CALONE
what is Calone?
Synthetic Ingredient For Perfumery Overview
Calone, Oceanone, watermelon ketone, or in IUPAC 8-methyl-1,5-Benzodioxepin-3-one is an unusual odorant that has an intense "sea-breeze" note with slight floral overtones. It has been used as a scent component since the 1980s for its watery, fresh, ozone accords, and as a more dominant note in several perfumes of the marine trend, beginning in the 1990s. In 2014, Plummer et al. reported the synthesis and fragrance properties of several related aliphatic analogs.
Discovery
It was first synthesized by J. J. Beereboom, D. P. Cameron, and C. R. Stephens from Pfizer in 1966.
Calone 1951 was invented by chemists from Pfizer, or, to be more precise, employees of the perfume company Camilli, Albert & Laloue, which was founded in Grasse in 1830, acquired by Coty in the same year, and then passed on to the Pfizer pharmaceutical group's control in 1963. The chemists were working with cyclic Ketones, including Benzodiazepines, as a part of big research to find an affordable tranquilizer, and they synthesized it in the end, it was marketed as benzodiazepine diazepam (Valium).
In the lab, there was a policy to name all new compounds by a special code, which included the first letters of the company name, the class of the invented compound, and its sequence number: Camilli+Albert+Laloue+ketone+=CALone. The substance registered by the number 1951 (methylbenzodioxepinone), was the only one that had a strong scent of watermelon. It was immediately patented just in case and during the next 20 years, Calone 1951 had been a marginal perfume ingredient it was used in trace amounts for flower accords, predominantly in creating the smell of lily-of-the-valley. When the patent had expired, Calone 1951 stepped into its glorious era: the first perfume with a significant amount of Calone (1.2%), Aramis New West for Her (1989), opened a new aquatic perfume trend. Different companies started to produce this compound, and it is now known by many names: Aquamore, Watermelon Ketone, Ozonor, Ozeone, Calone 161, or simply Calone. For your information the company Camilli, Albert & Laloue was acquired by a Société Marcel Blanc in 1985, and in 1996 became a part of the Finnish corporation Cultor. (M. Yudov)
Profile:
📂 CAS N° 28940-11-6
⚖️ MW — 178.18 g/mol
📝 Odor Type — Aquatic or Marine
📈 Odour Strength — Powerful
👃🏼 Odor Profile — It has an intense Marine, ozonic, sea-like smell. Pretty unique note, it can produce floral overtones. There can be a fruit aspect of melon/watermelon but it is very negligible to me.
👅 Flavor Profile — NOT FOR FLAVOR USE
⚗️ Uses: Calone can be used for its marine base note in the first place. But, it has also an important function in the ambergris reconstitution. It was used to make the REM accord along with Benzyl Salicylate and Patchouli. To make the aquatic note of Acqua Di Gio. To make the marine effect in Hugo and Fuel for Life.
In its pure form, Calone possesses a fresh, somewhat green, ozonic smell, with characteristic oyster and watermelon nuances. Сalvin Klein Escape (1991) with 0.8% of Calone, officially approved a new fashion for fresh aquatic scents. Hundreds of perfumes in which Calone was the leading note appeared, other ingredients were merely enhancing its different facets, especially its fresh metallic hues. After an intense 10-year-long fashion, everybody has gotten tired of Calone to the extent that many perfumes have been reformulated to decrease their "marine freshness", and some of them (for example, the already mentioned CK Escape) have lost it completely. (M. Yudov)
Sources:
National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 120101, 2H-1,5-Benzodioxepin-3(4H)-one, 7-methyl-. Retrieved November 25, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/2H-1_5-Benzodioxepin-3_4H_-one_-7-methyl.
C. M. Plummer, R. Gericke, P. Kraft, A. Raynor, J. Froese, T. Hudlicky, T. J. Rook, O. A. H. Jones and H. M. Hϋgel (4 Dec 2014). "Synthesis of Saturated Benzodioxepinone Analogues: Insight into the Importance of the Aromatic Ring Binding Motif for Marine Odorants". Eur. J. Org. Chem. 2015: 486–495. doi:10.1002/ejoc.201403142
Matvey Yudov, Calone: The Air of the 1990s.
https://www.fragrantica.com/news/Calone-The-Air-of-the-1990s-8150.html