 조성물.The method of claim 5,
The food composition is characterized in that the tromethamine salt of caffeic acid, the tromethamine salt of ferulic acid and the tromethamine salt of gallic acid are mixed in a weight ratio of 1: 1: 1.
상기 폴리페놀 트로메타민염은 DPPH(2,2-diphenyl-1-picrylhydrazyl) 라디칼 소거 활성을 갖는 것을 특징으로 하는 식품 조성물.According to claim 4,
The polyphenol tromethamine salt is a food composition, characterized in that it has a DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity.
상기 폴리페놀은 카페산, 페룰산 및 갈산으로부터 선택되는 적어도 어느 하나인 것을 특징으로 하는 화장료 조성물.According to claim 8,
The polyphenol is a cosmetic composition, characterized in that at least one selected from caffeic acid, ferulic acid and gallic acid.
상기 화장료 조성물은, 카페산 트로메타민염, 페룰산 트로메타민염 및 갈산의 트로메타민염을 중량비 기준으로 1:1:1의 비율로 포함하는 것을 특징으로 하는 화장료 조성물.According to claim 9,
The cosmetic composition comprises tromethamine salt of caffeic acid, tromethamine salt of ferulic acid and tromethamine salt of gallic acid in a weight ratio of 1:1:1.
상기 폴리페놀 트로메타민염은 DPPH(2,2-diphenyl-1-picrylhydrazyl) 라디칼 소거 활성을 갖는 것을 특징으로 하는 화장료 조성물.
According to claim 8,
The polyphenol tromethamine salt is a cosmetic composition, characterized in that it has DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity.
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