{{short description|Chemical compound}} {{Use dmy dates|date=July 2022}} {{Chembox | ImageFile = Calone V1.svg | ImageSize = 200px | PIN = 7-Methyl-2,4-dihydro-3''H''-1,5-benzodioxepin-3-one | OtherNames = Calone 1951; Watermelon ketone; Methylbenzodioxepinone |Section1={{Chembox Identifiers | ChemSpiderID = 107218 | InChI = 1/C10H10O3/c1-7-2-3-9-10(4-7)13-6-8(11)5-12-9/h2-4H,5-6H2,1H3 | InChIKey = SWUIQEBPZIHZQS-UHFFFAOYAC | CASNo = 28940-11-6 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 0NQ136C313 | PubChem = 120101 | SMILES = O=C1COc2c(OC1)cc(cc2)C }} |Section2={{Chembox Properties | C=10 | H=10 | O=3 | Appearance = white crystals, flakes or clumps | Density = | MeltingPtC= 35–41 | BoilingPt = | Odor = distinctive | Solubility = }} |Section3={{Chembox Hazards | MainHazards = irritant | FlashPt = | AutoignitionPt = }} }}
'''Calone''' or '''methylbenzodioxepinone''', trade-named '''Calone 1951''', is an organic compound with the formula {{chem2|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".<ref>{{cite book |doi=10.1002/14356007.t11_t02 |chapter=Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2016 |last1=Panten |first1=Johannes |last2=Surburg |first2=Horst |pages=1–45 |isbn=978-3-527-30673-2 }}</ref>
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).<ref>{{cite web |title=watermelon ketone|url=https://scentsandflavors.com/database/9dbb4f3d-ddc9-451f-82a7-4121d6393462|website=Scents and Flavors |publisher=Scents and Flavors |access-date=26 March 2026}}</ref> Calone is similar in structure to brown algae pheromones like ectocarpene and is also distantly related in structure to the benzodiazepine class of sedatives.<ref name="Yudov">{{cite web | last=Yudov | first=Matvey | title=Calone: The Air of the 1990s ~ Raw Materials ~ Fragrantica | website=fragrantica.com | url=https://www.fragrantica.com/news/Calone-The-Air-of-the-1990s-8150.html | access-date=2020-06-29}}</ref> 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.<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=2015 | issue = 3 | pages=486–495 | doi=10.1002/ejoc.201403142}}</ref> Swiss company Firmenich later released Cascalone, a sweet, watery version of calone with a transparent floral signature.<ref name=":0">{{Cite web |title=CASCALONE® |url=https://www.firmenich.com/product/cascaloner-pe-920000-0 |access-date=2023-12-23 |website=www.firmenich.com |language=en}}</ref>
==References== {{reflist}}
== External links == * [http://www.bojensen.net/EssentialOilsEng/EssentialOils05/EssentialOils05.htm Constituents of fragrances] * [http://www.thegoodscentscompany.com/data/rw1002351.html Watermelon ketone]
Category:Benzodioxepines Category:Ketones Category:Perfume ingredients