Around 1880 a new class of heterocyclic aromatic molecules was discovered by organic chemists and some of their members became very soon of a great interest for perfumers. The quinolines are virtually the 2 rings of naphtalene where one atom of carbon is replaced by nitrogen. The smell of their derivates is strong, earthy, smoky and very soon they contributed to new leather notes in perfumery. Iso butyl quinoline or IBQ is maybe the most famous today (after the overdose of Germaine Cellier) but other quinolines had also their moment of glory. They were part of many forgotten bases and contributed to several notes that are no more in favor these days: tobacco, mosses, animalic flowers.The methylquinolines - add one methyl group (CH3) to one of the 2 rings and you'll get 8 isomers with a strong civet, honey and lilac smell in different shades. Some were used in famous perfumes:
The alpha /2-methyl/ or Quinaldeine has tobacco-lilac shades.
The para /6-methyl has a very strong honey-civet and turkish tobacco note.
The meta /7-methyl / or Lilacine is the most floral and has a floral-honey-civet note to the lilac undertone
The ortho/8-methyl or Folianthine has a strong civet-honey note.
The most used were 7, then 6 and 8 and I found them in civet, honey bases, tobacco notes and in small shades in several floral notes.
Adding hydrogen in the first, nitrogen ring, or "saturating the ring" new products became interesting for the perfumer. They were the tetrahidro isomers and the most used is tetrahidro p-methyl quinoline called also Civettal because of its strong, sweet, animalic-civet note with a very good fixation. A product still available today at Givaudan.
The propyl quinolines - add one of the propyl groups (3 atoms of Carbon) to the basic shape of the family and you'll get some very interesting molecules with woody-earthy-mossy notes so valuable in classic perfumery.
The para / 6-isopropyl or Lichenol or Base 3 (Givaudan) is a famous and very old product. It smells woody, mossy, earty, rooty and is very tenacious. It was used in many classic accords with methylionones (orris), vetiver, oak moss and entered in many bases built around vetiver and mosses.
The butyl quinolines - add one of the butyl groups (4 atoms of Carbon) to the basic shape of the family and you'll enter the mossy-leathery shade so famous in classic masculine colognes that used and abused the IBQ.
The alpha isobutyl or 2-(2-methylpropyl) or Isobutyl Quinoline 2 (Givaudan) is strong, leather, woody and a classic material (IBQ) that gives radiation and strength.
The 6 (1-methylpropyl) isomer smells leather, green, woody, tobacco, and less dry. It can be found on the market as Pyralone (Givaudan) or Butyl Quinoleine Secondary (Givaudan) (in the second case as a mixture with small amounts of the 8(1-methylpropyl) isomer but the 6 represents around 84%)
The 8 sec-butyl or ortho sec-butyl is rarely used. It smells strong tobacco-Havana and "ash tray" beeing typical for "Nicotine odour".
(Sorry for so much chemistry but I wanted to show that isobutylquinoleine is not alone in the world of leather, tobacco, mossy and vintage notes. As an anecdote… you can smell also IBQ in Trésor by Lancôme. A very versatile family!)
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Fragrance is the 8th Art - Octavian Coifan - Le Parfum est le 8ème Art
