Fragrance Ingredient: Musks

It would not be an understatement to say that there is hardly a fragrance that does not contain at least one musk component. The power of musk to refine, balance, fix and accentuate compositions without adding a heavy note is exceptional, and no other ingredient can rivals musks in terms of their popularity and versatility. Musk forms the pedestal upon which the entire composition rests. It fuses sensuality and warmth even into the simplest of compositions, and there exist numerous fragrances based solely around musk.

The term musk/musky in perfumery refers not only to the specific ingredients, but also to the abstraction of complex odours of natural musk, which range from balmy, sweet, and powdery to fig-like, animalic, leathery, spicy, and woody. As Philip Kraft notes in his great overview of musks, “the more one studies its character [that of natural musk tincture], the more contrasting, vibrant and oscillating it becomes: repulsive–attractive, chemical–warm, sweaty–balmy, acrid–waxy, earthy–powdery, fatty–chocolate-like, pungent–leathery, resinous–spicy, fig-like, dry, nutty and woody, to give just some impressions” (144). The abstraction of these complex impressions into “warm, sweet, powdery and sensual” is what can be understood whenever “musky” tonality is mentioned. ...

The history of musk is old, mentioned in many ancient texts. Ancient Muslim mosques were said to have been built with the musk mixed into the mortar. As the sun shone on the building, it would have been filled with the beautiful scent. Natural musk (often referred to as Tonkin musk due to the fact that the best quality musk was Tonquin musk from Tibet and China) is the dried secretion from a sac in the abdomen of the musk deer (Moschus moschiferus L.) that at one time inhabited the area as far north as Lake Baikal. The cost of musk has always been exorbitant due to the fact that it took lives of a hundred and forty deer to produce a kilo of musk. In 1979, musk deers became protected by the Convention on International Trade in Endangered Species of Wild Fauna and Flora (CITES), and the importance of natural musk has declined further. Moreover, even prior to the signing of CITES, natural musk was eclipsed by the synthetic musk aroma-chemicals, which not only offered a more ethical solution, but also a more cost-efficient one.

However, musk deer is not the only natural source of the musk compounds. Ambrette seed oil, galbanum oil and angelica root oils allow for the isolation of elements that have a musky character. Thus, Jean-Claude Ellena explores the effect in his Angéliques sous la pluie (2000) for Frédéric Malle Editions de Parfums.

The discovery of the first synthetic musks is a by product of research on explosives. In 1888, Albert Baur, in the process of searching for new explosives noticed that the product of reaction of trinitrotoluene (TNT) and tert-butyl halides produced a pleasant odour. Musk Baur became the first synthetic musk, classified under the nitro musks category. In 1894 he produced Musk Ketone, which was said that resemble the natural musk fairly closely and until quite recently was among the popular perfume ingredients. The nitro musks (Musk Xylol, Musk Ketone, Musk Tibetene, Musk Ambrette, Moskene) possess a warm, powdery scent, with an ambery and animalic overlay. The sensual warmth of Musk Ketone as well as other nitro musks pervades the base of Chanel No. 5 (1921) and of many other fragrances from that period. Musk Ambrette’s heavy floral tone gave character to Nina Ricci L’Air du Temps (1948), and when it was withdrawn from the market in 1981, the reformulation of the fragrance ran into various problems, as the musk was not easy to replace.

Nitro musks fell out of favour in the 1980s not only because of the hazards associated with their production, but also due to their lack of stability. The new group of musks that arose were the polycyclic musks (Phantolide, Celestolide, Traesolide, Tonalide, Galaxolide), as well the macrocyclic musks (Habanolide, Thibetolide, Globalide, Velvione). In addition, various modern musks are becoming more and more important in the perfumery such as Helvetolide, Nirvanolide, and Muscenone. This list is hardly exhaustive, and it merely points out an incredible diversity among the synthetic musks, attesting to the popularity of these aroma-chemicals. From sweet powderiness of Galaxolide and metallic nuances of Habanolide to pear undertones of Helvetolide, the synthetic musks range dramatically in terms of their odour profiles.

The fruity side of the musks is explored by L’Artisan Parfumeur in the creation of Mûre et Musc (1978) and its sweeter, richer variant Mûre et Musc Extrême (1993). The addition of berry notes accentuates the fruity tonality of musk, leading to the harmonious composition. Woody and fruity accents of another musk ingredient, Moxalone, are juxtaposed with the sparkling grapefruit and red currant accord of Yves Saint Laurent Baby Doll (1999).

The radiant freshness accented by a metallic overtone made certain musks like Habanolide and Globalide particularly popular. These musks are sometimes referred to as white musks. The modern white musk accord was first created by Alberto Morillas’ Emporio Armani White for Her (2001), a combination of various white musks, exploring their elegant fresh facet in order to lend a gentle transparency to the composition. Emporio Armani White ornaments the glacier coolness of musks with tart sweetness of mandarin, spiciness of ginger, and verdancy of black currant, fig leaves and mint. Moreover, the white musk theme appears in fragrances like Thierry Mugler Cologne (2002), J.Lo Glow (2002) and Serge Lutens Clair de Musc (2003). The hot-ironed fabric feel of Habanolide lends elegance to the gourmand sweetness of Christian Dior Hypnotic Poison (1998).

Functional products are among the biggest consumers of musks, due to the fact that musks deposit well on fabrics during washing, and indeed a few musk odorants entered fine perfumery only after being made popular by the fabric softeners. Galaxolide is one such example. Interestingly enough, its association with freshly washed fabric was explored in Estée Lauder White Linen (1978), where it was used at the concentration of 20%. Its characteristic sweet and powdery warmth also pervades Lancôme Trésor and Caron Parfum Sacré.

In fine fragrances, due to the fact that the anosmia to musks is extremely widespread, even among the perfumers (indeed, rivaling even the very common anosmia to beta-ionones, which are responsible for the violet notes), the compositions usually include a cocktail of different musks, in order to ensure the unique effect of musk.

The search for the new musk odorants is always continuing, and my overview should be seen as a mere tip of the iceberg. The new great musk quest can lead researchers to the most unlikely places and can turn them into the alligator hunters! Thus, it was reported that a particular type of alligators emits a musky secretion, which was subsequently isolated. However, the alligator musk is not to be the next perfume ingredient as the compound turned out to be sweet and rosy, its musky undertone a sole product of impurities.

References: Calkin, Robert and J. Stephan Jellinek. Perfumery: Practice and Principles. John Wiley & Sons, Inc., New York, 1994.
Gautschi, Markus, Jerzy A. Bajgrowicz, and Philip Kraft. “Fragrance Chemistry—Milestones and Perspectives.” Chimia 55 (2001): 379-387.
Kraft, Philip. “Aroma Chemicals IV: Musks” in Chemistry and Technology of Flavors and Fragrances, ed. by David Rowe. Blackwell Publishing, UK, 2004.
Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Odds and Trends: Recent Developments in the Chemistry of Odorants, Angew. Chem. Int. Ed. 2000, 39, 2980–3010.

Comments

[parislondres]

Fascinating article dear V! I do enjoy some perfumes with musk. In Udaipur last year, a Gujarati perfumer with a tiny kiosk called Gujarati Perfumes in one of main market areas, showed me some musk that was thick and black in colour and he mixed some of that musk with saffron oil in front of me. The result was quite something.
If I can find it when I see you I will make sure you smell it. Potent stuff!

Hugs!

[kaie]

Great article! I love to read about this topic and I like many perfumes with musk very much, especially the white kind. I also like the musky note in Kenzo Flower.

[julien]

Great to read.
There are truly two types of musk:the animalistic one,we can find for example in Musc Koublai khan,very strong and uneasy to wear sometimes and the "white"one,pure,like Body shop or Clair de Musc.I also love musk with amber and vanilla from MUSC RAVAGEUR, it's like the smell of a perfect skin.

Have you tried Narciso rodriguez for her?
In france,women are so crazy about it and its musky scent.

[Håkan Nellmar]

Wonderful article! I learned a lot from it. Thank you.

[Laura]

This is SO interesting, V! I'm so glad to know more about this fascinating note/ingredient.

[Marcello]

Excellent job, V! I like the names of those poly- and macrocyclic musks. Do you know if they are trademarks?

[Katie]

Really a lot to chew on there, V. I do like my older scents that are clearly animal spiked, but I am quite happy and content with the fact that we have so very many animal-free options nowadays. I know some folks bemoan the perceived loss of the animal musk, yet I honestly think we make up for that scent-loss with an improved humanity for it.

I did not know that about explosives and synthetic musks. Wow. This gives a whole new layer of meaning to the phrase "bombshell perfume!"

[Test Subject]

I was also intriguied by the story of Albert Bauer and his experiments with TNT. I give him a lot of credit for exploring the use of his new compound in the fragrance industry. I suspect the average chemist would have simply noted that it smelled nice and left it at that.

[Håkan Nellmar]

Marcello, I'm sure the names are trademarks. Galaxolide, for instance, is IFF's name for hexahydro-4,6,6,7,8,8-hexamethyl cyclopenta-#-2-benzopyran.

[Tania]

Nice work, you busy researcher, you! Musks are fascinating. I can't figure out if their wide use in laundry detergents and the like is why I often think of musk scent as the smell of cleanness, or if they were selected for detergents because they smelled clean. Which came first?

By the way, I am so exhausted that I read "Nina Ricci L'Air du Temps" as "Ninja Ricci..."

[helg]

Hi there , dear V !

What I 'd really like to know , being a musk lover par excellence , is which musks are used in each composition , because the whole subject of synthetic musks is very dangerous for health and the environment I read (nitromusks etc ). Some polycyclic ones are deemed safer , I think , but how can one be sure of which is used each time? They always use poetic terms that pertain to smell and not composition.......
BTW , Narciso is a fabulous musk fragrance : quite something. If you haven't tried , I am sending some along pronto !!

[helg]

Forgot to say - what I mean is :"is there a safe perfumer's resource on which musk is used in which composition? "
The examples used here by you are excellent , but numerous of my favourite perfumes contain musks and I think it would be a wonderful resource if one classed them according to the musk ingredient used (just a thought) , provided one can have access to info of course.

[Tania]

By the way, I recall Chris Brosius mentioning (when we saw him in his shop) that they've recently found a way to extract musk safely from the musk deer without killing it, which could bring the use of natural musk back. Don't know how I feel about it. I still have a knee-jerk "poor little cute Bambi" feeling about the little critters, and knowing the ill treatment civet cats go through, I'd be skeptical about claims that the procedure is humane.

[mreenymo]

How on earth do you have time to research all of this and write these long, informative pieces?

I think you must be a genius! :):)

Hugs!

[Marcello]

Thanks, Håkan! Reason I ask is because the synthetic musks reminded me of an e-mail I received (recently) from Dr. Ralf Sieckmann. Three years ago he was involved in a legal battle against the Deutsches Patent- und Markenamt (the German patent and trademark office) re: "non-traditional marks". In this case (filed as RS C-273/00 on December 12, 2002) the European Court of Justice declared that:

"2. In respect of an olfactory sign, the requirements of graphic representability are not satisfied by a chemical formula, by a description in written words, by the deposit of an odour sample or by a combination of those elements".

"NOT satisfied by a chemical formula"... that bit sounded interesting, to say the least. When I read V's article, I wondered to what extent this is effective worldwide, and if manufacturers are always successful in registering their odorants.

Under the European ruling as stated above, the description "hexahydro-4,6,6,7,8,8-hexamethyl cyclopenta-#-2-benzopyran" is not sufficient to register Galaxolide as a trademark. To make things worse, some offices simply refuse to register smells as trademarks, like the Benelux Trademarks Office (BTO): http://www.bmb-bbm.org/gb/pages/faqantwoorden.html#4

All this is none of my competence, but I thought I'd share this with you. Since it's a bit off-topic here, I'll just add a link containing media reports on the Sieckmann case:
http://www.copat.de/markenformen/mn_eugh_kom.htm

[Test Subject]

Marcello, your comments were very interesting. I am no expert in fragrance patents or trademarks but I can share perspective from someone who has worked with technological intellectual property. There is certainly inconsistency in the way intellectual property is handled around the world. I'm sure you can patent a new synthetic molecule and it's method of synthesis or method of extraction. Trademarking is always more murky. I suspect it is easy to trademark the name of a molecule but much harder to trademark the actual smell of the molecule. Part of this must relate to the legal headache that would result. In essence, we have no objective way to discuss smell in a legal setting. For instance, we can't say that a smell is 5% different than another. Perhaps as the scientific community progresses in its understanding of olfaction we may one day have a quantitative measure. But for the time being, we rely on expert noses. Such evidence is intangible for a court of law. Anyway, I'm sharing the thoughts that pop into my head when I think about this issue. I hope there is some expert out there who can elaborate further.

[Rafael]

Once again, fascinating review dear V.
Some other great musk ingredients include ethylene brassilate (Musk T), Exaltolide and Cashmeran (diffusive, spicy, musky-like odor with strong floral reinforcement).
Surfing the net I found a very interesting article on musks (and phtalates) conducted by Greenpeace where the amount of different musk materials is stated for some very well known fragrances.

http://www.greenpeace.org/raw/content/international/press/reports/phthalates-and-artificial-musk.pdf

Dear V, do you think that for one of your next fragrance ingredients reviews, you could write something about the «acquatic» notes like Florhydral, Floralozone, Maritima, Scentenal, Calone, etc. It seems everybody hates the latter one after such repeated and extensive use!

My best, Rafael.

[BoisdeJasmin]

Dear N, thank you! Oh, I would love to smell that musk. Of course, you have also mentioned saffron, which I love. As far as I understand, Gujarat is one of the main jasmine growing areas in India. I would love to visit. So far, I have not made it past Delhi and Maharashtra.

[BoisdeJasmin]

Kaie, I love the musky note in Kenzo Flower as well. It has a very subtle pear nuance, which I like, and it uses some of the newest musk ingredients.

[BoisdeJasmin]

Julien, thank you. I think that you pointed the difference quite nicely. I like examples from both groups, although white musks took me longer to appreciate, and there are many compositions that overuse them. However, when they are done well (as in Emporio Armani White for Her), they shine.

I really grew to like Narciso Rodriguez for her, and you are inspiring me to revisit it.

[BoisdeJasmin]

Håkan, I am glad! It is fun to research these topics.

[BoisdeJasmin]

L, it is fascinating. I love to understand more on the science of fragrance, to read and to write about it.

[BoisdeJasmin]

Marcello, thank you! Yes, all of them are trademarks, and you can find out more on specific ingredients if you go to my perfume information page (I have links to most databases that are maintained by the fragrance suppliers).

[BoisdeJasmin]

Katie, I cannot agree more. I love the richness and complexity of musky bases of my fragrances from 20s-60s (natural musk was used till 1979 in fine perfumery), however I am all for ethical farming of ingredients. Moreover, there are many very good synthetic options.

Apparently, Musc Ravageur smells most like the natural musk tincture. Have you tried it?

Laughing out loud at your bombshell perfume reference!

[BoisdeJasmin]

P, I was intriguied by the story as well (and for the same reason you were). Fascinating how some discoveries take place.

[BoisdeJasmin]

Håkan, yes! For instance, Habanolide, Thibetolide, Velvione are the Givaudan trademarks.

[BoisdeJasmin]

T, chuckling over Ninja Ricci! Yes, you have been working very hard.

I think that musks in particular are favoured for laundry detergents is because they tend to have high hydrophobicity, which makes them adhere to fabric well during the wash. Many modern musks are also very clean smelling, which is not something one would say of the natural tincture.

[BoisdeJasmin]

E, NR for Her is a great musk. I have a few samples and a small bottle someone gave me a while ago. I really like it.

I doubt that you shall find that kind of information. However, do look through the link Rafael supplies below. It is quite information.

Nitro musks are no longer used, and there is no conclusive research on the topic of whether polycyclic musks have negative effects in the long term. Quoting from the article on musk by Philip Kraft, "As a consequence of their massive production
volumes, their excellent chemical stability, their non-biodegradability and their high
octanol/water partition coefficient, PCMs have bioaccumulated in fish and other marine
organisms, human fat and human milk [52]. Although no apparent toxicity has been
reported [10], possible long-term effects [53] are difficult to foresee, and more and
more PCM-free formulations appear on the market" (155).

At any rate, fragrance would be my last concern, because these musks are employed above all in the functional products.

[BoisdeJasmin]

E, I would love that kind of information, however I doubt that one can find it accessible all in one place. I am keeping my own little database, but the information in it comes from all of the articles I read, etc.

To be honest, I am not particularly concerned about the allergens in fragrances, as only a small amount of perfume is used anyway. Moreover, if you read enough on the topic, just about everything causes cancer. I do not know, maybe I just have too lighthearted of an approach to these things. Afterall, I lived through a Chernobyl accident in Ukraine.

[BoisdeJasmin]

T, I am also very skeptical about the humanity of that method.

[BoisdeJasmin]

R, hardly! This is just too interesting for me not to research the topic. I like to understand how things work (and smell). :)

[BoisdeJasmin]

Marcello, from what I understand (admittedly, little) and remember from my law school classes on intellectual property rights protection and trademarks, there are vast difference between the way the law is interpreted by the national courts, especially if you are talking about the European Court rulings. The trademarking of smell is also an extremely complicated topic.

Well, to make things more interesting: the same type of musk can be trademarked by different fragrance supplier companies. So, 15-pentadecanolide is sold as
Cyclopentadecanolide® by Symrise, Exaltolide® by Firmenich, Pentalide® by Soda Aromatics, and Thibetolide® by Givaudan.

[BoisdeJasmin]

P, thank you for such a great commentary on this topic. I think that you are right about the trademarking of smell. In these cases, it is not the smell that is trademarked though, as my aforementioned example of 15-pentadecanolide demonstrates. It is a very interesting topic, and I should probably read more on it.

[Test Subject]

With regards to musks and laundry detergent, I was interested by the comment about their hydrophobicity. I would have guessed that such character would tend to make them aggregate around any oils or grease rather than them having strong affinity for the fabric. But I guess I don't know much about the character of the fabrics themselves. Are the musks used only as odorants or do they actually have any cleaning function?

[BoisdeJasmin]

Dear Rafael, thank you for this fantastic link! I printed it out right away. I also like Cashmeran, and its ambery warmth seems quite special to me. Its floral side harmonized quite nicely with the jasmine in Thierry Mugler Alien.

I shall definitely have to write on aquatic florals and ozonic notes. I myself do not care for Calone, since it was so overused, however I still think that it is an interesting material.

[BoisdeJasmin]

P, I think that they are used for their scent alone, rather than for any cleaning function.

[dbeech]

Thanks for another fascinating research piece. I have always been intrigued by musk. After reading your article, I feel much more knowledgeable about this fragrance staple.

[BoisdeJasmin]

D, I am so glad to hear it! Musk is one of those notes that is present in every fragrance, and I am very intrigued by it too.

[helg]

Dear V ,

of course : the Chernobyl accident far surpasses anything of the kind of concern I raised ;-)
Thanks for your suggestions and the chance to find links here by knowledgable members who provide info.

[BoisdeJasmin]

Dear E,
I am glad that you found the links interesting and helpful. It is an important topic to research, and if it concerns you, you should do so. Happy to offer any help.

[lainey]

i was wondering if anyone where the musk in men's and women's aqua di gio comes from; is it the musk deer? also, can someone explain the term "white musk" again. i'm not sure i understand the difference between "white musk" and other types of musks. thanks so much!

[BoisdeJasmin]

Lainey, that musk is most definitely synthetic. Natural musk has hardly been used since 1979, and if so, only in very expensive fragrances.

There are numerous musk synthetics with varying odour profiles. White musk is just a description of certain musk synthetics which have a metallic, radiant freshness (white, clean) rather than balmy darkness. Hope that it helps to understand what white musk means.

[Louise]

Fascinating, informative article! As a musk lover since the early 1970s, I remember the sweetness and richness of animal musks in
oils such as RH Musk Oil.

The closest to those not-so-good for the deer old days, is perhaps the low-brow Coty Wild Musk Oil and the QVC shopping channel's Tova Signature.

I still miss the animal based musks, I'm sorry to admit though.

[BoisdeJasmin]

Louise, I am glad that you enjoyed it! I love the animalic sweetness too, to be honest. However, given the range of available synthetic musks, I am happy. Still, I would love to smell the real tincture at some point.

[bruno]

test

[aldona]

hi, does anyone know if the musk in Thierry Mugler's Angel is animalic? thank you :)

[anita loria]

Hi I work for Bloomingdales in new york, A woman past by me and she had a very nice musks fragrances on . I ONLY USE MUSKS, Iam 60 years young, she told me that she had musks body perfume, Please if you can email me some names of the musks that you have and how I can order them I would be very gratefull.
Thank you
Anita Loria
momhas5sons@aol.com

[Antique]

Hi. How it is possible to be registered? Me here to like.
Thanks.

[Jana Victoria]

Strange as it may seem, there is a delightful "musk" that comes from the ear wax of wolves. I have noticed it for many years-powdery, damp beeswax with Damascan rose. I do wolfdog rescue, and the more wolf in the animal, the stronger and more compelling the scent. My own ancient white wolf, Islay, has charmed many with his comforting scent. This is noticeable, of course, only as he is fairly clean and not covered in "wolf perfume", ie, dead things. I should add that this is different from the scent of fur, or of the more repulsive (to us) scent of wolves' marking glands.

Domestic dogs do not seem to have this same quality. I'm not sure if coyotes do, but I'll try to check next time one comes to rescue, if he or she cooperates!

[Boisdejasmin]

Jana Victoria, this is fascinating! Thank you for sharing. Wolves are such amazing animals.