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The Study of Optimal Conditions for Synthesis and Purification of 1, 2-Octanediol Galactoside

1, 2-Octanediol Galactoside 합성을 위한 최적 조건 및 정제 연구

  • Jung, Kyung-Hwan (Department of Biotechnology, Korea National University of Transportation)
  • 정경환 (한국교통대학교 생명공학전공)
  • Received : 2021.12.30
  • Accepted : 2022.02.24
  • Published : 2022.02.28

Abstract

1, 2-Octanediol (OD) as a cosmetic additive has been used simultaneously as a preservative and humectant. To solve the skin problem by 1, 2-octanediol (OD), we have synthesized 1, 2-octanediol galactoside (OD-gal) using Escherichia coli β-galactosidase (β-gal). Meanwhile, the optimal amount of β-gal, OD concentration, pH, and temperature for OD-gal synthesis were 4.5 U/ml, 150 mM, 7.0, and 37℃, respectively. Under these conditions, 150 mM OD was converted into about 55.9 mM OD-gal during 24 hours, in which the conversion yield (mole basis) was about 37.2%. In addition, OD-gal of 67.4 mg could be purified from a 9 ml reaction mixture, in which the overall synthesis yield from OD to the purified OD-gal was about 34.1% (weight basis) and 16.2% (mole basis), respectively. We are expecting that these results will be helpful to develop a safer additive in the cosmetic industry as basic data.

항균력과 보습력을 동시에 가지고 있는 화장품용 첨가제인 1, 2-octanediol (OD)의 피부 문제점을 개선하기 위하여 galactoside 유도체인 1, 2-octanediol galactoside (OD-gal)를 대장균 β-galactosidase (β-gal)을 이용하여 합성하였다. 이 때, β-gal은 4.5 U/ml, OD 농도는 150 mM, pH는 7.0, 그리고, 온도는 37℃가 OD로부터 OD-gal을 합성하는 최적 조건이었다. 이 조건에 24 시간 동안 150 mM의 OD로부터 약 55.9 mM의 OD-gal이 합성되었고, 이 때, conversion 수율(mole 기준)은 약 37.2% 였다. 또한, 9 ml의 반응액에서 67.4 mg의 순수한 OD-gal을 정제할 수 있었으며, 반응액에 들어 있는 OD에서부터 정제를 포함하는 전체 합성수율은 weight 기준으로는 약 34.1% 이고, mole 기준으로는 약 16.2% 정도였다. 이러한 연구결과는 보다 안전한 화장품용 첨가제로서 OD-gal의 산업화에 기초자료로서 도움을 줄 것으로 생각된다.

Keywords

Acknowledgement

본 연구는 2020년도 교육부의 재원으로 한국연구재단의 지원을 받아 수행된 지자체-대학 협력기반 지역혁신 사업의 결과입니다. 한국교통대학교 생명공학전공 안승혜, 이혜원, 신재혁, 오승준, 이재혁 학생과 (주)케이티피 진홍종 소장님이 본 연구에 도움을 주었습니다.

References

  1. N. Halla, I. P. Fernandes, S. A. Heleno, P. Costa, Z. Boucherit-Otmani, K. Boucherit, A. E. Rodrigues, I. C. F. R. Ferreira, M. F. Barreiro, "Cosmetics preservation: A review on present strategies", Molecules, Vol.23, No.7, pp. 1571, (2018). https://doi.org/10.3390/molecules23071571
  2. W. Johnson Jr., W. F. Bergfeld, D. V. Belsito, R. A. Hill, C. D. Klaassen, D. Liebler, J. G. Marks Jr., R. C Shank, T. J. Slaga, P. W. Snyder, F. A. Andersen, "Safety assessment of 1, 2-glycols as used in cosmetics", International Journal of Toxicology, Vol.31(Supplement 2), pp. 147S-168S, (2012). https://doi.org/10.1177/1091581812460409
  3. E. Lee, S. An, S. -A. Cho, Y. Yun, J. Han, Y. K. Hwang, H. K. Kim, T. R. Lee, "The influence of alkane chain length on the skin irritation potential of 1,2-alkanediols", International Journal of Cosmetic Science, Vol.33, Vol.5, pp. 421-425, (2011). https://doi.org/10.1111/j.1468-2494.2011.00646.x
  4. E. Q. Coelho, S. L. C. Wu, R. S. Nunes, V. M. S. Reis, "Contact urticaria following the use of a cosmetic containing caprylyl glycol: A case report", Contact Dermatitis, Vol.8, No.4, pp. 308-309, (2019).
  5. F. C. Kreeshan, J. D. L. Williams, "Allergic contact dermatitis to caprylyl glycol: A novel para-preservative allergen", Contact Dermatitis, Vol.83, No.5, pp. 418-419, (2020). https://doi.org/10.1111/cod.13628
  6. H. -Y. Lee, H. -J. Jin, S. H. An, H. W. Lee, K. -H. Jung, "Confirmation of enzymatic synthesis of 1, 2-octanediol galactoside using mass spectrometry and NMR spectroscopy", Journal of the Korean Applied Science and Technology, Vol.38, No.3, pp. 824-831, (2021). https://doi.org/10.12925/JKOCS.2021.38.3.824
  7. J. -S. Kim, H. -J. Jin, K. -H. Jung, "Comparative study of antimicrobial and cytotoxic effects of 1, 2-octanediol and 1, 2-octanediol galactoside", Journal of the Korean Applied Science and Technology, Vol.38, No.3, pp. 629-637, (2021). https://doi.org/10.12925/JKOCS.2021.38.3.629
  8. K. -H. Jung, "Antimicrobial activity of benzyl alcohol galactoside against Escherichia coli", Journal of Biotechnology and Bioindustry, Vol.9, No.1, pp. 1-8, (2021) https://doi.org/10.37503/jbb.2021.9.1
  9. K. -H. Jung, "Enhanced enzyme activities of inclusion bodies of recombinant β-galactosidase via the addition of inducer analog after L-arabinose induction in the araBAD promoter system of Escherichia coli", Journal of Microbiology and Biotechnology, Vol.18, No.3, pp. 434-442, (2008).
  10. Y. -O. Kim, K. -H. Jung, "β-Galactosidase-catalyzed synthesis of 1, 2-hexanediol galactoside and its purification using ethyl acetate extraction followed by silica gel chromatography", Journal of Korean Oil Chemists' Society, Vol.33, No.3, pp. 498-506, (2016). https://doi.org/10.12925/jkocs.2016.33.3.498
  11. K. -H. Jung, "Purifications of phenoxyethanol galactoside and chlorphenesin galactoside using solvent extraction followed by gel chromatography", Jouranl of Oil and Applied Science, Vol.34, No.4, pp. 954-961, (2017).
  12. K. -H. Jung, "Enzymatic synthesis of benzyl alcohol galactoside using Escherichia coli β-galactosidase", Journal of the Korean Applied Science and Technology, Vol.36, No.2, pp. 582-590, (2019). https://doi.org/10.12925/JKOCS.2019.36.2.582
  13. K. -H. Jung, "Optimal conditions for phenylethanol galactoside synthesis using Escherichia coli β-galactosidase", Journal of the Korean Applied Science and Technology, Vol.38, No.1, 99-106, (2021). https://doi.org/10.12925/JKOCS.2021.38.1.99
  14. S. E. Lee, T. M. Jo, H. -Y. Lee, J. Lee, K. -H. Jung, "β-Galactosidase-catalyzed synthesis of galactosyl chlorphenesin and its characterization", Applied Biochemistry and Biotechnology, Vol.171, No.6, pp. 1299-1312, (2013). https://doi.org/10.1007/s12010-013-0213-3
  15. S. E. Lee, H. -Y. Lee, K. -H. Jung, "Production of chlorphenesin galactoside by whole cells of β-galactosidase-containing Escherichia coli", Journal of Microbiology and Biotechnology, Vol.23, No.6, pp. 826-832, (2013). https://doi.org/10.4014/jmb.1211.11009
  16. K. -H. Jung, H. -Y. Lee, "Escherichia coli β-galactosidase-catalyzed synthesis of 2-phenoxyethanol galactoside and its characterization", Bioprocess and Biosystems Engineering, Vol.38, No.2, pp. 365-372, (2015). https://doi.org/10.1007/s00449-014-1276-4
  17. H. -Y. Lee, K. -H. Jung, "Enzymatic synthesis of 2-phenoxyethanol galactoside by whole cells of β-galactosidase-containing Escherichia coli", Journal of Microbiology and Biotechnology, Vol.24, No.9, pp. 1254-1259, (2014). https://doi.org/10.4014/jmb.1404.04004