You are about to enter the world of genius master perfumer, Arcadi Boix Camps, inadvertently talking about the compounds that likely make up the rum oil described by Rafael Arroyo in the 1940’s. I’ve had a lot of trouble getting anyone to pay attention to these compounds which often seem arbitrary. When described by a few notable chromatography based studies, they don’t exactly leap off the page.
Here, we find a character with the most intimate experience and he is immediately moved enough to wish he could introduce them to Plato! I personally used the world glorious over and over in a few birectifier case studies and was amazed to find fragments lurking in spirits more beautiful than the whole. Arcadi takes everything to a whole new level and teaches us why to pay attention (to rum oil) and how to be moved! Confronting rum oil is the next leg up for rum, and possibly many other spirits.
The title says stereo because we are in the challenging world of stereo chemistry, but luckily we can ignore much of it. Stereo chemistry is basically left or right handedness and other kinks and nodes that subtley differentiate families of molecules (3D arrangement). It leads to obnoxious names that describe the structure, but those aren’t important to us. The nose alone certainly knows enough and Arcadi helps illustrate that. He brings these head wrecking chemical nuances to life in an approachable way that will help us decode all the GCMS listicles getting dusty in library basements and behind paywalls. He convinces the distillery technician that they will want olfactometry for everything.
The following writings all come from the second edition of Perfumery: Techniques in Evolution. The text has sections based on eras (i.e. 1978,1985,1999) in Arcadi’s career and then finally a section titled: —No Creativity Without Philosophy or Poetry.
Only read the bold. Ignore everything else. (so as not to melt your brain) Damascone and damascenone are likely the foundation of Arroyo’s rum oil, but they were not identified in chemistry until years later. Damascenone also plays a role in defining Bourbon, but so does Ionone so I’ve also collected those snippets from Arcadi’s writings.
In a future post, I’ll examine how these compounds are all carotenoids and how they relate to spirits production as well as how they are presented in research papers. I’ll also propose a framework for birectifier assisted chromatography that will hopefully change how fast and economically the industry can work in this territory.
Nothing here is exactly chronological and there is a bit of repetition because of the sections are often collected writings.
In November 1978, 21 years ago, I introduced the first article of the series, I “Perfumery: Techniques in Evolution,” at the Fifth Convention of Perfumers in Spain. I was then a member of the Spanish Society of Cosmetic Chemists and The Professional Group of Perfumers, organizations that I quit some years later. I started talking about the word “evolution” as a key hallmark to understand our profession. At this time I described products like α-damascone, β-damascone damascenone, calone (watermelon ketone), all virtually unknown in 1978 by almost all the perfumers in the world. I stated that these chemicals were going to be the elements making the forthcoming evolution of perfumery possible, an evolution that was a real revolution already looming over the horizon. Well, I was right. In 1978 there was not a perfume with calone in it. Now, it is one of the most successful ingredients, one with which perfumers won’t be able to work without. Damascones and damascenone were known only through the patents, through scientific papers describing minor ingredients in bulgarian rose oil such as rose oxyde, neroloxyde, rose furan and p-menthen-9-al. At the time, these were used in bases such as cetylia, dorinia or damascenia. Most perfumers, except those working with the company that patented them, used these bases without knowing which chemicals were responsible for imparting the sought-after effects of radiant, fruity and rosy nuances.
Radiants [does rum oil give rum radiance?]
The family of the radiants is composed of products that strengthen, blend with, enhance, amplify, and have an influence over the other elements in a composition. Let us mention here the products we have already discussed: Muscone®, Exaltone®, Exaltolide®, Civetone®, Ambretolide®, Timberol®, and Hedione®. We are going to dwell on the following products, which, in my opinion, are brand new and thoroughly interesting—isodamasconel, alpha-damascone, beta-damascone, beta damascenone and the irones.
Most of these products have intense, fruity rose odors, but beta-damascenone, with its chemical formula 2,6,6 trimethyl-trans-crotonylcyclohexadiene 1,3, is perhaps the most revolutionary of this family of products. Present in the essential oil of Bulgarian rose as a minor component, its effects are of the greatest importance in determining the final odor of the natural product. Even in minimal closes, its effects are impressive. It imparts a freshness, naturalness, radiance, intensity, broadness, uniformity, and character to any perfume. We could almost say that it imparts the very subjective feeling of a perfume, wherever it is used. I am completely convinced that beta-damascenone will be one of the greatest aromatic compounds of the 1980s, and its incorporation into the great perfumes is assured.
The irones are well known by everybody. Their power to radiate and to embellish are enormous. We should indicate that by themselves they don’t necessarily have the odor of the absolute oil of orris. The natural absolute oil is a mixture of various isomers, the most important of which are the alpha, beta and gamma irones. Mixed just in the same proportions as is contained in the absolute oil of iris, they smell intensely of it. Rarely do you find an isomer in the pure state on the market because commercial products are already mixtures of these three very important isomers.
Let us mention as interesting, although totally different, the so-called alpha irone and Irone V. Their odor is different because their isomeric composition varies enormously. In general, alpha-irone has an odor very close to alpha-ionone, although its richness is a thousand times superior. Beta-irone is more spectacular. In any case the irones are classic products of unequal beauty, and when they have been well used they give an uncommon elegance. Their effect on woody notes and on the herbal-floral notes is indescribable.
Methylcyclopentenyl acetate, called Cyclopidene®, makes for important floral notes and creates great bases. Although it is a repetition, let us mention some aromatics of universal importance, the regal products of the subgroup: alpha damascone, isodamascone, beta damascenone and trans delta damascone. With the marketing of Nahema® by Guerlain, among other European and American products, the prediction I made in Part I that they would have an impact on perfumery has largely come true.
From my point of view, beta damascenone, isodamascone and trans delta damascone constituted an odor group in which beta damascenone is clearly the superior because of its unequaled beauty, its evanescent, sophisticated and difficult-to-catalogue note, and its radiance. Its effects will be more important, but only the good perfumers will know how to use this exciting aromatic as it should be used.
Alpha damascone, the most fruity and perhaps most metallic of the family, is also the most difficult to use. It enhances and gives a diffusion to floral blends, but its effect is also extraordinarily great with woody, amber, masculine notes, where it modifies extraordinarily the essence of cistus, and blends very well with tagétte, angelica and others. We have masterful applications.
[…] The bases Damascia, New Frutambria, and the Cetotabac series are personal examples of how β-damascenone behaves when mixed with incredibly new captive chemicals that improve either its rosy or herbaltobacco character. [I have experienced this in various birectifier fraction 5’s.]
β-Damascone – 1-(2,2,6-trimethyl-2-cyclohexen1-yl)-2-buten-1-one: As is well known, this is another great chemical in the series. β-Damascone is less herbal tobacco than β-damascenone, and pure rosy, if a bit less natural than β-damascenone. The material is extremely delicate, soft, fruity, floral, rose-like, and combines very well with other soft ingredients such as geranyl crotonate, cinnamyl propionate and isobutyrate, and cinnamic alcohol, among others. Its harmony is delicious; it is like dreaming with all the senses. When smelling it properly diluted, it even affects the mood by via relaxation, activating the hormones that help us feel pleasure. Our examples of using β-damascone with other novel and unused chemicals are the bases Dulci or 841/D and Vert de Magnolia 8758/D.
γ-Damascone -1-(2,2-dimethyl-6-methylenecyclohexyl)-2-buten-1-one: This ketone was kept captive until 2002. It is very rosy and delicate, as are all these rose ketones. It is also fruity-plum-apple and possesses an interesting black pepper effect in its top note that is missing from the other isomers. According to my experience, γ-damascone is the rose ketone that best blends with sandalwood chemicals. Its accords with nirvanol, javanol, Firsantol (Firmenich), Sandalore (Givaudan), Dartanol, Ebanol (Givaudan), Sandela (Givaudan). Mysoral and Polysantol (Finnenich) are really great. It is fruitier than the other damascones, but less long lasting. As in the case of β-damascone, I love to blend it with cinnamyl propionate and cinnamic alcohol—a great chemical, provided its quality is appropriately high (see sidebar).
The major question with all rose ketones is this: why do these materials have such a relaxing effect on the body? How do they bring pleasure to our strained souls? I do not have any scientific proof of these materials’ benefits, yet I (and many others) know them to be a reality. No doubt there are needs for stress remedies in our modern world: I believe our society promotes voluptuousness and consumption, the first of which brings apathy and indolence to our souls, while the second keeps us poor (that is to say, dependent). If only our culture and education ministers realized that the great secret of enlightenment and release from strain is to direct one’s vanity towards prudent, judicious and sensible objectives such as sensory beauty.
[My theory from experience is that some of these compounds have mildly psychotropic effects. I believe they can even change the feeling of inebriation and reduce a hangover by provoking a different immune response.]
α-Damascone 1-(2,6,6-trimethyl-2cyclohexen-1-yl)-2-buten-1-one: This is a very complex product. It smells floral, but less floral-rosy than β-damascone. It is also fruity, plum, apple and green, with a camphoraceous nuance. I like to mix this ketone with muguet and cyclamen chemicals such as Lilial, nerolidyl acetate, dimethyl benzyl carbinyl acetate, crotonate, isobutyrate and butyrate, myroxide, benzyl salycilate, Indo or (Symrise), Rosacetat, Jacintha or (Symrise), cyclamen aldehyde, and myrac aldehyde, among others. Unfortunately, the dimensions of this publication will not allow me to describe all the uses I have found in my life while working with α-damascone. As in the case of hedione, what is important here is the commercial quality, which rests on two enantiomers – (R)(+)-α-damascone, which is responsible for this related camphoraceous note, and the (S)-(-)-isomer, which is by far cleaner and around 100 times more intense than its enantiomer. This (S)-(-) isomer, found in tea, is one of the challenges now facing our chemists. It has been synthesized, and efforts are being devoted to produce it in an industrial scale. If success is achieved—and it will be, because those great chemists are extremely determined—a new era of creativity will come to us. Soon we will get the first perfume using this enantiomer separated and single. May I suggest the name of α-teascone for it? I am lucky because I have smelled this substance. The intensity of pleasure I felt as a result made me think of Plato. The material reminded me of what I’ve said elsewhere, in other writings: a “very small city, very, very small, isolated, very, very isolated and free from external influences.” I would have loved to show Plato β-damascenone, β-damascone, α-damascone, α-teascone and γ-damascone at 1 percent solution in alcohol and wait for his reaction. I believe it could be a great, utopic experience. Imagine one of the greatest men in all of Western Civilization smelling some of the best olfactory chemicals, which surely would move, motivate, touch and thrill his senses.
[Some rums have a strange camphoracious note in their fraction 5’s]
δ-Damascone -1-(2,6,6-trimethyl3-cyclohexen-1-yl)-but-2-en-1-one: This material is also called Dihydro oriffone TD. It is quite similar to α-damascone, but with a more striking metallic fruity nuance and less “cinnamic” impact. I say cinnamic because many shades of cinnamic alcohol are found in the diverse damascones. I believe δ-damascone smells closer to (R)-(+)-α-damascone than the described α-teascone. I like this chemical, although it is less linear and less clean than the other isomers. However, it is quite useful because of its striking fruity impact in functional perfumery.
α-Ionol: This is a great and ignored chemical. It is not far from cetonal, characteristically, but is weaker and less frankincense-like. α-Ionol is by far more green-violet than α-ionone, which is more floral-woody-fruity. α-Ionol has a very interesting tobacco tonality as well. Because there are so many, it is quite difficult to say what the best woodyoral and greenoral-violet chemicals are. To me they all possess advantages: top grades of diverse methylionone isomers, α-ionone, β-ionone (which is more orris-like), dihydro α-ionone (which is strongly amber with 1,000 different nuances), dihydro-β-ionone (more violet and less ambery), and dimethylionone, a great chemical. I believe that as in the case of musks, the best material is in fact the synergistic combination of several of them. Unfortunately, α-ionol is not widely used. This is a mistake because from within its charming molecule flows a torrent of floral character.
α-Ionyl acetate: This is less green than its corresponding alcohol, and is on the borderline between green-violet florals and woody florals, though it is more elegant. Mixtures of α-ionyl acetate, methylionones (especially the greater of them), cetone α, Raldeine AGV (Givaudan), Xandralia and Iralia, dimethylionone, methyl-α-ionone glycidate, vetyveryl acetate, Verto x Coeur and a touch of allyl ionone are simply great. They diffuse class and beauty. Even α-ionyl acetate and vetyveryl acetate alone together form a great accord of unsurpassed elegance. We have discovered dihydro-β-ionone and rediscovered β-ionone. A great tread forward will be to increasingly use this charming chemical, which is one of the greatest green-woodyoral materials I have smelled. Its mixture with ambergris chemicals like boronal, ambrinol and ambrinol oxide, ambrox or laevoCetalox (Firmenich), and the unknown and extremely interesting dihydro-γ-ionone is really exceptional. The woodyoral diffusion is tender and soft, and when the product is nally incorporated in a great perfume, the material will nally get its due.
Myrrhone — (E)-4-(2,2,cis-3-trans-6-tetramethyl-R-1-cyclohexyl)-3-buten-2-one: This is a totally unknown chemical, and one of the most beautiful I have ever smelled. While new, this product will absolutely influence the future of perfumery. It smells of a combination of irones, some of the finest parts of jasmine, Paradisone, epi methyl jasmonate and myrrh. Myrrhone is extremely fl floral, radiant, elegant—the result of the great research done by our industry’s chemists as is the case with Myrrhone, Helvetolide and its newer cyclaprop analogue, Paradisone, Pentambrette, dextro nor limbanol, nor dihydro-β-vetyvone, trans-α-bergamottenone, georgywood, Moxalone, Nirvanolide, muscenone δ, exaltenone, exaltone, exaltolide, habanolide, ambrettolide, ambrocenide, irone α, Limbanol, super muguet, anapear, Romandolide, Khusimone, woolfwood, the newest transoppositadienal, the rose ketone. Should I continue? I am approaching the notion of perfection, and “perfection” is a dangerous word. Can we remain humble (a condition of wisdom) when smelling such treasures that impart so much beauty? Did perfumers feel they’d arrived at perfection upon the discovery of the aliphatic aldehydes, isoamyl salycilate, vanillin, ethyl vanilline, heliotropin, and the ionones? Possibly. This phenomenon best describes how small we are when trying to get a handle on high concepts like “eternity,” a condition of the fine arts. But we must admit: art cannot be described. As I said before, Michelangelo knew Phidias, but not Marc Chagall, Poussin know Leonardo, but not Picasso, Protagoras knew the sophists, but not Plato, Plato knew Socrates, but not Marcus Aurelius, Julian the Apostate or Maximus. What is perfection? The eternal search for truth desperately required by the anonymous writer who wrote the poem in the first half of this installment? We should never lose our humility. Still, we have Myrrhone, and this for a perfumer must be an explosion of joy. Myrrhone is one of the most elegant chemicals. When smelling its delicacy, the eyes close, and dreams, for a while, seem as if they might come true. Its radiant, fl floral-woody and fl floral-resinous shades are paramount. It smells of the best part of sacred myrrh, and combines well with Cashmeran, Firsantol, dextro nor limbanol, Helvetolide, Javanol, Ambrocenide, Paradisone, Koavone, a touch of Zingerone, georgywood (a woody resinous chemical, too, although woodier and less radiant than Myrrhone). Iso E Super, Kohinool, Jasmine Lactone, Pentambrette, epi methyl jasmonate, the best musks (the cleanest and more crystalline). Myrrhone will affect the evolution of our art and science for the coming years. The material will be another Hedione, another Paradisone, another Helvetolide, another Cetone α, another Ionantheme 100 percent. We are reaching glory in perfumery and our dreams are coming true and have we not said that future belongs to those believing in their own dreams?
Isodamascone-1-(2,4,4-trimethylcyclohex-1-(2)-enyl-1)-2-buten-1-one: Presented by Dragoco in 1971, this material was the first of the related ketones to be commercialized. Its smell is good — a mixture of α and β-damascones that results from the fact that its commercial quality is a mixture of α and β-isodamascones. However, now the quality has changed; the material mainly contains α-isodamascone, which makes it more exciting than before. Isodamascone has a certain waxy, slight tonality similar to damascones and n-decanol, although this is not noticeable when not comparing it with the damascones. To me, the material is a very nice chemical, as all the damascones are. I like to compare isodamscone with γ-damascone (more peppery and fruity), β-damascone (more rosy and less fruity, but more subtle) and β-damascenone (more delicate, and most of all more rosy and herbal-tobacco-like). Its uses are similar to those of the related damascones.