Calone
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| Names | |
|---|---|
| Preferred IUPAC name
7-Methyl-2,4-dihydro-3H-1,5-benzodioxepin-3-one | |
| Other names
Calone 1951; Watermelon ketone; Methylbenzodioxepinone | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.044.823 |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C10H10O3 | |
| Molar mass | 178.187 g·mol−1 |
| Appearance | white crystals, flakes or clumps |
| Odor | distinctive |
| Melting point | 35–41 °C (95–106 °F; 308–314 K) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
irritant |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Calone or methylbenzodioxepinone, trade-named Calone 1951, is an organic compound with the formula CH3C6H3(OCH2)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
[edit]- ↑ 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.
- ↑ Armanino, N., Charpentier, J., Flachsmann, F., Goeke, A., Liniger, M., Kraft, P. (14 September 2020). "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. doi:10.1002/anie.202005719.
- ↑ "watermelon ketone". Scents and Flavors. Scents and Flavors. Retrieved 26 March 2026.
- ↑ Yudov, Matvey. "Calone: The Air of the 1990s ~ Raw Materials ~ Fragrantica". fragrantica.com. Retrieved 29 June 2020.
- ↑ 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 December 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ↑ "CASCALONE®". www.firmenich.com. Retrieved 23 December 2023.