Perfumery Materials: Pyrazines, Burnt/Caramelised/Maple Notes

One of the new trends that's gaining momentum as we speak is the one focusing on slightly "burnt", caramelised, overcooked notes that are remininscent of toast, sticky brunt toffee or maple-laced warm milk; a darker shade of gourmand if you will! Suffice to take a look at Jeux de Peau by Serge Lutens (shades of fresh toast) or Sensuous Noir by Estée Lauder (a crème brulée almost taste under the patchouli), not forgetting Minuit Noir by Lolita Lempicka which follows the path where L de Lempicka left off. Gourmand fragrances (a subset of orientals focusing on foodie notes) aren't going anywhere; even genuine gourmet food companies are issuing their own fragrances, if Payard is anything to go by. But a more nuanced, more sophisticated approach is ushering in, hooking up even die-hard purists.

But which materials are responsible for these flavours, these seemingly off-notes that nevertheless entice our taste buds as much as our intelligence?

One category is pyrazines, organic compounds with a ring structure of at least two elements. Naturally occuring in a variety of foodstuff (such as green peppers but also peas; plus they're used to enhance the "roast" factor of coffee and cured meats and to enhance the flavour of potato salad). In fragrance terms Lutens and Chris Sheldrake manipulated the roasted aroma of pyrazines into a composition that enhances the comfort factor with creamy sandalwood: eh voilà, Jeux de Peau was born!


Other molecules that render indispensable gourmand notes are:

Maltol or 3-hydroxy-2-methyl-4-pyrone...C₇H₈O_{3
.............................}
Although we have come to consider Ethylmaltol (see below) the standard "cotton candy" (candy floss) note of reference in perfumery, maltol is a naturally occuring chemical that can been found in chicory, cocoa, coffee, roasted malt, bread or even strawberry and which gives this spun caramelized effect we have come to associate with fair grounds.
Ethyl Maltol or 3-hydroxy-2-ethyl-4-pyrone...C₈H₁₀O_{3 ..............................}
Ethyl Maltol is the ethyl analog of Maltol, of course, but this time the molecule is synthesized in the lab and is not to be found in nature: hence the boosted effect; almost 500% more than simple maltol!
Smell Thierry Mugler's Angel, the trendsetter of ethylmaltol and patchouli orientals ~with a nod to childhood~ from 1992 and be prepared to be blown away by its potent spun sugar, cotton candy note!

Furaneol^(R) or 2,5-Dimethyl-4-hydroxy-3(2H)furanone ..C₆H₈O_{3
..........................}
This is a molecule which was taught to samba from the craddle: it naturally contributes largely into the chemical make-up of several tropical fruit (guava, lychee, pineapple) as well as other less exotic ones (strawberry, raspberry, tomato). The fact that it is used in roasted products as well (such as corn tacos, roasted almonds, popped pop-corn or roasted coffee) contributes to its perception as a "roasting" note. I hypothesize that it's at the heart of Dior's Miss Dior Chérie, a composition based on the tension between strawberry and freshly cooked pop-corn.

Cyclotene or 3-Methyl-2-cyclopenten-2-ol-l-one ..C₆H₈O_{2
..........................}
With Cyclotene we enter the maple section of notes: Although fenugreek solid extract is used to render a maple-suryp note (indeed it was the only extract source of caramel-maple notes till the discovery of these other ingredients), actual maple suryps are further aromatized with Cyclotene; thus creating the vivid association of the molecule's odour with our perception of how maple suryp smells like! Is it maple that smells of Cyclotene or Cyclotene that smells of maple? Naturally occuring in fenugreek seeds, it's also very common today in roasted sugary products such as coffee desserts, licorice sweets, desserts with roasted almonds and, apart from fenugreek seeds, it also occurs in cocoa and coffee.

Sotolon or 4,5-Dimethyl-3-hydroxy-2(5H)-furanone..C₆H₈O_{3
..........................}
Sotolon is the key ingredient in roasted fenugreek seed and brown sugar, which is as yummy a combination as any, hence its reference as "caramel furanone" or "sugar lactone" as well as "fenugreek lactone". When it's really concentrated, it takes on curry-like tonalities while on lower concentrations it can stay within the "caramelised sugar on the pan" range of odour.
But Sotolon also possesses notes that match boozy tonalities, as it's occuring in sake, rice wine, and botrytized wine. Remember the niche fragrance Botrytis by Ginestet, meant to reproduce the "noble rot" of a fungus on the Sauternes grapes? It's got Sotolon in it, blending the pain d' épices, candied fruits and honey notes into one seamless blend.
Although Sotolon is thousands of times more powerful than Cyclotene, the modern flavours industry is using the even more powerful maple furanone (one of the most potent flavor chemicals known to man) , this time for the enhancement of the flavour of soy sauce. Thankfully, this ingredient hasn't bombasted commercial fragrances yet, but who knows what the future holds.


Related reading on Perfume Shrine: Immortelle/Helichrysum: golden sunshine of the Med , Perfumery's Raw Materials

Ref: Leffingwell Photo of maple syrup by Martin Eager

Serge Lutens Jeux de Peau: fragrance review & draw

Horace had written* referring to his diet: "Me pascunt olivae, me cichorea, me malvae" ("As for me, olives, chicory, and mallows provide sustenance"). I don't know if I could supress my gluttony for "all the perfumes of Arabia" into a diet of only a few well-chosen ones, but Serge Lutens has a way into tempting me. Jeux de Peau, his newest (upcoming for the US) launch, is no exception. With vivid contrasts and a fascinating plot via Daedalean alleyways, it proves that the Master is still producing fragrances that can surprise and excite.


Jeux de Peau (pronounced Zø de POH) aka Skin Games, a fragrance for both genders, was supposed to smell of buttered toast, recalling Serge's quick run to the boulangerie across the road to pick up a baguette: "It gets me back to the 'don't forget to pick up the bread on the way back from school!' At the boulangerie at the end of the road, its captivating odour and its blond and warm light, a golden moment..." says Serge. Well, naughty, naughty Uncle, this is not what one would expect! The mercurial Serge actually hints at the humanity of the fragrance when he provocatively says "Eat, for this is my body"; especially if we consider that some human skins do smell like bread, the "dough" impression being a Ph variance.

Not that that this cryptic game would be unusual for any fan; in fact the fascination with the newest Lutensian opus comes exactly by its surprising character, at once a part of the Lutens-Sheldrake canon and a little apart; it's new and at the same time familiar, like seeing the photographs of antecedants and trying to pinpoint what part of the genetic roll of dice resulted in similarities with one's own offspring.
Starting to break down the composition of Jeux de Peau much talk has been conducted about the "burnt" note of pyrazines [see this lexicon on perfume effects according to notes/ingredients for definition] but I remain sceptical: Jeux de Peau doesn't really smell burnt or heavily roasted; more milky-spicy-golden in the sandalwood goodness that was Santal Blanc. It has a pronounced celery-pepper opening note, much like Chypre Rouge did, a trait that will certainly prove controversial, coupled with delectable milky-buttery notes which almost melt with pleasure on skin. The celery effect ~celery seeds were a common element in Mediaeval French cooking~ lasts for only about 5 minutes seguing into the main course: the buttery accords, alongside a distinctive, very pleasant chicory note.
Chicory, a bitterish-spicy smell, is a profoundly clever "note", if I am correct in surmissing it was the centre of the Jeux de Peau creation all along: It was substituting coffee in WWII, which might account for some of the memories of Serge, but it also evokes beer because producers add some in their stouts to lend flavour. Beer is so close to bread in olfactory terms that it's enough to put some on a pot on the stove for your guests to be fooled into thinking you're baking your own bread! (Not that you'd resort to such tricks, or would you?) Plus chicory root is 20% inulin which is very similar to starch. So the bread connection is there all right!
Immortelle/helichrysum notes (caramelic maple & spicy fenugreek facets) are allied to the familiar candied-dried fruits (apricot mainly, simply lovely!) which perfumer Chris Sheldrake has been respinning in novel and delecious combinations for Lutens ever since the inauguration of the Palais Royal niche line in 1992. This complex stage in Jeux de Peau by Lutens is sustained for a long, long time; it reminds me of rich Byzantine mosaics; tiny tesserae of glazed material surfacing and receding according to the angle from which you're viewing it.


If you like the core accords of Féminité du Bois or Boxeuses, you will probably detect them easily in Jeux de Peau. But the two diverge in other ways: there's no familiar plum, not much cedar, nor leather (as in the case of Boxeuses), while we can see that wheat & barley are evoked throughout that warm "gourmand" woody. If Serge hadn't mentioned he was inspired from his forays to the baker's clutching the baguette for home, we wouldn't be so insistent on searching for toast; a whiff of Crusader's pain au four it is and delectably so I might add.

If you're wondering if Jeux de Peau would suit you, apart from the wise advice I can offer to always sample a Lutens any fragrance ~just in case~ I can suggest that if you're a lover of other intellectual oriental woodies such as Like This by Etat Libre d'Orange or Tea for Two by L'Artisan, you have high chances of liking this one very much as well. It's rather odd that Jeux de Peau launches in spring, when it's the sort of snuggly fragrance you'd want to put on while wrapped in a cashmere blanket watching nonchalantly the logs in the fireplace change colours from brown to vermillon to bright red to ashen, but Lutensian fans are not very season-specific anyway.

A sample of the upcoming Jeux de Peau will be given away to a reader. State in the comments what is your most fragrant memory from childhood not involving actual fine fragrance and I will pick a random winner. Draw is open till Friday midnight.

Jeux de Peau belonging to the export range of oblong bottles is out in France as we speak (79 euros for 50ml Eau de Parfum), but will launch internationally on March 1st. The Perfume Shoppe in Canada is already taking pre-orders.

*Odes 31, ver 15, ca 30 BC

An intelligent essay on the scent, in French, on Ambre Gris. Photograph in black & white Le Petit Parisien by Willie Ronis via Art is not Dead. Bottle pic via duftarchiv.de
Disclosure: Initial sample was kindly procured by my reader Emanuella. Another sample was later sent by Lutens as part of their mailout, so that is given away to the readers.