Damascones : Perfume Ingredients

Damask_rose

If the light pouring through stained glass windows, dancing in vibrant red and orange and flickering on the skin, had a scent, it would be the fragrance of damascones, aroma materials derived from the Bulgarian rose oil (rosa damascena). Encompassing rosy and fruity aspects, damascones have a vibrant and potent scent, marked by woody and tobacco like qualities, depending on the type. Some derivatives of damascones have very interesting nuances, from green apple, stewed plums and ripe figs to nuts and woods. First isolated between 1970 and 1980, damascones and damascenons produced a true breakthrough given their fascinating olfactory profile and intense fragrance.

Nahema by Guerlain (1979) was one of the first fragrances to incorporate damascones into its rose veiled structure. Damascones decorate the rose notes in the way that gold jewelry enhances the beauty of princesses from the Arabian Nights tales by which Nahema was inspired. …

The rose petals drenched in peach nectar are simultaneously brightened and darkened by the plumy richness of alpha-damascone. Revealing the fruity, slightly green facet one moment and a lush flower the next, the rose accord of Nahema has an unusual and strong character. Sadly, Nahema was a big flop for Guerlain due to the fact that its strength and boldness were rather ahead of its time, yet Jean-Paul Guerlain mentions that Nahema will always remain his most innovative and proud creation.

Had Nahema made its debut in the mid-1980s, its success is likely to have been more certain. Indeed, one of the biggest successes of the 1980s was another damascone overdosed creation, Christian Dior Poison (1985). The damascones are a group of materials that are related to ionones. The synthesis of damascones is more difficult than that of ionones, this fact being reflected in their price. Because of their powerful and diffusive odors, they are usually used in very low concentrations. However, if one is interested in experiencing the potency of damascones when used in large concentrations, Poison is undoubtedly the best example. An overdose of alpha- and beta-damascones allows a warm wave of creamy tuberose crowned with vivid fruitiness to erupt from its black apple shaped bottle. While alpha-damascone is fruity and floral, with a distinct camphorous element, beta-damascone can be described as gourmand, with floral and tobacco-like aspects. Its honeyed plum facet complements the spicy heart of Poison, while offering a beautiful sweet prelude to the ambery base. However, I would mention that Poison is best experienced in Esprit de Parfum, since the remarkably cloying Eau de Toilette lacks the nuances that made Poison a legend.

Another legend from the 1980s, Yves Saint Laurent Paris (1983) marries the fruity notes of alpha-damascone with its beautiful green violet accord. Where the combination of rose and violet would have produced a dense powdery sensation, damascones infuse the composition with a transparent fruity brightness. In the same year, Guerlain released a damascone laced tuberose bouquet, Jardins de Bagatelle. Its long-lasting sweetness is punctuated by a burst of fruitiness, as if the flowers are layered over the stewed berry compote.

Another stunning example of damascones woven into the composition is Nombre Noir (1981) created by Jean-Yves Leroy for Shiseido under the artistic direction of Serge Lutens. A rose is abstracted by damascones into a vision of a dark jewel, the petals ossified by their peculiar woody note reminiscent of cork or the bark of an evergreen tree. This rose does not stray into the sweet and powdery domain, remaining somber, yet remarkably radiant as if held in the sunlight. At the same time, it unfolds in a languorous fashion, shedding one petal after another, in order to reveal a vibrant heart where rosy damascones meet the apricot leather richness of osmanthus.

The success of damascones and their affinity with various accords has inspired the synthesis of numerous analogs and derivatives covering a broad range of odor notes, from floral to woody, from rose to walnut. A very interesting and significant discovery was Dynascone, an impurity in alpha-damascone. The trendsetting Davidoff Cool Water (1988) is one of the fragrances exploiting its unique olfactory profile encompassing green, pineapple, hyacinth and metallic aspects.

Among the components of rose oil, damascones are the most important fragrant derivatives; however, they are not the only materials isolated from rose oil used in perfumery. In 1961, rose oxides were identified in rose oil (in 1957, they were discovered in the oil of geranium), a discovery that engendered a whole generation of fragrances that explored the floral and green aspects of these new aroma materials. Paco Rabanne Calandre (1968) built its metal accord around the rose oxides, softening and brightening the effect with the rose absolute, thus revealing a beautiful marriage between the natural and the synthetic derived from it. Yves Saint Laurent Rive Gauche (1971) constructs its heart accord following the direction of Calandre, resulting in a stunning composition where the powdery aldehydes gently caress the metallic coolness accented with rose and jasmine. Paco Rabanne Metal (1979) and Guy Laroche Drakkar Noir (1982) are among other fragrances relying on the green floral and herbaceous character of rose oxides.

The reason that the woody rose beauty of Nombre Noir can no longer be reproduced is because damascones and damascenones are considered to be sensitizers with their usage restricted to no more than 0.1%. Yet, damascones have continued to be used prominently. One of many examples of a masculine fragrance relying on damascones is Donna Karan Be Delicious for Men, where a luxurious fruity note reminiscent of baked apple touched by spicy sweetness is contrasted with the sparkling top accord and mossy base. In the reorchestration process of Lanvin Arpège, one of the dilemmas was the construction of a rose accord. While most women are used to the rose being accented with damascones, given their ability to lend a fruity sweetness to the floral notes, damascones were not yet discovered in 1927. Therefore, one can say with certainty that damascones and their various analogs will continue to play an important role in the development of modern perfumery.

References: Calkin, Robert and J. Stephan Jellinek. Perfumery: Practice and Principles. John Wiley & Sons, Inc., New York, 1994.
Gautschi, Markus, Jerzy A. Bajgrowicz, and Philip Kraft. “Fragrance Chemistry—Milestones and Perspectives.” Chimia 55 (2001): 379-387.
Kraft, Philip. “Aroma Chemicals IV: Musks” in Chemistry and Technology of Flavors and Fragrances, ed. by David Rowe. Blackwell Publishing, UK, 2004.
Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Odds and Trends: Recent Developments in the Chemistry of Odorants, Angew. Chem. Int. Ed. 2000, 39, 2980–3010.

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33 Comments

  • Marina: What a wonderfully detailed article!
    I say, yes to Damascones, no to Dynascones (and Cool Water specifically :-))
    Have a great week, V! February 13, 2006 at 8:23am Reply

  • kaie: Your articles on perfume ingredients are very interesting. Thank you for writing on the fascinating topic of damascones! February 13, 2006 at 9:37am Reply

  • N: Thank you dear V for this wonderful article.
    I am printing this out to read again.

    Hope you are well.

    Hugs! February 13, 2006 at 10:50am Reply

  • annE: Thank you for a fascinating article! I learn so much from you. February 13, 2006 at 11:09am Reply

  • Linda: V, I have been curious about Nombre Noir after hearing that it was Lutens’s first fragrance. It sounds wonderful! I see minis of NN on Ebay from time to time. Are they legit? I thought that its bottle was black. February 13, 2006 at 12:23pm Reply

  • CaitCait: I like this sort of article more than any othe on your blog. Your research is much appreciated. February 13, 2006 at 12:23pm Reply

  • Linda: Great article, by the way! I learned so much from it. February 13, 2006 at 12:23pm Reply

  • paru: This is a bit of a geeky question but what is the chemical composition of a damascone? I’m guessing the alpha and beta versions are just isomers? And why is the synthesis so difficult? February 13, 2006 at 1:05pm Reply

  • BoisdeJasmin: M, thank you. As for Cool Water, I think that the men’s version is great, but I personally do not like the women’s one. Granted, Cool Water is not something I would wear, because fougeres are usually too masculine for me, but I like it on a man. February 13, 2006 at 1:12pm Reply

  • BoisdeJasmin: Kaie, thank you. I also think that they are fascinating. February 13, 2006 at 1:17pm Reply

  • BoisdeJasmin: Have a great day, dear N! I hope that your week is starting well. February 13, 2006 at 1:17pm Reply

  • BoisdeJasmin: Ann, oh, I am so glad to hear this! I am glad that you enjoyed it. February 13, 2006 at 1:18pm Reply

  • BoisdeJasmin: L, yes, they should be legit, but my issue with those minis is that they are damaged. The juice is really fragile, and the black bottle would have guaranteed its preservation better. February 13, 2006 at 1:20pm Reply

  • BoisdeJasmin: C, well, we aim to please! :) February 13, 2006 at 1:21pm Reply

  • BoisdeJasmin: L, I am very happy to hear this! February 13, 2006 at 1:21pm Reply

  • Robin: Fascinating, V! See, I will end up knowing something about fragrance chemistry despite myself ;-) February 13, 2006 at 1:30pm Reply

  • Rafael: Hi V,

    Once again, a great review on fragrance ingredients. As far as I know, Damascone Beta was introduced by Firmenich in the market in 1975 when the Dorinia, Damascenia 185 and Cetylia® Base bases were launched. Damascone Alpha and Damascone Beta followed in 1979, and finally, Damascenone (an unsaturated analog of Damascone Beta) was introduced in 1982. This is a very powerful floral fruity note, that smells intensely natural, rose, plum, grape, raspberry and sugary. Pity you couldn’t comment more on this particular material. I recall an article on Damascenone published a couple of years ago at the Firmenich’s website, but unfortunately, it’s not there anymore.
    Hope you find this interesting.

    Regards, R. February 13, 2006 at 1:35pm Reply

  • BoisdeJasmin: P, the formula is C13H20O. The synthesis is complicated, because it requires several steps. For instance, one of the processes implemented in the 1970s involved starting from dehydrolinalool. There are a few other ways to get it, of course. Just to say, the synthesis of ionones by comparison is less costly, consisting of two steps, the synthesis of pseudoionone and cyclization of the acquired pseudoionone in the presence of an acidic catalyst, which then produces a mixture of ionones. February 13, 2006 at 1:47pm Reply

  • BoisdeJasmin: R, glad that you liked it! :) February 13, 2006 at 1:48pm Reply

  • BoisdeJasmin: Rafael, yes, you are right that Damascenone is a fascinating ingredient. To me, it smells more of natural roses than either alpha or beta-damascones, with a somewhat waxy element as well. Your description is great. Thank you for adding extra information, and I am glad that you liked the article. February 13, 2006 at 1:52pm Reply

  • paru: Thanks for the geeky answer! February 13, 2006 at 3:04pm Reply

  • BoisdeJasmin: Well, you wanted to know… Maybe, you might find it interesting to read more technical answers to these questions, so I would recommend any of the papers mentioned above. February 13, 2006 at 4:16pm Reply

  • violetnoir: I think you are brilliant!

    Hugs! February 13, 2006 at 4:29pm Reply

  • BoisdeJasmin: R, you are too kind! Hugs! February 13, 2006 at 5:42pm Reply

  • marchlion: Wow, what an interesting post — thank you!! I loved and wore Paris and Poison back in The Day — although I revisited them recently and, while I still find Paris lovely, I wouldn’t re-purchase them. I can’t decide whether they or my tastes have changed. I do think the original Poison (along with Giorgio) helped the no-perfume-in-the-office argument!

    Bored out of my mind the last time I was at the dept. store (smelling Curious and Baby Phat Goddess, lord help me) I grabbed the Arpege for some relief. It was … just stunning, reformulated or not.

    I am confused about the toxicity issue — are the other scents using a lower percentage than Nombre Noir, or will it eventually be banned entirely? February 13, 2006 at 8:43pm Reply

  • BoisdeJasmin: March, damascones are not toxic. I only know that they can cause photosensitivity (like citrus oils, for instance), therefore the concentration cannot be too high.

    I cannot agree more on Arpege. It is such a beautiful fragrance. Poison is difficult to wear, no doubts about it. It is so strong and diffusive. Well, almost any damascone has that property. A drop of Nombre Noir can last for an entire day and fill a whole room! February 13, 2006 at 9:10pm Reply

  • Viktor Nilsson: Thank you for this brilliant article, V! When you put certain fragrances in a chemical-historical context like this, they can never be the same to me again. It will even be a really intresting experience to try the horrible Cool Water again! Not that I think I will like it this time around, but I will probably learn something! And poison! Can’t wait to try it with all my new knowledge. February 13, 2006 at 9:14pm Reply

  • BoisdeJasmin: Viktor, I am very glad to hear this! I love knowing what goes into a fragrance and how the accords are constructed. Knowing this makes me appreciate and understand the art of creation better. February 13, 2006 at 11:58pm Reply

  • helg: This is one of your best articles. Chocefull of info. Thanks! February 14, 2006 at 7:32am Reply

  • BoisdeJasmin: E, thank you very much! I find it interesting to know what fragrances contain, and it is a pleasure to share. February 14, 2006 at 1:41pm Reply

  • uella: what are sensitizers? I own a full bottle of Nombre Noir 60ML, only used by me three times. February 17, 2006 at 5:13pm Reply

  • BoisdeJasmin: Damascones in concentrations over 0.1% are considered to have sensitizing potential by IFRA. Now, that has not stopped me from enjoying my Nombre Noir either. February 17, 2006 at 5:16pm Reply

  • Brian: Doesn’t Cool Water have Calone in it as well? I loved reading this article, as I’m about to get some Damascone. It was completely fascinating and very helpful. I’m still curious about how it really smells-I guess I will find out soon… October 14, 2011 at 2:12am Reply

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