Olfactory Chemistry: Norlimbanol- Mirror, Mirror Who’s The Woodiest Of Them All?

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Today’s perfume cliché was last year’s game changing raw material. One raw material, Norlimbanol, has followed this trajectory from its early exciting use in 2001 to today’s overused woody basenote. From a chemical point of view there are a couple of interesting aspects about its structure.

norlmibanol enaantiomers

One is that the structure you see above (+)-Norlimbanol is one of the most powerful woody notes in all of perfumery. If you just change the geometry by taking the bonds which have the solid wedge or the dashed wedge and reverse all three of them so the solid wedges are now dashed and the dashed wedge is now solid. You have (-)-Norlimbanol. So it is the same structure but the solid wedges are coming out of the page and the dashed wedges are going behind the page. These two structures are what are called enantiomers. They are mirror images of each other. That enantiomers have dramatically different properties is not just confined to perfume. This phenomenon extends to drug discovery as well. There are drugs where one enantiomer has the positive effect and the other enantiomer causes a bad side effect. Separation chemistry has evolved so much that separating these isomers has become easy and it allows for a chemist to isolate the specific enantiomer with the desired character almost at will. This is why even though it is a single enantiomer it is one of the more economical ingredients to be found in perfumery.

Norlimbanol was discovered by Firmenich chemists and patented in 2000. In 2001 perfumer Olivier Cresp would use it in two of the best designer perfumes ever released. M. Cresp didn’t just use Norlimbanol by itself he mixed a potent mix of Norlimbanol and two other synthetics Ambrox and Z-11. The two perfumes this mix was used in were Dolce & Gabbana Light Blue and Paco Rabanne Black XS. If the idea of strong long-lasting woody bases has become a cliché these were the two perfumes which popularized the concept. Nowadays Norlimbanol is often used by itself and because it has a great longevity and projection perfumers add it in because they believe this is what consumers want. I would say that the perfumer who takes the time to balance it out with other raw materials to deliver a specific effect can still use Norlimbanol effectively and creatively. Unfortunately those perfumes are few and far between especially on the department store counter. Next time you are there take a sniff of Light Blue or Black XS and keep in mind how Norlimbanol is used there. Then pick up any other perfume next to it that has a woody base and you will instantly see the difference.

Norlimbanol may have become trite due to overuse but it is still one of the most versatile and interesting synthetics on the perfumer’s palette.

Mark Behnke  

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