Calone

Structural formula
General
Surname	Calone
other names	7-methylbenzo [ b ] [1,4] dioxepin-3-one; 7-methyl-1,5-benzodioxepin-3-one; Watermelon ketones;
Molecular formula	C 10 H 10 O 3
External identifiers / databases
EC number	249-320-4
ECHA InfoCard	100,044,823
PubChem	120101
ChemSpider	107218
Wikidata	Q2934355
properties
Molar mass	178.187 g mol −1
Physical state	solid, white crystals
Melting point	38-41 ° C
boiling point	158 ° C
solubility	soluble in ethanol and dipropylene glycol ; slightly soluble in hot water, hardly soluble in cold water (471.5 mg l −1 at 25 ° C); almost insoluble in paraffin oil ;
safety instructions
GHS labeling of hazardous substances
H and P phrases	H: 302
	P: 264-270-301-330-501
Toxicological data	1556 mg / kg mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Calone or methylbenzodioxepinone , also known as Watermelon Ketone trade name Calone 1951 , was discovered in 1966 by the Pfizer company . It is used to create the smell of fresh sea air and nuances of the sea. Calone has a similar structure as some alicyclic C ₁₁ - hydrocarbons , such. B. Ectocarpenes, which are excreted as pheromones by brown algae .

Manufacturing

An industrial synthesis is based on 4- methylpyrocatechol , which is etherified in the first step by a Williamson reaction in the presence of sodium methylate with methyl bromoacetate . The ring closure then takes place in a Dieckmann condensation using sodium hydride . The target compound then results after saponification and subsequent acid-catalyzed decarboxylation .

A more recent synthesis takes place as a one-step variant from 1,3-dichloroacetone and 4-methylpyrocatechol in the presence of triethylamine and potassium iodide .

use

Calone is an unusual fragrance that smells like "sea breeze" with light floral hints. It has been used in several perfumes since the 1980s for its special smell, specifically in the wave of the marine trend in the US in the early 1990s.

A selection of perfumes containing calone:

Sun Men ( Jil Sander )
Hugo Element ( Hugo Boss )
Sun Bath (Jil Sander)
My Land (Trussardi)
Mare Pacifico (Linari)
Eternity Summer 2013 ( Calvin Klein )
Zeitgeist (JF Schwarzlose Berlin)
New West for Her (Aramis)
Neroli 36 (Le Labo)
Musc Monoï (Parfums de Nicolaï)
Oriental Essences - Fleurs de L'Himalaya (Rituals)
L'Eau d'Issey City Blossom (Issey Miyake)
Summer Sailing (Clean)
Eau Simple de Concombre (Phaedon)
Kenzo Homme Fresh (Kenzo)
Eryo Blue by Yves Rocher
Acqua di Giò (Armani)

Web links

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ The Good Scents company , accessed October 26, 2015.
↑ Kraft, P .; Bajgrowicz, JA; Denis, C .; Fráter, G .: All kinds of trends: the latest developments in rich chemistry in Angew. Chem. 112 (2000) 3106-3138, doi : 10.1002 / 1521-3757 (20000901) 112: 17 <3106 :: AID-ANGE3106> 3.0.CO; 2-P .
↑ Patent CN102584781 : Method for preparing and purifying calone. Published on 20120718 , Inventor: Yue, Zhizhou; Liang, Yukun; Xu, Bo. ‌
↑ Description of Calone in Parfumo , accessed October 31, 2015.
↑ Calone in Parfumo , accessed November 8, 2015.

[comp-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ The Good Scents company , accessed October 26, 2015.

[2] Kraft, P .; Bajgrowicz, JA; Denis, C .; Fráter, G .: All kinds of trends: the latest developments in rich chemistry in Angew. Chem. 112 (2000) 3106-3138, doi : 10.1002 / 1521-3757 (20000901) 112: 17 <3106 :: AID-ANGE3106> 3.0.CO; 2-P .

[3] Patent CN102584781 : Method for preparing and purifying calone. Published on 20120718 , Inventor: Yue, Zhizhou; Liang, Yukun; Xu, Bo. ‌

[4] Description of Calone in Parfumo , accessed October 31, 2015.

[5] Calone in Parfumo , accessed November 8, 2015.