Acetophenone (Yum)

I don't have much to say about acetophenone chemically - It is a useful (and very common) synthetic precursor. It's one of a relatively few chemicals that aren't used as a solvent that many labs keep around in liter bottles. The main reason I like it, though, is that it smells wonderful.


Predictably, it is used in perfumery. Like many single chemicals, its smell is puzzlingly hard to pin down (smells, such as coffee, where you definitively say "that's it," are very often mixtures). I'd describe it as something like orange blossom with a bit of artificial cherry/almond.

Acetophenone also is of note for its use in Luca Turin's experiment - a controversial dark-horse theory of olfaction that says vibrational levels (essentially what's given by an infrared absorption spectrum) of a molecule hold predictive power for odorant character. (The mainstream theory says molecular shape is the thing). In one experiment, he found that he could order a perdeuterated acetophenone (exchanging all the hydrogens for an isotope of hydrogen, deuterium). Turin and some others insist they smell different, others insist isotope-exchanged compounds are indistinguishable (see, e.g., here and here.).


More like this

I love reading lists of fragrance chemicals. The assignment of pleasant, qualitative fragrance descriptions to chemicals with hard-nosed, rigorous functional group names always makes me giggle a little. Acetophenone, for instance, smells of orange blossoms. Today, I came across one that has both in…
In today's issue of The New Yorker, John Lancaster reviews a new book called Perfumes: The Guide, by Luca Turin and Tania Sanchez. Olfaction (the sense of smell) is, as Lancaster notes, "a profound mystery". Why is it, for example, that two aromatic molecules with almost identical structures can…
Olfaction (smell) is the most mysterious of senses, and is wrongly regarded as insignificant by most people. The sense of taste, for example, consists in large part of smell - try holding your nose next time you eat - and the recent identification of putative pheromone receptors in humans suggests…
It is no secret that I enjoy smelly compounds... a lot. Here's a short list of what I seem to have covered at this blog (hits for "stinky" or "smell"). I'm sure I missed some I've already written up. If I haven't covered your favorite, post a request! Stinky: Tosyl Chloride Triethylammonium Acetate…

Have you ever made pivaloyl o-hydroxyacetophenone? What should be a morning's work to obtain crystals makes for an interesting week.

It is also one of the few chemicals whose name is made up of four three letter words. ace top hen one. Isn't that exciting!?

"with a bit of artificial cherry/almond."

Any chance that that is due to its structural similarity to benzaldehyde?

I always got a kind of cinnamaldehyde-y smell from acetohpenone.