Calone

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Calone
Calone V1.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
Appearancewhite crystals, flakes or clumps
Odor distinctive
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". [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. Calone is similar in structure to brown algae pheromones like ectocarpene and is also distantly related in structure to the benzodiazepine class of sedatives. [2]

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. [3] Swiss company Firmenich later released CASCALONE®, a sweet, watery version of calone with a transparent floral signature. [4]

Related Research Articles

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<span class="mw-page-title-main">Aldol condensation</span> Type of chemical reaction

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<span class="mw-page-title-main">Organolithium reagent</span> Chemical compounds containing C–Li bonds

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<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

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<span class="mw-page-title-main">Aroma compound</span> Chemical compound that has a smell or odor

An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.

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<span class="mw-page-title-main">Tropone</span> Chemical compound

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<span class="mw-page-title-main">Bis(trimethylsilyl)sulfide</span> Chemical compound

Bis(trimethylsilyl) sulfide is the chemical compound with the formula ((CH3)3Si)2S. Often abbreviated (tms)2S, this colourless, vile-smelling liquid is a useful aprotic source of "S2−" in chemical synthesis.

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<span class="mw-page-title-main">Trifluoroperacetic acid</span> Chemical compound

Trifluoroperacetic acid is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF
3
COOOH
. It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones. It is the most reactive of the organic peroxy acids, allowing it to successfully oxidise relatively unreactive alkenes to epoxides where other peroxy acids are ineffective. It can also oxidise the chalcogens in some functional groups, such as by transforming selenoethers to selones. It is a potentially explosive material and is not commercially available, but it can be quickly prepared as needed. Its use as a laboratory reagent was pioneered and developed by William D. Emmons.

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. Yudov, Matvey. "Calone: The Air of the 1990s ~ Raw Materials ~ Fragrantica". fragrantica.com. Retrieved 29 June 2020.
  3. 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)
  4. "CASCALONE®". www.firmenich.com. Retrieved 23 December 2023.