Raw Materials Aldehydes in Perfumery Mythology

Aldehydes in Perfumery Mythology

04/15/16 08:45:55 (28 comments)

by: Matvey Yudov

 

What are aldehydes in fact? The answer is not as simple as it may seem. Ask a sophisticated perfume lover and they will tell you all about synthetic materials with a smell that is hard to describe, which once made Chanel No. 5 so unusual, abstract and ground-breaking.

A chemist or even an ordinary high school student studying chemistry won’t think long and will tell you that an aldehyde is an organic compound containing the –CHO group, or aldehyde group. All the aldehydes have common chemical properties, for example, they are easily oxidized to corresponding acids. The “silver mirror reaction”, which you may remember from your chemistry lessons, is based on that oxidization – when the test glass is heated, a metal mirror-like coating is formed on its surface. The word “aldehyde” itself was coined by the German chemist Justus von Liebig as a contraction of the Latin alcohol dehydrogenatus, that is “alcohol without hydrogen”.

The trivial names for aldehydes* often has either the suffix “-al”, or the root “-aldehyde”, let us say “caterpillaral”, “gigglaldehyde”, “doughnut aldehyde”. Such substances as vanillin and heliotropin are also aldehydes, chemically speaking. And overall, a perfumer has numerous aldehydes with a variety of smells in stock: melonal smells of melon, adoxal – of sea and egg white, citronellal – of lemongrass, lyral – of lily-of-the-valley, triplal – of green grass. And of course, there are also cyclamen, cinnamic, anisic, cuminic, mandarine aldehydes.

All right, you say, but what's that got to do with Chanel? If there are so many aldehydes and they all have different smells what is this “aldehydic note”, what does it smell of, what aldehydes does Chanel No. 5 contain? Perfumers do love aldehydes and not so often do we call our loved ones by their full and proper names. Likewise, what perfumers are used to calling “aldehydes” are actually a subgroup and a special case: saturated aliphatic or so-called fatty aldehydes. Their names are usually based on the number of carbon atoms in a molecule. Thus, aldehyde C-7 or heptanal has seven carbon atoms, aldehyde C-10 or decanal has ten, as you may have guessed.

Chanel No. 5 contains a mixture of aldehydes C-10, C-11 and methylundecanal (aldehyde C-12 MNA). It's noteworthy that perfumers had used aldehydes long before this legendary fragrance was created [Chanel No.5 was launched in 1921]. Most experts in perfumery history agree that aldehydes were first used in Rêve D'Or by L.T. Piver, or rather in its new edition of 1905, created by Pierre Armigeant, and then in Quelques Fleurs Houbigant (1912) and Bouquet de Catherine (1913) by Moscow factory Alphonse Rallet & Co. As well as Chanel No. 5 these two were created by Ernest Beaux, a Moscow native by the way. But still, it is Chanel that has become the main aldehydic fragrance, giving birth to numerous copies and imitations.

Fatty aldehydes have a distinctive waxy smell, similar to the smell of a blown-out candle. Actually, the smell of candles is determined by fatty aldehydes, products of incomplete combustion of paraffin. The smell is very intense and strong; it only becomes pleasant when diluted down to 1% or less. Decanal (C-10) smells of zest, dodecanal (C-12) has some notes of lily and violet. The simplest aldehydes, formaldehyde and acetaldehyde, have very aggressive and unpleasant smells and nevertheless, flavourists use acetaldehyde for some of their flavours. Hexanal (C-6) already has some more or less pleasant green and apple notes. Fatty aldehydes with 15 and more carbon atoms have almost no smell at all.

The smell of the fatty aldehydes has another common property – a “soapy” aspect. For a very long time aldehydes have been heavily used in soap perfume, because of their low price, intensity of smell and ability to mask unpleasant nuances of a soap base smell. Very often aldehyde smell is associated with abstract cleanliness or the feel of freshly ironed linen.

It is important to understand that aldehydes are not artificial substances, results of human work. Lots of them occur in nature. For example, decanal can be found in citrus (up to 4% in orange oil) and conifer oils, in many flower oils and in abundance in coriander oil. Unsaturated aliphatic aldehydes also often found in nature and their smell is even more intense. For example, (E)-2-decenal determines coriander smell and it is a frequent component of stink bugs’ “chemical weapon”. Its epoxy derivative trans-4,5-epoxy-(E)-2-decenal gives blood its strongly marked metallic aspect. It is the smell that helps a predator to track down its prey.

In the wave of success of the first floral aldehydic fragrances, chemists were hard at work to synthesize new materials with similar olfactory properties. In 1905 French scientists E.E.Blaise & L.Huillon (Bull.Soc.Chim.Fr. 1905, 33, 928) synthesized γ-undecalacton and a little later, in 1908, the analogous work was published by two Russian chemists А.А. Zhukhov & P.I. Shestakov (Journal of the Russian Chemical Society 40, 830, 1908). The substance had a very interesting smell, reminiscent of a peach, warmed by the sun – fruity, waxy, with a creamy coconut nuance.

The producers decided to sell the substance under the name “aldehyde C-14” – to satisfy the perfumers’ craving for new “aldehydes with figures” on the one hand, and to lead astray the rivals on the other hand. Chemically speaking, it was not an aldehyde at all, but a lactone (cyclic ester) and the number of atoms in the molecule was not 14, but 11. As a Russian anecdote goes “Yes, you are absolutely right, only it was not chess, but bridge, and I haven’t won, but lost.” A pretty piece of business, isn't it!

So-called “aldehyde C-14” made its debut in 1919 in Guerlain Mitsouko. Soon it was followed by similar substances: so-called “aldehyde C-16” (“strawberry aldehyde”), “aldehyde C-18” (“coconut aldehyde”), “aldehyde C-20” (“raspberry aldehyde”) and others.

And, in the end, it turns out that nearly every third aroma material is an aldehyde, but some of the main aldehydes are not aldehydes at all.


*Chemists use several types of names. The first type is nomenclature or systematic names. It is a kind of cipher, an algorithm helping to recreate the structure of a substance, to understand what atoms are inside the molecule and how they are connected. Each name refers to its one and only corresponding structure and vice versa – each substance has just one systematic name. According to the nomenclature, aldehydes are to have the suffix “-al”. The only drawback of such names, but quite an important one, is their cumbersomeness. For example Iso E Super from my previous article should be called ”1-(1,2,3,4,5,6,7,8- octahydro-2,3,8,8,-tetramethyl-2-naphthyl) ethan-1-one”. Just try to imagine how daily life in laboratories would look like if chemists used only systematic names: “Dr. Jones, could you please pass me that flask with cis-3-dimethyl methoxy….”

That is why usually trivial names are used instead. A trivial name is a kind of nickname for a substance. It doesn’t tell us anything about its structure, but it is short and easy to remember. Vanillin, dichlorvos, promedol, paraben – all these are trivial names. Different companies may sell one and the same substance under different names, trade names that is. Thus, 2-(acetyloxy)benzoic acid is a systematic name, acetylsalicylic acid – a trivial name and aspirin is a trade name. Producers of synthetic perfumery materials love giving loud beautiful names to their goods. Very often aldehydes (real aldehydes) get the names with “-al” at the end. But clever market experts know about perfumers’ fancy for aldehydes and sometimes an “al” name is given something completely different. IFF’s Clonal is actually a nitrile, Givaudan’s captive Mystikal is a carboxylic acid. Just the same trick as the producers of “aldehyde C-14” once played.

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).

 



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esteban747
esteban747

Very informative and interesting piece.

Jan
29
2017
esteban747
esteban747

Very informative and interesting piece.

Jan
29
2017
antihero
antihero

I feel like I have just eaten a Warhead.
I guess I can't say "aldehydic" anymore in writing a review.

Thank you!

Jan
29
2017
Labaloo
Labaloo

Lovely! Thank you, Mat!

Jan
28
2017
nhledger
nhledger

another very interesting article Mat, thanks

Jul
29
2016
pkiler
pkiler

Thanks. We've just bedn having a discussion on the higher "aldehydes", C14 - C22, that are not even aldehydes...

Jun
19
2016
gordbrad
gordbrad

this is a wildly interesting and informative article. thanks!

Calvini--when i saw your comment about 'unhealthy' i made a disgusted noise. LEARN MORE: EVERYTHING AROUND YOU, even granola, baby tears, and unicorn sweat, IS MADE OF CHEMICALS.

There is no virtue in ignorance, and 99.99999% of modern scents use aromachemicals which have long histories of safety and careful testing. spreading fears about chemicals leads to such horrifying developments as the anti-vaxxers. READ AND LEARN MORE.

Apr
18
2016
Maeva
Maeva

Thank you for this informative and fascinating article, Mat!

In my ignorance, I didn't know that aldehydes and parabens were present in nature, and I didn't know that Chanel N. 5 wasn't the first aldehydic fragrance either. I even think Chanel itself claimed that it was. It's funny how aldehydes were mythologized at some point in history. But if the legend generates profits...

Now I can imagine why they named Avon's Lyrical like that in Europe (it was called Goddess in the US), because it contained Lyral.

Apr
17
2016
Calvini
Calvini

Wow.. The world of synthetic perfumery sure is complicated, and sounds extremely unhealthy -.-

Apr
17
2016
fullbottleworthy
fullbottleworthy

As a chemist, I really appreciate this article! Thank you so much for infusing science into the Fragrantica articles. I love it when I can get more exposure to fragrance chemistry, since I do not work with these types of molecules in my lab. As someone who knows all about aldehydes, I always wondered why we have this characteristic "aldehyde" smell in Chanel No 5 despite the fact that there are so many aldehydes with a wide range of scents. I think it's hilarious that they marketed the lactones as aldehydes because aldehydes were in demand! LOL Thank you for all this information!

Apr
16
2016
kishka
kishka

Very useful and knowledge of course is power. Helps to dispel some of the B******T in the perfume industry. My motto being - if you like the smell - then its good. Thankyou!

Apr
16
2016
ComfyCat
ComfyCat

Great article, Mat! I hope more like this are to come :))

Apr
16
2016
nurStress
nurStress

Parabens are esters of para-hydroxybenzoic acid. True, there are many different ones.

By the way they are mostly pretty harmless, you can find a big amount them in some berries like cranberries and blueberries. If those berries was not an indivisible God creation but human-made mixture, for example shampoo, it should be banned by regulation rules because of parabens :)

Apr
16
2016
odie
odie

Thank you for this informative and descriptive article. I did not know that a name like "paraben" was just a banal one and could be used to describe more than one substance that a company trades in. I learned may new concepts by reading this article Matt. It makes me more knowledgeable of what I am spraying/rolling on my sensitive skin

Apr
15
2016
HUEbris
HUEbris

What a great informative writing the perfumery wants to hide...

Apr
15
2016
hellovascent
hellovascent

And yet another article by Gospodin Yudov it is a sheer pleasure to read. Bolshoe spasibo.

Apr
15
2016
nikoleta1
nikoleta1

Wander what is % of synthetically formulated vs botanically extracted ingredients in perfumes? Probably most cheaper perfumes all synthetic, and niches are botanical?

Apr
15
2016
nurStress
nurStress

Thank you very much!

bibibling: what Zhukov and Shestakov have done was isomerisation of 10-undecenic acid in an acidic medium. That means that they wanted to obtain lactone. So they knew that what they have synthesized was γ-undecalactone, that's for sure. The term "aldehyde C-14" appears only when suppliers started to sell it to perfumers.

Apr
15
2016
Fragrant Desert
Fragrant Desert

Hahaha .. dumb on me. Floral Aldehydes are my favorite group and I'm still like "wha?" .. lots of chemistry is what I'll say.

Apr
15
2016
nikoleta1
nikoleta1

Very smart article, chemist's approach to explanation of aldehydes.

Apr
15
2016
joenick68
joenick68

Very good article, I'd wished I would been more into my chemistry lesson..

Apr
15
2016
bibibling
bibibling

Thank you for putting to bed the mythology that Chanel #5 gave birth to aldehydes and that all aldehydes only smell like whatever mysterious note Chanel #5 has.

I had no clue about those shameless naming practices though! I really feel like calling something "Aldehyde C-14" shouldn't be allowed. I mean what's stopping me from getting a bottle of cat pee and giving it the trivial name of sparklyglitterrosesandgumdropsal?

Do you know if there was a backlash against Zhukov and Shestakov for making a misleading name or were people too busy swooning over Mitsouko and rushing to make copycat 'aldehydes' to care?

Apr
15
2016
chayaruchama
chayaruchama

Thank you, thank you!

Apr
15
2016
Jane_Wonder
Jane_Wonder

wesleyhclark: did it in latin)

Apr
15
2016
wesleyhclark
wesleyhclark

Another fascinating article! You are my favorite writer. BUT... if you do the article in English, can you translate the graphics from Cyrillic into English, please?

Apr
15
2016
Perfumeaddict777
Perfumeaddict777

I didn't really know much about aldehydes except that it seemed to make perfume stronger and last longer. I appreciate this article, it's very interesting. Now i want to go out and test more perfumes with aldehydes and try to sniff out different kinds! Thank you

Apr
15
2016
perfumecritic
perfumecritic

What a great article, Mat! I learned so much from this and will undoubtedly have a greater appreciation for aldehydes in perfumery.

Apr
15
2016
henri345que
henri345que

Congratulations for the article Mat! Nice to see someone going further on aldehydes and showing that there is much more than the ones that are in Chanel No 5

Apr
15
2016

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