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February 13, 2006

Fragrance Ingredient: Damascones

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 odours, 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 odour 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 odour 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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