The Chemistry and Creative Legacy of Methyl Jasmonate and Hedione

Contact Author Christian Chapuis, Firmenich SA
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Dedicated to Drs. Edouard Demole and Valentin Rautenstrauch, on the occasion of their 80th and 75th birthdays, respectively.

Edouard Demole discovered methyl jasmonate in 1957, accomplished a synthesis of Hedione (from 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; on the occasion of Hedione’s 50th anniversary, we shall trace this landmark material’s hectic history and legacy.

Discovery and Chemistry In the late 1950s, Roger Firmenich instructed Demole to study in depth, as the subject of his doctoral thesis in E. Lederer’s laboratories (Institut de Biologie Physico-Chimique, Paris, 1955–1959), the concrete of Mediterranean jasmine (Jasminum grandifl orum L.), in order to discover and determine the missing structures responsible for this typical olfactive signature. At the same time, he also sent a sample to Leopold Ruzicka, as he was involved in a previous analysis in Geneva. Indeed, although more than 87% of the jasmine essential oil constituents had already been determined, the full olfactive reconstitution was still impossible. The fundamental element responsible for this material’s wonderful radiance and deep sweet floral character was hidden in the remaining unknown fraction. It should be noted that the price of one kilo of jasmine absolute, produced from ca. 1 ton of jasmine flowers and extracted with ethanol from 2.3 kg of jasmine concrete, could cost up to 20,000 CHF/Kg; at the time, world annual production was limited to ca. 6 tons of jasmine absolute. The decision to decode jasmine essential oil constituents was motivated by premium cost of the ingredient and the old saying, “No perfume without jasmine.” Up to the middle of the 20th century, ca. 80% of marketed fragrance compositions contained a basic note extracted from this precious handpicked flower; outstanding examples include Jasmin (Molinar, 1860), Jasmin de Corse (Coty, 1906), Arpège (Lanvin, 1927), Joy (Patou, 1935) and Miss Dior (Dior, 1947).

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