Raw Materials Tonka Beans and Coumarin

Tonka Beans and Coumarin

06/17/16 05:58:18 (23 comments)

by: Matvey Yudov

It is quite difficult to say what ingredient was the first synthetic material to be used in perfumery. The first "experimental" synthetic materials were narrow fractions of essential oils and isolates, individual materials which were isolated from natural sources. Benzaldehyde, which possesses a smell of bitter almond, is sometimes considered among the first synthetic fragrant substances. But much more often this memorable milestone is associated with the substance called Coumarin. Stricktly speaking, coumarin is not something entirely artificial.

Many plants contain coumarin. Besides tonka beans and vanilla, in high concentration coumarin is found in Galium verum, Angelica (Angelica archangelica L), Chinese cassia (Cinnamómum aromáticum), and Sweet grass (Hieróchloe odoráta). Many fruits contain coumarin, for example, sour cherry, strawberry, black currant and apricots. A big measure of coumarin in a plant makes it taste bitter and unattractive to most animals.

August Vogel isolated coumarin for the first time from tonka beans and sweet-clover (we will talk about this one later) in 1820. He mistook coumarin for benzoic acid. In the same year, the French pharmacist Nicholas Jean Baptiste Gaston Guibourt discovered the mistake and named the new compound "Coumarin" (from the French name for tonka beans, coumarou). In 1856, Friedrich Woehler determined the structure of coumarin, and in 1868, William Henry Perkin synthesized it for the first time in the lab. Ten years (1877) later he invented the industrial production of this substance. 

Кристаллы кумарина

Coumarin crystals

In 1884, Paul Parquet, the owner and perfumer of Houbigant, created the perfume Fougère Royale, which is believed to be the first perfume containing synthetic ingredients (its central accord was built of lavender, oak moss and coumarin). Fougère Royale was about 10% coumarin. From that very moment we begin the modern era in perfume history.* 

Fougère Royale has given its name to a very big perfume family of "fougeres". Fougere is almost the only "exclusively" masculine perfume genre which still exists and develops (although, according to the opinion of Jean-Paul Guerlain there were only two good fougere perfumes, Jicky and Mouchoir de Monsieur).

Структурная формула кумарина

 

About 90% of modern perfumes contain coumarin, you can easily detect it by reviewing the list of ingredients on the perfume packaging. I just made an experiment and randomly chose 10 perfumes and saw coumarin in the composition of 9 of them. Every second perfume has more than 1% of coumarin.

Ароматы, содержащие кумарин

The scent of coumarin is usually described as freshly mown hay. In low concentration coumarin really reminds somewhat of rotting hay, but in a big quantity it has a sweet gourmand, almond-vanillic aroma. Thus gourmand perfumes have it the most. In descriptive lists of perfume notes it might hide behind tonka beans, vanilla, marzipan or tobacco. So called С6 wound compounds, and cis-3-Hexenol among the first, are responsible for its fresh green grassy facet.

From a scientific point of view, coumarin is a lactone, an internal (cyclic) ester. Many lactones, used in perfumery, often have a characteristic fatty waxy scent, reminiscent of coconut and milk. Fragrant substances, which are similar to coumarin by structure, possess a similar scent: nutty, vanillic, creamy gourmand. The use of coumarin is restricted to 1.6% in the final perfume product, and even less, up to 0.1%, in cosmetic products. All similar compounds fall under the same regulations.

Одоранты с запахом бобов тонка

Among molecules with similar olfactory characteristics in the illustration above, I would distinguish Tonkene. This compound is a triumph of vibration theory by the renowned perfume critic and bio-chemist Luca Turin. The structure of this ingredient was obtained by a computer simulation on the quest to find a molecule similar to coumarin by its molecular vibration. This compund was synthesized and indeed it was very close by its scent profile to coumarin.

Tonka beans - fruits of Dipteryx odorata, a tropical tree native to Central and South America - contain 1-3% of coumarin. Tonka bean absolute contains 90% of coumarin. On aging tonka beans you can notice small white crystals; this is practically coumarin in its pure form! Tonka beans are used in making desserts, for air freshening and even as an insect repellent. As a flavoring, coumarin has been banned from the food industry in many countries, which I consider as an obvious overdoing; you can find it in absolutely legal cinnamon in the quantity of 1%.

Бобы тонка

Tonka beans, fruits of Dipteryx odorata

Coumarin has been widely used in flavoring of pipe-tobacco and cigarettes. Its sweet odor is now associated with tobacco scents. While a tobacco absolute does not contain any significant amount of coumarin, it is often paired with coumarin in tobacco accords in perfumes.

One of the most common horror stories about coumarin is that it is а rat poison. It is easy to understand the source of this errancy, but we need to learn a bit of history. It all started when a big disease outbrake connected with the deterioration of blood clotting in cattle was registered in North America at the beginning of the 20th century. It was detected that the silage that was fed to the infected cattle, was made of sweet clover (from the genus Melilotus). In the 1940's, the harmful compound of sweet clover was isolated, it was Dicoumarin, possessing strong anticoagulant properties. After that many similar compounds (4-Hydroxycoumarin derivatives) were described and isolated. In 1948, Warfarin was synthesized. This substance was patented as a rat poison which had enjoyed popularity until more modern rodenticides were invented. In the 1950's, Warfarin had become a popular anticoagulant to prevent thrombosis, heart attacks, strokes, and blood clots.

Варфарин

The Furanocoumarins, or Furocoumarins, also known as Phyto-Coumarins, occur in a variety of plants. They produce a photosensitizing effect. One of them is Bergapten from bergamot, which makes its oil phytotoxic. Even bigger amounts of Bergapten are found in Sosnowsky's hogweed or Heracleum sosnowskyi, a dangerous flowering weed. Bergapten easily penetrates the skin and causes severe sunburns.

Although coumarin has such scary relatives, it is still in a very high demand in perfumery and cooking (mainly in tonka beans and cinnamon).

 

*"…until modern perfumery began at the end of the nineteenth century, advances were limited to mixtures of natural extractions of local materials, with the occasional incursion of exotic resins and plants imported from distant lands at high prices." T. Sanchez, The Perfumes, The A-Z Guide.
 

Mat Yudov

Mat Yudov is a chemist, perfumer, and musician. Mat is a researcher and specialist in the chemistry of aromatic materials. He graduated from Moscow State University "Lomonosov" in 1999. He writes for the popular perfume blog leopoldray.blogspot.com (in Russian).

MEH



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LadyPilot
LadyPilot

I smelled coumarin during the raw ingredients exhibition 3 years ago - wonderul!!! My favorite perfume ingredient finally on its own - it was like a revelation to me!
Yes, this is strong stuff, sweet, vanilla, cocoa, almond and hay all together.
Thank you for this article, it reminded me of this amazing, cozy ingredient:)

Mar
11
2017
hope_ngwe
hope_ngwe

Interesting article.....it's funny just the other day I was checking list of ingredients in body butter I just purchased and it listed coumarin.

Mar
11
2017
BloomPerfume
BloomPerfume

oh, we've just done Vanilla et Co sample pack with samples of raw materials including tonka, coumarine, heliotropin, vanillin and ethyl maltol. To illustrate the use of tonka we selected PG4.1 Le Musc at La Peau (Parfumerie Generale) and Lumiere Blanche (Olfactive Studio). The pack is available worldwide from Bloom Perfumery's web-site.

Mar
10
2017
Michylaka
Michylaka

Great article! It was very informative. Thank you!

Mar
09
2017
wild_radish
wild_radish

I always look forward to Mat's articles. He really takes the highly subjective nature of scent and puts it into concrete science, making it all feel less abstract and more precise.

I always read coumarin with my nose as the waxy crumble of a vanilla shortbread cookie.

Mar
08
2017
nhledger
nhledger

Wow Mat that was really interesting! I failed science miserably at school, but ironically somehow managed to find myself in science-related jobs, working pathology, and then studied natural medicine....lastly I married a man with a chemistry degree! No surprise then that I find it all so fascinating. More please :-)

Jul
29
2016
ficusmuskus
ficusmuskus

Why is the use of coumarin restricted to 1.6% in the final perfume product?

Jun
20
2016
jeca
jeca

Hummingbirds are adorable creatures, they love flowers (maybe not aesthetically:-) as much as we do. They've got a character and I see them everyday here, in Southern California, they are inspiring. ;o)

The logo that Mathew used in his pictures we received as a gift from our generous reader from Belgium when we came to Milan.

Jun
20
2016
lemonzest
lemonzest

Thanks for this article. You should present more along this line - articles that discuss the science of smell.

Why is the hummingbird Fragrantica's logo? Hummingbirds have almost no sense of smell. They locate flowers by sight. Just wondering....

Jun
20
2016
hellovascent
hellovascent

Eshcho raz bol'shoe spasibo.

Jun
20
2016
hellovascent
hellovascent

еще раз большое спасибо

Jun
20
2016
mikemuscles21
mikemuscles21

Fascinating! Years ago, I use to be a pharmacy tech and I always wondered what the correlation was between Coumarin the medication and the fragrance ingredient.

Jun
18
2016
Buysblind
Buysblind

Very interesting article. Thank you!

Jun
17
2016
NebelGeîst
NebelGeîst

It should be added, that coumarin in higher doses can cause some milder symptoms of poisoning like vertigo, nausea, headaches and hypersomnia. But perfume and cosmetic alone would not reach that high amounts in the blood stream that usually should be necessary to do so.
It should be avoided by pregnant, nursing mothers and young children though, because it can be harmful to the development of the foetus and the nervous system of babies and young children causing neurological problems.
It might be demonized and I don't have problems with coumarin in my perfumes, but that doesn't mean it has no significant effects on the health (but more via peroral intake).

Jun
17
2016
drugstore classics
drugstore classics

Coumarin is indeed my a favorite note of mine! Tonka bean, vanilla, tobacco..... ahhhh.

<3 Blessings on August Vogel in 1820!

Jun
17
2016
Antagonistr
Antagonistr

Thanks for an information which is correct

Jun
17
2016
milkyway
milkyway

Such an informative and well-written article! Learned that a lot of my ideas about coumarin were pretty wrong. Want more of these!=)

Jun
17
2016
colettemichelle
colettemichelle

I love these articles where the author delves into the science behind certain scents or compounds. So fascinating that perfume isn't just an art, it's a science too. Here's a question though. Why do I hate tonka in some perfumes but LOVE others with coumarin?

Jun
17
2016
wesleyhclark
wesleyhclark

Oh. (Knocks head.) I never really noticed that this site had a logo or mascot!

Jun
17
2016
Kalitera
Kalitera

To wesleyhclark: I think it's just a way to present the logo of Fragrantica.

Jun
17
2016
mi55anthr0py
mi55anthr0py

I love these articles on the science behind perfumery!

Quick question: where'd you get the hummingbird patch?! *Covets*

Jun
17
2016
wesleyhclark
wesleyhclark

Fascinating, as usual! I like your articles best, but I guess I'll have to transliterate Cyrillic in order to get the graphics...

I don't understand the hummingbird patch.

Jun
17
2016
chayaruchama
chayaruchama

Fabulous, Matvey!

Jun
17
2016

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