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Phenol oxidation causes complications

Nature Reviews Chemistry volume 2, Article number: 0129 (2018) Cite this article

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This approach can capture reactive electrophiles ... that are generally very difficult to detect

2-Butene-1,4-dial is toxic because it can cleave or crosslink DNA, and can target albumin, prealbumin and transferrin proteins. Our bodies generate the dicarbonyl when cytochrome p450 encounters furan, which is present in cigarette smoke and exhaust fumes. Sedlak's team found that UV light irradiation of phenol causes it to degrade into products that include 2-butene-1,4-dial, a reaction that is faster in the presence of H2O2, when up to 2% of the reacting phenol gives 2-butene-1,4-dial. This (and potentially other polar products) had flown under our radar because they are not easily extracted from water and are present in low concentrations. The team got around this by irradiating aqueous phenol/H2O2, and then added aliquots to separate solutions of N-α-acetyl lysine and glutathione, as well as a solution of both N-α-acetyl lysine and N-acetyl cysteine. Such derivatization — an approach also used for screening drug metabolites — enables 2-butene-1,4-dial to be trapped as a stable adduct amenable to separation and quantification. “This approach can capture reactive electrophiles, especially polar, low molecular weight compounds that are generally very difficult to detect by conventional approaches such as liquid chromatography–tandem mass spectrometry”, notes Prasse. The amount of 2-butene-1,4-dial generated is indirectly determined by quantifying the N-substituted pyrroles and pyrrolin-2-ones that result from cyclization of the dicarbonyl onto the amines.

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References

  1. Prasse, C. et al. Unexpected transformation of dissolved phenols to toxic dicarbonyls by hydroxyl radicals and UV light. Proc. Natl Acad. Sci. USA https://doi.org/10.1073/pnas.1715821115 (2018).

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  1. David Schilter
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Schilter, D. Phenol oxidation causes complications. Nat Rev Chem 2, 0129 (2018). https://doi.org/10.1038/s41570-018-0129

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