An old base from Firmenich.

It was created in the 30′s, although it was possible to compose such accords back in the first decade of the 20th Century heliotropine was first synthetised in 1869, ionones in the 1890′s, methyl heptine/octine carbonate in 1900.


AD from a 30′s French trade paper


This is the very classical accord of violet, not quite reminiscent of the flower though. An elegant, powerful and longlasting violet, reminiscent of violet leaf absolute (that was possibly meant to replace).

I like to think that this very base shaped consumers for almost a century. This base is the archetype of perfumers’ violet  in fine fragrances and functional products as well. True-to-nature accords are easy to make using p-cresyl derivatives, indol and ionones as a foundation but unpleasant to the general customer.

Green, sweet, powdery, slighlty jasmine-like. You can have a beautiful example of such violet in Paris (Yves Saint Laurent), where I definitely smell this very accord (I cannot prove that Parmantheme was used though).

In Parmantheme I smell nonadienal and/or nonadienol as a powerful topnote: a green, cucumber-like, wet, oily note. This perception seems to be confirmed by S. Arctander in his monography on Nonadienal.

The base is founded on the main accord: methyl heptine/octine carbonate – ionones (an heavy dose!) – heliotropine – powdery musks. Some additional notes might be jasmin or rose.

A simple and beautiful composition that glorifies the green, violet leaf-like, extremely powerful methyl heptine/octine carbonate, quite difficult to use alone (and nearly banned by today’s IFRA standards).

I think that today Parmantheme features some methyl heptine/octine carbonate replacer.

Cultivar: mainly Femminello
Geographical origin: Sicily (Syracuse, Acireale and Palermo)

Lemon Oil Sfumatrice (Raw):

Pale yellow mobile oil.

Zesty, green, true-to-nature, light sparkling topnote of extraordinary beauty and subtlety. This fleeting note rapidly vanishes giving way to an intense pleasant sweet citral-like body very characteristic of this oil. Basenotes are pleasant, green, slightly aldehydic, soapy, and quite longlasting.

The term ‘Sfumatrice’ refers to the machinery used for cold-extracting the essential oil from the fruit. If you are interested in knowing more about these machines I suggest you to take a look to these manufacturers:
http://www.indelicato.it/azienda_uk.htm
http://www.speciale.it/english/home.html

Due to its furocoumarines content this product is limited to 2% in the finished product (leave-on products) by IFRA standards. You can download here the standard specific to this oil.

Furocoumarine-free – decolorized Lemon Oil:

Colourless mobile oil.

This quality closely resembles the cold pressed oil, especially in the middle notes, to a degree that is very difficult to differentiate between the two.

Light, green, subtle and natural refreshing topnote, a tad less sparkling than the ‘Sfumatrice’. Middle notes are typical sweet citral-like. Basenotes are less interesting and less longlasting than the raw oil, more citrusy, heavier and greener, but still refreshing and lemony in the overall aspect.

Free from any colour and phototoxic effect concerns.

To sum up: the two qualities are very close and almost equivalent. The ‘sfumatrice’ oil is more interesting (topnotes and dry-down in particular), however there may be phototoxic issues at high %. The FCF-decolorized oil is more versatile.


You might be interested in the supplier’s website (Simone Gatto), where you can find interesting information about citrus oils, varieties and extraction methods.


See the footnote on Bergamot Oil about old and oxidized oils.

I should add that, unlike oxidized bergamot oils, old oxidized lemon oils are much worse, smelling thicker, woody, almost caramelized. The light, fresh, joyful topnotes have disappeared completely. Basenotes smell turpentine-like.


 

Still life - photo: PerfumeChemicals.com

Still life – photo: PerfumeChemicals.com


Cultivar: Femminello, Castagnaro and Fantastico
Geographical origin: Calabria

Raw Bergamot Oil (cold pressed):

Green-yellow mobile oil.

At first it strikes you with a fresh zesty (lemony), green, aromatic topnote. It then evolves in a soft, sweet, velvety odour.

There is some sort of elegant coherence in the evolution that surprises me: a sparkling agrestic ouverture, which soon gives way to a soft, bright, fruity body. Then, it slowly settles down into a perfectly balanced leafy, fruity, powdery, almost silky-leathery base. A beautiful contrast of lights and shadows. A sulfury, sweet-harsh, radish-like, veiled animalic accent perfectly counterpoints the fresh sweetness of the body. An interesting note that is extremely natural and very characteristic of this oil.

Due to its furocoumarines content this product is limited to 0,4% in the finished product (leave-on products) by IFRA standards. You can download here the standard specific to this oil.

Furocoumarine-free – decolorized Bergamot Oil:

Colourless mobile oil.

Very similar to the raw quality. Less green-aromatic, less interesting and subdued topnotes. More vertical and fruitier (linalyl acetate-like) and rounder, but some linalool-rosewood-like notes tend to stand out. Some soapy, floral, octanol-like details… Less citrusy (less D-limonene-like). The body is very nice and almost as good as the raw oil. It may lack some sparkle and the rounded sweet-leafy cushion in the base is more delicate.

I would say that this one is the standard quality for bergamot oil used in perfumery. The one I have smelled more often.

Still a good choice (in particular when a colourless product is wanted) and without phototoxic issues.

To sum up: the main differences between the raw quality and the FCF-decolorized one are the zesty topnote, the citrusy-green body, and some soft, animal, sulfury basenote in the former; the neat, pleasant fruity, linalyl acetate-like note that brightens up and rounds the body in the latter.

bergamot oil colour comparison - blotter test


You might be interested in the supplier’s website (Simone Gatto), where you can find interesting information about citrus oils, varieties and extraction methods.


A note about old and oxidized oils.

Citrus oils are very fragile and exposure to oxygen and heat can damage their olfactory properties.
It is suggested to store them in the cold (5-10° C) and prevent oxidation by limiting exposure to air as much as possible.

Once you have smelled fresh expressed oils, you will understand how delicate the fine details of these products are and can suffer from poor storage.

On comparing some old oils (>24 months and improperly stored) with a fresh one, you can still be able to smell the citrusy character. However, the aromatic, fresh-lemony topnotes are almost vanished and the sparkling greeness is now replaced by some sort of sweet, lime-like, piney, varnish-like effect in the drydown. Still quite pleasant (if you were expecting to smell awful rotting notes, you’ll be reassured). But definitely the beautiful ephemeral topnotes are gone, replaced by a dull sweet-citrusy scent, and the sweet, leathery base overwhelmed by resinous off-notes.

I warmly suggest to buy only fresh expressed oils and to store them properly.

Silvanone Supra (Givaudan): a mixture of cyclopentadecanone and cyclohexadecanone (juniper lactone)
Romanone Extra (ACL Aromatics)

synonyms: nor-muscone, apo-muscone

Natural identical (found in muskrat).

Not to be confused with Exaltenone or Exaltolide.

White crystals.

Warm, diffusive musky, extremely fine, faceted, powdery, animal, greasy, natural musk-like odour.

Quite similar in odour to muscone, but more powerful and animal.

Nitromusks are sometimes defined as “animal”. While I quite agree on the fact that they possess a musk deer facet (they are warm and powdery, but also radiant, with some musky floralness) they don’t possess a truely dirty, greasy character.

Exaltone strikes with its greasy, warm animal musky odour.

@10% it is less dirty, more nuanced, somewhat metallic and much more similar to his brother muscone, or to exaltolide.

@1% finer. Best dilution. Every facet blooms and one can fully appreciate its elegant details: quite powdery, sort of ‘metallic’ (in a way that it recalls me of exaltolide), but still quite greasy and softly animal.

It is quite pricey, but is worth its weight in gold. I definitely love this molecule. And actually it costs about 3 times more than muscone (about the price of a jasmine absolute). This is the most astounding musk odourant I’ve ever smelled.

It was first synthesized in the 20′s (1926 patent, Chuit & Naef, Firmenich today) by L. Ruzicka, in an attempt to find a good substitute for natural musk. Exaltone is chemically very close to muscone; it only has one methyl function less.

In the 1927 “Notice sur l’Exaltone et autres produits à odoeur de musc”, it is explained why the name ‘Exaltone’ was chosen:

L’effet produit par l’exaltone dans une composition est le même que celui provoqué par le musc : son odeur s’allie merveilleusement à celle des autres produits de la composition et, contrairement à ce qui se produit avec l’emploi du “musc artificiel”, le résultat forme un ensemble des plus harmonieux; c’est justement en raison de sa propriété heureuse non seulement d’affiner, mais également et surtout d’exalter le parfum des compositions, que nous lui avons donné le nom d’exaltone.

Exaltone is capable of ‘exalting’ a composition and this property seemed to make this product a valuable candidate for replacing natural musk.

Reading this booklet one could get the feeling that natural musk extracts were not much prized for their “animal” odour, they would also have introduced unwanted, ammoniacal, rotting notes. The interest was in the smoothing, exalting effect coming from their musky odourants (such as muscone or civettone). A feeling that I also get when working with civet. However I am convinced that animal, greasy, dirty notes are sometimes really wanted and synthetical musks wouldn’t suffice alone (I am thinking about cuir, leather fragrances, or old chypres).

muscone-exaltone

Muscone and Exaltone seem at first quite different products, olfactively. The odour of muscone when pure is almost difficult to perceive (as many other musks). Exaltone, on the other hand, is a solid at room temperature and its odour when smelled pure is strongly musky, animal and greasy and quite powerful.

However, upon dilution the differences are smoothed down. They are quite similar, indeed. Muscone is rounder and, obviously, more true-to-nature. Exaltone, very similar to muscone, powdery, musky, rather sweet, has darker tones, a greasy accent and nice projection.

Interesting enough, Exaltone was eventually found in nature in the muskrat glands.

Very viscous (glucose-like consistency), colourless liquid.

Very often sold diluted at 50% in DEP, DPG, IPM, BB, etc. (hence the specification in the title)

Standard musk smelling, soft, long-lasting. Without any particular complexity, very linear.

Often used at very high % in perfume compositions: from 10-50% in the fragrance concentrate, in some cases even more), for its good performance (long lastiness, projection) and low cost. Its olfactive transparency explains pretty well how easy is to overdose this product.

Olfactively it is the kind of musk that smells “clean”, not surprisingly, since it is very much appreciated in functional perfumery (to a lesser extent today, when biodegradability concerns arise for this musk).
Indeed, it doesn’t possess any “animal”, dirty facet (unlike the surprisingly beautiful Exaltone, aka Romanone Extra or Silvanone Supra). But I think that the “clean” adjective is still quite misleading. I invite you to thoroughly study civet absolute (@1%) and compare it with the “clean” smelling civettone (the musky molecule found in civet). You will understand how, a part from the faecal, skatole-like accents of civet, the interesting and animalic notes are built upon the shining muskiness of civettone. Musks really add a third dimensions to animal odours and are a part of them.

It also doesn’t fit into the “powdery” musk category.

It is more close to the ambrette seed-like musks, like ambrettolide, Helvetolide, Romandolide, ethylene brassylate etc. with his sweet floralcy and velvety seedy woodiness.

In my essays I was often surprised how good this product performs in alcoholic perfumery, from 5% to 20%. It adds depth, wearability, without changing too much the odour profile of the composition. Surely, it is quite a “cheap”, boring choice in fine perfumery, were high price should account for quality or inventivness (some more interesting and original musks are available, but they can be pricey).

Needless to say, it blends perfectly well with almost any fragrance material. In my personal experience (the exception that proves the rule): I found it ugly and hard to blend with ambery-labdanum compositions, where an old-fashioned richness, opulence, thick sweetness is required. In this case Galaxolide (and similar musks) are to be used cautiously at low %, in order not to introduce a transparent, light verticalness that doesn’t fit very well (nitromusks, Muscenone, would fit better).


It has been suggested that Romandolide could replace Galaxolide.

I very much enjoy Romandolide and think that it closely resembles Galaxolide under various aspects.  Romandolide is slightly powdery, more ambrettolide-like, whereas Galaxolide bears some resemblance to Exaltolide. Romandolide has a particular green-bitter and metallic topnote that I find rather interesting for a musk, while Galaxolide is more neutral.

Romandolide also is quite cost-effective. Unfortunately, I am not able to speak about its performance in functional perfumery (where it could be an interesting asset), since this field requires a particular experience I don’t have.

I will test thoroughly the differences and similarities between the two musks (in alcoholic media) and post my thoughts in some months.

The following tips are based on my (little) personal experience. Some very interesting and punctual information I give is the result of resarches on excellent works, such as Steffen Arctander’s ‘Perfume and flavor materials of natural origin’ and others.

There are no general rules on how to tincture or infuse materials for perfumery use. Needless to say, each product has its own characteristics and requires changements in protocol. Here is a summary that unveils my thoughts and my little knowledge on the subject.

Tincturing process: grind the raw product and mix with alcohol, macerate, filter, age. For some products (when the alcohol takes longer to extract the odourant matter) filtration occurs after the ageing process (the material is left soak in the alcohol).

Infusion process: grind the raw product and mix with alcohol, heat under reflux, filter, freeze, refilter, age.

Infusion is a little more complicated to put in place, but faster. In the 60′s it was already considered old fashioned to prepare infusions, due to the process itself, not standardizable. In fact, when heat is applied, some reactions can take place, especially in the presence of acids and terpenes. The result is sometimes desirable: it is said to produce a mellower product.

First step: Grinding/comminuting the raw materials. In this case I am using a ceramic mortar. It is good for grinding hard products, for example: dried castoreum or hyraceum.

hyr-grind

Grinding of hyraceum in a ceramic mortar

But, sometimes, a hammer is a better tool… see starting from 2/3 of the video below. Castoreum pods can be very hard.

 

In the case of a TINCTURE, the next step is simply adding the ethanol (usually pure) in the right proportions (from 3 to 20% depending on the raw material) and let macerate from 1 week up to some months.

Steffen Arctander reports in his work that macerating 2 weeks is enough for vanilla beans. The tincture thus prepared is aged for some months before using.

I prepared a castoreum tincture @20% (in pure ethanol) that is still macerating after 2 years (i.e. the material is still soaking in the tincture). The same happened for a tonka beans and myrrh tincture (1 year untouched on the shelf). Curiously enough, I haven’t perceived any important changement in the odour profile in the extracts starting from 2-3 months maceration. I think that 1 month maceration should be enough for any material. But, to my knowledge, there isn’t any drawback in macerating for longer (unless you want to save time).

In the case of an INFUSION heat is applied. This process requires some glassware but is very simple to put in place. When preparing hyraceum and castoreum infusions heat is applied under reflux for 1 hour.

Refluxing a castoreum infusion

Refluxing process in preparing an infusion

The extract is then cooled down to room temp. and filtered. This is how the filter paper looks like after the first filtration of a 6% hyraceum infusion:

2014-04-24 13.00.10

Hyraceum infusion @6% filter paper #1

The infusion process takes one more step: the same extract is filtered again after cooling it down below 0°C for a day. This is how the filter paper now looks like:

2014-04-26 00.58.08

Hyraceum infusion @6% filter paper #2

The final product is free from any visible residues, the solution is clear and doesn’t show any cloudiness.

Hraceum infusion @6% after 'glaçage' and refiltration. It displays a beautiful reddish-ambery colour.

Hraceum infusion @6% after ‘glaçage’ and refiltration. It displays a beautiful reddish-ambery colour.

Note that some particules are soluble at room temp. and they can pass through the filter. Cooling down precipitates these impurities. This process is called ‘glaçage‘ in french, and is applied to any extract that requires hot solvents (producing absolutes). Remember that heat causes solvents to dissolve much more product than is generally possible at room temp. This will cause the extract to become cloudy upon cooling or after some time, eventually producing some annoying residues that precipitate down in the bottle.

For TINCTURES one filtration is enough.

It is possible to prepare tinctures of almost anything. Only flowers and very fresh materials don’t give a satisfactory result.
Think about vanilla, tonka, castoreum, ambergris, civet, hyraceum, (musk), olibanum, myrrh etc.

Tinture

Tinctures are rare nowadays, if not totally absent from the perfumer’s organ. An exception is vanilla tincture (there is at least one big company that still offers this product today, for perfumery use), or precious products that are still tinctured on a very small scale: ambergris or civet are the only example (absolutes of civet, castoreum and hyraceum are produced). Apolar solvent extraction totally replaced (approx. one hundred years ago) this simple, artisanal type of extraction, in favor of a more constant and concentrated product. Another drawback in tinctures is that ethanol absorbs water from the material (this can cause some trouble in dissolving essential oils or aromachemicals in a formulation).

tincturesIt is interesting enough to note that some resinoids or absolutes are produced more or less in this way, in a one-step process (by percolation), by replacing organic apolar solvents with ethanol which is then evaporated.

Here you have a list of tinctures I have prepared over time and some short comments:

Castoreum 3%, 6%, 20% Very nice result, polished and softer than some absolutes. 20% is a crazy strength for this product.
Benzoin 50% Benzoin is almost 100% soluble in alcohol (some residues are due to impurities). Heat will help dissolving the resin.
Tolu balsam 20% Apply heat until the balsam is completely solubilized.
Peru balsam 20% Completely soluble in alcohol without heat, almost no residues.
Galbanum 20% Apply heat until the balsam is solubilized, filter the residues (dust, organical matter).
Labdanum 20% Apply heat in order to help softening the resin. Filter. Very green odour, much different than the absolute.
Tonka 20% Interesting but not as beautiful as the absolute.
Vanilla 10%, 20% -
Olibanum 30% Nice, finer than the essential oil. Similar to the resinoid.
Myrrh 10% (in 70° ethanol), 20% (pure ethanol) Finer in 70° ethanol.
Hyraceum 3%, 6% -
Ambergris, different concentrations Be careful not to saturate or heat the tincture: ambrein may precipitate.
Civet, different concentrations -
Patchouli Poor results.
Ambrette seeds whole and crushed Very poor results.
Dried ylang flowers Useless.
Dried oak leafs Quite interesting.
Fresh violet leafs Very poor results. Better on ageing.
Seaweed (fucus vesciculosus) 20% Very nice results.
Sandalwood 10% Nice result, but inferior to the essential oil.
Orris root 30% (80° alcohol) Interesting, but inferior to any usual extract (concrète, resinoid or absolute).

Tinctures that are worth producing/having: ambergris, civet, castoreum, hyraceum, vanilla.

When I started preparing my first tinctures (4 years ago, now), I was obsessed with strength and I wanted to reach the saturation of the solution at any cost (I prepared civet tinctures @20%, ambergris @15%), but it didn’t turn very well. Especially for animal products, I warmly suggest to keep low concentrations (3%, 6%). Strength is to be carefully adjusted according to the power of the material. Naive it can be, this simple observation can make the difference. At lower concentrations powerful products can bloom and develop all their facets, while higher concentrations do not lend any additional feature and they are hard to dose or manipulate. A fitting example is civet: at high % it smells quite repulsive and mostly skatole, unrefined. At lower % a rounder, faceted product is obtained, developping the powdery, substantive muskiness civet is appreciated for.

In the particular case of benzoin or other resinous products, high concentrations can be reached without any harm. Anyway, for these products resinoids or absolutes are produced and tinctures are simply outdated. Civet absolute also performs very well.

Where supplies are scarce and batches irregular, as in the case of ambergris, tincturing still seems to be the best solution.

The tincture displays a nice ambery colour.

The tincture displays a nice ambery colour.

Vanilla tincture prepared using comminuted vanilla beans (Madagascar) @10% in pure ethyl alcohol.

The process is  trivial: maceration of the beans in alcohol at room temp. for 9 months and filtration.

The odour is quite satisfying, with a rich vanilla bouquet - similar to vanilla absolute though thinner and more volatile.

The topnotes are not very convincing due to a certain sweet-woody note of sweet almonds. The body is a nice rich, dense vanilla. The dryout is a creamy vanillin.

Not as beautiful as the resinoid or the absolute, but certainly easier to produce.

I am now investigating the undesirable nuance of almond – I’d prefer to get a darker, heavier, even greasy accent instead of an almondy feeling. This same note is also perceptible in the hot extract I made (infusion). I am now producing new extracts, in order to make a comparison. An update on this subject is in progress.

Heliotropyl acetone

Heliotropyl acetone

Not to be confused with: heliotropyl acetate.

White crystals.

Easily soluble in ethyl alcohol @10%.

Mild smelling, sweet, fruity, long-lasting raspberry-like odour.
I was expecting some resemblance  with heliotropine (sweet, powdery floralcy), but this one has a quite different odour profile.

It has very much in common with raspberry ketone: it possesses a jammy, red fruit-like character. Somewhat dry and woody, not much powdery. Rose ketone nuance.

It shuold be interesting in jasmine imitation bases. As suggested by S. Arctander for raspberry ketone, I think that Dulcinyl would also fit very well in a synthetic jasmine composition, bringing a realistic and elegant fruity juiciness very characteristic of some absolutes.
In his work he reports some resemblance with “the sweet-floral notes in Mimosa and Cassie“. Interesting to note that this product is called “Cassione” by Firmenich.

Colourless crystals.

Not ready soluble in ethanol (@2,5% only) or DPG (it forms a cloudy solution).

Floral, warm animalic (civetty), sweet honeyed, thickpowdery, sharp, slightly urinic smell.

Superior to any other p-Cresyl derivative in my opinion. Rounder and much floral than p-cresyl acetate (“horsey” notes) or p-cresol (jasmine-like): it bears a closer resemblance to narcisse, jasmin and violet. Also sweeter, higher-boiling (greater tenacity) and more delicate than the former.

It can easily mimic the violet with the sole addition of indole and ionones. The same for narcisse, being careful in replacing the ionones with methyl anthranilates and a hint of greeness. On paper and diluted, it is almost like smelling a dried out strip of jasmine absolute.

Interesting in a rose-jasmin complex: a warm animalic side married with a powdery phenylacetic acid (dirty honeyed) suggestion.
A short digression on an old perfume: JOY, Jean Patou. Warm and powdery, slightly harsh, intensely floral and jasmin, quite linear. I bet this molecule along with phenylacetic acid was used there (and a lot of Musk Ketone, rose and jasmin absolute, of course).

In jasmine reconstitution I would prefer p-cresol over p-cresyl acetate: it is sweeter and floral; in narcisse and tonkin musk imitation p-Cresyl acetate is my choice; while p-Cresyl phenylacetate elegantly and quite discreetly (in low dosage) fits in both (slightly too much floral for a musk accord, but nice in civet).

Definitely the richest, most floral, animalic, lively, nuanced and smooth p-cresyl derivative out of the three (I didn’t mentioned here p-cresyl methyl ether since it is the most different: thin, low-boiling and ylang-like).

Surely one of my favourite “floral” chemicals, along with indole, linalool and methyl anthranilate.

Molecular structure reference: S. Arctander works. Image created using ChemSketch.

Molecular structure reference: S. Arctander work. Image created using ChemSketch.

White flakes.

Warm, honeyed, metallic, sweaty odour, resembling rose with an animalic (castoreum) and jasmine-like nuance. Dry, medicinal, sweeter on dilution.

In traces it could lend interesting effects in jasmin, rose, cuir type fragrances, tobacco or animal accords.

This product doesn’t resemble civet on its own (in my opinion) but, as suggested in some works, I understand its use in civet imitation bases. Somehow dirty (not fecal): it is waxy, fatty, sweet and slightly acrid (tanned leather, vinegar, feet-like odour) and it could bring texture and roundness to the stronger skatole or indole.

What is surprising about this material is that it lasts forever on paper or tissue. According to S. Arctander’s Perfume and Flavor Chemicals, phenylacetic acid is

[...] one of the most tenacious odorants of all known and used perfumery materials. It will outlast Vanillin on a ‘blotter test’ and a 5% solution of Phenylacetic acid may last more than 3 years on a blotter [...]

Text printed on graph paper. The blurred effect was obtained with an alcoholic solution of phenylacetic acid and a tracing paper. Surely, you can't smell it, but the odour really adds something to it.

Text printed on graph paper. The blurred effect was obtained with alcohol and a tracing paper.

An old De Laire base (much probably reformulated today).

This base was created in the 20′s (1915-1926?) by the French company De Laire. In the 1939 de Laire’s ‘Notice des produits pour la parfumerie’ (a perfumery products catalog for their customers) the Amber 83 is described as follows:

“Produit de choix pour les notes orientales et parfums ambrés très aimés aujourd’hui.

Sa finesse, alliée à beaucoup de puissance et de ténacité, explique aisément le succès qu’il a rencontré dans des genres très différents d’emplois, en France comme à l’Etranger.
[...]
Son point de ramollissement assez bas nous permet cependant de le mouler en petits morceaux d’égales dimensions, et de couleur relativement claire [...]“

Translation: “The best product for oriental notes and ambery perfumes, very much enjoyed today.

Its subtlety, combined with much power and tenacity, easily explains the success it has achieved in many and very different uses, in France and abroad.
[...]
Nevertheless, its quite low softening point allows us moulding in small pieces of the same size, quite light in colour [...]

It is interesting to notice how the original amber was sold in a solid form, pale in colour.
This may suggest that much of the formula were nitromusks, vanillin and maybe resinoids (like benzoin).

The sample I have is physically different.

Appearance: pale yellow, pourable liquid (DPG’s like viscosity). May form a crystallin precipitate in the cold. This is sort of a diluted version of the original base that I suppose was a yellowish solid.

This is the archetypal “amber” of perfumery. Nothing in common with the ambergris, the sperm whale secretion.
This one is based on vanillin or similar products (a heavy dose), powdery musks, some patchouli (but not earthy and terpy), sandalwoodbalms (Tolu) and resins (labdanum, benzoin and styrax), plus a rosey, geranic note in the heart. Nutmeg and maybe cardamom lend some spiciness.
Everything is wrapped and smoothed out by the vanillin overdose. I also detect a civetty facet.
Long lasting and musky, powdery, vanilla absolute-like in the drydown, The sharp, incensey labdanum signature is still alive till the very end, discreetly.

A masterwork of balance, good structure, fine details, simplicity. Easy to recognize.

As almost any bases do, it needs incorporating into a fragrance, to give some boost and projection, especially in the very beginning. The high vanilla-musk dose is something that won’t come out easily, laying down close to the skin.

Here is a (solid) amber type formula from a 1931 book (Le livre du parfumeur – Félix Cola, chimiste-parfumeur), to give us an idea of the composition of such bases:

AMBRE SYNTHETIQUE N°3      
 
Musk Kétone     425 grammes
Muscambrette     100
Héliotropine     75
Vanilline       225
Résinoïde de Benjoin   100
Baume de Tolu     75
Ambréine absolue     50
Résinoïde d’encens     50
Vétyvert Bourbon     10
Patchouly     10
Acétylisoeugénol     110
Stéarine       170
        1400 grammes

Musk ambrette is now forbidden, but could be replaced by the flowery-type musk: ambrettolide, galaxolide or Romandolide (not powdery, but more ‘vegetal’ and clean in comparison to ancient musks, Romandolide in particular).
The ‘ambréine absolue’ is sort of a purified labdanum.
I don’t really know why stearin appears in the formula.

The composition in this photo was inspired by the Ambre 83 base. You can notice Tonka seeds, vanilla pods and geranium leafs. Photo: perfumechemicals.com

The still life in this photo was inspired by the Ambre 83 base. You can notice Tonka seeds, vanilla pods and geranium leafs. Photo: perfumechemicals.com

Pale yellow, ambery mobile liquid (denser than the redistilled quality).

Soft, sweetsawdust-like, patchouliy odour. Drier and more powdery than the redistilled one. Almost no trace of terpenic, mouldy, “cooked vegetable” notes.

In the opening it starts very softly, it has a very poor impact (if kept in cold you barely could tell you are smelling patchouli at all). Then, it opens up and blooms in a beautiful, well refined, cedary, dusty, camphory, clean patchouli. Fruity plum-like nuances. It’s less green-floral than the redistilled quality, but woodier. It does smell a little earthy, but in a clean way: without any mouldy effect.

I like to think this smells like a summery walk in the woods by night: you can detect dead leafs, wet wood and an earthy odour, while a cold humidity arising from the dark chills you to the bones. It also recalls me the smell of rain.

Modern (linear) and interesting. It is well-faceted and complex. I think it is special and different from a simply redistilled oil because here’s the intelligence of some mind that picked-up some fractions and put them together shaping a new character, different from any other patchouli oil.

I can also perceive an ambery (ambrox-like) captivating facet: woody, dry, musky and addicting. Do I detect an animal whiff? Maybe, or simply this oil recalls me some 70′s 80′s animalic bases (like the Animalis, Synarome) used not infrequently in those years in perfumes like Yatagan (Caron, 1976), Antaeus (Chanel, 1981) or Kouros (YSL, 1981): a patchouli-cedar theme, enriched by costus root castoreum and civetty notes, completed by fatty, incensey aldehydes (c12 MNA-like).

Long lasting and beautiful in the dry down. Dry and cedary, ambroxy, orris-like.

A 3D (sort of) gif I made. Photos taken in the woods near Versailles.

A 3D (sort of) gif. Photos were taken in the woods near Versailles.

Pale yellow, mobile liquid.

A very fine, smooth, silky patchouli oil. The terpy, mushroomy, earthy notes: erased in this redistilled quality.
It starts a little softer than the regular one: there’s only some distant green, leafy suggestion. It is velvety and rich in the heart. It dries out in a cedary, woody, dusty, ambery very patchouliy odour. It is indeed very long lasting.
I can smell some resemblance to narcisse absolute: its vegetable greenness, soft floralness (powdery and pollen-like) does suggest me an interesting and unexpected facet. Somehow hedione-like.

This is an intermediate quality between a regularly distilled oil and a fractioned one. Here the bouquet is lighter than the regular but finer. It is quite similar to the fractioned patchouli oil (see: Patchouli Coeur n.3 – IFF).

Very modern and linear. The most useful quality in my opinion: not too much chaotic or dirty in the top notes, ambery and velvety, elegant and simple all throughout the evaporation.

The IFF logo and name are a trademarks of IFF.

Green, fatty (aldehydic), acidic, rose ketone-like. Refreshing and juicy, really like biting an apple. Powdery and woody (similar to a patchouli coeur, Piconia or Verdox). Hints of floral fruitness. Well rounded and balanced throughout the evaporation. Maybe a little soapy, detergent-like (is my judgement somehow biased by my experience with functional products, that often contain such appley accords?). Quite a ‘perfumey’ apple, indeed.

On drying out the odour become more fruity, still dry and fatty, very apple-peel like. Hints of green, rose, geranium. Bright and sweet. Iris-powdery. On further evolution I can get whiffs of cinnamic alcohol-like molecules, sweet spicy, fruity and waxy, woody and very damascone or aldehyde C14-like.

Personally a very beautiful base, intelligently and technically well done. I like the many facets that refine the composition: the nice green accord and the beautiful waxy fatness. Moreover, it preserves its identity and character till the end.
Very much like the real thing, juicy and fleshy, astringent. Well balanced at any moment and nicely rounded, one can almost taste the peel and the flesh. As I said, a little bit ‘perfumey’… too sweet, not waxy and fatty enough at some point in the dry down.

But comparing a base to the object it mimics is often not satisfying. Considerations have to be made on the intended application: has been this base mostly conceived for functional products (a choice imposed by trends in perfumery)? Furthermore, would a copycat of nature be interesting enough on a technical point of view, would it stand itself like this base mostly unchanged and still alive for more than 12 hours?

My answer to the last question is simply: No. Not to talk about regulatory issues… nature actually has a much wider palette than a perfumer.
Concerning its use in fine fragrances: I think it would be good as well, since this base has many interesting facets that would come out even better in an hydroalcoholic menstruum, and possibly open smoothly on skin.

Pale yellow, mobile liquid.

Very fine and fresh, soft floral, with hesperidic nuances, well rounded. Slightly pungent, vert, terpy; evoluting from white fresh flowers to a metallic, rosey, ocimene-like, warm odour; very slightly indolic, but in a pleasant way, perfectly balanced.
A subtle, sweet tension produced by some linalyl acetate-like molecules, enlightens its aura. It somewhat recalls me the odour of wet, hot cotton tissue. It has a powdery, ‘clean’ aspect. After 15 minutes smelling it beautifully dries out and stabilises in a pronounced hesperidic bergamot-petitgrain-like whiff, and a tender flower suggesting hints of hay, tobacco, civet under a green fleshy and waxy veil.

Smelling this oil, discovering its facets throughout the evaporation curve is enchanting, a charming experience.

I like to ask me how one could use this product in a new, original way. Besides conventional compositions (colognes, chypres, fougères) or soliflores featuring orange blossom or rose, this material may need complete reinventing. It does smell just wonderful all alone, simply diluted in alcohol. It’s great in simple mixes (with woody, musky materials), but quite boring.. I think I should do some research on the flowery side of the perfumer’s palette. For example: it could be worth testing in some fine Narcisse, Lilac base, or leafy, green, imitation tea accord (its sweet fruitiness does fit well, indeed).

Mild smelling butyric, iso-valerate-like odour. It should be classified as fruity and classical plum-like. It exhibits a certain fresh sweeteness similar to some linalyl esters, but here a distinctive woody, dry, tobacco-y facet dominates the overall aspect. 

There might also be a rosey, green-metallic nuance. It is quite persistant, an heart note I would say.

Very nice in fruity accords: together with iso-amyl iso-valerate, bergamot eo or bergamot smelling chemicals (ethyl linalyl acetate), cassis absolute (or labienoxime 10%, cassyrane or other foxy, cat urine-smelling chemicals) and aldehyde c18/c14, it forms a sweet peachy bouquet.

In a fancy tobacco accord (preferably with tobacco absolute) it may constitute the plum-like note distinctive of some aromatised blends (plum juice concentrate).

Here’s a simple ambroxy/woody/burnt tobacco accord you can try with/without Datilat:

TOBACCO ABS
MOUSSE DE CHENE IFRA (with patchouli and ambroxid to form an easy and pleasant accord)
BENZYL SALICYLATE
ETHYL VANILLIN
COUMARIN/BICYCLONONALACTONE
BIRCH TAR (trace)
HEDIONE (for diluting and mellowing effects)
CIVET ABS (recalling some strong tobaccos)
AMBROXID (to make the all thing wearable)
PATCHOULI COEUR (I usually don’t like messy top-notes, this one I prefer)
COSMONE (nice velvety effect)
GUAIACWOOD EO
CLOVE (as a modifier)
+DATILAT and/or ISOAMYL ISOVALERATE (if using iso-amyl iso-valerate be sure to add some top-notes like mandarin or bergamot in order to round its effect. It is quite volatile and it could unbalance the accord)

In this first attempt I tried to extract the aromatic principles of roughly 0,5 kg Bourbon vanilla beans (from Madagascar) by hydrocarbon percolation. For this purpose I used n-hexane Scharlau 95% (120 euros 5 L canister). The extraction product is called an “oleoresin” (resinoid or concrète) because it carries a volatile fraction and odorless waxes and resins (I suggest you to read S. Arctander’s monograph on this subject: Vanilla oleoresin).

I bought extraction grade vanilla beans: water content is kept low.

I was quite satisfied with the overall “standard” odor quality of the starting material: “senza infamia e senza lode” (nor too bad nor too good). I only perceived a faint fermented type, volatile off-note when unpacking the beans. Apparently it was distilled off when evaporating the solvent, since it is not detectable in the oleoresin anymore (when disassembling the Soxhlet extractor after the process I was able to smell an acetic acid-like note on the top of the Dimroth condenser, while the recovered hexane did not carry such note).

In this first photo you can see the Soxhlet type apparatus I’ve set up for the extraction process:

Soxhlet apparatus

Soxhlet apparatus

Here’s a video of the soxhlet extraction process:


Comminuted Bourbon vanilla beans before extraction:

comminuted vanilla beans

comminuted vanilla beans

Comparison between exhausted (left) and fresh (right) vanilla beans. From this photo you can guess the extractive power of hexane: the vanilla on the left is drier and paler in color. It still carries some aromatic principles (not hydrocarbon-soluble material I presume).

exhausted (left) fresh comminuted vanilla beans (right)

exhausted (left) fresh (right) comminuted vanilla beans

A Soxhlet apparatus is designed in order to recirculate the solvent throughout the botanical material. The temperature at which the extract is exposed is the boiling temp. of the solvent used. At standard pressure n-hexane boils at 68° C (relatively low). The raw material is not directly in contact with the boiling solvent, thus preserving it a little bit from excessive heating.

In this first attempt I let the solvent recirculate 6 times (2 hours refluxing). The first run is, not surprisingly, the most charged with volatile materials, waxes and pigments (it is the darkest in color). The fourth is almost colorless.

I let the extraction liquor stand for a day and then filtered under gentle vacuum. This process results in a small loss of solvent. n-hexane is very volatile and vapors arise easily from the filter paper. It is the most troublesome phase of the process, when you are in strict contact with the solvent. I carried out this operation on the outside avoiding breathing too much vapors.

vacuum filtration

vacuum filtration

I then evaporated the solvent under vacuum (pressure between 150-300 millibar) at ~30° C. It is really tricky to evaporate all the solvent. The last traces are the most difficult to eliminate: the temperature increases and there is the risk of spoiling the extract.

recovered solvent (left) vanilla oleoresin (right)

recovered solvent (left) vanilla oleoresin (right)

A video I recorded of the evaporation process:


A rotatory evaporator would give better results: solvent recovery would be faster and more efficient.

I used a water vacuum pump: I can reach a pressure as low as 8 millibar, but in normal working conditions (heat, arising vapors) it is stable at around 150-200 millibar. A membrane pump would be more reliable.

An ice trap would also improve solvent recovery and avoid vapor leakage in the air (I used a Dimroth condenser and recovery was very good, I registered only minor losses through the vacuum pump).

The yield was quite good: 31 g oleoresin from 471 g of crude vanilla beans (6.7%). I was able to recover most of the solvent (major losses were due to filtration and adhering solvent on exhausted vanilla).

Vanilla oleoresin is a viscous, dark brown liquid not completely alcohol-soluble. It possesses a true-to-nature, rich and creamy vanilla aroma, with woody and licorice undertones and a tobacco nuance. It is not as powerful as a vanilla absolute, since it still contains odorless waxes and non-volatile material, but it possesses good tenacity.

I don’t appreciate headnotes from this oleoresin very much: they are quite smoky-bitter, overly sweet to my nose. It may be a factor of concentration (too high to fully appreciate the extract) or there could be solvent traces (a gassy nuance? Not quite sure). I assume that during solvent recovery the temperature increased too much in the last minutes (bitter, smoky, burnt odor detected?).

An hydrocarbon extraction followed by an hydro-alcoholic one should give better results: not complete alcohol solubility, but a much more complex and rich aroma quality.

Tightly controlling the temperature is essential to achieve satisfactory odor quality.

Not sure if it is a panteted molecule (IFF).

It is piercing, woody, resinous, musty and rosy in some ways. It is peculiar and interesting, not sure to have smelled anything that resembles this until now. Not at all ozonic (like Floralozone or Precyclemone B) nor marine, as stated in some descriptions; it has no lily of the valley-melon-like nuance. A little bit salty, maybe.
It is the odour you could find in a cellar, quite thin and volatile. This has not much body but is quite long-lasting. I very much appreciate its extremely dry, woody, musty, cork-like undertones.
It is quite powerful, difficult to use at more than 5%.

Sweet, tonka, almond-like, dry, woody odour. Lactonic nuance.

Its strength is better understood when properly diluted (usually at 5 or better 1%, in ethyl alcohol; anyway it will not dissolve at more than 8%). I usually keep it at a maximum concentration of 1% (fragrance concentrate), otherwise, it will grow and tend to overwhelm other notes.

It is a standard ingredient in chypres and fougères. It forms the classic ambrein accord together with vanillin, civet-like notes and bergamot.

Tonka bean absolute is quite obviously more complex and refined, it has soft, woodier, bitter, creamy, hay-tobacco-like, dark facets.

I have not yet found a good replacer for coumarin at this time. It could be Acetanisole (but it is thinner, sweeter, heliotropine-like in character). I really like Bicyclononalactone (closer to tonka, hay and hyraceum).

Powerful, thin, sweet, fresh, lavender-like, fruity, metallic, citrusy (linalyl acetate-like), clary sage-like, well recognizable odour.

Used in almost any manly fragrance, classic fougère accord, modern sweet-musky-chypré accord. From fine fragrances to functional products.

@ 100% intense, sweet, fruity, peary, green, ananas, oily, slightly waxy, fresh.

@ 10% pleasant, fresh, sweet, fruity, peary, metallic.

Used to introduce a modern fresh-fruity topnote. It blends well with iso e super and dihydromyrcenol in fougère accords.

Real nitromusk: warm, sweet, musky, dry, powdery, fruity, soft odour. Most polycyclic and macrocyclic musks lack that beautiful sweet-powdery undertone. Tends to discolor.
iso-Muscone and Velvione are examples of nitromusk-smelling non-nitromusks. They are safer than nitromusks but do not perfectly mimic that nuance.

Sandalmysore core
Santaliff

Medium-smelling, sweet, oily, slightly aromatic (dry fennel), sandalwood, musky, vibrant, woody odour. Effective in small amounts, it gives a natural milky, creamy, sandalwood-like nuance.

Powerful, sweet, milky, lactonic, coconut, coumarinic, powdery odour.
I used this in an imitation rum fragrance, where it surprisingly well mimics the effects of oak aged liquor: it provides a refined sweet, mellow, lactonic, woody, dry, musty nuance, and gives tenacity.

“Methyl Laitone 10% is one of the new “spiro”-lactones developed and patented by Givaudan. It is extremely powerful and very effective in all accords where a creamy, fruity volume is required. It provides “cosmetic” body to white flower notes such as jasmine, gardenia, tuberose and ylang ylang, and to fruity accords like peach and osmanthus. In sandalwood accords it provides milkiness. Coupling with coumarin and hay notes makes it extremely interesting and polyvalent. Its dry note is very noticeable, especially on humid and dry fabric.” (http://tinyurl.com/mlaitone10)

Medium smelling, sweet, powdery, milky, dry, typical vanilla odour, without any complexity, or dark shades. Useful in any composition. @ as little as .1%, whitout being perceptible as a single note it rounds off and mellows any fragrance.

gamma-Nonalactone

Intensely sweet, creamy and coconut-like odour. Oily, waxy and metallic undertones. Useful in many florals.
“Its intense sweetness and tenacity is often utilized along with that of Undecanolide (…) in Gardenia, Tuberose, Honeysuckle, Stephanotis, Plumeria, Jasmin and many other heavy floral types.” (Arctander)

gamma-Undecalactone

Medium-smelling, fruity, lactonic, peachy, sweet, oily, powdery. Effective in low concentrations, otherwise it tends to overwhelm other notes and give ‘opacity’. It may also be used in floral compositions, tuberose for instance.

Semisolid-viscous intensely yellow, blue fluorescent, mass.

Similar in odour to methyl anthranilate, but more sweet, oily, waxy, powdery and floral.
Useful for the same purposes as methyl anthranilate, where more tenacity and sweetness is desired. It is also more stable.

@ 100% pungent, chemical, thin sweet, heavy-flower, ylang, fruity, musty, grape.
@ 5% sweet, floral, ylang, orange blossom.

Useful in low concentrations in floral compositions, in imitation orange blossom, neroli, jasmine, tuberose, narcissus…
It reacts with aldehydes, forming condensation products (Schiff’s bases). Aurantiol is hydroxycitronellal+methyl anthranilate.

Very mild, almost non-smelling, nondescrpit, oily, sweet, floral odour. It tends to oxidize to benzaldehyde, which is strong-smelling and easily ruins its floral profile.
“Used in perfumery as a blender, in some florals quite extensively, Jasmin, Gardenia and Lilac may often be composed using Benzyl alcohol although this material is really dispensable in most cases.” (Arctander)

Quite powerful, similar to eugenol, but more fruity, floral, delicate, less woody-spicy. It strongly resembles carnation and it is usually found along with benzyl salicylate to form a classic accord.

Strong smelling, clove, spicy, woody odour. Bitter in too high concentrations, natural spicy, woody effects if properly diluted (usually @ around .1%). More refined, less woody, musty, green than natural clove oil.

Powerful, green, leafy, fresh, sweet, woody odour. It easily reminds of freshly crushed leaves, cut grass, green branches. In dilution it is more sweet and almost fruity. It gives a natural impact to fruity and floral compositions, imparting a realistic green effect.

Poweful, predominantly green, sweet, waxy, citrusy odour. Used in traces for an herbe coupée effect. It is less natural, more powerful than cis-3-hexenol, but it is more rounded and blends better with fruity-floral notes. 

Sweet, soft, pleasant, fresh, nondescript-flowery odour. It may resembles jasmine for its fruity-juiciness aspect. It is less refined, stronger than hexyl cinnamal. It is useful in any white-floral composition.

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