A Gardener’s Pride and Joy

Although this article arrives rather late, I have had it in mind to write about my lilies of the valley since the beginning of May when they were in bloom. During that time, bunches of these white porcelain bells could also be found wrapped in their green leaves and sold as bouquets. But since I much prefer the process of growing and coaxing a plant into blooms, especially one whose fragrance I have yet to smell in situ, I had planted their rootstocks or ‘pips’ in autumn last year. They lay dormant over the winter and only began to send out their leaves in mid-March when the weather warmed. A littler later, some flower stalks emerged, and I could enjoy the redolence of spring.

muguet pips

Pips emerging from dormancy in spring. The carpet of seedlings around the pips are violets, which also emerge from the seeds of last year.

The perennial lily of the valley or muguet (Convallaria majalis) returns every year to perfume the spring air. But despite its delicate-looking white bells, muguet is highly poisonous and, especially without blooms, often dangerously mistaken for the edible herb bear leek (Allium ursinum). Nonetheless, grow a small patch in a dedicated pot of its own for an olfactory pleasure and all the caution can be thrown in the wind.

Its ethereal scent smells fresh, obviously floral, even spicy, and with a watery green tone. I would describe it as a mix of rose, clove, jasmine, green saps, and musky sweetness. But in spite of these contrastingly opulent notes, the overall character of muguet is reserved, and it feels like a subtle and an elegant way of announcing spring. Lily of the valley, as such, has been a prime objective of perfumers who have tried to capture its mesmerising scent and, along with it, the allure of spring.

Lily of The Valley in Perfumery

Just as elusive as it is captivating, lily of the valley virtually refuses to be extracted. Steam distillation does not yield a desirable quality of essential oil and solvent extraction with either petroleum ether or butane, though sufficient to produce the concrete for research, gives too low a yield to be commercially tenable. Perfumers must therefore rely on their memory and headspace analysis of the natural scent to reconstitute and interpret lily of the valley with existing essential oils and aroma ingredients.

The first of such aroma chemicals were the aldehydes (-CHO), such as hydroxycitronellal, Lilial, and Lyral. These are some of the most well-known muguet odorants of this family. Hydroxycitronellal was the prototype; it encompasses all the facets of lily of the valley — despite itself not being naturally occurring. It had been discovered and marketed by Knoll & Co. in 1905, but soon various qualities from other manufacturers were available, such as Laurine (1906) and Cyclosia (1908). The next stage of muguet was, then, dominated by Lilial and Lyral, starting from the 1960s. They would eventually come to supplant hydroxycitronellal.

These muguet aldehydes found their use directly in a composition or alternatively in a compounded base. Hydroxycitronellal, for instance, first found its fame with the aldehydic floral perfume Quelques Fleurs (Houbigant, 1912). It had also been used to compound Lily 7 — a base comprising seven ingredients — which was employed in the composition of Arpège (Lanvin, 1927), another successful aldehydic floral perfume. Other classic perfumes such as Chanel N°5 (1921), Ma Griffe (Carven, 1946), L’Air du Temps (Nina Ricci, 1948), and Youth Dew (Estée Lauder, 1952) likewise benefited from this lily of the valley odorant. But hydroxycitronellal was just as popular in the enduring fragrance of Nivea Cream, which has notes of muguet, ylang ylang, rose, geranium, violet (ionones) as well as cinnamic and balsamic ones.

Later perfumes, however, relied more on the newly available odorants when they were first created. For example, Fidji (Guy Laroche, 1966) employed Lyral, imparting thus a green tone to its floral bouquet. Similarly, Calandre (Paco Rabanne, 1969) used Lyral in addition to hydroxycitronellal to give a green emphasis that accentuates its character of metallic rose. Even more so, the elaborate floral accord of Anaïs Anaïs (Cacharel, 1978) was based on hydroxycitronellal, Lilial, Lyral, and Cyclamen aldehyde. Interestingly, compositions such as Aromatics Elixir (Clinique, 1971), Coriandre (Jean Couturier, 1973), and Paloma Picasso (1984) used a combination of the muguet aldehydes partly for their floral notes that contrast beautifully with patchouli.

Interestingly, such muguet aldehydes was also used in the formation of Schiff bases. When an amine (-NH2) reacts with an aldehyde (-CHO), a Schiff base and water are formed. For example, methyl anthranilate reacts with hydroxycitronellal and Lyral to form Aurantiol and Lyrantiol, respectively. The Schiff bases produced can give odours of orange blossom, linden blossom, or tuberose. Perfumes such as Oscar (Oscar de la Renta, 1977), Poison (Dior, 1985), and Lou Lou (Cacharel, 1987) derived much of their sweet floral character in such a manner at the time.

Even in the last few years, the classic muguet aldehydes, such as hydroxycitronellal, Lilial, and Lyral could still be found. In adr_ett (Nomenclature, 2015), the lily of the valley, which lends a green floral touch to the fruity musk, was based on the combination of hydroxycitronellal and Lilial. And, as much as 12% Lyral was used in Inflorescence (Byredo, 2013) to build its lily of the valley character. Indeed, these muguet aldehydes have proved to be one of the enduring ingredients of perfumery.

But that is about to change.

Due to their skin-sensitising potential, these muguet aldehydes are facing restrictions. Hydroxycitronellal is allowed only up to certain concentrations depending on the end use, but Lilial and Lyral are severely restricted. According to the Scientific Committee on Consumer Safety (SCCS), Lilial is considered ‘not safe for use as fragrance ingredient in cosmetic leave-on and rise-off type products’ even at the concentrations set by the International Fragrance Association (IFRA), and Lyral ‘should not be used in consumer products’.

New odorants are therefore being developed to replace these restricted ones. Amongst them, the aldehydes  account for a broad range of muguet odour profiles that includes names like Dupical, Florhydral, Melafleur, Floral Super, Cyclemax, et cetera. There are also the alcohols (-OH), such as Mayol/Meijiff, Florol/Florosa, Mugetanol, Majantol, Lilyflore, Muguesia, and Super Muguet, and these are a sought-after class of muguet odorants because of their non-sensitising nature. Super Muguet, for instance, was first used in contrasting the fig accord of Marc Jacobs Men (2002), and it was later used in the oriental-gourmand Noir Pour Femme (Tom Ford, 2015). Amongst recently debuted ingredients, I had the chance to smell Mahonial, which offers a diffusive, creamy lily of the valley note reminiscent of the yellow blooms of Mahonia japonica, from whose name it is derived. Mahonial was first employed in the floral heart of Missoni (2015), and now one can smell its transparent yet creamy note in L’Homme (Prada, 2016) and La Femme (Prada, 2016), both containing Mahonial at approximately 4% and 2%, respectively.

As reflected in the many examples of perfumes, the muguet note is a part and parcel of many different styles of fragrances. It follows then that the quest for safe, stable, and impactful lily of the valley aroma chemicals must continue.

Lily of The Valley in Perfumes

The fresh watery appeal and creamy sensuality of muguet lend a special touch to a composition. For this reason, it is not limited to soliflore perfumes, and forms an important part in many styles of compositions.

But, of course, if one wishes to know how perfumers interpret lily of the valley, exploring soliflore perfumes is a good option. There have been several other muguet soliflores since the eighteenth century, from Lily of The Valley (Floris, 1750), Premier Mai (Houbigant, 1908), Muguet de Chaville (Cheramy, 1910), Muguet des Bois (Coty, 1941), Muguet du Bonheur (Caron, 1952), and Muguet de Guerlain (1998 by Jean-Paul Guerlain), to name a few. But I would rather offer a few favourite choices of this flower.

Naturally, one of these is the most well-known and appreciated lily of the valley: Diorissimo (1956). Considered to be the gold standard, its fresh green floral and surreptitious animalic notes conjure the vernal impression of damp woodlands covered in infinite patches of lily of the valley. In the current eau de toilette, its muguet has lost some radiance and its woodlands short on their animalic richness, but I think that its curious paradox of an ethereal flower with a veiled depth still rings true.

However, the lily of the valley that I find most captivating is far from the time-tested repertoire of classics. Muguet Porcelaine (Hermès, 2016), I feel, takes after the spirit of Diorissimo in simplicity and subtle depths, but its singular focus is where it diverges. Whereas Diorissimo is an impressionistic rendering of blooms in their woodlands, Muguet Porcelaine is a careful treatise dedicated solely to muguet, examining its accents and shades. Led by fresh accents of rose and clove, its green floral is not only depicted in detail, but also underpinned by watery melon and green sap that remain fresh until the dry down.

Other than the soliflores, the lily of the valley note, as evident in the examples heretofore, finds itself in various genres. Indispensable to the bouquet of the aldehydic florals, lily of the valley is a part of perfumes such as Chanel N°5, Arpège, Madame Rochas (1960), Calandre, Rive Gauche (Yves Saint Laurent, 1971), and White Linen (Estée Lauder, 1978). It is also found in the multiplex bouquets of L’Air du Temps, Fidji, and Anaïs Anaïs. Beyond these floral bouquets, it finds contrast and harmony in many interesting accords. In perfumes such as Aromatics Elixir, Coriandre, and Paloma Picasso, the lily of the valley accentuates the floral complex that is set against the patchouli and woods. This contrast between muguet and patchouli is also employed in the mellis accord of oriental perfumes such as Opium (Yves Saint Laurent, 1971) and Coco (Chanel, 1984). But the lily of the valley also shines brightly with green notes, where its green floral character finds harmony. In Chamade (Guerlain, 1969), a hint of muguet bridges between the green galbanum and hyacinth opening and the floral heart. This bridge between green galbanum and floral heart is similarly found in Chanel N°19 (1970). As the green notes are making a come-back, so too is the lily of the valley note, and this is seen in the green, dewy floral introduction of Miu Miu (2015).

But ultimately the perfume that has a special place in my memory of May is that of the lilies of the valley which I had coaxed into bloom. They were my pride and joy.

Sources: M. Meunier, Ind. Perfum., 5, 26, 1950; Naves and Mazuyer, Les Parfums Naturels, Paris (1939), p 250; Scent and Chemistry The Molecular World of Odors p 13, 108; SCCS Opinion on HICC SCCP/1456/11 revised 27 July 2012; SCCS Opinion on BMHCA SCCS/1540/14 revised 16 March 2016.

*Lilial is a tradename for butylphenyl methylproprional (BMHCA).

*Lyral is a tradename for hydroxyisohexyl 3-cyclohexene carboxaldehyde (HICC).

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Pinot Noir: A Wine Grape and Christian Dior Poison

Liquor notes are not new in perfumery. There is the red wine in Une Rose (Frédéric Malle, 2003), the rum in Monsieur. (Frédéric Malle, 2016) and Idole (Lubin, EdT 2005/ EdP 2011), and the whisky-cognac in Korrigan (Lubin, 2012). But, no, there is no wine in Poison (Dior, 1985), let alone the wine-evoking, fruity, sulphurous wine lees essential oil. Still, this flamboyant bomb actually shares an odorant with the Pinot noir wine grapes.

pinot noir bbc news

Pinot noir is a vineyard favourite that is notoriously difficult to grow and work with. It has the potential to make for the finest wine. And, key to this is the right time to harvest: when the grapes are ripe enough that the build-up of sugar diminishes and the aroma compounds accumulate. But because variations in temperature, rainfall, and soil condition fluctuate the rate at which aroma compounds accumulate, it never is as easy as simply harvesting the grapes when they are full of sugar and ready.

Yet, researchers from Oregon State University, Michael Qian and Fang Yuan, might have recently pioneered a way to decide when to pluck these bunches of ambrosia – by evaluating the concentrations of aroma chemicals. From early- and late-maturity Pinot noir grapes, the researchers identified 49 aroma compounds. Most of these remained at low concentrations throughout the growing season, but β-damascenone, vanillin, 4-vinylguaiacol, and 4-vinylphenol were determined to be in higher concentrations in the late-maturity harvest. To the researchers, these might serve as indicators of the ripeness of Pinot noir grapes.

poison ad yesterday's perfume

As an enthusiastic student of perfumery, however, I immediately thought of the milestones: Poison (Dior, 1985) and Jicky (Guerlain, 1889). As far as this post concerns, I shall discuss only Poison for now. The reported β-damascenone is a naturally occurring compound found in rose oil, raspberries, cooked apples, roman chamomiles, coffee, wine and even beer. It has a fruity-floral odour recalling dried fruits, raisins, plums, prunes, blackcurrants, and roses. In combination with other compounds, it also imparts a honeyed facet to rose oil. In Poison, legend has it that Nathalie, the assistant of perfumer Edouard Fléchier, might have erroneously increased the concentrations by ten times so that such a milestone was born, containing 0.04% α-damascone, 0.09% β-damascone, and 0.09% β-damascenone. Although I admittedly struggle with the intrusion of Poison from wherever I leave the blotter, a perfume that elicits strong opinions — be it aversion or ardour — surely has a character, and that should be found in any good perfumes. In the case of the damascones, they lend themselves to the fruit facet in the floral-oriental body of Poison and have since been catapulted from perfumery niceties to olfactory protagonists.

Sources: news.bbc.co.uk, yesterdaysperfume.typepad.com

  1. Yuan F, Qian MC. Aroma Potential in Early- and Late-Maturity Pinot noir Grapes Evaluated by Aroma Extract Dilution Analysis J. Agric. Food Chem., 2016, 64 (2), pp 443–450