Distant cousins: Lily of the Valley & Lily~part 1: Lily of the Valley

Although in nomenclature lily of the valley is easily confused with lily and its own varietal richness, the two are completely different flowers and in this scent guide I will try to analyse their olfactory differences, their participation in the bouquet of classic and modern fragrances, the materials used to render them in perfumery as well as a list of perfumes that highlight their graceful beauty. The first part deals with Lily of the Valley or Muguet, while the second part will deal with Lily.

The raindrenched earth after spring showers and the wet foliage remind me of the lyrics by songwriter George Brassens:

"Le premier mai c'est pas gai" / "The first of May isn’t cheerful"
"Je trime", a dit le muguet / "I slave away", the lily of the valley said
"Dix fois plus que d'habitude" /"Ten times more than usual"
"Regrettable servitude" / "A regrettable encumbrance"
Muguet, sois pas chicaneur / Lily of the valley, don't be a quibbler
Car tu donnes du bonheur / Because you make people happy
Brin d' muguet, tu es quelqu'un... / Nosegay of lily of the valley, you’re somebody...

~Georges Brassens, Discours Des Fleurs

May 1st has been inexctricably tied to Francophiles’ minds with one of the loveliest spring blossoms and its neo-Victorian image: lily of the valley (Lys des vallées) or, as the French commonly call it, muguet (pronounced mygɛ). And it’s for a reason: it’s the traditional flower offered on this day and one can routinely see street vendors selling nosegays on the French streets. The tradition goes back to Charles IX who on May 1st 1561 inaugurated the custom.It is also a symbolic gift for 13 years of marriage and is traditionally used in bridal bouquets thanks to its enticing scent.

Etymology and symbolism

The etymology of muguet is said to derive from muscade (nutmeg), since the smell of the flower has an indefinite nuance reminiscent to it, which became mugade, and finally muguet. A lucky symbol ~it means “return of happiness” in the language of flowers~ the delicate beauty of lily of the valley is however poisonous (especially its reddish fruit) due to convallatoxine, convallamarine, and convallarine; a brave irony on the part of Creation!
Lily of the valley/muguet (Convallaria majalis) is a herbaceous perennial plant prevalent in Asia, Europe and the Eastern USA, with characteristic bell-shaped little flowers, hence its other name May Bells. But its alternative names "Our Lady's tears" and "Male Lily" are more poetically evoctive: Legend wants Eve to have shed bitter tears after the Lapse from the Garden of Eden which falling onto the ground transformed into the white little blossoms. Another medieval legend wants Saint Leondard de Noblac, a knight in the court of Clovis I (of the Limousin region of France) and patron saint to prisoners of all kinds, to have battled with a dragon (a common medieval theme) in which his shed blood trasformed into lilies of the valley. But although one usually associates the delicate green floralncy of its aroma with females now, the term "Male Lily" has another explanation: It has been a favourite perfume for men ever since the 16th century, to the point that up till the 19th century the term muguet was linguistically used to denote an elegant young gentleman!
Another legend wants the Greek God Apollon to have tapestried the mount Parnassus with lilies of the valley so that the Muses wouldn’t hurt themselves if they fell...Classical antiquity paid great attention to the seasonal celebrations of nature and the zenith of the Roman celebrations of Flora, goddess of flowers, culminated on May 1st.

The role of lily of the valley in perfumery and construction of the accord

Lily of the valley is technically a green floral with rosy-lemony nuance*, whereas lily is a white, spicy floral. The former has known a profound and extensive use in perfumery, despite its resistance to natural extraction methods which yield a very miniscule amount of no great significance. Apart from soliflores (fragrances focusing on highlighting the beauty of one kind of flower), the lily of the valley accord has been adequately used in classical fragrances as a catalyst to “open up” and freshen the bouquet of the other floral essences in the heart, much like we allow fresh air to come in contact with an uncorked red wine to let it “breathe” and bring out its best. The effect is wonderfully put to use in Chanel No.19, Guerlain’s Chamade and Jean Patou’s L’Heure Attendue. Its lack of sweetness is also an important aspect in the creation of masculine fragrances: witness Chavelier d’Orsay, Équipage by Hermès, Insensé by Givenchy and Riverside Drive by Bond no.9 to name but a few.

The reconstitutions of lily of the valley note are based on either combinations of natural essences (usually citrus with jasmine, orange blossom or rose and green notes such as vetiver) or more commonly on synthetics. The classical ingredient is hydroxycitronellal, as well as the patended Lyral and Lilial, all coming under the spotlight of the latest restrictions on perfumery materials {you can read all about them here}. Lilial has a cyclamen facet to it, used in good effect in Paco Rabanne pour Homme. Super Muguet is another lily of the valley synthetic which surfaces in Marc Jacobs for men, as a clean facet under the figs. Kovanol is very close to hydroxicitronellal, which is interesting to note. Restricted by IFRA is also the newest Majantol {2,2-Dimethyl-3-(3-methylphenyl)-propanol}, while Muguesia or Mayol are also used to give this green floral smell of muguet. The name Mayol has an interesting background: it’s a nod to comedy singer Félix Mayol who put a boutonnière of the muguets he had been offered by his girlfriend Jenny Crook instead of his usual camelia on the 1st of May of 1895 before going out to sing!
Phenylethyl alcohol and benzyl acetate (the former rosier, the latter jasminer) as well as dimethylbenzenepropanol also contribute in the creation of bases which are used to render lily of the valley notes. It all depends on which impression the perfumer wishes to convey!
The clean, almost soapy nuances of lily of the valley has been traditionally exploited in soaps, which is why all too often lily of the valley as a fragrance note reads as “soapy” in your perfume. It’s also why it’s terribly difficult to render a convincing lily of the valley fine fragrance that does not evoke functional cleaning products, due to the exagerrated use they make of this aroma in that sector of the industry.

Iconic Lily of the Valley fragrances

The definitive lily of the valley fragrance used to be the masterful Diorissimo (1955) by trismegistus Edmond Roudnitska who is said to have planted a bed of them in his garden, so as to study the smell attentively and to evoke the indefinable atmosphere of spring. Lily of the valley used to be the lucky charm of Christian Dior himself, who always sew a twig into the hem of his creations to bring them luck. The juxtaposition of virginal, celestial greenness in the lily-of-the-valley crystal tones of Diorissimo with only a hint at improper smells through the deep, warmly powdery aspect of civet and indolic jasmine in the dry-down is nothing short of magical. Alas, the latest formulation of Diorissimo has taken away that animalic warmth, leaving it with only the clean facet.
Roudnitska himself however had been quite appreciative of the pure and delicate innocence of Muguet des Bois (Muguets of the Woods) by Coty (1942). Guerlain’s seasonal limited edition of Muguet is a rich, sweeter rendition that is partly inspired by the original Muguet of 1906, while Le Muguet by Annick Goutal (2001) is an ethereal and sharper interpretation, quite true to the blossom, if only rather fleeting in Eau de Toilette (alas the only offering). Début by parfums DelRae is an intensely lovely and sylphid-like lily of the valley composition by Michel Roudnitska, which shines like ivory pearls on a long smooth neck. For those who prefer a soft and creamy treatment of the note, I suggest they try Muguet de Bonheur by Caron (1952).

Fragrances with prominent Lily of the Valley notes (in alphabetical order, click links for reviews):

Acaciosa by Caron
Anais Anais by Cacharel (along with lily)
Antilope by Weil
Aqua Allegoria Herba Fresca by Guerlain
Aqua Allegoria Lilia Bella by Guerlain
Be Delicious by Donna Karan
Capricci by Nina Ricci
Chamade by Guerlain (along with hyacinth)
Clair de Musc by Serge Lutens
Climat by Lancôme
Dazzling Silver by Estee Lauder
Début by DelRae
Dior me, Dior me not by Dior (limited edition of 2004, along with sweet pea)
Diorissimo by Christian Dior
Eau d’Argent by Montana
Eclipse by Parfums De Nicolaï
Envy by Gucci
Helmut Lang Eau de Cologne and Eau de Parfum (discontinued)
Jessica Mc Clintock by Jessica Mc Clintock
Koto by Shiseido
Laura by Laura Biagotti
Lauren by Ralph Lauren
Le Muguet by Annick Goutal
Le Muguet de Rosine by Les Parfums de Rosine (discontinued)
Lily by Dior (limited edition of 1999)
Lily of the Valley by Crabtree and Evelyn
Lily of the Valley by Floris
Lily of the Valley by Penhaligon’s
Lily of the Valley by Taylor of London
Lily of the Valley by Winds of Windsor
Lily of the Valley by Yardley
Miss Dior by Christian Dior
Miss Worth by Worth
Mughetto by L'Erbolario
Mughetto by Santa Maria Novela
Mughetto di Primavera by I profumi di Firenze
Muguet by Cotswold Perfumery
Muguet by Guerlain (limited edition, launches for May 1st only each year)
Muguet by Molinard
Muguet by Slatkin
Muguet de Bois by Coty
Muguet de bois by Yves Rocher
Muguet de Bonheur by Caron
Muguet de Mai by Roger & Gallet (discontinued)
Odalisque by Parfums De Nicolaï
Remember Me by Dior (limited edition of 2000)
Sampaquita by Ormonde Jayne
Tiare by Chantecaille
Urban Lily by Strange Invisible Perfumes
W by Banana Republic
XS pour Elle Paco Rabanne

*In a study on the headspace of lily-of-the-valley flowers using GC-MS and GC-sniffing/GC-olfactometry techniques, Brumke, Ritter and Schmaus from the company Dragoco (today Symrise, Germany) identified some 23 compounds contributing to the lily-of-the-valley fragrance, among these several newly detected trace constituents. The odorants could be divided into floral-rosy-citrusy notes: citronellol (9.6 %), geraniol (8.4%), nerol (1.3 %), citronellyl acetate (1.1 %), geranyl acetate (3.3 %), geranial + benzyl acetate (0.96 %), neral (0.02 %), benzyl acohol (35 %), phenethyl alcohol (0.78 %), phenylacetonitrile (3.0 %), farnesol (1.9 %) and 2,3-dihydrofarnesol (0.88 %), green-grassy notes: (Z)-3-hexen-1-ol (11 %), (Z)-3-hexenyl acetate (7.8 %), (Z)-3-hexenal (trace) and (E)-2-hexenal
(0.18 %), green pea and galbanum-like notes: 2-isopropyl-3-methoxypyrazine (trace) and 2-isobutyl-3-methoxypyrazine (trace), fatty, waxy, aldehydic notes: octanal (0.15 %), nonanal (0.1 %), decanal (0.07 %) and fruity, raspberry notes: beta-ionone (trace). In another study of lily-of-the-valley, phenylacetaldehyde oxime was identified (source Bo Jensen).

Muguet pic via mes-passions.over.blog.net
Adrien Barrère, illustration of F.Mayol, chromolithographie via imageandnarrative.be, Diorissimo bottle via Dior

Iso E Super, its merits, its faults, Geza Schoen and Jean Claude Ellena

The chemistry of fragrances seems like an arcane side-path in the vast avenue of pretty smells. Those who venture there are either chemists, eternal students or people reading perfume boards. On those last ones, Iso E Super is nom du jour due to recent rumours of restricting its use to specific ratios in products (and they're many!) and due to its increasing popularity, some of it attached to the work of master perfumer Jean Claude Ellena who has experimented with its magic properties many a time in the past to glorious effect: Terre d'Hermès, Poivre Samarkande and Déclaration are utilizing lots of it, exploring minimalism: the play of scents note-for-note with no sentimentality attached. Even an entire composition, Molecule 01 by perfumer Geza Schöen of niche brand Escentric Molecules (his Escentric 01 also features it in high ratios along with pink pepper, lime peel, orris and incense) is composed of nothing else but it, diluted in solvent, because the perfumer loved it so! I am hereby reminding you that he is the perfumer who created HSIDEWS for artist Sissel Tolaas and he has collaborated with the London-based niche brand Ormonde Jayne. The theory behind Molecule 01 and IsoE Super was that it would create an appealing effect to those smelling it on the wearer without it being perceived as a "perfume"; the ultimate skin-scent, much like natural ambergris to which it mimics certain aspects would act. Another scent which officially contains it is Maitresse by Agent Provocateur, while the masculine fragrance Fahrenheit by Dior (1988) iincludes a 25% Iso E Super in the compound. In the legendary woody oriental Féminité du Bois by Shiseido, under the maestro Serge Lutens's direction, the material serves as an harmoniser between the plummy effect of the fruits with the violet ionones and the cedarwood bottom notes. Iso E Super is used in so many fragrances today that it would be hard to compile an actual list that would not bore everyone silly! But what the hell is Iso E Super?, you might ask. Let's take matters at the top.

Iso E Super® is the trademark name of aromachemical 7-acetyl, 1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethyl naphthalene and I guess it's pretty obvious why it's called that instead of its long organic chemistry name. According to International Fragrances and Flavors Iso E Super is

"Smooth, woody, amber with unique aspects giving a ''velvet'' like sensation. Used to impart fullness and subtle strength to fragrances. Superb floralizer found in the majority of newer fine fragrances and also useful in soaps. Richer in the desirable gamma isomer than isocyclemone e".

Arborone is the odor active enantiomer of Iso E Super, with its clean woody and pleasing aroma.[1] The uses of Iso-E Super are legion: from bleach and deo sticks to soaps, shampoos, laundry detergents and fine fragrance. Given that its colour is almost transparent to very light yellow it poses no problems in being incorporated in formulae and is also used in the pharmaceutical industry.
Despite the IFF being the company to trademark it, Chinese companies such as Zhejiang Winsun Imp. & Exp. Co., Ltd. do provide it at a concentration of 90% for various uses. Home-made mixes would suggest one part Iso-E Super to 9 parts base, such as dipropylene glycol/perfumer's alcohol (therefore a 10% concentration). Although neat use on skin isn't recommended, minor "accidents" of spillage have not produced anything sinister. Taking in mind that it is quite inexpensive, it is perhaps of interest for apprentices and amateurs alike to experiment themselves at high dilution.

Smelling it in itself one is surprised by how almost non-existent a smell Iso-E Super has; not something one would describe as a smell in so many words, it's unapologetically synthetic and perhaps vaguely cedar-like, slightly sweet. It seems to vanish very quickly and resurface on skin in intervals from time to time very discreetly: The heat of the skin is intergral to its volatilising properly and it seems that any test on paper would not give an accurate perception of its true nature. It is however quite recognisable once you get to sample it and you will have fun detecting it in many major fragrances on the market todat. This subtle "skin-scent" effect is what in perfume-lingo is used to evoke that a fragrance stays close to the skin, not projecting in a wide radius; but also that it has some skin compatibility effect that makes it smell not like a usual perfume. Therefore IsoE Super soon gained the reputation of it acting like a pheromone, that invisible aroma that is supposed to attract same species potential sexual partners and ensures recognition of compatibility between mates. Plainly explained, pheromones act to the vomero nasal organ ensuring that pigs mate with pigs and not rhinoceruses for instance! Much as the matter is exciting and intriguing hower, the scientific community has not been able to conclusively establish validity in the theory of pheromones working in humans so far, although popular mythology is rampant with examples of products aimed to achieve this magical attraction (such as Androstenol, Androstadienone, and Androsterone). In an interview given by perfumer Geza Schöen on the creation of Molecule 01, he intimated:

"When I was introduced to ISO E Super in 1990 I gave it to a friend of mine to wear. We went out to this bar in our hometown and it took only a few minutes until this woman steered straight into our direction to inquire about who smelled so lovely! Since then I knew that this stuff is special indeed. I suggested it to the guy who was in charge of Diesel back then and he said that he felt that this is a bit too much - even for them!" [2]

He's quick to elaborate however that it does not act as a pheromone (that's a misconception if scientifically examined) but that simply it's "not possible not to like it", as no one has ever commented he/she doesn't like its particular smell per se.

Perhaps the most vexing matter to perfume enthusiasts however has been how Iso E Super is one of the 14 chemicals that have been recommended for study by the National Toxicology Program (NTP) with impending restrictions on its use. Ever since as early as 2000 the matter has been in discussion. In a letter by Betty Bridges, RN Fragranced Products Information Network (http://www.fpinva.org/) addressed to Dr. Scott A. Masten, Ph.D. from the Office of Chemical Nomination and Selection, Environmental Toxicology Program of the National Institute of Environmental Health Sciences in 2002 we read the following:

"International Flavors and Fragrance's suggested use levels of Iso E Super is up to 10% of the fragrance formula and is recommended for use in a variety of products (IFF, 2002). Isocyclemone E's (a material with a different ratio of isomers, same CAS# 54464-57-2) suggested use level is up to 30% and is recommended in a variety of applications.(IFF, 2002) [...] Considering Iso E Super's similar structure to AETT and AHTN, two polycyclic musk compounds with known concerns, it is likely that Iso E Super and other chemically similar materials would also bioaccumulate in human tissue, persist in the environment, and have health concerns. There are concerns related to AHTN causing liver toxicity and discoloration. Galaxolide, another polycyclic musk has similarconcerns, but to a lessor degree (SCCNFP, 2000) Chromogenic properties have been associated with neurotoxicity (Sabri, 2002)"

Before publication of the 43rd amendment issued by IFRA it had been rumoured that Iso E Super should be a restricted raw material. This doesn't mean that it is not to be used any more as novices often assume erronesouly. It simply means that it should be incorporated in a formula below a certain level for it to be commerialised (and of course one could do whatever they pleased if they made a do-it-yourself formula at their own labs/homes!). On the other hand another aroma material, Boisvelone (C16H26O) closely related to Iso E Super (but reportedly a little more elegant; I haven't tried it myself while one source[3] reports it as the exact same thing) has disappeared from commercial use. According to one perfumer currently teaching [4] however, a feminine "alcoholic" product (that means an eau de toilette, eau de parfum or extrait de parfum ~generally any product with an alcohol base) there is a limit of approximately 20% of Iso E Super in the final product. Although it might seem like a lot, if you are composing an Eau de Parfum, which means a 15-20% dilution, you're well within limits still even if the entire fragrance consists of Iso E Super. Luckily for all of us, the latest amendement of IFRA can be downloaded here and it seems to make us sigh a sigh of relief for now: Iso E Super is not yet restricted. ** [Please see addition on the bottom for current info on IFRA approved ratio]

Hot on the heels of the sinister rumours was the prevalent concern of perfume lovers whether the fragrances that feature it (with Jean Claude Ellena's most prominently) would suffer from it. It was only the other day that the matter was brought again to the table on this very venue, while discussing Déclaration by Cartier, one of the most influential of Ellena's fragrances. Since the objective of Perfume Shrine is to be very clear in what is only a hypothesis on our part and what is a matter of fact, we took things in our hands to further investigate and the resulting message is even more assuaging, discouraging you from frantic stocking-up of fragrances which you would fear would be unrecognisably altered. The fragrances by Jean Claude Ellena will not be altered or influenced by any -as yet only suggested for the future- restrictions of Iso-E Super ratio as they are already well below the ratio proposed for the restrictions. The information is official and comes from mr. Jean Claude Ellena himself. I hope this article proves useful to you!

Here is a table of Top Ten Fragrances with Regard to Their Content in Iso E Super
No., Fragrance Name (Company, launch year), Iso E Super
[NB. the percentage is in regards to compound, not diluted ready to use product]

1 Molecule 01 (escentric molecules, 2005) 100%
2 Perles de Lalique (Lalique, 2007) 80%
3 Poivre Samarcande (Herme`s, 2004) 71%
4 Escentric 01 (escentric molecules, 2005) 65%
5 Terre d'Hermes (Hermes, 2006) 55%
6 Incense Kyoto (comme des garcons, 2002) 55%
7 Incense Jaisalmer (comme des garcons, 2002) 51%
8 Fierce for Men (Abercrombie & Fitch, 2002) 48%
9 Kenzo Air (Kenzo, 2003) 48%
10 Encre noire (Lalique, 2006) 45%

Ref for table: Schon G. 2008. 'Escentric' molecules. Chemistry & Biodiversity. 5 (6) :1154-8. In June 2008. Verlag Helvetica Chimica Acta AG,Zurich


EDIT TO ADD/AMEND 2011: At the time of writing this was the correct info. As of 2011 however the IFRA industry regulating body has set a maximum dilution limit of 21.4% in the compound. Jean Claude Ellena's scents and the majority of scents using it are relatively safe, as a mere 1% in the formula in enough to provide the qualities it's famed for, but it is the updated info for anyone caring to use it in their own formulae.


References:
[1]Helvetica Chimica Acta, Volume 82, Issue 7, Date: July 7, 1999, Pages: 1016-1024
[2]I heart Berlin.de
[3]Nextbio.com
[4]J'aime le parfum!

Pics from Iheartberlin.de and Hermes.

The Golden Red Sunshine of Saffron 2: Chemistry and Production

The sophisticated, bitter, almost iodine taste of saffron is a constant source of fascination to me. Crocus sativus, a member of the iris family and a similar-looking flower to the latter, contains the deep red style (the female sexual organ and the central part of the blossom) and the yellow stamina (the male sexual organ which doesn't possess a taste of its own). How can this complex, somewhat hay-like odour be possible through such an unlikely material? The answer lies in the chemicals picrocrocin and safranal.
The bitter glucoside picrocrocin (deriving from the Greek word πικρός/picros and approximately 4% in dried saffron) is responsible for saffron's flavour and is a precursor of safranal. Essentially it's the marriage of the terpene aldehyde safranal (systematic name: 2,6,6-trimethylcyclohexa-1,3-diene-1- carboxaldehyde) and a carbohydrate which accounts for its formation. Saffron contains several carotenoids in fact: α- and β-carotene, lycopin and zeaxanthin. Safranal is a volatile oil, less bitter than picrocrocin and often comprises up to 70% of dry saffron's volatile fraction. It's hereby interesting to note that the related safraleine has been used by perfumers to render the hint of a leather note in some fragrances, accounting for a note of mixed shoe polish/black cherry/air conditioning refrigerating fluid (as referenced in our Production of Leather Notes article in our Leather Series).
But the most intense chemical in saffron's odour profile is 2-hydroxy-4,4,6-trimethyl-2,5-cyclohexadien-1-one, which although is less quantitatively represented, contributes more intensely than saffranol in saffron's aroma. Saffron's rich golden-yellow hue on the other hand is due to the carotenoid α-crocin. You can see this in action if you take a couple of stigmata and infuse them in a cup of hot water: you will have a richly yellow-golden liquid in your hands with a very pleasing aroma.

The harvest of the purple-hued flowers of crocus sativus is a long and arduous process that involves picking the stigmata by hand. Seeing the purple carpets of blossoms with my own eyes I couldn't help myself from sighing from the sheer beauty of it: The flowers range from incandescent to dusky as the sun changes angles on the horizon and the wind blows among the petals. Old women with 'babushka'-style foulards to protect themselves from the rays pick them slowly one by one, filling basket after basket. Dried, the stigmata are gently heated and along with enzymatic action, picrocrocin yields D-glucose and the above mentioned safranal. The aromatic potential is just one glimpse away.

The history of saffron is no doubt fascinating and to this day saffron remains an expensive commodity, cultivated from the Western Mediterranean (Spain) to India (Kashmir). More than 80% of the global production (approximately reduced from 300 to 140 tons a year although according to same sources exportation is on the rise) is accountable to Spain (La Mancha region) and Iran. Saffron is not antithetical to cooler climates nevertheless. As we had referenced in the previous installment of the Saffron Series, the English town of Saffron Walden in Essex got its very name from local production in the 16th century ~yet the former saffron cultivation sites were eventually abandoned and the only remaining saffron producer north of the Mediterranean today is the 1200m-high Mund, a small Swiss village in the Wallis canton, which produces a few kilograms per year.
Outside Europe, Iran is most productive, especially lately, finally overcoming the Spanish yield. Smaller amounts are harvested in Turkey and India with Kashmiri saffron possessing a very high reputation, yet hardly available outside India.
In Greece, saffron is a product of Protected Designation Of Origin and of Protected Geographical Indication. The Greek Red Saffron is classified as the highest quality saffron worldwide, as it lacks the bitter edge of the Iranian variety. The Co-Operative of the Kozani region in Northern Greece is selling their own organic version, hand-picked in whole stigmata, while the well-known Greek brand Korres (who joined the above co-operative with a 42.8% share) is also issuing their own packaging of organic saffron stigmata for the Greek and European market. Indeed the increasing scope of saffron as exploited by Korres can be seen in their newest Eau de Toilette for men, tagged Saffrom Amber/Agarwood/Cardamom. The illustruous heritage of saffron has reverted to its place of origin through the medium of today's technology!

Related reading on Perfume Shrine: the Saffron Series

Pic of crocus sativus via irana.ir, pic of crocus harvesting via Kozani Co-operative.

Myth Debunking 1: What Are Aldehydes, How do Aldehydes Smell and Chanel No.5

Ask any aspiring perfumista about aldehydes and you will hear that they are synthetic materials first used in Chanel No.5, that thanks to them this is the first and the prototype of synthetic fragrances and that aldehydes themselves have a champagne-like, sparkly, fizzy odor that makes the fragrance fly off the skin. This is what they have been told time and again. Ask any seasoned perfumephile and you will hear that aldehydes have a waxy, citrusy or rosy aroma, like snuffed-out candles (Luca Turin was instrumental to that with his references appearing in “Emperor of Scent”). The truth? It’s a little more complicated than either!

It’s a fact that aldehydes became famous through their introduction in copious amounts into the formula of Chanel No.5 in 1921. However No.5 is definitely NOT the first fragrance to feature synthetic aldehydes :

~"Though Chanel No. 5 is recognized as the first Aldehydic fragrance, created in the mid-twenties, the truth is that the first Aldehydic fragrance was Rêve D'Or(Golden Dream), [1]created in 1905 by Armingeat." (sic[2]).

Nor is No.5 the first modern perfume to feature synthetic components (that honor belongs to Fougère Royale -Royal Fern- by Paul Parquet for Houbigant in 1882). Aldehydes themselves are organic compounds present in various natural materials (for instance natural citrus essences such as the one from orange rind, rose oil, pine essence, citronella and cinnamon bark ~they even appear in bovine heart muscle!). Several essence reconstitutions by chemists involved using aldehydes as various types can also be synthesized in the laboratory.

Aldehydes (same as ketones) are organic compounds which incorporate a carbonyl functional group (that's C=O). The carbon atom of this group has two remaining bonds that may be occupied by hydrogen or alkyl or aryl substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde. If neither is hydrogen, the compound is a ketone. The majority of aldehydes and ketones have strong odors. Ketones generally have a pleasant smell and they are frequently found in perfumes (e.g. muscone in musk-smelling colognes). They are also used in food flavorings. Aldehydes vary in smell with most of the lower molecular weight smelling bad (rotten fruits), yet some of the higher molecular weight aldehydes and aromatic aldehydes smell quite pleasant and are thus used in perfumery. Formaldehyde is the simplest aldehyde with a central carbon atom bound to two hydrogen atoms (H2C=O). Discovered in Russia by A. M. Butlerov in 1859 it is very reactive, used in dyes, medical drugs, insecticides and famously as a preservative and embalming fluid.
Aliphatic aldehydes possess intriguing smells outside the realm of simplistically nice: butyraldehyde for example smells of rancid butter (from βούτυρο/butyro which means "butter" in Greek)! Acetaldehyde is the name of the shortest carbon chain aldehyde and is one of the oldest known aldehydes (first made in 1774 by Carl Wilhelm Scheele). Its structure however was not completely understood until Justus von Liebig determined the constitution of acetaldehyde 60 years later, described its preparation from ethanol, and baptised this chemical group “aldehydes”.

Hardly a fragrance exists without some kind of aldehyde in it, which incidentally makes insisting the greatness of No.5 is due to its synthetic materials comparable to saying that the Pyramids are monumental because of their shape alone. It is the cleverness of marketing and the propagation of a myth that No.5 was meant to evoke an unnatural smell (because supposedly Coco Chanel insisted that she wanted a perfume smelling of a woman and not of flowers ~"women do not want to smell of a bed of roses") which gave rise to this confusion. Chanel No.5 and No.22 later owe their vivid sprakle to a specific subgroup of aldehydes which are called “fatty”: strings of carbon atoms (between 8 and 13) coded in accordance to that number of atoms (ie.C8) with nomenclature deriving from Greek numerics, such as octanal from οκτώ/octo (=eight), in which each of the 8 carbon atoms is connected to two hydrogen atoms. The “bouquet” of aldehydes C10, C11, and C12 in Chanel No.5 became so popular that all consequent “aldehydic fragrances” used that sequence of aldehydes, giving a fizzy perfume-y scent that is quite characteristic with the direct result of having the perfume lover confused as to how aldehydes themselves smell. Fatty aldehydes have a citrusy or floral note, and a pronounced fatty/waxy/soapy tone which is very apparent if you consider a modern fragrance that uses them in high ratio: Sicily by Dolce & Gabbana. The soapy feel is unmistakeable! As an exercise compare that smell with your Chanel No.5: you will pick up the soapy facets in that one as well. Another reason that they read as “soap” is exactly because they have been used in the production of soap for years to give that fresh lemony feel.

Most widely used aldehydes in perfumery are C7 (heptanal, naturally occuring in clary sage and possessing a herbal green odour), C8 (octanal, orange-like), C9 (nonanal, smelling of roses), C10 (decanal, powerfully evocative of orange rind; Citral, a more complicated 10-carbon aldehyde, has the odor of lemons), C11 (undecanal , “clean” aldehydic, naturally present in coriander leaf oil~also used is unsaturated C11 undecen-1-al), C12 (Lauryl aldehyde evocative of lilacs or violets), C13 (waxy, with grapefruit tone)and the infamous C14 peach-skin note of Mitsouko: technically not an aldehyde, but a lactone ~gamma undecalactone.

Often the compounds are patented under commercial names; therefore their true nature remains arcane even to perfume lovers who might have seen them mentioned. For instance Triplal, a patented molecule by IFF: its chemical name is 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde. Its smell? Powerfully green and herbal, like crushing ligustra leaves between fingers. None of the characteristic aldehydes of Chanel No.5!
One interesting ingredient is phenylacetaldehyde which has a pronounced green note (top in natural narcissus and thus used to recreate a narcissus note in perfumery). The hydrocinnamic aldehydes are another family of materials from the manipulation of benzene and their odor profile resembles lily of the valley (muguet) and cyclamen. One of them is the famous Lilial (patented name for lily aldehyde; also known as Lilistralis), widely used in the replication of that elusive natural essence, lily of the valley. Another is Cyclamen aldehyde (usually produced with cumene as a starting material).
Aromatic aldehydes have very complex chemical structures but are the easiest to identify by smell. Anisaldehyde smells like licorice. Benzaldehyde on the other hand, has an odour profile of almonds and has several chemical constituents: cinnamaldehyde, amylcinnamic aldehyde, hexylcinnamic aldehyde. Condensation of benzaldehyde with other aldehydes gives a series of α-substituted cinnamlaldehydes, the lowest member of which is used in the production of cinnamyl alcohol, very important in the production of spicy perfumes (cinnamon note). Higher members, on the other hand, such as amylcinnamic aldehydes (ACA) and hexylcinnamic aldehyde (HCA) project a fatty jasmine impression despite their abscence from natural jasmine oils! Most synthetic jasmine perfumes today use one or both because they are inexpensive (Their fibre-substantive qualities also make them perfect candidates for laundry detergents and fabric conditionners). The hawthorn or aubépine note, rendered synthetically in perfumes for several decades, is produced via anisic aldehyde (p-methoxy benzaldehyde) and it has been sublimely woven into the gauzy cloth of Après L’Ondée by Guerlain (where it sings along with heliotropin). Additionally, the aldehyde vanillin is a constituent in many vanilla-scented perfumes. So nothing is as simplistic as one might assume!

Aldehydic fragrances include (click links to read corresponding articles/reviews): Chanel No.5 and No.22, Lanvin Arpège, Guerlain Liu and Véga, Worth Je Reviens, Millot Crèpe de Chine , Balecianga Le Dix, Revillon Detchema, Caron Fleurs de Rocaille (not Fleur, singular), Infini and Nocturnes, Myrurgia Joya, Jean-Charles Brosseau Ombre Rose , Molyneux Vivre, Lancome Climat, Givenchy L’Interdit, Piguet Baghari, Madame Rochas and Mystère by Rochas, Rive Gauche by Yves Saint Laurent , Paco Rabanne Calandre, Estée Lauder Estée, White Linen, Pure White Linen, Van Cleef & Arpels First, Nina by Nina Ricci (the old formula in the ribbed bottle), E.Coudray Musc et Freesia, Bill Blass Nude and Amazing, Hermès Amazone, D& Sicily, Divine L’Ame Soeur, Serge Lutens La Myrrhe, Frederic Malle Iris Poudre, Ferré by Ferré, Agent Provocateur Maitresse, Annick Goutal Folavril, Le Labo Aldehyde 44.
Hermès Calèche is poised between floral aldehydic and floral chypre in some taxonomies.

[1]Bernand Chant, British Society of Perfumers 1982
[2]Armigeat is perfumer Pierre Armigeant (1874-1955) who composed Floramye and Azurea for L.T.Piver

Painting Gueridon 1913 by Georges Braques, courtesy of allposters.com. Chanel makeup ad via Bellasugar.

Dans Tes Bras by Frederic Malle: fragrance review

It would not be an overstatement to say that the “library” comprised of Frédéric Malle edited tomes of olfactory literature is one of the most stimulating lines in modern perfumery. Now perfumer Maurice Roucel gives us another volume to gnaw our teeth on, Dans Tes Bras (In Your Arms). Their previous collaboration on Musc Ravageur (2000), a best-selling vanillic oriental that despite the name has more of a pronounced spicy, sensual accord than the musky effluvium of a warm body à la Muscs Kublaï Khän, managed to entice even those afraid of the risqué intimacy of the latter.

Inspirations
Dans Tes Bras aims for a new interpretation of sexiness:

“The deep and lasting odor of warm skin, with all of its salty hints and rich overtones. A fragrance carved with hefty chunks of cashmeran, sandalwood, musk and patchouli, reinforced with salicylates and incense, softened with heliotrope, colored with a violet accord. An intimate but deep sensuality, an exalted skin scent, the real essence of the perfume”.

Dans Tes Bras communicates seduction and generosity in an amalgam of masculine-like nuances simultaneously clean and dirty, like a man confident of his prowess enough to show a tender side as well.

Scent Profile

The habitually damsel-like violet note is treated here as an unforeseen touch of freshly turned soil with the merest sprinkle of powderiness due to heliotropin, the unifying element with Roucel’s much sweeter and tartly fruity Insolence Eau de Toilette, its hairspray-opening and all. Green bittersweet patchouli and abstract woods create a bodily landscape of earthy delights which blooms with every passing minute. I do not significantly perceive frankincense smoke, even though it is there, while Six’s impression of fields of mushrooms is another image for the wet undergrowth that arrested my perception: favorably. The creamy, discreetly musky summation stays poised on skin for hours radiating warmth. In sum Dans Tes Bras makes me yearn to don a pair of breeches and trudge along bucolic sceneries of still humid, autumnal beds of decaying leaves accompanied by roborant company.

Maurice Roucel, an autodidact starting at Chanel’s Fragrances Laboratory in 1973, is a sensuous aesthete, with streamlined formulae as his signature evident in such marvels as 24 Faubourg, L de Lolita Lempicka and the missile-in-the-air Insolence. It is therefore of great interest to see how he proceeded with Dans Tes Bras.

Composing Dans Tes Bras

Violet, a symbol of ancient Athens where it was used in scenting wine and Napoleon Bonaparte’s favorite flower, is a complicated matter in perfumery for two reasons: First the natural extract of viola odorata (sweet violet/English violet), although it exists, is rarely used for reasons of cost and versatility. Secondly because there is a distinction between violet flower and violet leaf: the two have a world of difference in terms of odor profile, but that’s not always clear in fragrance descriptions. The flowers have a sweet, powdery ~and when fresh slightly spicy~ note, while the leaf is earthy, green with a cut-grass feel.

The symbolism of violets as emblematic of death at an early age is apparent in the John Everett Millais painting "The Death of Ophelia" and violets which stood for constancy or devotion were traditionally used in mourning. Most people however associate violet with Parma Violets, a violet-flavoured confectionary manufactured by the Derbyshire-based company Swizzels Matlow; or alternatively, depending on cultural memories, with Violettes de Toulouse, violets preserved by a coating of egg white and crystallised sugar still made commercially at Toulouse, France. These tender, playful associations might account for the popularity of several sweet florals in the market, such as Drôle de Rose, Lipstick Rose and indeed Insolence.In violets along with terpenes, a major component of the scent is a ketone compound called ionone, which temporarily desensitises the receptors in the nose; this prevents any further scent being detected from the flower. Ionones were first isolated from the Parma violet by Tiemann and Kruger in 1893. The discovery of ionones enabled cheap and extensive production of violet scents, cataclysming the market with inexpensive violet colognes which became au courant. The ionones palette ranges from the scent of fresh blossoms to mild woodsy sweet-floral tonalities, while methyl ionones possess a stronger woodsy nuance, similar to iris rhizomes, binding woody and floral notes perfectly such as in the masterful Lutens creations Féminité du Bois and Bois de Violette. And let’s not forget that Roucel was the composer of the mournful, cooly wistful Iris Silver Mist for Lutens focused on the nitrile Irival too!

Violet Leaf absolute on the other hand smells herbaceous with an oily earthy nuance and naturally includes salicylates, more on which below. Octin esters and methyl heptin carbonate are used to render the floral green violet leaf odour with watery accents of melon and cucumber, customary in many modern masculine fragrances and the family of fougères (an aromatic group based on the accord of lavender-coumarin-oakmoss). It also gave the older version of Farhenheit its distinctive feel. If you want to get a good impression of violet leaf in a contemporary composition, smell Eau de Cartier. Several of the greener violet fragrances in the market such as Verte Violette by L’artisan or La Violette by Annick Goutal explore those aspects.
In Dans Tes Bras the tone comes from Iraldeine, a base that helps recreate the freshness of violet flowers. The aromachemical α-n-methyl ionone became commercially available around 1935 in Haarmann & Reimer's Iraldeine Alpha rein and Givaudan's Raldeine A (the main constituent of Fath’s legendary Iris Gris) which Ernest Beaux ~good friends with Leon Givaudan~ is said to have included in 25% concentration in the long-lost Mademoiselle Chanel No.1 from 1942-1946 (as analysed and publicized in 2007 in Perfumer & Flavorist magazine).

Benzyl Salicylate (benzyl ortho hydroxy benzoate) is an almost colourless liquid that has a mild balsamic, sweetly floral note possessing excellent blending capabilities. Often used as the foundation for heavy florals such as ylang, gardenia, jasmine, lily etc., it is also used in functional products such as soap, shampoo and fabric softener. Along with Methyl Salicylate, salicylates “turn the most banal floral composition into a real perfume, with majestic weight and sweep” divulges Luca Turin. However some people are anosmic to it, including some perfumers. Guy Robert could not smell benzyl salicylate at all, but could instantly recognize its presence in perfume: “I recognize it as if it were a friend seen from behind in a crowd, by the cut of his shoulders”. Indeed in the words of nose Bernand Chant “it produces a diffusing, blooming effect very pleasing to the public”. Many orchid fragrances are built on salicylates, while the mysterious emerald glow of the vintage Je Reviens is also due to them. Coupled with eugenol and isoeugenol, the effect becomes almost carnation-like with its clove tint. The magic of benzyl salicylate can be best experienced in the archetypal floral bouquet of L’air du Temps featuring an overdose of the ingredient. Its progeny included Wind Song, Norell, Estée, Charlie, even Angel! However the recent restrictions on the use of benzyl salicylates have taken their toll on many floral fragrances, L’air du Temps included, which simply do not smell as they used to.

Methyl salicylate (salicylic acid methyl ester or oil of wintergreen ~because it is present in lots of evergreens such as birch and also rhododendrons~ and commonly featured in arthritis and muscle body rubs but also in Life Savers) has a green glow with camporeous aspects. Naturally occuring in tuberose, jasmine and hyacinth absolutes, as well as ylang ylang and neroli oil, it provides that characteristic eucalyptus-mint nuance of Tubéreuse Criminelle and to a lesser degree Carnal Flower. It is also a big ingredient in birch tar, used in Russia in treating leather and therefore associated with Cuir-de-Russie-themed fragrances, modernly interpreted in Dzing! and Bulgari Black. Also present in cassie absolute, so it seems to be the bridge between those and Une Fleur de Cassie; the connection being that acacia bark (the inspiration behind the latter) was also used in treating leather, in France.

Finally Cashmere Woods or Cashmeran, a favorite of both Roucel and Malle, is a IFF patented, complex aromachemical that provides a beautiful, velours note with diffuse nuances of earthy-wood and spicy notes (pine, patchouli), fruits and flowers (heliotrope, red fruits, apples and jasmine) and is softly musky-vanillic, entering Dans Tes Bras at the appropriate dosage. It's featured in Ysatis, Amarige, Michael, Lacroix Rouge, Perles de Lalique, Beautiful Love and many more.

Dans Tes Bras is thus an excellent example of a fragrance in which analysis makes for much better understanding and appreciation.

Official Notes:bergamot, cloves, salicylates, violet, jasmine, sandalwood, patchouli, frankincense, cashmeran, heliotrope, white musk

Dans Tes Bras has been available in Europe since September ’08 and will become available in the US this coming October, in Eau de Parfum bottles of 50ml/1.7oz and 100ml/3.4oz through the appointed select doors and the Editions des Parfums site.

Pic of actor Ken Watanabee originally uploaded on MUA, I believe it's by Anne Leibovich. Bottle pic via F.Malle

An Iris Problem: How to Build One

I got a most interesting mail the other day: Someone who is clearly very much a perfume lover and whom I knew before through the blog was asking me what I thought was a perfumer's perfect way to build a masterful iris. It surprised me because I am not a perfumer myself, but intrigued my nerdy tendencies enough to devote a post to it.
I have to put a disclaimer here that the post will feature some chemistry and might be perhaps a little boring for those of you who'd rather read ethereally poetic reviews about fragrances or some comedic spoof take on popular trends. But despite all that and knowing it won't be too popular, I thought it was worth addressing and I promise I will try to state it as simply as possible and even include a small index at the bottom for your ease.

Our reader has been reading what many of you have too: The Emperor of Scent by Chandler Burr, Luca Turin's Secret of Scent and Perfumes, the Guide, many online perfume blogs and boards...the works! Based on that and some knowledge of chemistry on the reader's part, those are the questions posed:

"I know α-n-methyl ionone (aka Givaudan's Raldeine A) was the chief component featured in Iris Gris. I also remember that one also needs irones; they are crucial, since it's this group of compounds that give orris its distinctive aroma.
Now, problem number one: which irone isomer(s) {1} should one use? I know orris emits at least three irones: cis-gamma, cis-alpha, trans-alpha irones. Octavian mentioned alpha irone in his Iris Gris entry (didn't mention which enantiomer {2} was used in Iris Gris). So what would be your pick? Is there a commercial blend, say, from IFF, that produces a good irone bouquet?
Then there are the interesting molecules....I remember Chandler Burr mentioning something about methyl ionones, which is a bit confusing since I assume ionones must have a methyl group stuck with them as well. Is this necessary? In addition, Dr. Luca Turin also talked about Maurice Roucel's ingenious use of Irival (produced by IFF), a nitrile{3} that gives Iris Silver Mist it's interesting quality. Now I'm lost..."

The question is interesting because it goes to the heart of the matter: in order to build a solid, good, true iris, where should the perfumer look?

To my understanding, irones are higher analogues of ionones, because they contain an additional methyl group in the cyclohexane group.
Although irones are indeed present in natural orris, it seems that production of a-irone has become standard, starting from a-pinene via the Caroll re-arrangement. [Basically the schema is going like this for anyone taking notes: A-pinene goes through decarbonylation, gives methyl trimethulcyclobutyl ketone, they add acetylene, there goes the Caroll re-arrangement, we get (trimethylcyclobutyl) heptadienone, pyrolysis is induced, giving methylated ψ-ionone and through cyclization this gives α-irone.]
Let me at this point clarify regarding the Greek letters (α: alpha, β: beta, γ: gamma) in the nomenclature of irones (as well as ionones and damascones) that they refer to the position of the double bond after the ring closure, while n- and iso- to the position of the alkyl group (assuming something other than acetone is used in condesation).

I suspect this ease of production is the reason why we have been flooded with iris fragrances the last couple of years: like Octavian pointed out, it has become easy to synthesize, not to mention it is a great marketability tool in a milieu which thrives on semi-info (the perfume lover usually knows that iris is the most expensive natural ingredient). Two birds in one shot!

But wait: what was that interesting molecule that Chandler Burr was referenced to mention? It must be a-iso-methylionone which had been erroneously mentioned as γ-irone in some old texts. At least, I suppose so... Therefore another irone, used to produce an iris effect.

Concerning Iris Silver Mist and Irival, let me set this straight. The info is not that Irival gives the fragrance its very specific iris scent (I just checked Luca's book before I typed this), but that it has been used in conjunction with other things to produce the ethereal, sad and grey rooty effect that we smell in Iris Silver Mist. Maurice Roucel, the perfumer behind it, used every ingredient he had acess to that had an iris descriptor attached to it, prompted by Lutens who urged him to produce an iris to the max.
There are possibly myriads of ingredients that have an iris descriptor attached to them (meaning they have some nuance of iris in their odour profile); if one reads lists of ingredients one sees that. To reference an example: Like we say that oudh has a musty woody but also nutty nuance when we smell it, the same applies for other ingredients, some complex like natural essences and some less so like single molecules. Roucel probably used all the ones available to him at the time and in the company he was working with.

Basically what I have concluded is that there is no single molecule that alone could account for a sublime effect on any perfume, be it an iris one, a certain jasmine effect or the surreal ones such as those based on dusty lamp and linen drying in the wind notes. Although we're often made to think that chemists discover magical aromachemicals/single molecules (and they do) which in bullet-form could almost fuel a rocket, to bring an analogy, I think that it has to do with context as well. The interaction of different ingredients with each other accounts for many pleasurable and not so pleasurable sensations and therein lies the artistry of perfumery. Rose and patchouly for instance do wonderful things to one another, which is probably why they are often combined. But with what different effects: smell Voleur de Roses side by side with Aromatics Elixir. The result is dissimilar. They are both based on this accord, but they go in different directions from there. Otherwise every chemist would be a perfumer! It takes however something more than that to become the latter.

The secret of producing a masterpiece iris -or anything else for that matter- lies in the artistry of the formula and the sleight of hand of its creator.

Index:
{1}.Isomers are compounds with the same molecular formula but different structural formulae.
{2}.Enantiomers, like their Greek etymology alludes to, are stereoisomers which have a mirror image of each other, much like one's own hands (the same, but somehow opposite).
{3}.A nitrile is any organic compound which has a -C≡N functional group (that is a carbon and a trible bonded nitrogen).

Pic of perfumer Alberto Morillas courtesy of Basenotes.net