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Calone 1951; Watermelon ketone; Methylbenzodioxepinone
3D model (JSmol)
|Molar mass||178.19 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Calone or methylbenzodioxepinone, trade-named Calone 1951, also known in the industry as "watermelon ketone", was discovered by Pfizer in 1966. It is used to give the olfactory impression of a fresh seashore through the marine and ozone nuances. Calone is similar in structure of certain alicyclic C11-hydrocarbons like ectocarpene, excreted by some species of brown algae as pheromones.
Calone is an unusual odorant which 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 and co-workers reported the synthesis and fragrance properties of several related aliphatic analogues. 
- 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.