Featured Research

from universities, journals, and other organizations

Chemical reaction could streamline manufacture of pharmaceuticals and other compounds

Date:
July 22, 2013
Source:
University of Texas at Austin
Summary:
Researchers have discovered a new chemical reaction that has the potential to lower the cost and streamline the manufacture of compounds ranging from agricultural chemicals to pharmaceutical drugs. The reaction resolves a long-standing challenge in organic chemistry in creating phenolic compounds from aromatic hydrocarbons quickly and cheaply.

The crab represents the chemical phthaloyl peroxide. The claws are the reactive regions of the molecule that undergo the reaction. The crab is grabbing a molecule (forming the carbon-oxygen bond) then tearing a hydrogen atom off.
Credit: Image was created by Mingjun Quan, based on a design by Changxia Yuan.

Researchers at The University of Texas at Austin have discovered a new chemical reaction that has the potential to lower the cost and streamline the manufacture of compounds ranging from agricultural chemicals to pharmaceutical drugs.

Related Articles


The reaction resolves a long-standing challenge in organic chemistry in creating phenolic compounds from aromatic hydrocarbons quickly and cheaply.

Phenolic compounds, or phenols, are broadly used as disinfectants, fungicides and drugs to treat many ailments such as Parkinson's disease. Creating a phenol seems deceptively simple. All it requires is replacing a hydrogen molecule on an aromatic hydrocarbon with an oxygen molecule.

"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," said Dionicio Siegel, an assistant professor of chemistry in the College of Natural Sciences at The University of Texas at Austin.

The secret that Siegel and his colleagues discovered is a substance called phthaloyl peroxide. This chemical was studied in the late 1950s and early 1960s, but it has been largely ignored during the intervening years.

The scientists were conducting basic studies on phthaloyl peroxide, building on previous research, and decided to use it to tackle the age-old problem of transforming aromatic hydrocarbons into phenols.

The advantage to using phthaloyl peroxide is that the reaction does not require the use of acids or catalysts to work, and it can add oxygen to a wide variety of starting materials.

"There are no special conditions," said Siegel. "You just combine the reagents, mix them and go. It's very simple and straight forward."

The paper describing this discovery was published last week in Nature.

The new process can be applied to other problems in organic chemistry. One particular area of interest is creating metabolites to drugs. Metabolites are the products left after the body finishes breaking down, or metabolizing, a substance. When testing drugs, scientists need to take into account not just how the drug itself reacts in the body, but also how the metabolites react.

"We've had a long-standing interest in accessing metabolites of drugs or compounds that are used in biological systems," said Siegel. "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."

Another area where Siegel and his colleagues are applying what they have learned is in developing even more reactive agents that will expand the scope of chemicals that can be transformed. Siegel hopes to get this new process into the hands of others quickly. He is working with chemical supply companies to market the phthaloyl peroxide compound and/or the precursors and make it available to people in research and the pharmaceutical industry.

"It hasn't even come out yet," said Siegel, "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 paper, 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.


Story Source:

The above story is based on materials provided by University of Texas at Austin. The original article was written by Steve Franklin. Note: Materials may be edited for content and length.


Journal Reference:

  1. Changxia Yuan, Yong Liang, Taylor Hernandez, Adrian Berriochoa, Kendall N. Houk, Dionicio Siegel. Metal-free oxidation of aromatic carbon–hydrogen bonds through a reverse-rebound mechanism. Nature, 2013; 499 (7457): 192 DOI: 10.1038/nature12284

Cite This Page:

University of Texas at Austin. "Chemical reaction could streamline manufacture of pharmaceuticals and other compounds." ScienceDaily. ScienceDaily, 22 July 2013. <www.sciencedaily.com/releases/2013/07/130722152741.htm>.
University of Texas at Austin. (2013, July 22). Chemical reaction could streamline manufacture of pharmaceuticals and other compounds. ScienceDaily. Retrieved October 30, 2014 from www.sciencedaily.com/releases/2013/07/130722152741.htm
University of Texas at Austin. "Chemical reaction could streamline manufacture of pharmaceuticals and other compounds." ScienceDaily. www.sciencedaily.com/releases/2013/07/130722152741.htm (accessed October 30, 2014).

Share This



More Matter & Energy News

Thursday, October 30, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

Mind-Controlled Prosthetic Arm Restores Amputee Dexterity

Mind-Controlled Prosthetic Arm Restores Amputee Dexterity

Reuters - Innovations Video Online (Oct. 29, 2014) A Swedish amputee who became the first person to ever receive a brain controlled prosthetic arm is able to manipulate and handle delicate objects with an unprecedented level of dexterity. The device is connected directly to his bone, nerves and muscles, giving him the ability to control it with his thoughts. Matthew Stock reports. Video provided by Reuters
Powered by NewsLook.com
Robots Get Funky on the Dance Floor

Robots Get Funky on the Dance Floor

AP (Oct. 29, 2014) Dancing, spinning and fighting robots are showing off their agility at "Robocomp" in Krakow. (Oct. 29) Video provided by AP
Powered by NewsLook.com
Saharan Solar Project to Power Europe

Saharan Solar Project to Power Europe

Reuters - Business Video Online (Oct. 29, 2014) A solar energy project in the Tunisian Sahara aims to generate enough clean energy by 2018 to power two million European homes. Matt Stock reports. Video provided by Reuters
Powered by NewsLook.com
Lowe's Testing Robot Sales Assistants in California Store

Lowe's Testing Robot Sales Assistants in California Store

Buzz60 (Oct. 29, 2014) Lowe’s is testing out what it’s describing as a robotic shopping assistant in one of its Orchard Supply Hardware Stores in California. Jen Markham explains. Video provided by Buzz60
Powered by NewsLook.com

Search ScienceDaily

Number of stories in archives: 140,361

Find with keyword(s):
Enter a keyword or phrase to search ScienceDaily for related topics and research stories.

Save/Print:
Share:

Breaking News:

Strange & Offbeat Stories


Space & Time

Matter & Energy

Computers & Math

In Other News

... from NewsDaily.com

Science News

Health News

Environment News

Technology News



Save/Print:
Share:

Free Subscriptions


Get the latest science news with ScienceDaily's free email newsletters, updated daily and weekly. Or view hourly updated newsfeeds in your RSS reader:

Get Social & Mobile


Keep up to date with the latest news from ScienceDaily via social networks and mobile apps:

Have Feedback?


Tell us what you think of ScienceDaily -- we welcome both positive and negative comments. Have any problems using the site? Questions?
Mobile: iPhone Android Web
Follow: Facebook Twitter Google+
Subscribe: RSS Feeds Email Newsletters
Latest Headlines Health & Medicine Mind & Brain Space & Time Matter & Energy Computers & Math Plants & Animals Earth & Climate Fossils & Ruins