Chemistry:Calone
Calone or methylbenzodioxepinone, trade-named Calone 1951, is an organic compound with the formula CH
3C
6H
3(OCH
2)
2CO. A white solid, it is a derivative of 4-methylcatechol. In the fragrance industry it is known as "watermelon ketone" or simply "calone".[1][2]
It was discovered by Pfizer in 1966. It is used to give the olfactory impression of a fresh seashore through the marine and ozone nuances (specifically, as fresh, watery, clean, melon, green, marine, and ozone).[3] Calone is similar in structure to brown algae pheromones like ectocarpene and is also distantly related in structure to the drug diazepam.[4]
Calone is an unusual chemical compound which has an intense "sea-breeze" note with slight floral and fruit 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 analogues.[5] Swiss company Firmenich later released the isopropyl homologue of this substance under the brand name Cascalone - a sweet, watery version of calone with a transparent floral signature.[6]
References
- ↑ Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
- ↑ "What’s Hot, What’s Not: The Trends of the Past 20 Years in the Chemistry of Odorants". Angewandte Chemie International Edition 59 (38): 16310–16344. 14 September 2020. doi:10.1002/anie.202005719. https://onlinelibrary.wiley.com/doi/10.1002/anie.202005719.
- ↑ "watermelon ketone". Scents and Flavors. https://scentsandflavors.com/database/9dbb4f3d-ddc9-451f-82a7-4121d6393462.
- ↑ Yudov, Matvey. "Calone: The Air of the 1990s ~ Raw Materials ~ Fragrantica". https://www.fragrantica.com/news/Calone-The-Air-of-the-1990s-8150.html.
- ↑ 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 (3): 486–495. doi:10.1002/ejoc.201403142.
- ↑ "CASCALONE®" (in en). https://www.firmenich.com/product/cascaloner-pe-920000-0.
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