Monday, November 24

The Schiff(er) effect

Is there any molecule that smells like blonde hair, like Claudia Schiffer, like all the stereotypes in the yellow orange spectrum? We might search a lot but at least there is a physical evidence, the color of the molecules. Schiff bases, usually bright yellow, are a chemical function with a carbon nitrogen double bond and the nitrogen connected to another carbon from an alkyl/aryl group - R1R2C=N-R3
To keep simple - a Schiff base is the child of a primary amine (NH2) and an aldehyde. They have a crucial role in perfumery and there are many of them - put by the perfumer or "obtained" inside a perfume under several conditions (the time and the presence of those molecule able to react).
With only methyl anthranilate or indole (the most used) and the great amount of aldehydes a lot of Schiff bases were obtained and used in fragrances. Many of them have a strong orange flower note with all possible accents, from fresh to green, pungent, fruity. They last for ever while in pure form they are very viscous. There are several ways to prepare them and many are very simple. If you put in a bottle the amount required by the reaction and heat a little … the smell will change and a new "scent" with a very yellow color will appear.
Schiff bases are used in tuberose and white flower notes. Giorgio could be considered the King of those bases.
Widely used are the products obtained from the orange flower-grape smelling Methyl Anthranilate and lily of the valley aldehydes like Hidroxycitronellal for Aurantiol, Lilial, Lyral but also with Canthoxal, Anisaldehyde, Triplal. They have power and tenacity while the orange flower note is one of the most diffusing! You cannot escape from a Schiff Base.:) Aurantiol is one of the most used from this family, but there are many other, sometime "secret", not available on the market and put into bases (though easy to produce). Some time ago I evaluated no less than 50 molecules of that type and it's not easy to find yourself inside. Citral plus indol result appears in at least 2 masterpieces created before the 60's.
Giorgio is of course the crown jewel, but I've got the feeling that more and more new fragrances are into this direction. First I noticed the smell in Paris streets, than I made an "investigation" in the celebrity scents universe where to my surprise I found it again. A Schiff base is not like vanillin - you cannot put it everywhere! Schiff base plus damascones and some spices are in the heart of one of the giants of XXth century. A bomb! Pure Poison (Dior) is a modern example: to me it's closer to Giorgio than to Poison. The latest Christina Aguilera is also a variation around this theme, so popular in the 80's.

Photo - Aurantiol molecule
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Fragrance is the 8th Art - Octavian Coifan - Le Parfum est le 8ème Art
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