What is Hydroxyquinoline? - Uses & Overview

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

In this lesson, we will be learning about a specific organic compound known as hydroxyquinoline. Our primary points of discussion will be on its structure, an overview of how it's synthesized, and some of the more common uses it finds application in.

A Bandage that's a Liquid?

Let's imagine that one day you're out playing with your 5-year-old cousin in the woods. She stumbles on a tree root and gets a cut on her arm. You reach into your pocket, not for a band-aid, but a small tube that contains a magic potion (or at least that's what you tell her). She's quite surprised that when you squeeze out the jelly-like substance it starts to dry, stop the bleeding, and actually makes her arm feel better! That's when you share the secret and tell her that it's called a liquid bandage and that it negates the need for a band-aid!

Although our liquid bandage certainly seems like magic, it can actually be explained by some simple organic chemistry. The organic compound that's used in liquid bandages is known as a hydroxyquinoline, which is the subject of our current lesson. Let's get started!

Hydroxyquinoline Structure

The first obvious thing we need to discuss is the structure of a hydroxyquinoline so that we'll know how to recognize them. In general, a hydroxyquinoline is a derivative of the heterocycle quinoline, with a hydroxy (-OH) group attached to one of the carbon atoms. That sounds complicated, so let's break it down into simpler terms. A heterocycle is a compound that contains a ring, and the prefix -hetero means that there is an atom within the ring that's NOT carbon. In the case of a quinoline, the atom that's not carbon is nitrogen.

A lot of hydroxyquinoline compounds exist, but luckily they are only different in the placement of the hydroxy group on various carbons throughout the ring system. For example, 2-hydroxyquinoline, 4-hydroxyquinoline, and 8-hydroxyquinoline are common isomers (same chemical formula but different atom connectivity) that simply have the hydroxy group connected at different points on the ring. Notice the common quinoline core that each compound shares.


Structures of 2-hydroxy, 4-hydroxy, and 8-hydroxyquinoline
null


Synthesis

Now that we know what hydroxyquinoline look like, let's talk about the most common way they can be made in the lab. 8-Hydroxyquinoline can be conveniently made by simply reacting glycerol with 2-aminophenol in the presence of sulfuric acid. This reaction is called a Skraup synthesis, named after the Czech chemist Zdenko Hans Skraup. The nice thing about this reaction is that it constructs a hydroxyquinoline using cheap and commercially available starting materials.


8-Hydroxyquinoline synthesis by the reaction of glycerol with 2-aminophenol, also known as a Skraup synthesis
null


Uses

Liquid bandages can be used in the place of band-aids. They bind to your skin while creating a protective layer that not only keeps dirt and germs out, but helps keep moisture in to promote healing of a wound. What's interesting is that liquid bandages contain an alcohol solution of 8-hydroxyquinoline as the active ingredient.

To unlock this lesson you must be a Study.com Member.
Create your account

Register to view this lesson

Are you a student or a teacher?

Unlock Your Education

See for yourself why 30 million people use Study.com

Become a Study.com member and start learning now.
Become a Member  Back
What teachers are saying about Study.com
Try it risk-free for 30 days

Earning College Credit

Did you know… We have over 200 college courses that prepare you to earn credit by exam that is accepted by over 1,500 colleges and universities. You can test out of the first two years of college and save thousands off your degree. Anyone can earn credit-by-exam regardless of age or education level.

To learn more, visit our Earning Credit Page

Transferring credit to the school of your choice

Not sure what college you want to attend yet? Study.com has thousands of articles about every imaginable degree, area of study and career path that can help you find the school that's right for you.

Create an account to start this course today
Try it risk-free for 30 days!
Create an account
Support