Students isolate two iridoid monoterpene diastereoisomers for NMR characterization. Commerically available essential oil of catnip, Nepeta cataria, is comprised primarily of two diastereomeric nepetalactones (1 and 2) . These compounds trigger olfactory driven stimulatory responses in many felines. Reactivity-based separation takes advantage of the selective saponification of the enollactone in the (Z,E)-isomer (1) affording aldehyde-lactol (3a-3b) upon acidification. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/239nm/uploads/15982_fig.1_copy.w3k_gel_sem.jpg' alt='' /> (E,Z)-nepetalactone (2) resists mild hydrolysis. Solubility differences allow for simple separation of lactone (2) from the carboxylate form of (3a) and subsequent p-TSA mediated dehydration of lactol returns pure (1) .

Isolation and reactivity-based separation of nepetalactone diastereoisomers from catnip oil in an advanced undergraduate laboratory

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.