Ethyl-β-cyclodextrin can be widely used for controlled release of drugs, but its application is greatly limited due to the use of toxic ethylation reagents such as diethyl sulfate, chloroethane, and iodoethane in previous synthesis processes. This article expands the application range of ethyl-β-cyclodextrin by using green ethylation reagent instead of previously toxic ethyl reagents to synthesize ethyl-βcyclodextrin. Ethyl-β-cyclodextrins were studied by reaction with diethyl carbonate and β-cyclodextrin in DMF using anhydrous potassium carbonate as catalyst, During the reaction process, in order to avoid oxidation, the samples were kept in a protective atmosphere of N2 flow. A new green synthesis process for ethyl-cyclodextrins, using silica gel chromatography to synthesize and purify four substituted 6-O-ethyl-cyclodextrins. Their structures were characterized by IR, MS, 1H-NMR, and 13C-NMR. The final product with a yield of 4% was obtained by chromatographic separation using acetonitrile-concd aq NH3-H2O-EtOAc (6:1:3:1) as the eluent. IR data indicate that the obtained product is the expected product. 13C-NMR characterization indicates that the substitution position of the product is at position 6, 1H-NMR, and MS characterization indicate that the degree of substitution of the product is 4. This synthesis method takes full advantage of the spatial selectivity of β-cyclodextrin. The method is green and simple. The target product is synthesized in one step, which is superior to previous reports.
| Published in | Science Journal of Chemistry (Volume 12, Issue 2) |
| DOI | 10.11648/j.sjc.20241202.11 |
| Page(s) | 27-31 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Diethyl Carbonate, β-Cyclodextrin, NMR, Ethylation, MS
| [1] | Wang J., Yang F., Materials Letters. 2021, 1-4. |
| [2] | Lu J., Huang W., JIA Y., CAI L., Ion Exchange and Adsorption. 2024, 1, 37-45. |
| [3] | Yonghui S., Linnan J., Yong C., Yu L., Chinese Chemical Letters, 2024, 108644, 1-6. |
| [4] | Gan Y., Zhang B., Zhang Y., Ling S. Science Journal of Chemistry. 2021, 9, 68-71. |
| [5] | Gan Y, ZHANG B, ZHANG Yi, LING S, Guangzhou Chemical Industry. 2021, 23, 63-64. |
| [6] | Sinha, V. R.; Amita, N.; Rachna, K. Pharmaceutical Technology. 2002, 10, 36-46. |
| [7] | Fumitoshi, H.; Masahiko, K.; Yasuhide, H.; Tadanobu, U.; Kaneto, U.; Masaki, Y. Pharm. Res-DORD. 1993, 10, 208-213. |
| [8] | Veronique, L.-L.; Denis, W.; Monique, C.; Dominique, D. International Journal of Pharmaceutics. 1996, 141, 117-124. |
| [9] | Eun, S. l.; Hyeok, L.; Jung, J. K. U. S. Patent 2008/0286375 A1, 2008. |
| [10] | Kazuaki, H.; Humitoshi, H.; Kaneto U. Carbohydr. Res. 2000, 329, 597–607. |
| [11] | J indrich, J., Josef, P.; Bengt L.; Pia, S.; Kazuaki, H. Carbohydr. Res. 1995, 266, 75-80. |
| [12] | Lemesle, L.; Wouessidjewe, D.; Taverna, M.; Ferrier, D.; Perly; B.; Duchene, D. J. Pharm Sci-US. 1997, 86, 1051-1056. |
| [13] | Sandip, K. H.; Amrita, C.; Pranb, K. B.; Partha, C. Green Chem. 2009, 11, 169-176. |
| [14] | Zhen, Z.; Xinbin, M.; Pingbo, Z.; Yeming, L.; Shengping, W. Journal of Molecular Catalysis A: Chemical. 2007, 266, 202–206. |
| [15] | Yongjiang G., Asian J Chem. 2014, 14, 4395-4398. |
APA Style
Yongjiang, G., Xiangping, W., Zhen, Z., Yimin, Z. (2024). A Novel Preparation and Purification of Ethyl-β-Cyclodextrins. Science Journal of Chemistry, 12(2), 27-31. https://doi.org/10.11648/j.sjc.20241202.11
ACS Style
Yongjiang, G.; Xiangping, W.; Zhen, Z.; Yimin, Z. A Novel Preparation and Purification of Ethyl-β-Cyclodextrins. Sci. J. Chem. 2024, 12(2), 27-31. doi: 10.11648/j.sjc.20241202.11
AMA Style
Yongjiang G, Xiangping W, Zhen Z, Yimin Z. A Novel Preparation and Purification of Ethyl-β-Cyclodextrins. Sci J Chem. 2024;12(2):27-31. doi: 10.11648/j.sjc.20241202.11
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Download@article{10.11648/j.sjc.20241202.11,
author = {Gan Yongjiang and Wei Xiangping and Zhou Zhen and Zhang Yimin},
title = {A Novel Preparation and Purification of Ethyl-β-Cyclodextrins
},
journal = {Science Journal of Chemistry},
volume = {12},
number = {2},
pages = {27-31},
doi = {10.11648/j.sjc.20241202.11},
url = {https://doi.org/10.11648/j.sjc.20241202.11},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20241202.11},
abstract = {Ethyl-β-cyclodextrin can be widely used for controlled release of drugs, but its application is greatly limited due to the use of toxic ethylation reagents such as diethyl sulfate, chloroethane, and iodoethane in previous synthesis processes. This article expands the application range of ethyl-β-cyclodextrin by using green ethylation reagent instead of previously toxic ethyl reagents to synthesize ethyl-βcyclodextrin. Ethyl-β-cyclodextrins were studied by reaction with diethyl carbonate and β-cyclodextrin in DMF using anhydrous potassium carbonate as catalyst, During the reaction process, in order to avoid oxidation, the samples were kept in a protective atmosphere of N2 flow. A new green synthesis process for ethyl-cyclodextrins, using silica gel chromatography to synthesize and purify four substituted 6-O-ethyl-cyclodextrins. Their structures were characterized by IR, MS, 1H-NMR, and 13C-NMR. The final product with a yield of 4% was obtained by chromatographic separation using acetonitrile-concd aq NH3-H2O-EtOAc (6:1:3:1) as the eluent. IR data indicate that the obtained product is the expected product. 13C-NMR characterization indicates that the substitution position of the product is at position 6, 1H-NMR, and MS characterization indicate that the degree of substitution of the product is 4. This synthesis method takes full advantage of the spatial selectivity of β-cyclodextrin. The method is green and simple. The target product is synthesized in one step, which is superior to previous reports.
},
year = {2024}
}
TY - JOUR T1 - A Novel Preparation and Purification of Ethyl-β-Cyclodextrins AU - Gan Yongjiang AU - Wei Xiangping AU - Zhou Zhen AU - Zhang Yimin Y1 - 2024/04/29 PY - 2024 N1 - https://doi.org/10.11648/j.sjc.20241202.11 DO - 10.11648/j.sjc.20241202.11 T2 - Science Journal of Chemistry JF - Science Journal of Chemistry JO - Science Journal of Chemistry SP - 27 EP - 31 PB - Science Publishing Group SN - 2330-099X UR - https://doi.org/10.11648/j.sjc.20241202.11 AB - Ethyl-β-cyclodextrin can be widely used for controlled release of drugs, but its application is greatly limited due to the use of toxic ethylation reagents such as diethyl sulfate, chloroethane, and iodoethane in previous synthesis processes. This article expands the application range of ethyl-β-cyclodextrin by using green ethylation reagent instead of previously toxic ethyl reagents to synthesize ethyl-βcyclodextrin. Ethyl-β-cyclodextrins were studied by reaction with diethyl carbonate and β-cyclodextrin in DMF using anhydrous potassium carbonate as catalyst, During the reaction process, in order to avoid oxidation, the samples were kept in a protective atmosphere of N2 flow. A new green synthesis process for ethyl-cyclodextrins, using silica gel chromatography to synthesize and purify four substituted 6-O-ethyl-cyclodextrins. Their structures were characterized by IR, MS, 1H-NMR, and 13C-NMR. The final product with a yield of 4% was obtained by chromatographic separation using acetonitrile-concd aq NH3-H2O-EtOAc (6:1:3:1) as the eluent. IR data indicate that the obtained product is the expected product. 13C-NMR characterization indicates that the substitution position of the product is at position 6, 1H-NMR, and MS characterization indicate that the degree of substitution of the product is 4. This synthesis method takes full advantage of the spatial selectivity of β-cyclodextrin. The method is green and simple. The target product is synthesized in one step, which is superior to previous reports. VL - 12 IS - 2 ER -
Shanwei Vocational and Technical College, School of Public Teaching, Shanwei, China; Jingchu University of Technology, College of Chemical Engineering and Pharmacy, Jingmen, China
