Calone

Calone
Names
IUPAC name
7-Methylbenzo[b][1,4]dioxepin-3-one
Other names
Calone 1951; Watermelon ketone; Methylbenzodioxepinone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.823
Properties
C10H10O3
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).
Infobox references

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. [1]

References

  1. 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.
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