Guerlain Apres L'Ondee: fragrance review

What's in a name? What's in a material? Shakespeare's immortal line has a lot to account for. Lots of scents with heliotrope pose as "almond" or "marzipan" or "powder with tonka". These are all scents with a kinship that runs deeper than initially thought of. The synthesized material that is dosed into compositions that take heliotrope as a starting point is quite strong and can be an overwhelming molecule to work with if one isn't careful and discreet. One of the first major fragrances to make judicious use of it, in a light enough composition, so as to wear it inconspicuously, was Après l'Ondée by Guerlain, "after the spring shower" as the name implies.  

"Ça se porte léger" (this wears lightly) is the motto behind the concept of these Guerlain creations that aim to offer gouaches rather than oil paintings. It's more akin to the pale, hazy colorations on a Monet sky than the almost fauve brushwork and vivid color palette on a Van Gogh, to bring an art analogue. If one were to look for a fauve heliotrope, one would rather turn to Cacharel's Loulou.

Zaira Alfaro on Flickr via

I personally find Après l'Ondée a rather quiet fragrance indeed, almost timid, with a sweetish air that is not immediately thought of as feminine (quite different than the airs that current feminines exhibit!), with lots of heliotropin to stand for cassie, which is the predominant element. Some heliotrope scents also recall cherry pie, or lilac and powder, but not Après l'Ondée. Even the almond is not particularly identified as almond, it's a haze of lightly warmed, blurred, hazy notes, a cloud of a distant scent.

The violets, like you might have heard, are quite fleeting in this Guerlain perfume, especially in more recent incarnations which are warmer and cuddlier than the older ones, notably the extrait de parfum in the Louis XV style bottle. The anisic note on the top note is also a brilliant addition (created through the use of benzylaldehyde, it would be recreated more forcibly in L'heure Bleue some years later), since it brings a chill cooling off the first spray and balances the warmer, almond paste flavor of the heliotrope in the heart.

Après l'Ondée is also rather less known than L'Heure Bleue, so even Guerlain wearers on the street might not identify it right off, which is always a good thing in my books; it would also obliterate your qualms about it being perceived as solely feminine.

The Smell of the Earth After the Rain: Geosmin, Petrichor & Other Wonders

The first heavy drops of rain fell on the thirsty ground yesterday after a hot, hot summer that scorched our conscience. It seemed like release, like tears falling after a gigantic pressure mounting inside that had overflown, ready to burst.

"With the first drop of rain the summer was killed. Soaked were the words which starlight had born. Words that were meant just for you." writes Odysseas Elytis. 

This sweet melancholy of autumn is inextricably tied to the pit pat of the raindrops on the window pane, much as it sounds corny. Like many, I adore the ambience after the rain; when everything seems washed, purged, the green leaves and flowers shiny fresh with droplets hanging onto them refracted into myriads of rainbows in the emerging light; with the distinct smell of the earth that has soaked the water and brought out a scent at once musty and refreshing, a scent that is ancient and at the same time of the moment, galvanizing, a scent of the divine and the pagan. But what makes that delicious scent, popular enough to be first unapologetically encapsulated into a fragrance to sell by Christopher Brosius in his Fragrance Library for Demeter by the eerie name "Dirt"? The answer is more enjoyably lyrical.

via http://lifeofpri.blogspot.com

Petrichor is the name of the scent of rain on dry earth, which aided by the compound geosmin contributes to that delectable ambience of upturned earth and musty deliciousness which walkers of the woods have been known to enjoy with all their might. Due to poetic justice, I suppose, and because everything is paid upon at the cashier eventually in this world, both words have a Greek origin: "Petrichor" literally means the fluid in the veins of the gods hitting stone (from the words πέτρα i.e. stone and ιχώρ i.e. the mythical lifeblood of the Gods). "Geosmin" is simpler, more to the point: from the Greek word for earth, γαία (deriv. γεο-) and οσμήν i.e. smell; simply put, "the smell of the earth". The term "petrichor" was coined in 1964 by two Australian researchers, Bear and Thomas, for an article in the scientific journal Nature. In their article, it is argued that certain plants exude an oil during dry periods which is then absorbed by clay-based soils and by rock. The hitting of the ground during the rain releases this oil alongside geosmin, a germacranoid sesquiterpene or a trans-1,10-dimethyl-trans-9-decalol for the more chemically minded ~or simply a by-product of microorganisms, which acts as a metabolite.

Geosmin is produced by a number of microorganisms amongst which the mycelial soil bacteria Streptomyces. Geosmin is exactly that distinct smell that soil gives off when disturbed or just rained upon and its human detection threshold is so low (allowing almost all to savor it) and so pleasant, it is used to confer an earthy scent to perfumes! But careful: in flavor, by contrast, geosmin can turn a glass of water or wine (or fruits or vegetables) musty and unpleasant for consumption. Even lightning contributes to the scent of the earth after the rain nevertheless; the presence of ozone is electrifying, producing that energetic, come what may, putting on boots and clutching a cane walk in the woods mood one doesn't know they had in them until it actually happens. This is the magic turn of the screw that makes fragrances such as Creed's classic Green Irish Tweed (with the infinitely matching name to this fervent desire) and the quirky enchanted forest of Ormonde Woman work so well.

Several perfumers try to recreate that complex smell of the forest floor; upturned, a little decayed, yet at the same time fresh, cooling, a sort of clean all the same. Great vetiver fragrances, such as Guerlain's classic Vetiver and Vetiver pour Elle, Route du Vetiver by Maitre Parfumeur et Gantier , Chanel's Sycomore, Lalique Encre Noire or F.Malle's Vetiver Extraordinaire mingle that particular freshness that the exotic grass root of vetiver possesses alongside a smokier, mustier background which brings on a crepuscular tinge. Some patchouli fragrances, notably Voleur de Roses by L'Artisan Parfumeur utilize the more wine-like facets of the rose and the Indian leaf material to render a scent that approximates well a garden after the rain. Herbal accents and iris notes alongside grassy-musty ingredients (such as vetiver, angelica, wormwood or oakmoss) also produce this effect as in Roadster by Cartier, L'Artisan Parfumeur Timbuktu, the stupendous Derby by Guerlain, Angeliques sous la Pluie (F.Malle) and Dior Homme.

It's interesting to note that geosmin doesn't just contribute to the smelly landscape but could be a way of promoting sporulation as it occurs where humidity is involved. "Camels may well smell out an oasis by sniffing the air for traces of the fragrant metabolite. While camels quench their thirst, hordes of Streptomyces spores will be supped with the water or will find a way to stick onto the animals’ hides. In this way, spores can be carried for miles. In the same way, some cacti flowers may also use the geosmin scent to fool insects, in a sort of fragrant mimicry. Indeed, insects are attracted to the plants in the hope of a little refreshment, and in their quest for water, they actually serve as pollinators!"[source]

As with everything involving smell, there's more than meets the nose...

 
Music clip "With the First Drop of the Rain", lyrics by Greek nobelist poet Odysseas Elytis, set to music by Manos Hadjidakis and sung by Dimitris Psarianos.

Perfumery Material: Cashmeran/ Blonde Woods

Thanks to its pliability, which fits like a glove many diverse compositions of different fragrance families, or thanks to its diffusiveness and tenacity, Cashmeran or blonde woods is a molecule which forms the core of many a modern perfume formula; a synthetic not found in nature but copiously used in products we use every day from soap to shampoo and deodorant.

Chemistry 
The proper name of Cashmeran is 1,2,3,5,6,7-hexahydro-1,2,3,3-pentamethyl-4h-inden-4-one. You might also come across it as "musk indanone" or "indomuscone". Though commonly refered to as "blonde woods" in perfume speak, the reality is that the ingredient Cashmeran (an International Flavors and Fragrances appelation) is actually a musk component with a yellow, trickly texture. Its scent profile takes over a vast sea between woods and ambers, abstract and indefinable. Not currently under the allergens list controled by IFRA it is used in a variety of products. There are som concerns that excessive use of polycyclic musks might do some liver damage, but we're probably talking massive amounts here.

The name Cashmeran derives from its tactile feel which recalls the smoothness and softness of cashmere wool.  Among the first perfumes to use it in a considerable degree were Loulou by Cacharel (1987) and Paco Rabanne Sport (1986).
as is Sexy Graffiti by Escada (2002). Tempting though it may be to imagine that modern best-seller Cashmere Mist by Donna Karan (1994) is full of it, in reality the powdery soft perfume doesn't use it.

Insoluble in water and hydrophobic, Cashmeran is therefore a prime target for use in functional perfumery too, since it won't rinse out: detergents, fabric softener, alcoholic lotions, deodorants, shampoos, you name it... But fine perfumery has profited of its advantages as well.

Scent Profile: Abstract, Musky, Woody, Concrete Hit by Rain
The diffusive, musky-woody scent is reminiscent of concrete (especially the abstract woody scent that concrete gives when hit upon by rain, a cityscape in the rain), also lightly spicy, lightly powdery. Though perfumers sometimes describe it to also have apple and pine facets I admit I haven't detected those myself. It is however used as a powerful floralizer as it aids the expansion and diffusion of floral notes, especially accords of jasmine, as in Thierry Mugler's Alien (it's also used in Womanity) or the lighter Flora Nerolia by Guerlain (where it's married to neroli and frankincense as well). Other cult fragrances to feature it prominently include the discontinued Feu d'Issey and Kenzo's Jungle L'Elephante and Jungle Le Tigre.
In Histoires de Parfums' Tuberose Trilogy, Gislain chose to include the note in the Tubereuse Virginale offering, where blond woods coexist with naturally cohabitating, heady white flowers on a base of patchouli and vanilla. Dans tes Bras by Editions de Parfums Frederic Malle contains a hefty dose of Cashmeran alongside the violet nuances and so does his Une Fleur de Cassie, while Wonderwood by Comme des Garcons, Diptyque's Eau Particuliere, Nasomatto Duro, Byredo La Tulipe and Al Khatt by Xerjoff Shooting Stars collection are a few more niche offerings exploiting Cashmeran's diffusiveness. Perfumer Mathilde Laurent, currently in-house perfumer for Cartier, has a particular fondness for it.

How to Incorporate Cashmeran into Perfumes 
Blending well with other modern ingredients (ambroxan, allyl amyl glycolate, damascones, ethyl maltol...) as well as natural ingredients (frankincense, clary sage, citrus, geraniol, linalool, patchouli, tonka bean, vetiver, etc.), Cashmeran presents a vista of options for the creative perfumer.

It can serve woody or warm musk compositions (see Miami Glow by JLo), formulae resting on rose and saffron, tobacco or oud masculine blends (see Nomaoud by Comptoir Sud Pacifique or Byredo's Accord Oud), even perfumes with jonquil or cassie. It can even aid aqueous olfactory scapes, such as in Armani's Acqua di Gioia Essenza!
Tocca Florence, Tom Ford White Patchouli, Step into Sexy by Avon, Philosophy Love, Blumarine Innamorata, Kylie Minogue Dazzling Darling, Hugo Boss Hugo (in the flask bottle), Anna Sui Night of Fancy, Oriflame Paradise and Burberry Body are a few more of f the fragrances featuring this musk-woody component.

Another one of the advantages of this fairly inexpensive musky component is that it has a medium potency in volume projection, but a long trail that surpasses a full day's length. Being a mild sensitiser, its ratio is currently restricted to no more than 2% of the compound.

It's clear we will be seeing it more and more admitted as such in official perfume press releases in the years to come.

Definition: Creamy, Milky, Lactonic, Butyric in Fragrances

What does "creamy" mean to you in relation to fragrance? Is it the rich, sundae vanilla feeling you get while licking a cone, the thick yet refined taste of a bavaroise or is it the beachy tropical scent you get from a lush floral perfume? And what about lactonic? You hear this term brandished a lot, especially in relation to vintage fragrances, but where does it lead you? What does lactonic mean and how do you differentiate between it and "milky"? And, oh gods, where does "butyric scent" come into all of this? Let's try to define some confusing perfume terms on Perfume Shrine once again.

Creamy fragrances are more in reality more straight-forward than you'd expect: The term "creaminess" usually denotes a rich feeling, infused with silky, sensuous and lightly or more heavily sweet notes which may derive from soft vanilla, sandalwood, or coconut and sometimes from rich, lush florals that naturally have nectarous qualities, such as jasmine or honeysuckle. Vanilla in itself is usually described as creamy: Indeed Vanilla tahitensis pods have a complex odour profile, with notes of raisin, musk, cherry, lactones and anisic aldehydes.
Often tropical florals combine with coconut and coconut milk to produce that suntan lotion feel that we describe as "creamy". These would also fall under the umbrella of "exotic", as many people's vision of exotica is tan skin, dark almond shaped eyes and the scents that are exuded in meridians where leis are worn around the neck at all occasions. Delta jasmolactone exhibiting a coconut facet (and a creamy tuberose basenote as well) makes it a natural match for this sort of thing.
Fragrances of this type include Juste un Rêve by Patricia de Nicolai, Datura Noir by Serge Lutens, Champaca Absolute by Tom Ford Private Line, Gai Mattiolo Exotic Paradise LEI (coconut, vanilla and exotic flowers) and Jil Sander Sun Delight (with frangipani and vanilla). Ylang & Vanille in the Guerlain Aqua Allegoria line is a small gem of creamy floralcy: the naturally piercingly sweet scent of ylang is given a meringue treatment via fluffy vanilla and the eau de toilette concentration never allows it to become cloying or suffocating. Even the dicontinued Sensi by Armani was great in this game of uniting flowers with soft, tactile woods.

Almond fragrances when air-spun and given the dessert, gourmand treatment with lots of heliotropin, instead of the more medicinal bitter almond iterations (as in Hypnotic Poison by Dior), can fall under the "creamy, soft" spectrum as well: Try Heliotrope by Etro or the very friendly Cinema by Yves Saint Laurent. A popular choice in the genre is Comptoir Sud Pacifique's Vanille Amande. Their silky veil is soft, enveloping, tactile. When coupled with a lot of vanilla and some musk they can become almost a visible cloud around you, such as in Ava Luxe Love's True Bluish Light. On the same page, Lea by Calypso St.Barth is a cult choice and Sweet Oriental Dream by Montale (with its shades of loukhoum) is among the best in the niche line. Tilt the axis into woody-creamy and you get Sensuous by Lauder; a literal name for once.
An elegant version of this genre, holding the sugar at an optimum medium, is Eau Claire de Merveilles by Hermes; a more mainstream one Omnia by Bulgari. Men are not forgotten in this field: Pi by Givenchy and Rochas Man in the phallically siggestive rocket-bottle are great examples of creamy fragrances for men.

Among modern molecules, Methyl Laitone (patented by Givaudan, from "lait", French for milk) is a powerful aroma-material with a diffusive, milky, coconut-like coumarinic odour character. Its use as a milk note in soap formulae is now a given, but it also aids in providing a creamy scent to perfumes too.

It's detabateable whether creamy and milky are the same, though: The difference isn't just a game for scholars. The condensed milk sweetness and "fattiness" of certain gourmand fragrances, such as the latest caramelic benjoin-rich Candy by Prada, can evoke visions of both clotted cream and milk desserts and rice-puddings, melding the two notions into one. Jo Malone utilizes the cozy, familiar note of condensed milk in black tea in her Tea Collection Sweet Milk. Kenzo Amour goes the way of a rice pudding: it's lighter than a pannacota, and has a steamy rice note in there too. Organza Indencence by Givenchy has a custard-like base, sprinkled with cinnamon, while Saffran Troublant by L'Artisan Parfumeur is like a milk dessert hued a vivid crocus-yellow by saffron served in bowls dressed in sturdy suede. Flora Bella by Lalique hides a milky facet under the soft, clean, fabric-softener violet core, while Etro's Etra is a milky floral as pretty and polite as this genre gets.
Sandalwood from the Mysore region in India in particular is famous for having a rich, satisfying milky scent. But smell a pure sandalwood-focused fragrance, such as Santal Blanc by Serge Lutens and see how a "milky scent" can be subtler, drier, less sugary than "creamy"; more opalescent than fatty glistening. Contrast now with a heavy bad-ass sandalwood perfume (boosted by powerful synthetic Polysantol), such as Samsara by Guerlain, and you are at a crossroads: that one's creamy rather than milky, va va voom sexy and enhanced by the richness of jasmine. Smell a virile, masculine sandalwood, ie. Santal 33 by Le Labo and you're back at square one; not a hint of cream in sight. No single ingredient can sattisfyingly give the full effect, obviously.

Take things too far on the dairy scales and you end up with "butyric". The word comes from the Greek for butter: βούτυρον/butyron. Usually butyric smells are due to either a single molecule (butyric acid) or, in the case of butyric esters, to part of a molecule. Butyric refers to a sharp cheesy scent, reminiscent of parmesan cheese (or even vomit and really stale, stinky socks; take your pick!), but some butyric esters, such as ethyl 2 methyl butyrate which has a fruity facet like pear or apples, are used in perfumery (and in the flavouring industry as well). And yet, and yet... irony has a place in perfumery; it's the buttery taste of tuberose-drama-queen Fracas by Piguet that makes it the unforgettable classic that it is! 

"Lactonic" however is specific perfumery jargon. It's not just a descriptor, hence I differentiate. (Though the feeling can read as "milky" or "creamy" too, as you can see further on!) Picture  lactonic as a subgroup of the greater milky/creamy continent, reached through specific vessels (called lactones).
Lactonic fragrances derive their name from Latin for milk (lac, hence lacto- etc.), and lactones are cyclic esters, a very specific chemical compound group, uniting an alcohol group and a carboxylic acid group in the same molecule. Therefore describing a fragrance as "lactonic" transcedes mere smell evocation and enters the spectre of analytic chemistry.

Why the confusing name, then?

Because they're produced via the dehydration of lactic acid, which occurs in...sour milk (and is found also in some dairy products such as yoghurt and kefir etc). You could begin to see the connection if you get the brilliantly synthetic Rush by Gucci, a lactonic modern chypre rich in a patchouli-vetiver-vanilla base and squint just so; a hint of sourness is its crowning glory. This is also the weird baby-vomit "note" in the iconoclastic Le Feu d'Issey (possibly accounting for the fragrance's commercial flop!).
Far from smelling sour, however, lactonic fragrances fall under 2 main schools, according to which of the most popular lactones they're using: milk lactone/cocolactone (i.e. 5,6-decenoic acid) or peach lactone.

A classic example of the latter is Caron's Fleurs de Rocaille or Mitsouko by Guerlain; Mitsouko's infamous peach-skin heart note in particular is due to undecalactone (referred colloquially as "aldehyde C14"). Peach lactone can sometimes veer into coconut territory smell-wise, thus giving rise to "creamy" descriptors! Indeed gamma-nonalactone is the popular coconut additive in suntan lotion.
On the other hand, demethylmarmelo lactone has a milky, butter cake scent, as does delta decalactone which has facets of coconut.
Milk lactone or cocolactone has a silky, balsamic almost burnt butter odour which pairs exceedingly well with white flowers (jasmine, gardenia), as it is reminiscent of naturally occuring jasmolactones, hence its use in white floral blends. Dis-moi Mirroir, in the more esoteric Mirroir line by Thierry Mugler, is a characteristic example showcasing a white flower top (orange blossom) and a white floral heart (lily) plus peachy lactones (smelling of apricot and peach) flying over a milk lactone base, producing a milky-fruity floral.
Massoia lactone is an individual case, as it produces a note that is poised between woody and coconut; it is what will be featured in the upcoming Santal Massoia by Hermès in the more upmarket Hermessence line.

But not all lactones are created equal: the whole group of octathionolactones has a fungi smell, reminiscent of the refrigerated mushrooms aroma of some white flowers, such as gardenia and tuberose.These flowers also exhibit creamy facets side by side, so the whole issue of describing a fragrance is far more complex than expected; as with most things in life, it all depends on context and proportions!

Related reading on PerfumeShrine:  

If you haven't caught on the Perfumery Definitions series till now, please visit:

• Definition: Indolic vs. Non Indolic
• Definition: Phenolic, Terpenic, Camphorous
• Definition: Powdery & Dry in Fragrances
• Definition: Resinous & Balsamic
• Definition: Soapy in Fragrances
• Definition: Which Material Produces Which Note/Effect?

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Perfumery Material: Sandalwood & Synthetic Substitutes

"None but the Mali Mountains contain Sandalwood" is written in an ancient Buddhist scripture. We know this is not the case, but the essence produced by Santalum album (a member of the Santalaceae family) has captured the imagination of man for 4000 years. Sandalwood is the natural product par excellence: a scent so fine, so rich and yet with a fresh top note, so creamy sweet and so enduring that it has inspired generations of men and women to harvest its precious, sacred trunk in order to imbue products for personal and public use with its fine aroma. I vividly remember the sandalwood soaps I received as a gift when an impressionable teenager by a well travelled, older cousin: the creamy, woody, incense-y ambience was irresistible, to the point that a bar was tucked intact in my drawer of small tops to produce a spontaneous "aaah" of rediscovery each time it was pulled out.

Japanese temple incense is most often infused with the aroma of sandalwood in tandem with agarwood. Indian incense often is nothing but. From soap to shaving cream and from essence oil to fine fragrances, sandalwood is one of the most traditional and yet still popular "notes" in all of perfumery.

As I bathe my skin with real Mysore sandalwood soap, stockpiled a while ago as mentioned, I can very well see why: the suds retain a smell that is beautifully nuanced, clean yet rich, midway between masculine and feminine, with a beautiful lingering effect of polished creaminess on silky pyjamas and dressing gowns.

The production of sandalwood essence 

It is a time consuming process and depends on the maturity of the trees, the length of distillation time and the experience of the person distilling. Most time-honoured method of extraction of sandalwood oil has been hydro-distillation, lately phazed out by steam distillation and CO2 extraction (which is more realistic to the raw material of the wood, due to the reduction in heat processing)

The endangerement of natural Indian sandalwood
Especially in the famous Mysore region of Karnataca and of Tamil Nadu where they're protected by state law, even as early as the 1980s, the depletion of the trees due to over-harvesting has had several adverse effects:

1) sandalwood oil is one of the most-often adulterated essential oils; 

2) the cost of sandalwood oil is rising dramatically (about 25% per year); 

3) due to the value of sandalwood oil, the trees are being illegally cut, leading to the waste of this precious resource as trees that are too young are cut, or trees are cut but the roots are left to rot (the roots are the most valuable part of the tree from which to extract the oil). Additionally, this illegal poaching has lead to several murders of forestry officials and other crimes indicative of the black market; 

4) the resource is becoming scarce. The current production of sandalwood trees is not enough to meet the demand of consumers. The trees are difficult to propagate and must grow for at least 30 years to become suitable for harvesting. The forestry departments in India are regulating the amount of material that is cut and sold, but there are many demands for other use of the land – for example, cattle grazing, the need for wood to keep people employed, etc. [1]

This situation has required the gradual substitution of this precious ingredient in fine fragrance with synthetic varieties (gradually and to the rhythm of depletion of any given brand's inventory of raw materials), such as isobornyl cyclohexanol. Some of them are quite costly in themselves and beautiful to smell, as evidenced below, possessing some of the beloved "creamy", milky facets of natural sandalwood. From a technical standpoint the natural consistutents of sandalwood comprise terpenes, terpenols and terpenals, i.e.terpenoid alcohols.

• Sandalwood-Smelling Synthetic Ingredients

Several sandalwood synthetics nowadays comprise part of a perfumer's palette for both their technical merits (they are capsule forms of the effect of an otherwise very dense and demanding essence that is amazingly complex in nature), as well as for their isolated facets that boost one aesthetic choice over others, according to said perfumer's mood. Sometimes they can even co-exist as in the case of Guerlain's Samsara, the beautiful balance of natural and synthetic in one.

Among those synthetic sandalwood notes, Polysantol, a former Firmenich trademark, is quite popular thanks to its intense diffusion and realistic replication. Otherwise known as santol pentenol due to its structure it enters many a fragrance composition imparting herbal and almost tropical nuances with an animalic touch.
Beta santalol or technically (-)-(1'S,2'R,4'R)-(Z)-beta-santalol (interestingly its positive entaniomer is odourless) is also a nature identical typical sandalwood note. It's the reverse case for the enantiomers of alpha Photosantol, the positive being strong and diffusive, the negative weak. Process producing sandalwood organoleptic substances from camphogenic aldehydes produce the prized Firsantol, another Firmenich trademark and a favourite with perfumer and writer Arcadi Boix Camps. Levosandol by Takasago introduces a sharper, more austere cedar note within the creamy sandalwood impression picture. Ebanol [(1S,2'S,3'R)-Ebanol], a Givaudan trademark, on the other hand is noted for its potency. Symrise proposes its Fleursandol which has a very strong, animalic-laced sandalwood note with floral elements surfacing. Other sandalwood substitutes present various unexpected facets, from the very clean with phenolic/guaiac notes on top and cashmeran notes at the finish like some enantiomers of HomoPolysantol to the waxy, leathery of other enantiomers of the same ingredient. The quest for sandalwood substitutes is under way as we speak with several patents from Japanese companies under way and is only going to accelarate in the coming years, despite the illegal poaching in Mysore of immature trees or the import of sandalwood from other regions of the Far East.

A recent addition is a synth blend smelling of sandalwood tagged "HipNote Sandalwood", composed by Tru Fragrance (formerly Romane Fragrances), claimed by the company producing it to be picked by perfumer Harry Fremont of Firmenich no less: “The use of synthetic substitutes within the fragrance world, like those found in "HipNote Sandalwood" and many of the season’s product launches, are essential in assisting in sustainability efforts, helping to ensure the fragrance development process does not destroy natural resources. By using these synthetic blends, we are able to eliminate any allergens that are found in nature and create consistency across different batches of the same fragrance product,” adds Amy Braden, director of product development for Tru Fragrances. The limited edition HipNote Sandalwood is available by request in limited quantities via “Hipnozes by Tru Fragrance” on Facebook, a dynamic, interactive online community which you can visit at www.facebook.com/Hipnozes

 

• Other Sandalwood Varieties of Different Origin

But not all perfumers or all fragrances aim to merely replicate that classic Indian sandalwood scent: In Le Labo's case in Santal 33 for instance they're quite clear on using Australian sandalwood (Santalum spicatum), which is a different variety than Mysore sandalwood (Santalum album): indeed the Australian variety is more pungent, sharper in its dryness, with less density, almost metallic in its fine smokiness, still compatible to scent of skin.

Another sandalwood tree variant sometimes used for its rich essence oil is Amyris balsamifera, or West Indian sandalwood or simply amyris: Though not a true sandalwood, it still bears the nuanced, distinctive smell and is useful in soap production (and increasingly fine fragrance, such as the latest Francis Kurkdjian Amyris duo of fragrances) where the Indian variety would rocket the cost to stratospheric heights.  

Finally the New Caledonian sandalwood variety is yet another species with a scent profile between that of the Australian and the Mysore varieties and it looks like it's going to be supremely popular in the near future.

LIST OF FRAGRANCES WITH PROMINENT SANDALWOOD (in alphabetical order):

01 Nomad by Odin New York

1725 Casanova by Histoires de Parfums

Alain Delon pour Homme

Aramis by Aramis

Arsene Lupin Dandy by Guerlain

Arsene Lupin Voyou by Guerlain

Barbara Bui Le Parfum

Basala by Shiseido

Bel Ami by Hermes

Belle d'Opium by Yves Saint Laurent

Black Jeans by Versace

Bleu by Paul & Joe

Bleu de Chanel

Bois de Santal by Keiko Mecheri

Bois de Turquie by Maître Parfumeur et Gantier

Bois des Iles by Chanel

Boucheron femme by Boucheron

Bronze Goddess by Estee Lauder

Bulgari Black by Bvlgari

Burberry for Men

By Man by D&G

Cannabis Santal by Fresh

Cefiro by Floris

Chaos by Donna Karan

Chinatown by Bond no.9

Classic 1920 by Bois 1920

Comme des Garcons by Comme des Garcons

Contradiction for Men by Calvin Klein

Dolce Vita by Dior

Eau de Monsieur by Annick Goutal

Eau de Sandalwood by Le Jardin Retrouve

Eau de Santal Extreme by Floris

Egoiste by Chanel

Fahrenheit by Dior

Fete d'Hiver by Ayala Moriel

Ginger Essence by Origins

Hasu-no Hana by Grossmith

Idole de Lubin

Jazz by Yves Saint Laurent

Le Male by J.P.Gaultier

Le Roi Santal by Comptoir Sud Pacifique

Les Saisons: Automne by Van Cleef & Arpels

Loulou by Cacharel

Macassar by Rochas

Magical Moon by Hanae Mori

Maharadjah by Patricia de Nicolai

Mahora by Guerlain

No.1 for women by Clive Christian
Original Santal by Creed

Pleasures Sandalwood Amber Splash by Estee Lauder  
Samsara by Guerlain  
Sandalwood by Elizabeth Arden
Sandalwood by Pacifica

Sandalo by Lorenzo Villoresi
Santal by L'Artisan Parfumeur

Santal by Roger & Gallet  
Santal 33 by Le Labo
Santal blanc by Serge Lutens
Santal de Mysore by Serge Lutens
Santal Majuscule by Serge Lutens

Santal Imperial by Creed

Santal Noble by Maitre Parfumeur et Gantier

Santalum by Profumum
Tam Dao by Diptyque

Ref: Christian Chapuis, In the Quest for a Virtual Pseudo Receptor for Sandalwood-Like Odorants, Part I, Chemistry & Biodiversity, Volume 1, Issue 7, July 2004 [1] Eden botanicals

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

Perfumery Material: Osmanthus

Osmanthus fragrans (Sweet Osmanthus) or 桂花/ guìhuā in Chinese and金木犀/ Kinmokusei in Japanese is another member of the Oleaceae family (like olive or lilac) and its fresh and highly fragrant aroma is a natural wonder professing a nuanced texture. Also known as "Tea Olive" (because olive is the pre-eminent member of the Oleaceae family) it is the emblem flower of Hangzhou, China. It is especially valued as an additive for tea and other beverages in the Far East where usually the aromatic extract comes from the golden yellow flowers variety. This is because the variant Osmanthus fragrans Lour. var thunbergii has more carotenoids in its chemical make-up which contribute both to the sunnier colouring as well as the enhanced aroma.
The flowers are also used to produce osmanthus-scented jam (called guì huā jiàng)

Osmanthus absolute is an expensive raw material for the perfumer, but worth investing in due to its unique olfactory profile: Highly fragrant and succulent in its peachy-apricoty top note it is nothing short of mouthwatering. The effect of the natural flower is undoubtedly enhanced with a synthesized apricoty creamy note (benzylaldehyde, aldehyde C16, amyl butyrate), giving an almost velours effect. The essence of osmanthus naturally contains cis-jasmone (a white floral note), gamma-decalactone and various delta-lactones (peachy-milky notes) as well as several ionones derivates, which accounts for its violet-like sweetness.

Fragrances featuring a prominent osmanthus note:

Aubusson Desiderade
Aubusson Histoire d'Amour
Ayala Moriel Kinmokusei
Badgley Mischka by Badley Mischka
Bidjan DNA
Calvin Klein Escape
Davidoff Echo for women
Elizabeth Arden Sunflowers
Estee Lauder Beautiful Love
Escada Sunny Frutti
Fendi Theorema
Gap Dream
Givenchy L'Interdit (2003 re-issue)
Gucci Flora
Hermes Osmanthe Yunnan
Hove Tea Olive
Jean Patou 1000
Keiko Mecheri Osmanthus
Kenzo Jungle Le Tigre
Lancome Benghal (travel exclusive)
Marcela Borghese Il Bacio
Michael Kors by Micheal Kors
Narciso Rodriguez Narciso for Her (recreated note)
Nina Ricci Deci Dela
Oleg Cassini Cassini
Ormonde Jayne Osmanthus
Oscar de la Renta Volupte
Parfums d'Empire Osmanthus interdite
Providence Perfumes Osmanthus Oolong
Roger & Gallet Fleurs d'Osmanthus
Serge Lutens Datura Noir
The Different Company Osmanthus
Tous Touch

Ref: Sisido, K.; S. Ktirozumi, K. Utimoto and T. Isida, Fragrant Flower Constituents of Osmanthus fragrans

Photo of Osmanthus fragrans via jam343/flickr (some rights reserved)

Three Cheers for Perfume Chemistry

Much as perfumery has often been the marketing story of virgins amassing jasmine petals at the crack of dawn in endless emerald fields on exotic lands (and it is a lovely image), some synthetic molecules created in the lab have irrevocably revolutionized the fragrance industry as we know it: Hedione, Galaxolide and Calone for instance have left a footprint as big as the Yeti’s in modern perfumery, accounting in some cases for a big percentage within a formula in and of themselves (see Trésor and Cool Water or the odd case of Dune for instance ~also the iconic fragrances touched by hedione).


Sometimes these molecules were arrived at years before they were popularised in mainstream compositions the consumer buys off the counter today: Calone for instance, which catapulted the "marine scents" trend in the 1990s, was patended as "Calone 1951" in as early as 1966 by the pharmaceuticals collusus Pfizer. Sometimes, on the other hand, new molecules are the very reason why specific styles of fragrances multiply like Gremlins: see the recent cases of Ambrox and synthetic oud.

Damascones and ionones have brought their own particular challenges and risk-taking through the course of the 20th century, ending in beautiful specimens (examples include Nahéma, Féminité du Bois, Nombre Noir). I have always had a soft spot for nitromusks myself, which I absolutely love in vintage creations due to their intimate and warm character, but of course science and the industry go on and we must adapt with the times...

I like to think that we’re upon a Brave New World in which the not-forgotten old artistry of naturals alongside the sleight of hand, that relies in the proper dosage of synthetics, will produce astounding and unprecedented results: Safraleine is a beautiful example, exactly because it brings on both spicy and subtly leathery facets to the fore with a restrained hand. We’re seeing a new sophisticated generation of aqueous and “ozonic” molecules too, away from the obvious “watermelon slap” of Calone: Scentenal (Firmenich), Cyclemone A and Floralozone (both IFF); for instance the latteris featured in otherwise earthy Vétiver Extraordinaire in Editions des Parfums Frederic Malle, where it juxtaposes freshness to the mustiness of the grass.

Alternatively, in some cases, modern technology aims to replicate retro effects which we used to miss due to depletion of the original and shortage of technical solutions. Let me mention some examples:
White Moss is an IFF patent to create a green-mossy accord at the base of some nouveau chypres such as Lauder’s Private Collection Jasmine White Moss. I think it’s an excellent addition to IFF's already impressive stable as it manages to bypass the “problem” of oakmoss restrictions (as inflicted by the industry-self-regulating body IFRA) while at the same time smelling as a proper green chypre base-accord should (comparable to the original Cristalle for instance).
Jovanol by Givaudan is creating the creaminess and intense lasting power which we had come to associate with the “creaminess” of sandalwood, its lactonic facet ~perfume speak for that warm, milky cozy, cuddly effect that older Orientals and woody fragrances with a preponderance on Mysore sandalwood used to have. The anisic note which we have come to associate with anisaldehyde and retro effects such as those in L'Heure Bleue is given new lease by Givaudan's captive Toscanol (which is in its turn substitutes the similar chavanol), used to mollify lavender compositions. And who can disregard Cashmeran, that tactile "cashmere woods" note embraced so lovingly by both mainstream fragrances (DK Cashmere Mist, Alien by Mugler, CKin2u, Fleur de Cristal by Lalique) as well as niche (The Beautiful Mind series Intelligence & Fantasy)? Its encompassing woody-musky-soft and sensual profile makes it a passe-partout ingredient.

I like one small detail about musks in particular, how the newest mascrocyclic Cosmone by Givaudan (a warm musk with a nuance of ambergris, smell in DelRae's Panache for instance) is taking on the expanse and beauty of the Cosmos to graft it unto its name. One better from the previous Galaxolide which was also astro-inspired in regards to nomenclature! And the ironic touch that it’s used in a fragrance bearing such a cunning name as Pi Neo, which means "new" in Greek. Isn’t perfumery dreamy?

picture of perfumer at Lever Laboratories in New Jersey, c.1950 via howstuffworks.com

Perfumery Material: Hedione (Luminous/Transparent Jasmine)

 Smelling hedione, I'm struck by its beautiful, limpid and luminous character which resembles the beautiful citrusy floral note of a magnolia blossom blossoming under sunny skies.
Hedione or methyl dihydrojasmonate is an aromachemical (patented as Hedione by aroma-producing company Firmenich) that is often used in composition in substitution for jasmine absolute, but also for the sake of its own fresh-citrusy and green tonality.

Hedione lacks the clotted cream density of natural jasmine, recalling much more the living vine in the warmth of summer mornings and for that reason it is considered a beautiful material that offers quite a bit in the production of fine perfumes.

Perfumer Lyn Harris, nose of the brand Miller Harris and also the independent nose behind many well-known creations not credited to her name, calls it “transparent jasmine” and attributes to it the capacity to give fizz to citrus notes much “like champagne”. (See? it’s not only aldehydes which do that!)

According to Christian Chapuis of Firmenich SA, Edouard Demole discovered methyl jasmonate in 1957, accomplished a synthesis of Hedione (from the Greek word ηδονή/hedone, meaning agreeable and pleasant) in 1958, synthesized methyl jasmonate in 1959, placed both materials under intellectual protection in 1960, and published these discoveries in 1962. "This simple timeline belies a more complex history of chemistry and creation".
First used in the classic men’s cologne Eau Sauvage, composed by Edmond Roudnitska in 1966, hedione had been isolated from jasmine absolute and went on to revolutionize men’s scents with the inclusion of a green floral note. Eau Sauvage was so successful that many women went on to adopt it as their own personal fragrance leading the house of Dior to the subsequent introduction of Diorella in 1972, composed by the same legendary nose, blending the green floral with hints of peach, honeysuckle, rose and cyclamen in addition to the herbal citrusy notes of the masculine counterpart, all anchored by a base of cool vetiver, patchouli and oakmoss, lending a mysterious, aloof and twilit air to women who went for it.

Ten years after its introduction to perfumery, in 1976, it was the turn of Jean Claude Ellena to coax hedione in a composition that exploited its fresh and lively character to great aplomb in the production of First by jewelry house Van Cleef & Arpels (the name derived from the fact that it was their first fragrant offering, but also the first scent to come out of a jeweler too ~subsequently many followed in its tracks with notable success). In it, Ellena used 10 times the concentration of hedione used in Eau Sauvage, married to natural jasmine as well as rose de mai (rosa centifollia, which is also a "crystalline" variety), narcissus, orris, ylang ylang and a hint of carnation with the flying trapeze of aldehydes on top and the plush of vetiver, amber and vanilla at the bottom which accounted for a luminous and luxurious floral.

Hedione also makes a memorable appearance in many other perfumes, such as the classic Chamade by Guerlain (introduced in 1969), Chanel no.19 (1970) and Must by Cartier (1981) and in many of the modern airy fragrances such as CKone, Blush by Marc Jacobs, the shared scent Paco by Paco Rabanne or ~surprisingly~ in the bombastic Angel by Thierry Mugler, in which it is used as a fresh top note along with helional! Perhaps if you want to feel it used in spades smell L'Eau d'Issey by Issey Miyake: the aquatic/ozonic notes cannot hide its radiance.
Its uses are legion, especially since it acts as a supreme smoothener of the rest of the ingredients. In Terre d'Hermes, perfumer Jean Claude Ellena uses lots of it to bring out the softer side of hesperidic bergamot and to fan out the woodier aspects.

High-cis Hedione is an isomer which gives a jasmine tea profile (not surprisingly, as the component naturally occurs in tea), more diffusive and less floral and thus useful in masculine blends, but it costs more than regular hedione and poses problems of stability in acidic environments. Some of the Bulgari "tea" scents, such as Bulgari Eau au Thé Rouge and Bulgari Eau au Thé Blanc are good reference points if you want to smell this in action.
Despite hedione's unlikeness to natural jasmine absolute and essential oil (which are much lusher, narcotic and indolic), perfumers have used it to supreme results in the history of fine fragrance of the last 40 years, occassionaly using it up to 35% concentrations, although it's more usual to be featured in ratios of 2-15%.

Related reading on Perfume Shrine: Perfumery Materials, The Jasmine Series

pic of jasmine via Gracemagazine. Bottle of First via zensoaps.com

Perfumery Material: Coumarin, Tonka Bean & the Fougere accord

Open any perfume guide with fragrance "notes" or any online discussion or blog post on perfume description and you're bound to stumble on coumarin; one of the most common materials in many fine fragrances but also several body products, cosmetics and functional products. Its rich history goes back to the beginnings of modern perfumery in the late 19th century, bringing us right at the moment of the nascent concept of perfumery as a mix of organic chemistry and nature's exploitation. Coumarin as such is a synthesized material in most perfumes, but it's also found in abundance in natural products, such as tonka beans (Dipteryx odorata) where it is the principle aromatic constituent (1-3%). In fact the name derives from "cumaru", an Amazonian dialect name for the Tonka bean tree.

• Origin & function of coumarin

Chemically, coumarin is a benzopyrone (1-benzopyran-2-one) which, apart from tonka beans, also occurs naturally in vanilla grass (Anthoxanthum odoratum), sweet woodruff (Galium odoratum), sweet clover (Meliotus L.), sweet grass (Hierochloe odorata) and cassia cinnamon (Cinnamomum aromaticum) among other species. In short, it's rather sweet, as you might have surmissed by now, and evokes cut grasses. You'd be correct to assume both facts, but that's not all: Although coumarin in perfumery does add a certain sweet note of mown hay or freshly cut grass with vanilla overtones, it's really bitterish in flavour in high concentrations (its -now banned- inclusion in food would attest that). Therefore theorizing its plant origin one would assume it's produced by plants in order to defend themselves from predation. After all it's also present in cherries, strawberries, and apricots, prime targets for birds. You might have even seen it featured in your rodent pesticide: don't be alarmed (coumarin is included in miniscule quantities in foodstuff anyway), but now you know why!

• History of coumarin discovery & synthesis

Natural perfumers used and continue to use tonka bean absolute and tonka in powder form, as well as deer's tongue, a herb with brittle leaves to render a coumarin note. But the story of coumarin is largely one of organic chemistry. The component was isolated by A.Vogel in 1820, but the laboratory synthesis of coumarin first happened in 1868 from coal tar by W.H.Perkin (who gave his name to "the Perkin reaction" used to produce it). It took another year to produce it in an industrial scale at Haarmann & Reimer. The consequent memorable inclusion of synthesized coumarin in Jicky (Guerlain 1889) and earlier in Fougère Royale (Houbigant 1882) was the kickstart of a whole new fragrance family: the fougère, thanks to Paul Parquet's composition for Houbigant. Fougère Royale contained a staggering 10% coumarin of the finished formula! How one can dream a bit while reading Guy de Maupassant describing this fragrance as "prodigious evocation of forests, of lands, not via their flora but via their greenery"...

• The Fougere fragrance family

Fougère fragrances evoke the smell of ferns at least as we imagine them to be, as by themselves they don't have a particularly noticeable odour (Paul Parquet said that if they could, they'd smell of Fougere Royale). But the concept of a scent that is herbaceous, infused with aromatic lavender ~a popular material for both sexes at the end of the 19th century thanks to its propriety in the "clean" sense of the world~ and which leaves a malleable, soft, enveloping, yet discreet aura on the wearer was lacking: The era was still using the Victorian soliflores. Funnily enough, even those had their own categorisation; violets or roses for the respectable lady, jasmine and tuberose for the courtesan. Fougère scents were on the cusp between approved and revolutionary, creating a very desirable pull.
The other principle constituents in the accord are lavender and oakmoss: It was only natural; lavender by itself contains coumarin in its aromatic makeup. Thus the triad comprising the main accord of the rising fougère (i.e.lavender-oakmoss-coumarin, played together like a musical chord) made coumarin itself quite popular: many classic or influential masculine colognes owe their character to it, starting of course with Jicky and continuing with Azzaro pour Homme (1978), Fahrenheit by Dior (1988), Dolce & Gabanna pour homme (1994), and Gucci pour Homme (2003).
From there coumarin infiltrated its way into many modern fragrances belonging in other families. But it was its pliability and usefulness, like a trusty Swiss knife, which made it the perfumers' darling: Are there more contrasting fragrances than the icy aldehydic Rive Gauche (YSL 1970) and the intense floral Amarige (Givenchy 1991)? Perfumers tell me that coumarin ends up in some degree in 90% of all fragrances; and in concentrations exceeding 1% it accounts for over half of the fragrances in the market!!

• The odour profile of coumarin

Coumarin is a water-insoluble crystallized powder which has an odour that is pleasant, soft and warm, evoking cut grass or new mown hay, but it's more complex than that; it sometimes even veers into a smell of fresh paint! This is what gives Jicky its bracing almost "petrol" opening which alienates some people. Originally biosynthesized via hydroxylation, glycolisis and cinnamic acid cyclization, nowadays coumarin is produced via more sophisticated techniques.
Coumarin conjures warm notes of tobacco (useful in masculine formulae) and because it also has caramel overtones, alternatively it can be married to vanillic components (such as vanilla, benzoin or some of the other oriental balsams, such as Tolu balsam or Peru balsam, as well as ethylvanillin) in order to play down and sophisticate their foody aspects: see it in action in orientals such as the discontinued Venezia by Laura Biagotti, Lolita au Masculin(Lempicka) or Casmir by Chopard.
In dilution coumarin projects with soft hazelnut or almond facets underneath the hay, even licorice; smell Lolita Lempicka (1997). But in higher concentration it also has spicy fresh and herbaceous facets, no doubt reminiscent of its primary role in different grasses. In combination with vanillin and bergamot, we're veering into chypre territory: Elixir des Merveilles is a no man's land with its chypre tonalities and gourmand facets.
Its versatility and its ability to "fix" smell and make it last longer allows coumarin to enter amber or woody blends (witness Samsara or Vetiver by Guerlain) as well and even heighten the appeal of spicy materials: in fact it marries very well with cinnamon or clove. Pi by Givenchy is a sweet spicy woody with lots of tonka bean, or smell L de Lolita Lempicka by Maurice Roucel. Usually, indeed coumarin is mentioned in the form of tonka beans in the traditional lists of "notes"/pyramids for fragrances (see this Index for more ingredients contributing to which "note") but it can also hide underneath grassy notes, clover, lavender, or tobacco. Modern perfumers pair it with synthetic woody-amber notes such as Kephalis and Iso-E Super to surprising results. A wonderful material indeed!

• Fragrances featuring discernible amounts of coumarin

Addict (Dior)
A*men (Thierry Mugler)
Amarige (Gievnchy)
Angel ~all concentrations, esp. extrait de parfum(Thierry Mugler)
Angel Sunessence (T.Mugler)
Angel La Rose (T.Mugler)
Antidote (Victor & Rolf)
Azzaro pour Homme (Loris Azzaro)
Azzaro Elixir Bois Precieux (L.Azzaro)
Blue Jeans (Versace)
Bois des Iles (Chanel)
Brit (Burberry)
Chic for Men (Carolina Herrera)
Coco (Chanel)
Coco Mademoiselle (Chanel)
Contradiction (Calvin Klein)
Etoile de Rem (Reminiscence)
Fahrenheit (Dior)
Fieno (Santa Maria Novela)
Fougere Royal (Houbigant)
Florissa (Floris)
Gloria (Cacharel)
Jasmin Noir (Bulgari)
Jicky (Guerlain)
Joop! Homme (Joop)
Kouros (Yves Saint Laurent)
Lavande (Molinard)
L de Lolita Lempicka
Lolita Lempicka (L.Lempicka)
Le Male (Jean Paul Gaultier)
Musc (Molinard)
Navy (Lily Bermuda)
Pi (Givenchy)
Rive Gauche (YSL)
Samsara (Guerlain)
Tonka Imperiale (Guerlain)
Venezia (Laura Biagotti)
Versace pour Homme (Versace)

Related reading on Perfume Shrine: Perfumery Materials one by one

source of coumarin pic via The Health Nut Corner, ad for Houbigant via Punmiris and Jicky collage via Perfumesbighouse