Scent vs. structure: Vanillin and its derivatives

CHED 437

Rachel Mansfield, ecsuhai@transy.edu and Eva Csuhai, ecsuhai@transy.edu. Division of Natural Sciences and Mathematics, Transylvania University, 300 North Broadway, Lexington, KY 40508
We have taken a molecule of a known scent and replaced a substituent with various new groups to form a new scent. We test this new scent for its effect on human perception. Specifically, we used vanillin, 3-methoxy-4-hydroxybenzaldehyde, a pleasurable scent, as a starting material. By using the Williamson-synthesis of ethers, we replaced the hydrogen from the hydroxyl group with a range of R groups containing carbon chains ranging in size from two to six carbons. The products were purified using column chromatography and tested to see what effect the substitution had on the scent. A random group of college students were asked to smell the different products as well as the starting material, vanillin, and answer a variety of questions about the scents. This allowed us to see the effect of the alkyl-substitution pattern on the pleasantness or unpleasantness of the scents.