Organic synthesis

2,5-Dimethyl-2,5-di(tert-butylperoxy)hexane (also known as Trigonox 101) is an important bifunctional peroxide that can be used to prepare super-toughened poly(lactic acid) (PLA)/poly(ethylene-co-vinyl acetate) (EVA) blends. It can also be used for crosslinking natural rubber, synthetic rubber and thermoplastic polyolefins.

In the field of medicine

2,5-Dimethyl-2,5-di(tert-butylperoxy)hexane has potential pharmacological activity, and molecular docking results indicate that there is a potential interaction between the peroxide and certain biological targets (such as breast cancer receptor 3hb5-oxidoreductase and prostate cancer mutant 2q7k-hormone). In addition to the potential cytotoxic activity, the anti-diabetic activity of organic peroxides has also been studied. Docking results showed that peroxide binds to the active sites of diabetes-related enzymes such as α-amylase, pancreatic lipase, and β-glucosidase with low binding energy. This suggests that peroxide has a potential role in diabetes treatment.

In addition, the interaction between peroxide and the antioxidant protein IHD2 (2HCK) was explored. These computational studies suggest that peroxide may play a pharmacological role in the treatment of Helicobacter pylori (H. pylori) infection. The docking energy between peroxide and the H. pylori adhesin HopQ type I bound to the N-terminal domain of human CEACAM1 suggests that peroxide may be a potential target for inhibiting H. pylori infection. It is worth noting that these findings are based on computational methods and molecular docking studies, and further in vitro and in vivo experimental verification is required.

Thermal Decomposition

The bifunctional dialkylperoxide 2,5-Dimethyl-2,5-di(tert-butylperoxy)hexane was thermally decomposed in various solvents at 353 to 383 K, and the generated radicals were trapped using DMPO, PBN-d14, and 2,4,6-tri-tert-butylnitrosobenzene (TTBNB). It was found that the tert-butyloxy radical was released after the cleavage of the O—O bond (and the methyl radical was released by β-cleavage). During the thermal decomposition of 2,5-Dimethyl-2,5-di(tert-butylperoxy)hexane, a ·CH2R radical was trapped, which was attributed to the 3-methyl-3-(tert-butylperoxy)butyl radical.

References:

[1] NING ZHANG  Xiang L. Morphology and properties of super-toughened bio-based poly(lactic acid)/poly(ethylene-co-vinyl acetate) blends by peroxide-induced dynamic vulcanization and interfacial compatibilization[J]. Polymer Testing, 2016, 56: Pages 354-363. DOI:10.1016/j.polymertesting.2016.11.003.

[2] EL-WAHAB M A, EL-DESOUKY M G. In silico antibacterial, anticancer, antioxidant, antidiabetic activity predictions of the dual organic peroxide 2,5-dimethyl-2,5-di(tert-butyl peroxyl)hexane[J]. Main Group Chemistry, 2023, 210 1. DOI:10.3233/mgc-230095.

[3] PIERRE G. MEKARBANE &nbsp;Brian J T. ESR spin-trap study of the radicals present during the thermolysis of some novel dialkyl peroxides[J]. Magnetic Resonance in Chemistry, 2001, 39 1: 9-14. DOI:10.1002/1097-458X(200101)39:1\<9::AID-MRC776\>3.0.CO;2-3.