Olfactory Chemistry: Macrocyclic Musks- A Whiter Shade of Musk

When it comes to musk it is not like we as chemists don’t know the chemical structure of the natural source. In 1926 Leopold Ruzicka isolated and chemically identified the molecule found in the musk deer which primarily gave musk its smell and he called it Muscone.

muscone exaltone

In the structure above what you see is a 15-membered ring of carbon and importantly the bold wedge attached to the CH3 represents a methyl group which is coming up from the plane of the page. If that wedge was dashed that would indicate the geometry was going behind the plane of the page this is how we show three-dimensional geometry on the page. This orientation is very important because if that wedge was dashed and the methyl group was oriented differently the odor profile of muscone is significantly lowered. It is exactly the difficulty of getting this geometry just right that gives synthetic chemists so much difficulty in making molecules easily. In 1926 Dr. Ruzicka didn’t even try because he discovered if you just leave the methyl group off and  synthesized the rest of the large ring you still had an acceptable musky profile. Thus was the first synthetic macrocyclic musk created, Exaltone.

musk graph

These all-carbon large rings were difficult to synthesize but if you replaced one of the carbons in the ring with oxygen or added additional oxygen, those were much easier to make. These molecules are called lactones and the smaller versions of these also play a large part in perfumery.  As you can see in the table above the same issue with the muscone still existed as if the methyl group was pointed away the odor profile was much more muted.

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Dr. Robert Grubbs and Nobel Prize

The big breakthrough for the all-carbon macrocyclic musks came in the 1990’s when Prof. Robert Grubbs published a technique called catalytic ring-closing metathesis. That’s a lot of words but what it comes down to is now there was a chemical reaction which allowed a synthetic chemist the ability to form almost any size carbon ring imaginable. This is one of the most powerful synthetic methodologies of the last thirty years and Dr. Grubbs received the 2005 Nobel Prize in Chemistry for this work. It fired the imagination of chemists everywhere and in the fragrance industry it sparked a bit of a race into which firm could produce and patent the best synthetic musk.

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Alberto Morillas

As for the use of these macrocyclic musks these are the musks most commonly referred to as “white musks”. The term was coined by perfumer Alberto Morillas as he combined a number of these musks to create a “cotton and linen” accord for Emporio Armani White for Her in 2001 and called it a white musk accord in the press release. M. Morillas would use the same white musk cocktail in one of my all-time favorite fragrances Thierry Mugler Cologne later that year.

These musks are also the musks that some people are not able to discern in a fragrance. We term that as being anosmic to musk but that is far too general a term. These very large molecular weight molecules hold a special property that we don’t understand very well which causes certain people to not detect them. The same people who can’t detect these macrocyclic musks can often smell either of the polycyclic or nitro musks and anosmia to those is far less common.

Mark Behnke

New Perfume Review Amouage Journey Woman and Journey Man- The First Steps of the Second Cycle

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My admiration for Christopher Chong has been writ large across numerous reviews of the Amouage fragrances he is the Creative Director for. His vision has made Amouage into one of the great perfume houses of this century. I believe this collection he is responsible for creating has only peers, and damn few of them. Throughout my time corresponding with Mr. Chong and the influences which motivate him I have come to “know” him, though we have never actually met. With last year’s release of Fate Woman and Fate Man “the first cycle of the Amouage narrative” came to an end. Now with the release of Journey Woman and Journey Man we begin the second cycle which will delve into Mr. Chong’s life and is subtitled ‘Portraits of a Life’.

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Christopher Chong

Mr. Chong was inspired by Shanghai Deco and Chinese film noir. The common thread to both of these is a weaving of distinctly western elements into an eastern undertaking. During the 1920’s and 30’s there were many striking examples of art deco buildings erected in Shanghai. When I look at this purely western form of architecture it is striking to me how well it meshes with its eastern surroundings. There seems to be no disconnection. The same can be said of Chinese cinema over the last 100 years as it has evolved by adding its own flair to traditional movie tropes and then, interestingly to me, these new interpretations find their way back into Hollywood releases. This is the theme of Journey Woman and Man the meshing of distinct western influences like noir and deco with a Chinese aesthetic to create something wholly unique. The perfumers Mr. Chong chose to help him bring this to life are Alberto Morillas and Pierre Negrin.

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Shanghai Park Hotel

Journey Woman feels very Deco inspired to me as it has jasmine tea, saffron, cypriol, and osmanthus provide the eastern details on the solidity of the western foundation of honey, cedar, and tobacco. When I asked Mr. Chong what it was about Deco that drew him to it he responded, “my reason for loving it is quite simple. I love the form, shape, and the period.” As a result Journey Woman is a fragrance which carries an unusual simplicity for Amouage but the “form” and the “shape” of this perfume is fascinating for those clean architectural lines.

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The Paramount in Shanghai

Journey Woman might have the softest opening of any Amouage fragrance to date, based on the opening moments I would bet many would not suspect it was an Amouage fragrance. The top notes of jasmine tea, nutmeg, apricot, and osmanthus provide luxuriance without heft. It lilts and draws you in with the intersection of so many beautiful notes precisely positioned. Honey and jasmine provides a bit more volume as Journey Woman begins to arise from the early delicacy and now begins to take more shape. The honey in particular provides a matrix for the osmanthus to blossom upon and the jasmine tea transforms into jasmine sambac in all of its full indolic glory. Cedar is used to start refining the emerging shape into eventual form. The base notes achieve the melding of west and east as tobacco, saffron, vanilla, and cypriol all flow together into a smooth montage of both sets of influences.

I suspect many are going to be surprised at this light Amouage perfume. I would encourage you to not try Journey Woman with prior expectations weighing you down. Embrace this new beginning of the second cycle and you will be heartily rewarded.

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Maggie Cheung as actress Ruan Lingyiu in "Centre Stage"

If you need something a little more “Amouage” to help you start the second cycle Journey Man will provide that transition. Journey Man feels very cinematic to me it could even have a logo “composed in Technicolor”. Mr. Chong has been a fan of Chinese movies for his entire life and he wrote to me, “I was brought up with all kinds of Chinese Cinema…for me it means entertainment and family time.” It is an almost universal thing to sit in a movie theatre watching larger than life images and losing yourself in the story unspooling from the projector behind you. Journey Man unspools in larger than life accords of Sichuan pepper, neroli bigarade, juniper berries, along with the tobacco and cypriol we saw in Journey Woman.

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Bruce Lee

The use of the Sichuan pepper in the top notes of Journey Man may feel like it is in living color but it is also very Chinese. It is also the smell of home cooking to Mr. Chong I suspect which makes it appropriate to be the opening note. It is stirred in with a very green cardamom and an incredible neroli bigarade. This creates an interplay of shadow and light flickering to life. Shadow wins for a while as juniper berries and incense take over. Geraniol and rose push back against the twilight while a haze of tobacco hovers above it all. Journey Man tells most of its story right here and it is where it lingers on my skin for many hours as the olfactory chiaroscuro continues to evolve throughout the day. The base notes are a fit denouement as tonka, cyrpriol, and ambrox finish things off.

Journey Man is much more typical of what many have come to think of as an Amouage fragrance. I found it very comforting despite the characteristic intensity. I definitely felt this biopic of Mr. Chong’s life come to reality on the olfactory silver screen.

Journey Woman had 12-14 hour longevity and Journey Man 10-12 hour longevity on me. The sillage for both was average.

I am so looking forward to the remainder of the fragrances in this second cycle. As Lao Tzu says, “A journey of a thousand miles begins with a single step.” Journey Woman and Journey Man have taken two confident steps into this new journey of Mr Chong’s and Amouage.

Disclosure: This review was based on bottles of Journey Woman and Journey Man provided by Amouage.

Mark Behnke