Calone or methylbenzodioxepinone, trade-named Calone 1951, also known in the industry as "watermelon ketone", was discovered by

Pfizer Pfizer Inc. ( ) is an American multinational pharmaceutical and biotechnology corporation headquartered on 42nd Street in Manhattan, New York City. The company was established in 1849 in New York by two German entrepreneurs, Charles Pfize ...

in 1966. It is used to give the

olfactory The sense of smell, or olfaction, is the special sense through which smells (or odors) are perceived. The sense of smell has many functions, including detecting desirable foods, hazards, and pheromones, and plays a role in taste. In humans, i ...

impression of a fresh seashore through the

marine Marine is an adjective meaning of or pertaining to the sea or ocean. Marine or marines may refer to: Ocean * Maritime (disambiguation) * Marine art * Marine biology * Marine debris * Marine habitats * Marine life * Marine pollution Military * ...

and ozone nuances. Calone is similar in structure to

brown algae Brown algae (singular: alga), comprising the class Phaeophyceae, are a large group of multicellular algae, including many seaweeds located in colder waters within the Northern Hemisphere. Brown algae are the major seaweeds of the temperate an ...

pheromones like

ectocarpene Ectocarpene is a sexual attractant, or pheromone, found with several species of brown algae (Phaeophyceae). The substance has a fruity scent and can be sensed by humans when millions of algae gametes swarm the seawater and the females start emitti ...

and is also distantly related in structure to the benzodiazepine class of sedatives. 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

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. ...

s of the marine trend, beginning in the 1990s. In 2014, Plummer ''et al.'' reported the synthesis and fragrance properties of several related aliphatic analogues. {{cite journal , title = Synthesis of Saturated Benzodioxepinone Analogues: Insight into the Importance of the Aromatic Ring Binding Motif for Marine Odorants , author = C. M. Plummer, R. Gericke, P. Kraft, A. Raynor, J. Froese, T. Hudlicky, T. J. Rook, O. A. H. Jones and H. M. Hϋgel , journal = Eur. J. Org. Chem. , date = 4 Dec 2014 , volume=2015 , issue = 3 , pages=486–495 , doi=10.1002/ejoc.201403142

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Constituents of fragrances

Perfume ingredients Ketones Benzodioxepines