[논문]보존제로서 선형 1,2-알킬아미노프로판디올의 합성과 항균활성

차경온; 곽상운; 정국인; 김영호

doi:10.14478/ace.2022.1052

보존제로서 선형 1,2-알킬아미노프로판디올의 합성과 항균활성
Synthesis of Linear 1,2-Alkylaminopropanediols as Preservatives and Antimicrobial Activity 원문보기

공업화학 = Applied chemistry for engineering, v.33 no.4, 2022년, pp.394 - 401

차경온 (충남대학교 응용화학공학과) , 곽상운 (충남대학교 응용화학공학과) , 정국인 ((주) 비제이바이오켐) , 김영호 (충남대학교 응용화학공학과)

초록
AI-Helper

알킬 사슬의 탄소 수가 10개, 12개, 14개 및 16개인 직쇄상 1,2-알칸디올의 친수성을 향상할 목적으로 1,2-알킬아미노프로판디올(1,2-alkylaminopropanediol, 1,2-AAP)의 합성을 설계하였다. 1,2-AAP는 40 ℃ 에탄올(ethanol) 용매에서 2 h동안 3-모노클로로-1,2-프로판디올(3-monochloro-1,2-propanediol, 3-MCPD)과 10, 12, 14 및 16의 탄소 수를 갖는 선형 알킬아민 화합물과의 반응에 의해 합성하였다. 합성한 4 종류 1,2-AAP의 수율과 순도는 각각 51~58%와 85~99% 범위인 것으로 나타났다. 정제된 페이스트 또는 고체 합성물로 pH 7까지 산(HCl)을 가하여 4 종류 1,2-AAP의 아민염을 제조한 다음, 용해성과 항균효과를 시험하였다. 물에 대한 용해 농도는 1,2-데실아미노프로판디올(1,2-decylaminopropanediol, 1,2-DAP)이 100%, 1,2-도데실아미노프로판디올(1,2-dodecylaminopropanediol, 1,2-DDAP)이 50%, 1,2-테트라데실아미노프로판디올(1,2-tetradecylaminopropanediol, 1,2-TDAP)이 0.1%이었으며, 1,2-헥사데실아미노프로판디올(1,2-hexadecylaminopropanediol, 1,2-HDAP)은 용해되지 않았다. 항균 효과는 알킬 사슬의 길이가 증가할수록 향상되었다. 응용을 위해 1,2-AAP가 적용된 로션(화장품 제형)에서 보존효과를 확인한 결과 0.005~0.2% 범위의 낮은 농도에서 매우 우수한 항균력을 보였다.

Abstract ▼ AI-Helper

The synthesis of 1,2-alkylaminopropanediols (1,2-AAPs) was designed to improve the hydrophilicity of linear 1,2-alkanediols having 10, 12, 14, and 16 carbon atoms in the alkyl chain. 1,2-AAPs were synthesized by reacting 3-monochloro-1,2-propanediol (3-MCPD) with linear alkylamines having 10, 12, 14 or 16 carbon atoms in an ethanol solvent at 40℃ for 2 h. The yield and purity of four types of 1,2-AAPs synthesized were found to be in the range of 51-58% and 85-99%, respectively. The amine salts of four types of 1,2-AAPs were prepared from a purified paste or solid compound by adding an acidic solution (HCl) to pH 7, and then their solubilities and antibacterial effects were tested. 1,2-decylaminopropanediol, 1,2-dodecylaminopropanediol, and 1,2-tetradecylaminopropanediol were all dissolved in water at concentrations of 100%, 50%, and 0.1%, respectively, however 1,2-hexadecylaminopropanediol was not. The antibacterial effect was improved as the length of the alkyl chain increased. As a result of confirming the preservative effect of the lotion (cosmetic formulation) applied with 1,2-AAP for application, it showed very strong antibacterial activity at low concentrations ranging from 0.005% to 0.2%.

주제어

표/그림 (10)

그림 Figure 1. Design of 1,2-alkanediol derivatives with antimicrobial activity. ⓐ Retention of diol structure: key structure of Hinge role in microbial cell membrane. ⓑ Longer alkyl group design: the longer the alkyl group, the better the preservative power at low concentrations. ⓒ A hydrophilic group (amine group) is placed to compensate for the solubility caused by the lengthening of the alkyl group[20].
그림 Scheme 1. Synthesis of 1,2-Alkylaminopropanediol (1,2-AAP).
표 Table 1. Types and Characteristics of 1,2-Alkanediol according to Carbon Number
표 Table 2. Composition of Experimental Lotions Base[20]
그림 Figure 2. Gas chromatogram of (a) 3-MCPD, (b) 1,2-DAP, (c) 1,2-DDAP, (d) 1,2-TDAP and (e) 1,2-HDAP products after completion of the reaction.
그림 Figure 3. H¹-NMR spectrums of (a) 1,2-DAP, (b) 1,2-DDAP, (c) 1,2-TDAP and (d) 1,2-HDAP products.
그림 Figure 4. Water solubilization limit concentration of 1,2-DAP, 1,2-DDAP, 1,2-TDAP and 1,2-HDAP.
그림 Figure 5. Solubilization limit concentration of 1,2-TDAP and 1,2-HDAP in aqueous solution containing 1,2-DDAP.
그림 Figure 6. MIC(%) and MBC(%) values of single preservatives against (a) E. coli, (b) S. aureus, (c) P. aeruginosa, (d) C. albicans, and (e) A. brasiliensis.
표 Table 3. Challenge Test of Single and Mixed Preservatives in Cosmetic Emulsion

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