A new chemical reaction has been developed by researchers at The University of Texas at Austin that has the potential to lower the cost and streamline the manufacture of a number of compounds from agricultural chemicals to pharmaceutical drugs. This new process resolves a long-standing problem in organic chemistry in making phenolic compounds from aromatic hydrocarbons quickly and cheaply.
Phenols (phenolic compounds) are used as disinfectants, fungicides and drugs. Making a phenol would at first glance seem to be a simple endeavor. It requires replacing a hydrogen atom on an aromatic hydrocarbon with an oxygen atom.
According to Dionicio Siegel, an assistant professor of chemistry in the College of Natural Sciences at The University of Texas at Austin, “This is a chemical transformation that is underdeveloped and at the same time pivotal in the production of many chemicals important to life as we know it.” Siegel and his colleagues have discovered a substance known as phthaloyl peroxide. This molecule was studied in the late 1950s and early 1960s, but has essentially been ignored all this time. The advantage of using phthaloyl peroixde is that this reaction doesn’t require the use of acids or catalysts to work. Moreover, it can add oxygen to a wide range of starting materials. Siegel goes on to say, “You just combine the reagents, mix them and go. It’s very simple and straight forward”.
Of particular interest is to be able to make drug metabolites. Metabolites are the breakdown products of a substance. It is important to know how a drug reacts in the body, but it is also important to know how its metabolites react.
Siegel points out, “We’ve had a long-standing interest in accessing metabolites of drugs or compounds that are used in biological systems. Just as it’s important that the drug doesn’t have deleterious side effects, it’s equally important that the metabolite doesn’t have an effect. You need to be able to test them, and there’s not really a direct way to access metabolites other than using liver microsomes, and that’s not efficient and it doesn’t always work.”
Siegel and his colleagues are applying what they have learned to develop more reactive agents that will expand the types of chemicals that can be transformed. They hope to make this procedure available to others as quickly as possible. Siegel is working with chemical companies to market phthaloyl peroxide and/or precursors for use in research and the pharmaceutical sector. Siegel remarks, “It hasn’t come out yet, but there are a lot of people that are already picking up the technique and working on it.”
Siegel is a co-author on the article in Nature, along with his graduate student, Changxia Yuan, and two undergraduate researchers, Taylor Hernandez and Adrian Berriochoa. Two other co-authors, Kendall Houk and Yong Liang, are from the University of California, Los Angeles.