Calone

Calone
Names
Preferred IUPAC name
7-Methyl-2,4-dihydro-3H-1,5-benzodioxepin-3-one
Other names
Calone 1951; Watermelon ketone; Methylbenzodioxepinone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.823 Edit this at Wikidata
UNII
  • 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
Appearance white crystals, flakes or clumps
Odor distinctive
Melting point 35–41 °C (95–106 °F; 308–314 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 irritant
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, is an organic compound with the formula CH3C6H3(OCH2)2CO. A white solid, it is a derivative of 4-methylcatechol. In the fragrance industry it is known as "watermelon ketone" or simply "calone".[1]

It was discovered by Pfizer in 1966. It is used to give the olfactory impression of a fresh seashore through the marine and ozone nuances (specifically, as fresh, watery, clean, melon, green, marine, and ozone).[2] Calone is similar in structure to brown algae pheromones like ectocarpene and is also distantly related in structure to the drug diazepam.[3]

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 perfumes of the marine trend, beginning in the 1990s. In 2014, Plummer et al. reported the synthesis and fragrance properties of several related aliphatic analogues.[4] Swiss company Firmenich later released the isopropyl homologue of this substance under the brand name Cascalone - a sweet, watery version of calone with a transparent floral signature.[5]

References

  1. ^ Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
  2. ^ "watermelon ketone". Scents and Flavors. Scents and Flavors. Retrieved 26 March 2026.
  3. ^ Yudov, Matvey. "Calone: The Air of the 1990s ~ Raw Materials ~ Fragrantica". fragrantica.com. Retrieved 29 June 2020.
  4. ^ 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 December 2014). "Synthesis of Saturated Benzodioxepinone Analogues: Insight into the Importance of the Aromatic Ring Binding Motif for Marine Odorants". Eur. J. Org. Chem. 2015 (3): 486–495. doi:10.1002/ejoc.201403142.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ "CASCALONE®". www.firmenich.com. Retrieved 23 December 2023.

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