# Calone

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> Markdown URL: https://mediated.wiki/source/Calone.md
> Source: https://en.wikipedia.org/wiki/Calone
> Source revision: 1345634372
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{{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](/source/organic_compound) with the formula {{chem2|CH3C6H3(OCH2)2CO}}. A white solid, it is a derivative of [4-methylcatechol](/source/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](/source/Pfizer) in 1966. It is used to give the [olfactory](/source/olfactory) impression of a fresh seashore through the [marine](/source/Marine_(ocean)) 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](/source/brown_algae) pheromones like [ectocarpene](/source/ectocarpene) and is also distantly related in structure to the [benzodiazepine class of sedatives](/source/benzodiazepine).<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 [perfume](/source/perfume)s of the marine trend, beginning in the 1990s. In 2014, Plummer ''et al.'' reported the synthesis and fragrance properties of several related [aliphatic](/source/Aliphatic_compound) 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](/source/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

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Adapted from the Wikipedia article [Calone](https://en.wikipedia.org/wiki/Calone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Calone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.