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'''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 (ocean)|marine]] and ozone nuances. Calone is similar in structure of certain alicyclic C11-[[hydrocarbon]]s like [[ectocarpene]], excreted by some species of [[brown algae]] as [[pheromone]]s.
'''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 (ocean)|marine]] and ozone nuances. Calone is similar in structure of certain alicyclic C11-[[hydrocarbon]]s like [[ectocarpene]], excreted by some species of [[brown algae]] as [[pheromone]]s.
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 [[perfume]]s of the marine trend, beginning in the 1990s.
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 [[perfume]]s of the marine trend, beginning in the 1990s. In 2014, Plummer and co-workers reported the synthesis and fragrance properties of several related analogues. <ref name=Plummer>{{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=4 | pages=486–495 | doi=10.1002/ejoc.201403142}}</ref>


== External links ==
== External links ==

Revision as of 03:14, 18 April 2017

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 Edit this at Wikidata
  • InChI=1/C10H10O3/c1-7-2-3-9-10(4-7)13-6-8(11)5-12-9/h2-4H,5-6H2,1H3
    Key: SWUIQEBPZIHZQS-UHFFFAOYAC
  • O=C1COc2c(OC1)cc(cc2)C
Properties
C10H10O3
Molar mass 178.187 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 analogues. [1]

  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. 4: 486–495. doi:10.1002/ejoc.201403142.{{cite journal}}: CS1 maint: multiple names: authors list (link)