KR20200058840A - Synthesis method for high purity allyl isothiocyanate and cosmetic composition comprising high purity allyl isothiocyanate - Google Patents
Synthesis method for high purity allyl isothiocyanate and cosmetic composition comprising high purity allyl isothiocyanate Download PDFInfo
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Abstract
Description
고순도의 이소티안산알릴 화합물 합성방법 및 상기 합성방법에 따른 이소티안산알릴 화합물을 유효성분으로 함유하는 기능성 화장료조성물에 관한 것이다.The present invention relates to a method for synthesizing a high-purity allyl isocyanate compound and a functional cosmetic composition containing the allyl isothiocyanate compound according to the synthesis method as an active ingredient.
고추냉이는 일본이 원산지인 다년생 향신료로 우리나라에서는 울릉도에서 자생하고 있으며, 최근에는 춘천, 평창, 철원 등지에서 지하수를 이용한 물재배 양식으로 소규모 재배되고 있다.Horseradish is a perennial spice native to Japan. It is native to Ulleungdo in Korea. Recently, it was cultivated on a small scale in Chuncheon, Pyeongchang, and Cheorwon using groundwater.
고추냉이의 매운맛 성분 중에는 이소티안산알릴이 포함되며, 주로 고추냉이의 뿌리에 존재한다. 이소티안산알릴 화합물은 건위, 진통, 식욕촉진, 항암 및 항혈전응고 방지 등의 효과 있는 것으로 알려져있으며, 최근 연구보고에 따르면, 비듬균, 여드름균 및 헬리코박터균에 대한 항균 활성이 뛰어난 것으로 확인되었다.Among the spicy ingredients of horseradish, allyl isocyanate is present, and it is mainly present in the root of horseradish. Allyl isocyanate compound is known to have effects such as dry stomach, pain relief, appetite promoting, anti-cancer and anti-thrombotic coagulation, and according to a recent research report, it has been confirmed that it has excellent antibacterial activity against dandruff, acne, and Helicobacter bacteria.
그러나 고추냉이에서 이소티안산알릴을 직접 추출하는 방식은 값비싼 원자재와 고추냉이 뿌리에서 0.04~0.5% 수준의 적은 양으로 추출됨에 따라, 상업적으로 이용하기에는 절대적으로 부족하여 국내에서는 이소티안산알릴을 외국에서 전량 수입하고 있으며, 일부 소량의 비누와 방향제에만 사용되고 있다.However, the method of directly extracting allyl isothiocyanate from horseradish was absolutely insufficient for commercial use, as it was extracted in small amounts of 0.04 ~ 0.5% from expensive raw materials and horseradish root. It is imported from all over the world, and is only used in some small amounts of soap and fragrances.
이러한 문제점을 해결하기 위한 방법으로 등록특허 제10-0676892호에서는 유기합성을 통한 이소티안산알릴을 대량생산 기술이 보고되었으나, 상기 방법은 티오시안산 화합물이 먼저 생성된 후 이소티안산으로 이성질체화되어 합성됨에 따라, 불순물인 5%의 티오시안산알릴이 포함되어 있어 최대 95% 이상의 순도를 나타내지 못하므로, 상기 방법으로 합성된 이소티안산알릴은 착향제로만 사용되고 있다.As a method for solving this problem, in the patent registration No. 10-0676892, a technique for mass production of allyl isothiocyanate through organic synthesis has been reported, but the method isomerized with isothio acid after the thiocyanate compound is first generated. As it is synthesized, allyl thiocyanate, which is an impurity, contains 5% of allyl, and thus does not exhibit a purity of up to 95% or more.
이에 따라, 우수한 생리활성을 나타내는 이소티안산알릴을 다양한 제품에 적용시키기 위해서는 99% 이상의 순수한 이소티안산알릴 합성방법에 대한 연구가 필요한 실정이다.Accordingly, in order to apply allyl isothiocyanate, which exhibits excellent physiological activity, to various products, studies on the synthesis method of allyl isothiocyanate over 99% are necessary.
종래의 이소티안산알릴 유기합성 방법은 5% 이상의 불순물을 함유하여 의료품이나 치료제 및 식품 첨가제로의 사용이 제한적임에 따라, 이소티안산알릴을 고순도로 합성하기 위한 신규한 이소티안산알릴 합성방법을 제공하고자 한다.The conventional method for synthesizing organic allyl isothiocyanate is a novel method for synthesizing allyl isothiocyanate for synthesizing allyl isothiocyanate with high purity, since its use as a medical product, therapeutic agent, and food additive is limited by containing 5% or more impurities. Want to provide
본 발명은 알릴아민 화합물과 이황화탄소를 반응시켜 화학식 1-1의 화합물을 합성하는 단계(제1단계); 상기 화학식 1-1의 화합물을 톨루엔설포닐 화합물과 반응시켜 화학식 1-2의 화합물을 합성하는 단계(제2단계); 및 상기 화학식 1-2의 화합물에 염 화합물을 처리하여 이소티안산알릴을 합성하는 단계(제3단계)를 포함하는 이소티안산알릴의 합성방법을 제공한다.The present invention comprises the steps of synthesizing a compound of Formula 1-1 by reacting an allylamine compound with carbon disulfide (first step); Reacting the compound of Formula 1-1 with a toluenesulfonyl compound to synthesize a compound of Formula 1-2 (second step); And it provides a method for synthesizing allyl isothiocyanate comprising the step of synthesizing allyl isothiocyanate (third step) by treating a salt compound to the compound of Formula 1-2.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
또한, 본 발명은 상기 합성방법에 따른 이소티안산알릴을 유효성분을 함유하는 화장료 조성물을 제공한다.In addition, the present invention provides a cosmetic composition containing allyl isothiocyanate according to the above synthetic method as an active ingredient.
본 발명에 따르면, 알릴아민을 출발물질로 이용하여 3단계 합성방법을 통하여 합성된 이소티안산알릴의 순도가 99%인 것으로 확인됨에 따라, 상기 합성방법으로 합성된 고순도의 이소티안산알릴은 아토피 또는 여드름을 예방하거나 개선하기 위한 기능성 화장품 조성물로 제공될 수 있다.According to the present invention, as it is confirmed that the purity of allyl isothiocyanate synthesized through a three-step synthesis method using allylamine as a starting material is 99%, allyl isocyanate of high purity synthesized by the synthesis method is atopy Or it may be provided as a functional cosmetic composition for preventing or improving acne.
도 1은 이소티안산알릴 구조이다.
도 2는 고순도의 이소티안산알릴 합성 메커니즘이다.1 is an allyl isothiocyanate structure.
Figure 2 is a high purity allyl isothiocyanate synthesis mechanism.
이하, 본 발명을 보다 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
종래의 이소티안산알릴 유기합성 방법은 5% 이상의 불순물을 함유하여 의료품이나 치료제 및 식품 첨가제로의 사용이 제한적임에 따라, 본 발명자들은 알릴아민을 출발 물질한 3단계 합성방법을 통하여 고순도의 이소티안산알릴 화합물을 제조하여 본 발명을 완성하였다.According to the conventional method of organic synthesis of allyl isothiocyanate, the use of it as a medical product, a therapeutic agent, and a food additive is limited because it contains 5% or more impurities, and thus the present inventors provide high-purity isocyanate through a three-step synthesis method starting from allylamine. Allyl thianate compound was prepared to complete the present invention.
본 발명은 알릴아민 화합물과 이황화탄소를 반응시켜 화학식 1-1의 화합물을 합성하는 단계(제1단계); The present invention comprises the steps of synthesizing a compound of Formula 1-1 by reacting an allylamine compound with carbon disulfide (first step);
상기 화학식 1-1의 화합물을 톨루엔설포닐 화합물과 반응시켜 화학식 1-2의 화합물을 합성하는 단계(제2단계); 및 Reacting the compound of Formula 1-1 with a toluenesulfonyl compound to synthesize a compound of Formula 1-2 (second step); And
상기 화학식 1-2의 화합물에 염 화합물을 처리하여 이소티안산알릴을 합성하는 단계(제3단계)를 포함하는 이소티안산알릴의 합성방법을 제공할 수 있다.A method for synthesizing allyl isothiocyanate comprising the step of synthesizing allyl isothiocyanate (third step) by treating the compound of Formula 1-2 with a salt compound may be provided.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
상기 톨루엔설포닐 화합물은 톨루엔설포닐 클로라이드일 수 있다.The toluenesulfonyl compound may be toluenesulfonyl chloride.
본 발명은 상기 합성방법에 따른 이소티안산알릴을 유효성분을 함유하는 화장료 조성물을 제공할 수 있다.The present invention can provide a cosmetic composition containing allyl isothiocyanate according to the above synthetic method as an active ingredient.
상기 이소티안산알릴은 아토피 치료 또는 개선 효과를 갖는 것일 수 있다.Allyl isothiocyanate may have an atopy treatment or improvement effect.
상기 이소티안산알릴은 항균 효과를 갖는 것일 수 있다.Allyl isocyanate may have an antibacterial effect.
상기 이소티안산알릴은 여드름 개선 효과를 갖는 것일 수 있다.The allyl isocyanate may have an effect of improving acne.
상기 화장료 조성물은 유효성분인 이소티안산알릴 외에 안정화제, 용해화제, 비타민, 안료 및 향료와 같은 통상적인 보조제, 그리고 담체를 포함할 수 있다.The cosmetic composition may include a stabilizer, a solubilizing agent, a common auxiliary agent such as vitamins, pigments, and fragrances, and a carrier in addition to allyl isothiocyanate as an active ingredient.
상기 화장료 조성물은 당업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는, 썬 크림, 유연 화장수, 수렴 화장수, 영양 화장수, 영양 크림, 마사지 크림, 에센스, 아이 크림, 팩, 스프레이 또는 파우더의 제형으로 제조될 수 있다.The cosmetic composition may be prepared in any formulation conventionally prepared in the art, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, oils, powder foundations, emulsion foundations, It may be formulated as a wax foundation and spray, but is not limited thereto. More specifically, it can be prepared in the form of a sun cream, soft lotion, converging lotion, nutrition lotion, nutrition cream, massage cream, essence, eye cream, pack, spray or powder.
상기 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로서 동물성유, 식물성유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜,실리콘, 벤토나이트, 실리카, 탈크 또는 산화아연 등이 이용될 수 있다.When the formulation is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicon, bentonite, silica, talc or zinc oxide may be used as a carrier component. .
상기 제형이 파우더 또는 스프레이인 경우에는 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록시드, 칼슘 실리케이트 또는 폴리아미드 파우더가 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로플루오로히드로카본, 프로판/부탄 또는 디메틸 에테르와 같은 추진체를 포함할 수 있다.When the formulation is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder can be used as a carrier component, and in the case of a spray, additionally chlorofluorohydrocarbon, propane / butane Or propellants such as dimethyl ether.
상기 제형이 용액 또는 유탁액인 경우에는 담체 성분으로서 용매, 용해 화제 또는 유탁화제가 이용되고, 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알코올, 벤질 벤조에이트, 프로필렌 글리콜, 1,3-부틸글리콜 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다.When the formulation is a solution or emulsion, a solvent, solubilizer or emulsifier is used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3 -Fatty acid esters of butyl glycol oil, glycerol aliphatic esters, polyethylene glycol or sorbitan.
상기 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올 또는 프로필렌글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다.When the formulation is a suspension, liquid diluents such as water, ethanol or propylene glycol as carrier components, ethoxylated isostearyl alcohol, suspensions such as polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, microcrystalline cellulose , Aluminum metahydroxide, bentonite, agar or trakant, and the like.
이하, 본 발명의 이해를 돕기 위하여 실시예를 들어 상세하게 설명하기로 한다. 다만 하기의 실시예는 본 발명의 내용을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다. 본 발명의 실시예는 당업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples will be described in detail to help understanding of the present invention. However, the following examples are merely illustrative of the contents of the present invention, and the scope of the present invention is not limited to the following examples. The embodiments of the present invention are provided to more fully describe the present invention to those skilled in the art.
<< 실시예Example 1> 1> 이소티안산알릴Allyl isotian (( AITAIT ) 합성) synthesis
하기 반응식 1과 같은 과정으로 이소티안산알릴을 합성하였다.Allyl isothiocyanate was synthesized in the same manner as in
[반응식 1][Scheme 1]
이상으로 본 발명 내용의 특정한 부분을 상세히 기술하였는 바, 당업계의 통상의 지식을 가진 자에게 있어서, 이러한 구체적 기술은 단지 바람직한 실시양태일 뿐이며, 이에 의해 본 발명의 범위가 제한되는 것이 아닌 점은 명백할 것이다. 따라서 본 발명의 실질적인 범위는 첨부된 청구항들과 그것들의 등가물에 의하여 정의된다고 할 것이다.Since the specific parts of the present invention have been described in detail above, for those skilled in the art, it is clear that such specific technology is only a preferred embodiment, and the scope of the present invention is not limited thereby. something to do. Therefore, the substantial scope of the present invention will be defined by the appended claims and their equivalents.
Claims (5)
상기 화학식 1-1의 화합물을 톨루엔설포닐 화합물과 반응시켜 화학식 1-2의 화합물을 합성하는 단계(제2단계); 및
상기 화학식 1-2의 화합물에 염 화합물을 처리하여 이소티안산알릴을 합성하는 단계(제3단계)를 포함하는 이소티안산알릴의 합성방법.
[화학식 1-1]
[화학식 1-2]
Reacting the compound of Formula 1-1 with a toluenesulfonyl compound to synthesize a compound of Formula 1-2 (second step); And
A method for synthesizing allyl isothiocyanate comprising the step of synthesizing allyl isothiocyanate (the third step) by treating the compound of Formula 1-2 with a salt compound.
[Formula 1-1]
[Formula 1-2]
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100676892B1 (en) | 2005-10-26 | 2007-02-02 | 강릉대학교산학협력단 | Synthesis method for allyl isothiocyanate |
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2018
- 2018-11-20 KR KR1020180143451A patent/KR20200058840A/en not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100676892B1 (en) | 2005-10-26 | 2007-02-02 | 강릉대학교산학협력단 | Synthesis method for allyl isothiocyanate |
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