23726-92-3

Usage

Uses

Used in the Food Industry:
(Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one is used as a food spice for formulating rose essence, adding a distinct and pleasant aroma to various food products.
Used in the Fragrance Industry:
(Z)-beta-damascone is used as a key ingredient in the creation of perfumes and other fragrances, providing a natural and captivating rose-like scent.
Used in the Flavor Industry:
(Z)-1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-buten-1-one is also utilized in the flavor industry to enhance the taste and aroma of various products, such as beverages, confectionery, and other consumables, by imparting a fruity and floral note.

Synthesis

(Z)-beta-damascone can be synthesized by the reaction of ethyl crocinate and allyl lithium, followed by catalytic isomerization.

InChI:InChI=1/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7H,6,8-9H2,1-4H3/b7-5-

Upstream product

• 49815-58-9 6,6-dimethyl-2-methyl-1-cyclohexene-1-carboxylic acid methyl ester 
• 2622-05-1 allylmagnesium bromide 
• 35124-05-1 2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol 
• 49815-59-0 4-(2',6',6'-trimethyl-1'-cyclohexenyl)-1,6-heptadien-4-ol 
• 79-77-6 (E)-β-ionone 
• 139609-00-0 1-<3-(2,6,6-Trimethyl-1-cyclohexen-1-yl)oxiranyl>ethanone 
• 139609-02-2 α-Methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)oxiranemethanol 
• 139609-04-4 2-(1-Bromoethyl)-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)oxirane 
• 23726-91-2 beta damascone 
• 67-63-0 isopropyl alcohol 

Relevant academic research and scientific papers

172. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone

The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β-cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf.Scheme 2).These studies have established an order of β-cleavage for 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl-2-propenyl, and benzyl groups in alkoxides 49a-56a and have allowed a comparison between the β-cleavage reaction and the oxy-Cope rearrangement in alkoxides 74a-83a.As illustrative synthetic applications, a two-step preparation of propenyl ketones 15-42 from carboxylic esters is described, together with syntheses of ar-turmerone (48), α-damascone ((E)-71), β-damascone ((E)-109), and β-damascenone ((E)-111).

Synthesis of (E)-1-Propenyl Ketones from Carboxylic Esters and Carboxamides by Use of Mixed Organolithium-Magnesium Reagents

The novel reagents formed by combination of allylmagnesium chloride and a strong non-nucleophilic lithium base (LiNR2) convert non- or slowly enolizable carboxylic esters or carboxamides into 2-propenyl ketones which are protected from further reaction by their in situ conversion into enolates.This modified Grignard reaction is applied to efficient syntheses of α-damascone, β-damascone, β-damascenone, and various other (E)-1-propenyl ketones.

Photochemistry of dienones. Part 12. Photochemistry of (E)-α- and (E)-β-damascone

The photochemistry of (E)-α- and (E)-β-damascone has been studied.Upon triplet-sensitized irradiation, both compounds exclusively undergo (E)-(Z) isomerization. (E)-β-damascone, upon direct irradiation with λ 254, 300 or 350 nm in non-alcoholic solvents, exhibits only (E)-(Z) isomerization.However, in an alcoholic solvent, direct irradiation induces cyclization and subsequent solvent incorporation, with formation of exo-8-alkoxy-1,5,5-endo-9-tetramethyl-cis-bicyclononan-7-one (12). (E)-α-damascone, upon direct irradiation, exhibits α-cleavage with subsequent formation of the 1,3-acyl shift product, and equal amounts of the dimerization products of the allylic radical, viz. 9 and 10.The 1,3-acyl shift product again undergoes photo-α-cleavage and the only products, upon prolonged irradiation, are the bicyclohexenyls 9 and 10.