Essentials of Fragrance Chemistry

By Matthew Tittensor, Nicholas Lang, and Sohum Sanghvi

Two more common hygiene products are perfume and cologne.  We know that these sprays smell nice and permeate throughout a room, but what is it that gives them their scent and more importantly why does it disperse?  In today’s blog post we will get into this by discussing the organic structures of esters, specific scents, commercial uses for esters, and the process of diffusion.

http://l.yimg.com/ck/image/A1442/1442224/300_1442224.jpg

           An ester follows the format follows the format of the image to the right, with the R group being any hydrocarbon.  This is written a RCO2R’.  The alcohol component makes up the basis of the alkyl component and R’OH’s root name and is based on the longest chain with an OH attached to it. Meanwhile, RCO2H is the carboxylic acid, from which the –oate in the name is derived from.  The full name for an ester is an alkyl alkanoate. Now that the nomenclature is out of the way, what do esters smell like and would they be used in perfumes?

Esters often have a pleasant fruity aroma as can be seen in the chart to the right.  However, that does not necessarily make them ideal for perfumes.  Most simple esters give off these pleasant smells, but problems arise because they are not prepared to handle the sweat that a human body releases.  This sweat hydrolyzes the simple ester and can replace this seemingly nice smell with a harsh one.  A common example is that butyric acid smells like rancid butter, but ethyl butyrate, an ester it can be derived from, smells like pineapples.  This is one reason that simple esters are not utilized in the perfume industry.  However, perfumeries get around this by often including many esters in their products as well as essential oils to prevent the hydrolysis of the esters.  Esters serve a role in the food and beverage industry as well.

           Would you rather eat a delicious food that smells rancid or a mediocre food that smells delicious, if you did not know how each one tasted?  This is a problem that major manufacturers come to face when they make their products.  These companies utilize a combination of esters and essential oils as well to produce a scent that is please to both smell and taste.  It is not so simple as getting one pleasant odor and taste either, as the human has over 9000 taste receptors on its tongue and smell plays a large role in perception of taste.  To create an ideal, it takes a lot of testing and a wide variety of organic and synthesized compounds to be used.

           Diffusion is the movement of molecules from an area that contains a higher concentration to one with a lower concentration of the molecule.  These molecules are already in constant motion and move in random directions due to the random collisions that they experience with each other and other particles.  The net movement is always towards the lower concentrated expanse as more collisions occur on a more highly concentrated zone, making it more likely for the molecule to be pushed over to the other area.  Dynamic Equilibrium only comes to exist after the concentration gradient, difference in molecule distribution, is removed.  This applies to perfumes and colognes as they emanate from their more highly concentrated location on the wrist or neck to the areas surrounding the wearer.  This creates a nice scent around the user and fulfills the purpose of removing or covering up body odors.

http://www.hartnell.edu/tutorials/biology/images/cell%20environment%20diffusion%20fig.jpg

We have taken a look at the concept of esters, specific scents, commercial uses for esters, and basics about the process of diffusion. Using the right ester is vital for obtaining the scent that is wanted, and diffusion is important for making sure the scent remains on the user and covers the body odors. In our next blog post, we will continue our discussion on fragrances and continue to unveil interesting chemistry behind perfumes and colognes.

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