Calone

Calone
Names
	IUPAC name 7-Methylbenzo[b][1,4]dioxepin-3-one
	Other names Calone 1951; Watermelon ketone; Methylbenzodioxepinone
Identifiers
CAS Number	28940-11-6;
3D model (JSmol)	Interactive image;
ChemSpider	107218;
ECHA InfoCard	100.044.823
PubChem CID	120101;
CompTox Dashboard (EPA)	DTXSID0047165 ;
	InChI 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;
	SMILES O=C1COc2c(OC1)cc(cc2)C;
Properties
Chemical formula	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). 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

^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

[Plummer-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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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