1,2,7,8-Diepoxyoctane – general description and preparation
General description of 1,2,7,8-Diepoxyoctane:
1,2,7,8-Diepoxyoctane [2426-07-5] is aliphatic compound with a boiling point of 120 °C at 28 Torr. [1] It is highly toxic oil which can cause cancer and linking of DNA.[2]
It is commonly used as linking agent in the preparation of hyaluronic acid hydrogels which are kind of promising body filler for tissue engineering [3] or in enhancing thermal stability of Candida antarctica Lipase B enzyme.[4] This enzyme is widely used as catalyst in industrial processes.
Preparation:
1,2,7,8-Diepoxyoctane can be synthesized by epoxidation of 1,7-octadiene using peracids such as m-CPBA. Alternatively, it can be obtained via enzymatic epoxidation catalyzed by Pseudomonas oleovorans.[5][6]
Product categorization (Chemical groups):
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[1]J. L. Everett, G. A. R. Kon, J. Am. Chem. Soc. 1950, 0, 3131 – 3135. Doi: 10.1039/JR9500003131
[2] M. J. Yunes, S. E. Charnecki, J. J. Marden, J. T. Millard, Chem. Res. Toxicol. 1996, 9, 994-1000 Doi: https://doi.org/10.1021/tx960059c; P. C. Jurs, J. T. Chou, M. Yuan, J. Med. Chem. 1979, 22, 476 – 483. Doi: 10.1021/jm00191a004; C. E. Voogg, J. J. Steil, J. J. J. A. A. Jacobs, Mutat. Res. 1981, 80, 269 – 282. Doi: https://doi.org/10.1016/0165-1218(81)90108-7.
[3] Z. Li, X. Ma, D. Fan, C. Zhu, L. Zhao, Y. Liu, L. Chang, Mater. Res. Innov. 2015, 19, 268 – 272. Doi: https://doi.org/10.1179/1432891715Z.0000000001983.
[4] N. Miletić, K. Loos, Aust. J. Chem. 2009, 62, 799 – 805. Doi: 10.1071/CH09033.
[5] K. Martina, M. Caporaso, S. Tagliapietra, G. Heropoulos, O. Rosati, G. Cravotto, Carbohydr. Res. 2011, 17, 2677 – 2682. Doi: https://doi.org/10.1016/j.carres.2011.09.018, H. J. Park, J. J. Kim, H. R. Kim, E. K. Lee, E. S. Kim, Ch. S. Jeong, A. Moon, S. H. Lee, Bioorg. Med. Chem. 2011, 19, 4004 – 4013. Doi: https://doi.org/10.1016/j.bmc.2011.05.020.
[6]R. D. Schwartz, C. J. Mccoy, Appl. Environ. Microbiol. 1976, 31, 78 – 82. https://journals.asm.org/doi/pdf/10.1128/aem.31.1.78-82.1976
[2] M. J. Yunes, S. E. Charnecki, J. J. Marden, J. T. Millard, Chem. Res. Toxicol. 1996, 9, 994-1000 Doi: https://doi.org/10.1021/tx960059c; P. C. Jurs, J. T. Chou, M. Yuan, J. Med. Chem. 1979, 22, 476 – 483. Doi: 10.1021/jm00191a004; C. E. Voogg, J. J. Steil, J. J. J. A. A. Jacobs, Mutat. Res. 1981, 80, 269 – 282. Doi: https://doi.org/10.1016/0165-1218(81)90108-7.
[3] Z. Li, X. Ma, D. Fan, C. Zhu, L. Zhao, Y. Liu, L. Chang, Mater. Res. Innov. 2015, 19, 268 – 272. Doi: https://doi.org/10.1179/1432891715Z.0000000001983.
[4] N. Miletić, K. Loos, Aust. J. Chem. 2009, 62, 799 – 805. Doi: 10.1071/CH09033.
[5] K. Martina, M. Caporaso, S. Tagliapietra, G. Heropoulos, O. Rosati, G. Cravotto, Carbohydr. Res. 2011, 17, 2677 – 2682. Doi: https://doi.org/10.1016/j.carres.2011.09.018, H. J. Park, J. J. Kim, H. R. Kim, E. K. Lee, E. S. Kim, Ch. S. Jeong, A. Moon, S. H. Lee, Bioorg. Med. Chem. 2011, 19, 4004 – 4013. Doi: https://doi.org/10.1016/j.bmc.2011.05.020.
[6]R. D. Schwartz, C. J. Mccoy, Appl. Environ. Microbiol. 1976, 31, 78 – 82. https://journals.asm.org/doi/pdf/10.1128/aem.31.1.78-82.1976