6-Isobutyl Quinoline

GreenLeathery
Written By Giuseppe Coglienti

6-Isobutyl Quinoline

Synthetic ingredient for Perfumery Overview

The 19th century was a boiling, exuberant cauldron of possibility for chemistry. Amidst the bubbling flasks and scientific breakthroughs, a remarkable aromatic molecule emerged, ready to leave an indelible mark on the world of perfumery.

Like stepping into the tiger’s den, we embark on a captivating journey through time, delving into the secrets and allure of the historical compound. From its humble origins to its formative role in fragrances, we uncover the fascinating history and mystique that surround 6-Isobutyl Quinoline. Join us on this journey to unravel the captivating story of this aromatic marvel, where chemistry, artistry, and olfactory intrigue intertwine in a dance of scents and sensations.

The Intricate History of Quinoline

The enduring tale of 6-Isobutyl Quinoline began in 1834, well before its discovery, attributed to the work of Friedlieb Ferdinand Runge, a German chemist. Runge was widely regarded as one of the pioneering industrial chemists of his time, having made significant discoveries, and having isolated various compounds including alkaloids like quinine, atropine, catechol, and caffeine, throughout his lifetime.

In 1833, Runge was hired as a technical director by a company called Produktenfabrik, in Oranienburg. His task was to conduct a series of research and find uses for coal tar oil, a byproduct of the manufacturing of illuminating gas. During these productive years of research, Runge made several significant discoveries. He identified phenol and aniline, developed a new method of synthetic dyeing, and most importantly, isolated and discovered an oily substance which he named Leukol. Derived from the Greek word “λευκό ελαίου” meaning “white oil”, Leukol was a transparent, odorous material obtained from coal tar, a byproduct of coke and coal gas production. Unbeknownst to Runge, he had just discovered what would later be recognized as Quinoline.

In 1842, a significant development took place when the French scientist Charles Fréderéric Gerhardt successfully obtained an intriguing odorous liquid. This breakthrough occurred when Gerhardt decided to heat quinia and strychnine with potassium hydroxide, leading to the creation of a substance strikingly reminiscent of Leukol, which Gerhardt named Quinoline.

A few years after its Christening in 1842, the discovery of this new compound sparked the interest of one of the most influential chemists of the 19th century: Auguste Laurent.

Laurent, a close friend and collaborator of Gerhardt, noticed conflicting compositions attributed to Quinoline, Leukol, and other nitrogen derivates. This prompted him to undertake a thorough and rigorous analysis of these compounds.

Through his research, Laurent observed that certain formulas of several compounds did not align with his rule for nitrogen compounds which state that the sum of hydrogen, nitrogen, and their respective replacements present in a nitrogenated substance’s equivalent should be divisible by four. Gerhardt’s proposed formula for Quinoline, C38H20N2O2, as well as the formula suggested by the German chemist August Wilhelm von Hoffmann for Leukol, C36H16N2, were deemed incoherent by Laurent.

Recognizing the inconsistency, Laurent reached out to both Gerhardt and Hoffmann, requesting them to repeat their respective experiments to assess the validity of their claims. Between 1845 and 1846, Gerhardt revised the formula for Quinoline to C36H14N2, while Hoffmann discovered that Leukol was the exact correspondent to Quinoline, leading him to conclude that both compounds were, in fact, one and the same.

Despite being initially observed in 1834, the development of a synthesis method for Quinoline took an additional forty-five years. In 1880 the Czech chemist Zdenko Hans Skraup postulated a possible synthesis method for the compound. The so-called Skraup Synthesis, also known as Skraup reaction, consisted of heating aniline and glycerol with an oxidant agent such as nitrobenzene to yield quinoline (more specifically the reaction requires the involvement of a nucleophilic 1,4-addition of aniline to acrole, which is formed in situ by the dehydration of glycerol. The intermediate cyclises under the influence of concentrated sulphuric acid, forming 1,2-dihydroquinoline, which then undergoes oxidation, becoming quinoline.) Nitrobenzene can be utilized as both the solvent and oxidizing agent, and Arsenic Acid may be used in place of nitrobenzene, causing a milder reaction.

The synthesis of Quinoline propelled the compound to new levels of prominence in various fields including pharmaceuticals, various industrial applications, and the production of synthetic dyes, and also became highly sought after as a solvent and chemical reagent for its high-boiling point. While this may hold true for the aforementioned fields, in perfumery Quinoline was still an undiscovered and certainly underappreciated element, yet imbued with the promising scent of untapped potential.

In fact, between 1876 and 1878, Edgar de Laire established a pioneering chemical firm called Fabriques de Laire, which focused on the creation of synthetic aromatic materials, perfume bases, and the blending of synthetic molecules with natural raw materials. In 1895, de Laire’s wife, Madame Marie Thérèse de Laire, opened a new branch of the company dedicated to the production of aromatic compounds. It was thanks to Madame de Laire that, at the dawn of the 20th century, Mousse de Saxe was born.

The exact date of creation and commercialization of the accord is debated due to a lack of specific documentation. However, the base holds significant importance, not only for its lasting impact on the world of perfumery, but also because it was the first base and perfume to utilize 6-Isobutyl Quinoline. This derivate of Quinoline contributed to the creation of the legendary base with its dark, earthy, leathery, and nutty notes, featuring characteristic shades of vetiver and oakmoss.

While not directly related to Mousse de Saxe or 6-Isobutyl Quinoline, it is worth mentioning that Fabriques de Laire also launched the iconic base Amber 89 in 1889. The synthetic perfume base was created combining synthetic vanillin and exquisite natural materials such as vetiver, patchouli and jasmine.

In 1921, unbeknownst to anyone, the perfume house Molinard concocted and commercialized a fragrance that would shake the very foundations of the world of perfumery. Habanita, in fact, would later be recognized as one of the most important achievements, not only for the company, but for the industry as a whole. The ambitious perfume was initially developed as a “cigarette fragrance” and featured top notes of raspberry, peach, orange blossoms, and bergamot, middle notes of heliotrope, orris root, rose, Lilac, Jasmine and Ylang-Ylang, and base notes of leather, vanilla, musk, oakmoss, cedar, and amber. To impart Habanita with its distinctive tobacco and leather-like notes, the master perfumers decided to use 6-Isobutyl Quinoline, resulting in a shockingly well-rounded fragrance.

In 1922, Parfums Caron, a French perfume house founded in 1904 by Ernest Daltroff, created an essence that had the ability to bottle the festiveness, and luxurious scents associated with fur coats, and incense typical of the Christmas period. To impart a more animalistic, intense, and leathery aspect to the fragrance, the perfumers at Parfums Caron opted to use Mousse de Sax as a base.

After a four-year collaboration that resulted in the creation and commercialization of Chanel No. 5, the Russian perfumer Ernest Beaux whent on to create a new leathery fragrance for Chanel. In 1924, Cuir de Russie Parfum continued the tradition of fragrances that embraced the use of the harsh, odorous molecule, combining a lathery, animalistic base, with delicate floral notes.

Although the impact of Fabriques de Laire and its bases can still be felt in the field of perfumery, the de Laire company no longer exists. It was acquired by Florasynth in 1985, which was subsequently bought by H&R in 1987. In 2003, H&R transformed into what is now known as Symrise. Despite the changes, Symrise continues to perpetuate the legacy of de Laire, striving to innovate and expand the boundaries of perfumery while paying homage to its rich history

Generic Introduction to Quinoline

When discussing Quinoline or one of its specific variants, it is important to recognize that there numerous compounds stemming from this particular molecule. So, in order to gain a better understanding of 6-Isobutil Quinoline, let us briefly explore the nature of Quinoline itself.

Quinoline is a N-base (nitrogenous base), colorless, bicyclic, heterocyclic, and hygroscopic compound which, if exposed to the light, acquires a yellowish to brown appearance, and bears a pungent amine-like odor. The compound is formed by two ring-like structures (heterocyclic and bicyclic) which contain atoms of at least two different members and has the ability to attract and holding water molecules (hygroscopic) through absorption or adsorption.

As previously specified, Quinoline was first observed in coal tar, a byproduct of the production of coke and coal gas from coal. It can also be found in certain other products derived from fossil fuels. Additionally, Quinoline can be formed through the combustion of various substances, including tobacco.

The surprising versatility of the compound has led to a significant departure from its early days in the world of chemistry. While Quinoline is still utilized as an industrial dye and solvent, it has found diverse applications in modern times. It serves as a reagent for decarboxylation and is widely used in pharmaceuticals, including antiseptics, fungicides, and is well-known for its antimalarial, antibacterial, and antiglaucoma properties. Additionally, one of Quinoline’s variants, known as Quinoline Yellow, has been utilized as a food additive and, in the European Union, is identified by the E number E104.

6-Isobutyl Quinoline

6-Isobutyl Quinoline is one of the many alcohol-soluble, fragrant, synthetic, and peculiar variants of Quinoline. Throughout history, due to its specific olfactory profile, the compound has been used in surprisingly curious perfumes, that aimed to evoke rather unusual sensations. Although one might find validation of this claim solely by examining the list of perfumes that incorporated the molecule in their bases, one of the most interesting descriptions of the compound comes from a respected authority in the field of perfumery: Michael Edwards.

During his description of Mousse de Saxe, the first base in which 6-Isobutyl Quinoline was used, Edwards described it in his book ‘Perfume Legends: French Feminine Fragrances’ (1998) as possessing the “smell of a tiger’s lair”. This description masterfully encapsulate the fundamental primal essence of the molecule, effectively conveying the rough, warm, and overwhelming notes of the fragrance.

Tyger Tyger, burning bright, In the forests of the night; What immortal hand or eye, Could frame thy fearful symmetry?

William Blake - The Tyger (1794)

The distinctive olfactory profile of 6-Isobutyl Quinoline is characterized by earthy, nutty, vetiver, green, and oakmoss notes, with a particularly powerful leather-like facet. When opting to use 6-Isobutyl Quinoline in perfumery, due to its overpowering, incisive odor, it becomes necessary to dilute or accompany the molecule with other ingredients or bases that could blend with its floral, green and earthy notes, while mitigating its harsh aspects. An example in this approach is seen in Marie Thérèse’s production of Mousse de Saxe, during which she paired the molecule with abundant quantities of a geranium base, rose, vanillin, violent ionones, sandalwood, nitro-musks, and anisyl acetate. These ingredients not only provided de Laire with the means to mellow the otherwise sharp tone of 6-Isobutyl Quinoline, but also tamed its proverbial tiger, giving her control over its lair and domesticating it, complementing its floral notes and exalting the other facets of the concoction.

Although 6-Isobutyl Quinoline is not as widely used as other variants of the same molecule, its legacy is perpetuated by the skilled hands of the Symrise perfumers who, to this day, continue to produce the legendary base Mousse de Saxe. These lingering fragrant memories of a bygone era in perfumery offer the public an intoxicating sense of possibility, suggesting that, what is now just a faint reminiscence, may soon reclaim its prominent position on the stage of perfumery.

Giuseppe Coglienti https://Scentspiracy.com
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