Musk Series 3: The Many Permutations of Musk

In all of perfume speak, "musk" and "musky" has got to be the most casually utilized term, often taking on hidden nuances inadvertedly to the speaker, based on their own perception of the odoriferous molecules creating the impression. We had touched upon this issue while discussing the cultural perception of musk (Musk Series Part 1), peppered with anecdotes. We had also tried to shed some light into the differences between the natural essence (produced from the deer Moschus moschiferous L.) and the vast array of synthetic musks in the industry today on this article (Musk Series Part 2).

In the words of Philip Kraft “the more one studies [musk] 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” [1]. Still, beyond our interpretation (surely a personal matter) and the more clandestine issue of which ingredients are actually utilized in any given perfume, anyone immersing themselves into the fascinating subject of musks stumbles on another obstacle: What about the denominations that the companies and online boutiques give to their musks and musk notes themselves? What is "white musk", "black musk", "Egyptian musk" and so on and on to infinity? Let's try to find out in this guide.

White musk
The easiest to tackle, because of its ubiquity. You have probably seen the term in single-standing fragrances at the drugstore, such as the famous Jovan White Musk, and you have probably seen it in relation to the continuing success of The Body Shop's White Musk. The latter is comprised of the synthetic musks Galaxolide (7,7%), Tonalide (1,6%) a little Cashmeran (0,1%) for a total of 9.4% of white musks. Galaxolide (an International Fragrances & Flavours synthetic molecule with staggering popularity in the industry in both fine fragrance and functional products) gives a a clean, but also musky flowery-woody odour with a sweet, powdery nuance: You're probably well familiar with it through fabric softeners such as Comfort and Soflan and through detergents like Coral. White musk in perfumery therefore has become synonymous with a "clean", soapy and somewhat biting impression, with a passing floral tonality. Globalide (another musk synthetic, also called Habanolide) is often used in white musk compositions: A metallic smelling, fresh radiant musk which opens up the bouquet. Indeed its coupling with Helvetolide in Emporio Armani White For Her, by Alberto Morillas in 2001, gave rise to the term "white musk" as official perfume lingo beyond the brand names of yore ~its olfactory profile opposed to the balmy darkness of the prior nitromusks. The same synthetic (Globalide) enters the aldehydic musk Glow by Jennifer Lopez, accenting the fresh white floral components of the formula, while it also gives the cooly herbal-soapy feel of Mugler's Cologne and the baby-soft"clean" of Clair de Musc by Serge Lutens. It also outlives the blackberry top notes of the popular Trish McEvoy #9 Blackberry Musk.

Egyptian Musk
Even though the adjective might make you think that these musks come in their own little sarcophagi chanting in an unknown language, the reality is far removed from such exoticism. Simply put, Egyptian musk does not originate in Egypt, but is simply a variant of a musk blend in which the clean, scrubbed-skin nuance is the dominant part. The laundry day feel is there, much like with white musk (see above) but in general the effect is less screetchy and subtler to detect. Famous examples in use include the perennial Narciso For Her, where the fractialised patchouli (keeping the cleaner aspects) and the synthetic white flowers are highlighted by the clean muskiness of the base and smoothed out by a recent amber molecule, Amberlyn and a hint of honey. The Cuban born designer was inspired by an Egyptian musk oil he used to buy in New York City along his friend and muse Caroline Bessette-Kennedy. (It turns out it was Abdul Kareem's Egyptian Musk). The Egyptian musk part is easier to detect it if you test the Musk For Her by Narciso Rodriguez in the same line of fragrances (for a breakdown of the confusing concentrations of the line, please refer to this guide). There, Egyptian Musk stands almost solely on its own. They have recently updated the line with specific Musk editions.
The combination with "clean" patchouli seems to be an approved shortcut for this variant. Reading through this recipe for homemade Egyptian Musk, you come across the mention of patchouli leaves and rose petals entering the composition in a vegetal-base oil.
Several indie perfumers such as Ava Luxe, Dawn Spencer Hurwitz, Sonoma Scent Studio, as well as etailers (the likes of Nemat, Sweetcakes, Utopia Oils et al) make Egyptian musk fragrances. Its popularity has to do with its sheer subtlety, it would never offend a scent-phobic environment and it is pleasant to have around when you don't feel like perfume. The popular Egyptian Goddess oil from Auric Blends is a good example of a plain, unadulterated Egyptian musk with no other tonalities included: it smells a lot like fabric softener! You might also encounter this as "Pearl Musk" such as chez Ava Luxe, who offers both this and an Egyptian Musk version.

African Musk
Despite the "wild" evoking name, African musks usually are variations on the theme of Egyptian musk, soft, clean, inoffensive with an inclusion of sweet vanilla which makes them even cuddlier.

Red Musk
A chromatic variation in the name which was inspired by the "white" adjective, it bears an incense note reminiscent of the Eastern temples. Several etailers provide "red musks".

Black Musk
Similar concept with red musk, but this time with a woody, somewhat dirtier background, although not exactly animalic.

Blue Musk
Another variation poised on colour colding, this is close to white musks, with perhaps a sweeter musky nuance, a little softer and close to African Musk. If a manufacturer makes both Blue Musk and African Musk, it would be advised to try out before investing in both.

China Musk
Inspired by Body Time's China Rain, China musk types usually feature a distinct aldehydic and green top which brings on a refreshing feeling. Halfway between the metallic feel of white musks and the suaveness of Egyptian musks, China musks are saturated with light and are very pleasant. Ava Luxe makes an exceptional speciment termed China Musk.

Oriental Musk
A slight tweek on the China Musk idea (see above). Usually brought by jasmine inclusions and powdery background. Ava Luxe has one in her line.

Tunisian Musk
Generally the term refers to a sweet variation on the clean Egyptian theme (see above). Some manufacturers offer both Egyptian and Tunisian versions, so there is a slight twist in there. Dawn Spencer Hurwitz as well as TheParfumerie.com offer their versions.

Turkish Musk
Inspired by the traditions of tea and exotic leathers brought through the Silk Road to Constantinople, perfumers have come up with a musk blend that uses tarry topnotes to denote black tea and leathery nuances. Drier than the African-termed musks and with a little bit of sophistication, while still a wearable musk for layering or wearing alone. Dawn Spencer Hurwitz has a nice offering in this category.

Tibetan or Himalyan Musk
A variation seemingly close to the real Tonkin musk tincture but in reality not even close. These are warmer, sweetish interpretations presented by etailers and street vendors which can be very pleasant and inviting with good lasting power and hushed tonalities. Nemat makes a lovely Himalayan Musk oil which is supreme for wearing alone or layering purposes under other fragrances or oils to make them warmer and softer.

Nude Musk
I took the term used by Ava Luxe's fragrance to denote this category which also includes Perfect Veil by Creative Scentualisation and Sonoma Scent Studio Opal (for a comparison review of all three, click here) just because it's so erotically charged. This is a category which is meant to smell like "your skin but better", obviously a very popular demand and considered quite sexy (the skin-on-skin concept). It takes a lightly citrusy top (bergamot) and rounds it out through sandalwood and other creamy notes, blending into the skin where it smells as if you rolled into bed after a shower: That would be the scent you'd leave on the sheets. Suggestive, I know...The permutation with sandalwood was famously introduced in the 1970s with Bonne Belle's Skin Musk, Sarah Jessica Parker's longtime standby (this is now made with a slight reorchestration by Parfums du Coeur).

Wild Card musks (or anything goes...)
Some of the musks which you will encounter in your galivanting among fragrance lines are imaginatively named with poetic overtones leaving you wondering what they entail. Dawn Spencer Hurwitz has a whole array of unusual musks. Among them she makes a terrific animalic musk called Almadina Musk, which although reminiscent of the Arabian Al Madina, is in fact a leathery (lots of castoreum) and green marvel which projects with swagger and is highly recommended as a stand-alone fragrance. The Body Shop has a similar case of a musk which is not really musky: Japanese Musk is really a chypre in the manner of powdery chypres of old (see Ma Griffe); starched, cool, delightful and wonderful on a handkerchief tucked inside a purse.
DSH Special Formula X is a skin-friendly and erotic perfume that evokes boyish musks of yore, presented in the plain and longer lasting Extreme version. Dawn's Old School Musk is reminiscent of the 70s specimens specifically, such as Kiehl's as well as Houbigant's and Dana's, slightly greener and animalic. The touch of ambergris at the base makes it a bit like salt-water dipped skin.
The Fragrance Shop boasts an Almadina Musk too which they describe as "a spicy bitter musk with animalic undertones". Coty on the other hand makes the wonderful old barber-shop evocative Wild Musk which has a fougere overlay over the musky base. A retro fragrance with warm, inviting and lightly masculine accents, superb! Sonoma Scent Studio makes a spicy musk, called Sienna Musk, which is truly wonderful. (for a full review, please refer to this link)

Although mentioned in passing above, some etailers such as The Perfumerie.com feature lots of ethnically named musks, such Nigerian Musk (green-ish and named as a variant of Egyptian obviously; same with Tunisian, Indian etc). Generally they indicate what kind of "blend" they fit into, but trying out is always recommended first. As with everything...

The Musk Series will continue with lots of other interesting info and reviews.

[1] Kraft, Philip. “Aroma Chemicals IV: Musks” in Chemistry and Technology of Flavors and Fragrances, ed. by David Rowe. Blackwell Publishing, UK, 2004
Photograph of Lisa Lion by Robert Mapplethorpe. Perfume pics via parfum de pub

Musk Series 2: The Natural and Everything about Synthetic Musks

The beauty of musk's scent is that when you smell it on a person's skin, it's hard to tell where one aroma ends and the other begins. "I can feel you on my skin", says one lover to another...The fascinating subject of musk, its origin, its synthetic replication and the multiple variations, surfaces from time to time when we wonder what is hidden in our favourite fragrances ~and not only...

"Not limited to strong perfumes of questionable taste, musk is in fact the basic ingredient of practically all perfumes, from the most expensive and refined French florals to the sleaziest reek of high school hoochies. Everything in your medicine cabinet contains musk: soaps, shampoos, powders, cosmetics, bath oils, even your toothpaste. It is an ingredient in household cleansers, laundry detergents, insect repellents, and almost every other commercial product that requires fragrance - including food. Does the label say "artificially flavored?" Musk is added to fruit flavors, vanilla, chocolates, licorice, hard candy, chewing gum..."[1]

So where do these musks come from and what are synthetic/white musks?

Short History of Musk Use
Musk is the essence coming from a glandular secretion of the male Tibetan musk deer (Moschus moschiferus L), considered an aphrodisiac (as well as a spiritual fragrance in the Muslim world) in the past. It also fixes and balances a composition , refining it in the most plesasurable and sensuous way and allowing floral and resinous ingredients to flourish in it. Its first historical appearence is in the 5th century BC when it is mentioned in the Talmud (Brachot 43.) as an animal-based fragrance. Despite mentions of the supreme smell of the panther, the creature with the most divine scent imagineable according to the ancient Greeks, no reference per se is made in classical antiquity. In the 6th-century Greek explorer Cosmas Indicopleustes references it as a raw material of Indian origin. It took the Arabs and Byzantine perfume makers for it to rise as an aphrodisiac especiall during the height of the Abbasid Empire. The spice and silk route soon took the aromatic essence aboard and the string of languages that reprised the Sanskrit muṣká (denoting testicle, the source of the musk pod) ~via Middle Persian mušk, Late Greek μόσχος (moschos), Late Latin muscus, Middle French musc and all the way into Middle English muske~ is a journey into its aromatic signposts. In the 1970s musks soared: "In response to the "back-to-nature" ethos of the hippie movement, American perfumers on both coasts sought alternatives to traditional French perfumes. Around 1970, both The Body Shop* in Berkeley, CA, and Kiehl's in New York City introduced single-note "essential oil" fragrances". [2]

*In 1987 The Body Shop was taken over by a huge English firm of the same name, taking over the Musk oil that was synthesized in the 1970s and re-introducing it as White Musk, which is comprised of Galaxolide (7,7%), Tonalide (1,6%) a little Cashmeran (0,1%)for a total of 9.4% of white musks.

Origin and Scent of Natural Deer Musk
The musk deer (moschus moschiferus) is a small, inofensive creature living in Pakistan, India, Tibet, China, Siberia and Mongolia and only the mature male can produce musky odour in rutting season. The best quality musk used to come from Tibet (Tonquin/Tonkin musk) and China, while products from India and Siberia were considered of inferior quality. The practice of extracting the musk pods from the deer however is very difficult, as they're close to the testicles of the animal, and becomes fatally cruel (a kilo of musk necessitated the loss of between 30 to 50 deer), rendering the practice nowadays extinct. (According to Christopher Brosius however , there are currently ways of extracting it without harming the deer being examined ,which could bring back the practice of using real musk). The precious pods (worth twice their weight in gold) were dried in the sun, on hot stones, or by putting them in hot oil. The resulting black granular "musk grain" is used in alcoholic dilution, called tincture.
Natural musk in its raw state is pungent, with a strong pervasive urinous (ammoniac) smell that borders on the somewhat fecal and needs storage and considerable dilution for it to unfold all its potential. Still, The cultural perception of musk varies significantly, often swayed by the smeller's twisted impression of what they are smelling, as discussed in our Musk Series Part 1. Most common descriptors state animalic, earthy and woody notes or baby's skin scent, yet when perfumers talk about musk they refer to muscone, the very core of the musk essence devoid of the other ingredients that are included in natural musk (such as ammonia, cholesterol and animalic compounds with resinous odoriferous characteristics).

Other Natural Sources of Musk
The matter is further complicated by the reference of musk in relation to other animals from which glandular substastances are exracted: Ondatra zibethicus, the muskrat (ondantra zibethicus) a rodent, the Musk Duck (Biziura lobata), the muskox, the musk shrew, the musk beetle (Aromia moschata), African Civet (Civettictis civetta), the musk turtle, the alligator of Central America, and often people refer to the animalics of civet cats (civettictis civetta) or castoreum from beavers as animals' musk, further confusing the terms (those last two animals produce animal substances that have different odour profiles). Even a particular type of alligator emits a musky secretion, but it proved to be non-functional for this type of odour aim as it is mainly rosy.

Some plants also have musky smelling compounds, usually of a lactonic macrocyclic nature, such as Angelica archangelica (containing 12-methyl-13-tridecanolide and Exaltolide) or Abelmoschus moschatus (ambrette seeds) produce musky smelling macrocyclic lactonic compounds which enrich fragrant compositions and are a handy if expensive resource for niche and natural perfumers. The former is amply explored in Angeliques sous la Pluie by Jean Claude Ellena for F.Malle. The latter is highlighted in Chanel Les Exclusifs No.18 and Musc Nomade by Annick Goutal. Other sources include musk flower (Mimulus moschatus), and muskwood (Olearia argophylla), to a much smaller degree. Even galbanum, a bitter green grass not usually associated with milky sweet musky smells, contains musk components (14-pentadecanolide and 15-hexadecanolide).
Interestingly, animal derived musks are all ketones, while plant-derived musks are large-ringed lactones.

The Rise of Synthetic Musks: History and Classification
Musk deers became a protected endangered species by the Convention on the International Trade in Endangered Species of Wild Flora and Fauna (CITES) in 1979, rendering natural musk almost obsolete in perfumery (The erratic quantities used by a handful of perfumers come from either old stock ~musk only gains in complexity with storage and doesn't lose its aroma for centuries~ or illegal poaching). Therefore all musk used in perfumery today is synthetic apart from only a handful exceptions which are usually small artisanal perfumers (who are often not at liberty to be open about it due to ethical concerns from consumers).
Although "white musk" is a prevalent epithet used as a blanket-term, the reality is somewhat more complex. The high cost and scarcity of natural musk had always been a concern for the fragrance industry and it was a happy accidental discovery when in 1888, Baur discovered the nitromusks. He had actually been working on explosives, hence the "nitro" prefix, when he discovered that the molecules actually smelled nice: the warm, sweet ambience recalled the scent of muscone. The first nitromusk was thus baptized Musk Bauer in honour of this occurence and a frantic exploration of these aromatic molecules started with the aim of replicating the elusive smell of natural musk. Follow-up nitro-musks, notably musk ketone and musk xylene, are rich, expansive-smelling and very warm; they can be savoured in vintage extraits and colognes, notably in Chanel No.5 (at a staggering 10% concentration) where they shine with their come-hither whisper. Later developments effectuated different kinds of musks.
Synthetic musks can be therefore divided into three major classes — aromatic nitro musks, polycyclic musk compounds, and macrocyclic musk compounds. The first two groups have broad uses in industry ranging from cosmetics to detergents but their continuous presence in human tissue and environmental samples coupled with carcinogenic properties has created concern resulting in a ban or reduction of their use in most countries. Macrocyclic musk compounds are generally considered safer and have replaced the nitro-musks (abandonded since the early 80s) and slowly phasing out the polycyclics. For those concerned with the dangers, WWF has an interesting article downloadable as PDF on this link. (primarily against musk ketone, musk xylene ~both nitromusks~ and polycyclics)
Synthetic musks are essential in modern perfumery forming the base note of most perfume formulae.

• Nitro-musks

Albert Baur came up with the first synthetic musk in 1888 by condensing toluene with isobutyl bromide in the presence of aluminium chloride, and nitrating the product, the process a collateral effect of trying for a more effective form of trinitrotoluene (TNT). The odour of this first nitro musk, Musk Baur or Tonquinol, depends upon the symmetry of the three nitro groups. Following Musk Baur, he developed another three synthetics: Musk Xylene, Musk Ketone (beautifully animalistic in the base of vintage Chanel No.5) and Musk Ambrette, which dominated in perfumery for the next 50 years. L'Air du Temps by Nina Ricci beautifully juxtaposes the warmth of musk ambrette with sunny salicylates and the piquancy of spicy notes (eugenol-isoeuegenol). Another nitro-musk that is less popular is Moskene.

• Polycyclic musks

Polycyclic musks are thus named due to the presence of more than one ring in the molecular structure and their popularity rose after WWII and the discovery of ambral (a non-nitro musk), when the photo-toxicity and molecular instability in alkline media of nitromusks became a concern, necessitating the removal of the nitro group. Givaudan, the aromachemicals company, thus managed to created Phantolidein 1951 via Kurt Fuchs; it was a less potent molecule, but very stable and suitable to use in detergents (musks are hydrophobic, thus rendering them supreme candidates for laundry detergent products, as they don't wash off). Further development resulted in Galaxolide (HHCB), perhaps the most popular synthetic musk in the polycyclic group, as well as Celestolide (or Crysolide), Fixolide, and Tonalide (Musk Plus, AHTN). Galaxolide from IFF has a clean, but also musky flowery-woody odour with a sweet, powdery nuance. It was first synthesized in 1965, gaining popularity in dosages up to 40% in fabric softeners such as Comfort and Soflan and in detergents like Coral at 27 by the end of the decade. Fine fragrances didn't escape its intrusion, for instance Trésor by Sophia Grosjsman for Lancôme with its 21,4% of Galaxolide. Its powdery, starched-cottons feel is exploited to memorable effect along with aldehydes in the original White Linen by E.Lauder (at 20% concentration) and it even enters Caron's incense-y Parfum Sacre! It's also in 13% concentration in Ralph by Ralph Lauren. Indeed the most widely used "clean musk" in the industry is a simple combination of Galaxolide and Adoxal.
However apart from hydrophibic, polycyclics are also lipophilic, as was first discovered in the early 1990s, building up in the bodies of humans and wildlife over time (Daughton 1999).
Traesolide is another synthetic polycyclic musk used as a fragrance ingredient in a variety of consumer products, including soaps, perfumes, and cosmetics and even though Traseolide is not as commonly used as other polycyclics, such as Galaxolide and Tonalide, it has been detected in breast milk, adipose tissue, and blood in humans (Rimkus 1996; TNO 2004; Duedahl-Olesen 2005). They're being steadily replaced by newer molecules.

• Macrocyclic musks

Macrocyclic musks are a class of synthetics consisting of a single ring composed of more than 6 carbons (often 10-15) and amongst artificial musk they most resemble the primary odoriferous compound from Tonkin musk, Muscone, with fewer environmental and health concerns so far. They also generally considered expensive ingredients, used in quality products. The synthesis of muscone only became possible in 1926 by Leopold Ruzicka, but until the late 1990s the difficult process and subsequent high price made it unpopular. Interstingly 50% of the general population are anosmic (unable to smell) to macrocyclic musks, because they have an exceptionally high molecular weight! So if someone can smell the musk in your fragrance but you cannot, consider the chance you're anosmic to the macrocyclics in it. Therefore perfumers often utilize a cocktail of musky notes to bypass this problem.
Ethylene brassylate (or Musk T) is a brassilic ester with floral woody facets, commonly used in cosmetics, because it acts as an odour neutraliser to the other chemicals used, as well as in fine fragrance. Notably it is featured in Dove's Cleansing Towelettes, as well as Olay, Cover Girl, Max Factor and The Body Shop foundations.
Globalide (Habanolide) is a metallic smelling, fresh radiant musk: Smell it in Emporio Armani White For Her, coupled with Helvetolide (please see below), where it forms the signature of nose Alberto Morillas in 2001, giving rise to the term "white musk" ~as opposed to the balmy darkness of the prior nitromusks. Or try it in the ultra-popular aldehydic musk Glow by Jennifer Lopez, accenting the fresh white floral components of the formula; the cooly herbal-soapy Cologne by Mugler and the baby-soft"clean" of Clair de Musc by Serge Lutens. It also balances the sweeter calorific elements in Hypnotic Poison by Christian Dior.
Ambrettolide is lightly sweetly-musky, uniquely vegetal with bordeline floral tones possessing exceptional diffusion which comes through from the very top notes through the base of the fragrance! Although it naturally occurs in ambrette seeds (prefered by niche brands or natural perfumers), it is usually synthesized in the lab. Other popular macrocyclics are Thibetolide (Exaltolide) ~more detectable by women than by men~ and Velvione, the latter from "velvet" and "ketone", referencing the velvety softness resembling older nitromusks and famously comprising almost the entirety of Helmut Lang's Velvione cologne formula.

• Alicyclic musks

Alicyclic musks, are novel musks hailed as the 4th generation and known as cycloakyl ester or linear musks. They were introduced in 1975 via Cyclomusk. Contrary to aromatic (nitro), polycyclic and macrocyclic musks they consist of modified akyl esters. Firmenich first manufactured Helvetolide in large commercial scale in the 1990, its name evocative of Helvetia, aka Switzerland. Its unique fruity facet (nuances of pear along with ambrette) makes it especially congenial to fruity blends which were popularised by the late 1990s. The fruity aspects of some musk compounds were first explored in L'Artisan Parfumeur's Mûre et Musc in the late 1970s backed by blackberry notes and from then on they literally blossomed. Romandolide, another popular Firmenich molecule is an alicyclic musk with more ambrette than fruity facets compared to Helvetolide and close to Galaxolide and was introduced in 2000.

One interesting case is IFF's Allyl Amyl Glycolate (iso-amyl oxyacetic acid allylester), one of my less prefered musk variants (Chandler Burr describes it as “a combination of the smell of processed pineapple and the tin of the can it comes in”), a clear liquid that can be used in any blend. It possesses sharp green facets with a top resembling the bitter touch of galbanum and a sweet pineapple fruity note. First discovered in 1936, it lagged unnoticed until it was popularised via Italian detergents in the late 1960s. Its use in Camay soap made it familiar and thus it entered fine perfumery: Trace amounts can be found in Alliage by E.Lauder while higher doses can be found in Drakkar Noir by Guy Laroche (1%)and Cool Water by Davidoff (3% which is very high for a powerful synthetic such as this). Trésor, Eternity, and Boss Elements Aqua also use it for its harmonization with the greener notes (lily of the valley, violet leaf).

Newer musks are constantly created, often with imaginative and inspiring names.
Nirvanolide, a chemical produced by Givaudan has a clean sweetly powdery and slightly animalic odour close to the restricted older Musk Ketone. You can smell it in the perfume Forever Elizabeth created by David Apel where it is used in 6.7% concentration. Another chemical with an odour close to Musk Ketone is Muscenone, possessing a very elegant and diffusive musk odour.
Firmenich offers two musk blends, Auratouch 911382 and Auranone 911383. The base of these products contains a captive* musk with a berry top note that performs like a polycyclic musk. Auratouch 911382 is a strong layered musk base with a substantive drydown and contains only triethyl citrate as a solvent. Meanwhile, the base of Auranone 911383—a strong substantive musk base with a delicate floral and somewhat animalic character—has strong ambrette connotations and contains no solvents, or polycyclic or nitro musks.
Meanwhile, the base of Auranone 911383 is a subtle but substantitve assemblage of some of Firmenich's finest musks with ambrette and animalic facets, blended with soft floral notes, devoid of polycyclic or nitro musks. Created around Romandolide, the captive alicyclic is paired with Habanolide, Exaltolide Total, Muscenone and Helvetolide to produce a hard-core musk with traces of sandalwood, amber, violet and powdery notes.
Givaudan has two new synthetic musks: Cosmone and Serenolide. Cosmone, is a single molecule the first C14-macrocyclic musk commercially available, which has a nitro-musk character of great warmth and diffusion which blends well with all kinds of accords. This biodegradable molecule, in addition to Nirvanolide, enlarges Givaudan’s range of environmentally friendly macrocyclic musks and can be smelled in Pi Neo by Givenchy (2008). Serenolide is an elegant white musk with sweet fruity connotations providing warm and soft velvety notes that blend well with all kinds of trendy fruity accords.
Musk R1 (originally from Quest International) is an example of an oxa-macrolide with sensual, powdery musky character.

The fascinating world of musks is far from over: We will return with classifications, descriptions and reviews of musky fragrances on the market!

*Captives are molecules which are patented by companies for their exclusive use for a number of years. 

Related reading on Perfume Shrine: Musk Series 1: a Cultural Perception of Musk, Musk Series 3: The Many Permutations of Musk (musk "types")


Ref:
Rowe, David J. (Ed.); Philip Kraft (2004). "Chapter 7. Aroma Chemicals IV: Musks". Chemistry and Technology of Flavours and Fragrances. Blackwell
Charles (Ed.), Sell; Charles Sell (2005).The Chmistry of Fragrances Chapter 4. Ingredients for the Modern Perfumery Industry". Royal Society of Chemistry Publishing.
Robert R. Calkin and J. Stephen Jellinek, Perfumery Practice & Principles
PChirality & Odour PerceptionJohn C. Leffingwell, Ph.D.
Perfume & Flavorist magazine, Musks in Fragrance Blending
Jenny van Veenen Perfume Making
Aromax blog

[1] [2]Epistola S.Fowler: Musk


Painting Lovers by a Tree Mughal, Muhammad Shah period, about 1725 via lokvani.com. Pics via mikndfully.org, Natural Health Crafters, homotography.blogspot.com

Musk Series 1: A Cultural Perception of Musk

Guy de Maupassant notes in Bel Ami:

"The old woman in her turn kissed her daughter-in-law with hostile reserve. No, this was not the daughter-in-law of her dreams; the plumb, fresh housewife, rosy-cheeked like an apple and round like a brood mare. She looked like a hussy, the fine lady with her furbelows and her musk. For the old girl all perfumes were musk."

In another story (One Evening) Maupassant attributes rather different connotations to musk:

"As for me, I was moved and powerfully interested, and in the darkness I could see that little woman, that little, fair, lively, artful woman, as if I had known her personally. I saw her selling her books, talking with the men whom her childish ways attracted, and in her delicate, doll-like head, I could see little crafty ideas, silly ideas, the dreams which a milliner smelling of musk attached to all heroes of romantic adventures".

Musk weaves its thick, ensnaring plot to even grace French roads with its sonorous name. In Greek the term "musk" is called μόσχος (MOS-chos) and it denotes (in both noun and verb form) any delightful aroma, from culinary to personal!
For all its rich history and ubiquity to the vernacular, musk remains a great mystery making even perfume lovers exasperate on its multiple facets and shady nature. Some, daunted by the odorant's sheer animal nature in some compositions such as Muscs Kublai Khan by Serge Lutens, reference "Post-coital genitals", "Caligula's couch", "balls' sweat", "the armpit of a camel driver who has not been near running water in a week" (the latter by Tania Sanchez in her early MUA days) and other highly entertaining descriptors. Kiehl's Original Musk, "wears its seductive intent on its sleeve" and Musc Ravageur tries to say it all at hello.
Those musks are generally termed "dirty" or "animalic musks", even "skanky" (both in reference to the little critter and the vulgar ladies thus called) in perfume-community-lingo; they tend to reflect the intimate aura of private parts and private acts and if you have any apprehension to smells that might offend your workplace or your conservative entourage, you might give them a miss. Nevertheless to a whole bunch of enthusiasts ~myself among them~ the smell is fur-like, cozy, intimate and transcedentaly primal. Not sweaty or fecal exactly, yet with a "lived-in" quality which is inescapeably delicious.

A vast array of different musks, termed "clean musks", are available for exploring for anyone afraid of the former, their scent often reminiscent of fabric softener, your laundry detergent or even shampoo and refined body powder. Serge Lutens has the polar opposite to Muscs Kublai Khan in Clair de Musc. Some of them often take the guise of "white musk", a code-name to signify a lightly floral musk "base", The Body Shop's White Musk being the most famous example. A reviewer at Fragrantica referring to Alyssa Ashley Musk (1969) notes:

"My perception of AA Musk is a very babylike, milky, powderish scent, completely non-defined by certain age or sex or the consumer."

Perfect Veil by Creative Scentualisation, a combo of citrus, vanilla, sandalwood and musk, is termed "a casual, clean-smelling-skin scent" on Makeup Alley, a huge review site. Noa with its sparse formula is "fit for virgins and nuns" per Susan Irvine, a sentiment due to the transparent laundry-day white musks at its base. Allesandro del'Aqua and Helmut Lang make for a fascinating study in musk in their respective eponymous creations.
In some cases musks in a well-rounded composition manage to smell at once dirty and clean, like a human being in various stages of disarray. Such is the case with Chanel No.5: Its intense accord of ylang-ylang and musk, boosted by the soapy ppssshht of aldehydes (a group of predominantly synthetics that were used extensively in soaps and go well with musks) along with classical rose-jasmine, is the very core of sexy. Modern musky florals with woody bases such as Narciso For Her and Lovely by Sarah Jessica Parker utilize a cooler sensation, but with the same duality inherent. Imagine your dog and its own musky odor: Doesn't its true essence come out when just out of the shower?
But, herein lies the question, like a savvy member on Perfume of Life asked recently: "how on earth did musk, a term derived from the Sanskrit word for "testicles" because of its origins, come to be associated with cleanliness?"
What is musk in terms of smell and what accounts for its varied perception?
Musk of course originates from the Sanskrit muṣká meaning "testicle," coming as it did from the genital glands of the Musk Deer (moschus moschiferus); two pouches were extracted from the animal through cruel methods that resulted in its demise and the subsequent banning of the practice. The precious pods were opened to exude their aromatic effluvium, worth twice its weight in gold, and used as a powerful fixative and enhancer in perfumes & incense since antiquity. Musk odorants as a group however include glandular secretions from other animals as well, numerous plants emitting similar fragrances (ambrette seed being the most popular, highlighted beautifully in Musc Nomade by Isabelle Doyen for Goutal; also rosa moschata), and artificial substances with similar odors synthesized in the lab. But what perfumers refer to as "musk" is in realityits odorous principle, muscone (or muskone), or 3-methylcyclopentadecanone. Its chemical structure was first analysed by Lavoslav Ružička: Muscone is a 15-membered ring ketone with one methyl substituent in the 3rd position.

Still the fascinating reality is that human "reading" of musks differs widely. What is nectar to one can be anathema to another! Cast your mind back to Napoléon and Joséphine de Beauharnais: At the Directoire period the vogue for animalics (civet, musk, castoreum and ambergris) had given way to a new freshness, ushered in by the Revolution which stigmatised the "dirty" aromatics in relation to the decadent aristocrats who were guilotined. Only a defying elite, the Incroyables and Merveilleuses hung on to them, extravagant in style, wanting to emulate classical antiquity: Their nickname became les muscadins! Napoléon loathed musk and prefered to douse himself in Eau de Cologne and rosemary essence dilutions. His women, he preferred them in violets. The scorned Joséphine in an act of cunning revenge, when she was bypassed for another woman, doused her walls at Malmaison with her favourite musk essence, making her presence painfully unforgetable. Rumour had it that a hundred years later the scent was still perceptible! The Arabs knew a thing or two of musk's tremendous lasting power when they used crushed musk and rose in the mortar of their mosques so that the buildings would exude aromatic delight when warmed by the sun. But why the different reaction to musks?

The answer is twofold: Biological and psychological/cultural. In humans, odor perception phenotypes (MSHM1 and MSHM2) often account for specific hyperosmias (a heightened perception of odorants), the best studied examples being to musk and the sweaty odorant isovaleric acid. A great explanation why one's body odour might be inoffensive to one yet very repulsive/potent to another! Recent reseach going against established biology is that musk perception and sensitivity to it does not variate according to a woman's menstrual cycle like with some other odorants. Le Magnen in 1952 working with a dilution of Exaltolide (a synthetic musk) had found that women had significantly lower thresholds for it than men, 50% of the latter having difficulty in smelling it per se [1]
On the other hand, musk components (both natural and synthesized) are by their very nature very large molecules, bordeline undetactable due to that fact, making a large segment of the population anosmic (i.e.odor-blind) to some or other type. This is usually addressed by the perfume industry by employing an eventaille of various musk components of different molecular weights, so that if one doesn't click on the brain's receptor, another will. The most common anosmias are towards Androstenone (a sex pheromone possessing a musky facet) and Galaxolide (a very common synthetic "clean" musk), while there seems to be evidence of recessive inheritance for pentadecalactone sensitivity in humans; the inability to smell musk behaves as a recessive autosomal trait in a study of families.

The perception of any odorant however has to do with CONTEXT, as proven by the associations of wintergreen in the US vs the UK, "beach" scents and household products in different cultures. Ergo, it's largely cultural rather than biological. Real musk (the best is Tonquin) from musk deer has a rather urinous smell in itself with pungent, borderline fecal tonalities in its raw state, NOTHING like what you encounter in perfumes termed "musk" (even by top brands). Yet diluted and mixed with floral essences (try it with rose) it becomes a warm underground murmur of intimacy. A caress...
Historically, musk synthetics were used en masse in detergents and fabric softeners, roughly at the middle of the 20th century and onwards, to mask the more displeasing chemical nuances, due to their superb hydrophobic properties (ie. musks didn't wash off) and their low price (they were synthesized on the cheap). Thus the association of the "warm" smell of clean clothes out of the washing-machine as well as the lingering smell on the clothes themselves became an association with cleanness itself! That warm "cotton" feel you like in clean laundry? Musks! Funny for a product that initially signified the glandular secretion of a rutting deer's improper parts, isn't it? There is a pleiad of synthetic musk ingredients in the market, not just one or two types (on which we will revert in detail) and therefore there is no blanket term or description for them (not even "white musk" is sufficiently accurate), as every one of those molecules has a different olfactory profile: some smel "cleaner" like dryer sheets, some more metallic, some powdery even, others still with a fruity overlay, some have a vegetal or animalic quality. Hence the confusion of the consumer, who doesn't know what to expect from a "musky" fragrance (or reporting liking some in certain fragrances and detesting others to their puzzlement).

The popularity of said scented products led to the introduction of those functional musk notes in fine fragrance: The increasingly lower percentage of real natural musk in them, resulted in a paloply of "musks" which approximated the feeling of musk rather than the smell itself. Such musks were popular in the 70s especially (following the hippy movement, as a natural progression). The "dirty" association that several Baby Boomers have with musk is not exactly related to musk itself: Talking with American independent perfumer Dawn Spencer Hurwitz, she intelligently proposed that often the association is to the dense patchouli-clouds and unwashed parts (body odor) of the hippies of their youth, as the (incidental) added layer of musk oil was par for the course for the Woodstock era and beyond. The 1970s musks tagged their product with animal magnetism: "It's what attracts!" proclaimed a Jovan advertisement progressing well into the 80s and 90s.

Functional fragrance musks were incorporated in several other types of products as the years passed: soaps, shampoos, powders, deodorants, you name it! 99% of fine fragrances today contain some type of synthetic musk to anchor notes down, especially now that the other animalics are absent; this happens whether the note is "perceived" as musk or not and regardless of being stated as a note or not in the official descriptions. Since most of them fall under the "clean musks" umbrella ~and what's more under a screechy variant of them on top~, we can expect that generation Y will have no mental associations with any of the "skanky" musks and will come to regard the symbol (musk) as the collateral signification (laundry day) rather than the primal one (animal magnetism). The most interesting mental path of them all, nevertheless, is how the companies have incorporated the latter illusion in their ad copy without including the scent of it at all, rather opting for the equivalent of a line of warm cottons drying in the breeze. "Clean musks" are marketed as attractants, as powerful aphrodisiacs, as sexually inviting, thus equating "clean" with sexy! In a culture where personal grooming is a trillion dollar business it somehow logically follows.

Perhaps it was Charles Baudelaire who saw the duality of musk best: fresh yet intimate, and dedicated it to his "dearest, fairest woman" in his Hymn in Fleurs du Mal: "Sachet, ever fresh, that perfumes the atmosphere of a dear nook; Forgotten censer smoldering secretly through the night; Everlasting love, how can I Describe you truthfully? Grain of musk that lies unseen, in the depths of my eternity."[2]


[1]D.M.Stoddart, The scented ape: the biology and culture of human odour
[2]translation William Aggeler, The Flowers of Evil (Fresno, CA: Academy Library Guild, 1954) Pics via wikimedia commons, parfum de pub, mongoose.wordpress.com, Nude Painting by Amedeo Modigliani via apolloart.com.

This is part of a series on the note of "musk" and its various types. Please also refer to: Part 2: Natural Deer Musk (Tonquin Musk), how does it smell and info on Synthetic Musk Substitutes and Part 3: The Many Permutations of Musk (Musk Types on the Market)

Musk and Civet in Food: Challenging our Perceptions

 The seductive power of animalic essences in fragrances has been well known among people tuned into perfumes, especially of a vintage nature when true animalics were used in the formula. However how surprised would you be if you found out that not only your eau de toilette or extrait de parfum contained them, but also the delicacies that pass your lips? Yes, actual food and drink containing animalic essences such as musk or civet.

Musk was tentatively touched in one of the discussions I followed with some interest on a popular fragrance board the other day, as I had already experiences with the subject at hand: musk-flavoured candy, (called "musk candy" in Australia or "musk sticks" in other permutations) which seemed to create repulsion rather than attraction. Since everything in our medicine cabinet contains some form of synthesized musk (from soaps to cosmetics through bath oils and even the stuff we brush our teeth with!) and it's perenially a favourite of the functional fragrance industry to put in household cleansers, laundry detergents, and insect repellents, does it come as any surprise that artifically-flavoured food is also being aromatized with certain synthetic musk variants? Musk is an added component in fruit flavors, in chocolates, licorice, candies, chewing gum and even vanilla flavourings or puddings. 
The cozy, inviting smell of musk which we associate with warm, living and heaving human skin has an illustrious ancenstry that can be traced back to the Silk Route. Legends touch upon the tales of Chinese concubines being fed natural* musk-flavoured food so that during lovemaking their skin would sweat pure essence acting as a powerful aphrodisiac.

Is it any wonder then it has appeared even in a Lifesavers single flavour? That particular "musk candy" is an Australian idiosyncratic delicacy, much like Vegemite (the yeasty spread that rivals the British equivalent Marmite in the terrain of acquired taste). There also appears to be some form of edible Musk Sticks, by [supermarket private brand, as I learn from my Aussie readers] Coles, which appear to replicate the odour of incense sticks aromatized with musk. There is also the Beechies "musk gum" variety and Baba "musk melon candy". It's a whole industry!

Having been on the receiving end of a gift package that also entailed those "Musk Lifesavers", albeit of a different packaging (solid red with white lettering) and maker (not Nestle) than those linked above, sent by an Australian friend I can attest that soli-musk candies are not repulsive or nauseating. They're tinged with a "clean" soapy lace of almost aldehydic aftertaste that is certainly strange to encounter in a hard candy but which once you try you can appreciate for what it is.

Perhaps coming from a culture that traditionally and continuously has indulged in odours and flavours such as turpentine (the undertone of some ouzo varieties), of anise and mastic (used in several local liquors but also neat in bread and dough products), of cumin (an essential component of meatballs and pasturma) and of garlic (too numerous recipes to mention) along with an experimental spirit in cuisine that embraces squids, kalamari, octupus and snails cooked in red wine in all their squishy glory, as well as ripe cheeses that have mould, these come as no big surprise to me. And my musk affinities firmly in place, accounting for collecting musk fragrances of every possible nuance from the opalescent to the fetid, you might be warned that your own experience might be different. Still, it is an interesting proposition and worth keeping in mind should you find yourself faced with the option of tasting for yourself.

And what about civet in recipes, that fecal-smelling aroma that derives from the anal glands of the civet cat, farmed in Ethiopia and small erratic groups in other exotic locales at the moment? Civet highly diluted in fragrance formulae can have a marvellous effect of opening the bouquet, especially of floral blends, and thus adding texture, depth and radiance. An animalic touch that cannot be pinpointed as fecal as it truly is in concentration, yet is unmistakeably there: if you need proof open a vintage flacon of Jicky extrait de parfum and wait for it to make its pronounced magic appearence.

Although civet essence is not as wondrously diversified in synthesized forms as that of musk because the extraction of civet aromatic essence does not entail killing the animal ~and therefore has not had the chance to enter our plates in comparable droves~ civet does make an infamous appearence in drink: in coffee. This very special and most expensive coffee (£100 - £300 per lb. at time of writing), named Kopi Luwak, is produced by feeding the civet cats coffee berries which cannot be digested along with their food (much like we'd naturally dispose the bran of whole-grain cereals) and waiting for them to come out the natural way. The passing through the anal region stimulates the production of the anal glands secreting the valuable civet essence that is so prized in perfumery, so the beans gain a whole new dimension of animalic aroma. Further treating by roasting produces a coffee brew that is said to be among the very best, good to the last dropping so to speak. I admit although I have been intrigued by the idea for years and searching high and low for it locally among batches of Jamaican Blue Mountain and other assorted exclusive imports, it was only by the powers of the Internet and the intervention of a penpal that I came upon this link. I think I will take the plunge, bypassing the raw product we're invited to clean and roast ourselves, rather opting for a generous pouch. If on the other hand civet cats are too exotic for you, there is also weasel coffee - made from berries which have been regurgitated by, you guessed it, weasels.

And for those wondering, castoreum is also featured as a flavouring, in chewing gum and cigarettes no less, but its restricted use of the natural essence has probably put a stop to the practice. As to ambergris/grey amber, the divine marine/brine-like essence coming from the expulged cuttlefish residue in the digestive track of sperm whales, found floating in the ocean, I would be standing in line to taste something aromatized with its refined aroma. Brillat-Savarin recommended an infusion called "chocolate ambre" which was essentially chocolate drink heavily aromatized with ambregris. Heaven...

*The natural musk essence comes from Moschus moschiferus moschiferus or musk deer from the Himalayas but the cruelty necessitated for extracting the musk pouch from its genital region resulting in killing the animal has effected a prohibition on its hunting. Today musk essences at almost 100% are produced synthetically.

Pic Against the Grain by thatotherguy/flickr. Cartoon of civet coffee production spoof provided by Concord on MUA. 

Related reading on Perfume Shrine: The Musk Series (everything about the musk note, natural or synthetic, its cultural aspirations, its various musky fragrance types on the market)