화학공학소재연구정보센터
Applied Chemistry for Engineering, Vol.33, No.4, 394-401, August, 2022
보존제로서 선형 1,2-알킬아미노프로판디올의 합성과 항균활성
Synthesis of Linear 1,2-Alkylaminopropanediols as Preservatives and Antimicrobial Activity
E-mail:
초록
알킬 사슬의 탄소 수가 10개, 12개, 14개 및 16개인 직쇄상 1,2-알칸디올의 친수성을 향상할 목적으로 1,2-알킬아미노 프로판디올(1,2-alkylaminopropanediol, 1,2-AAP)의 합성을 설계하였다. 1,2-AAP는 40 °C 에탄올(ethanol) 용매에서 2 h동 안 3-모노클로로-1,2-프로판디올(3-monochloro-1,2-propanediol, 3-MCPD)과 10, 12, 14 및 16의 탄소 수를 갖는 선형 알킬 아민 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-테트라데실아미노 프로판디올(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 위 해 1,2-AAP가 적용된 로션(화장품 제형)에서 보존효과를 확인한 결과 0.005~0.2% 범위의 낮은 농도에서 매우 우수한 항균력을 보였다.
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° C 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%.
  1. Ryu MS, Effect of Antiseptics for Prevention of Microbial Contamination in Cosmetics, Master Dissertation, Sungkyunkwan University, Seoul, Korea (1990).
  2. Hiom SJ, Preservation of medicines and cosmetics. In: Fraise AP, Lambert PA, Maillard JY (eds.).Preservation & Sterilization, 4th ed., 484-486, Wiley-Blackwell, Oxford, UK (2004).
  3. Soni MG, Carabin IG, Burdock GA, Food Chem. Toxicol., 43, 985 (2005)
  4. Darbre PD, Harvey PW, J. Appl. Toxicol., 28, 561 (2008)
  5. Poudrier JK, J. Am. Coll. Toxicol., 9, 259 (1990)
  6. Dreno B, Zuberbier T, Gelmetti C, Gontijo G, Marinovich M, J. Eur. Acad. Dermatol. Venereol., 33, 15 (2019)
  7. Geier J, Lessmann H, Schnuch A, Uter W, Contact Derm., 67, 334 (2012)
  8. Croshaw B, J. Soc. Cosmet. Chem., 28, 3 (1977)
  9. Kunicka‐Styczyńska A, Sikora M, Kalemba D, J. Appl. Microbiol., 107, 1903 (2009)
  10. Andersen FA, Int. J. Toxicol., 27, 1 (2008)
  11. Sigg M, Daniels R, Pharmaceutics, 12, 1117 (2020)
  12. Mekata H, J. Soc. Cosmet. Chem. Jpn., 51, 2 (2017)
  13. Levy SB, Dulichan AM, Helman M, Cutan. Ocul. Toxicol., 28, 23 (2009)
  14. Gaonkar TA, Geraldo I, Shintre M, Modak SM, J. Hosp. Infect., 63, 412 (2006)
  15. Lee E, An S, Cho SA, Yun Y, Han J, Hwang YK, Lee TR, Int. J. Cosmet. Sci., 33, 421 (2011)
  16. Yoo IK, Kim JI, Kang YK, Comput. Theor. Chem., 1064, 15 (2015)
  17. Ziosi P, Manfredini S, Vandini A, Vertuani S, Fraternali M, Cosmet. Toilet., 128, 538 (2013)
  18. Warner KS, Li SK, Higuchi WI, J. Pharm. Sci., 90, 1143 (2001)
  19. Kim JI, Study on the Challenge Test and Safety Assessments of 1,2-Alkanediols in Cosmetics, PhD Dissertation, Hannam University, Daejeon, Korea (2016).
  20. Cha KO, Kwak SW, Jeong KI, Kim YH, Appl. Chem. Eng., 33, 179 (2022)
  21. Siegert W, Househ. Pers. Care Today, 8, 32 (2013)
  22. Schambil F, Schwuger MJ, Interfacial and colloidal properties. In: Falbe J (ed.). Surfactants in Consumer Products, 170-177, Springer, Berlin, Germany (1987).
  23. Choi JJ, Cho WG, Rang MJ, Korean Chem. Eng. Res., 46, 799 (2008)
  24. Okukawa M, Watanabe T, Miura M, Konno H, Yano S, Nonomura Y, J. Oleo. Sci., 68, 759 (2019)