23068-96-4

Usage

Uses

Used in Fragrance and Flavor Industry:
Ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate is used as a key ingredient in the production of fragrances and flavors due to its distinctive fruity and sweet, floral scent. It adds depth and complexity to the aroma profiles of various products, enhancing their appeal to consumers.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate serves as a versatile intermediate in the synthesis of other organic compounds. Its unique chemical structure allows it to be a building block for the development of new drugs and pharmaceutical formulations.
Used as a Solvent:
Ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate is also utilized as a solvent in various chemical processes. Its ability to dissolve a wide range of substances makes it a valuable component in the production of different chemical products and formulations.
Used in Synthesis of Other Organic Compounds:
As an intermediate in the synthesis of other organic compounds, ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate plays a crucial role in the development of new chemical entities. Its unique properties and reactivity contribute to the creation of innovative materials and compounds for various industries.

InChI:InChI=1/C12H18O3/c1-5-15-11(14)10-8(2)6-9(13)7-12(10,3)4/h6,10H,5,7H2,1-4H3

Upstream product

• 35044-52-1 ethyl 2-acetyl-3-methylbut-2-enoate 
• 141-97-9 ethyl acetoacetate 
• 23069-06-9 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-carbonsaeure-ethylester 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 141-79-7 4-methyl-pent-3-en-2-one 

Downstream Products

• 51769-11-0 Ethyl 2,6,6-trimethyl-4-hydroxy-2-cyclohexene-1-carboxylate 
• 28815-33-0 2,6,6-trimethyl-4-oxo-cyclohex-2-enecarboxylic acid 
• 70416-88-5 2,6,6-trimethyl-cyclohexa-2,4-dienecarboxylic acid 
• 94092-46-3 2,6,6-Trimethyl-4-oxo-3-propyl-cyclohex-2-en-carbonsaeure-aethylester 
• 96812-60-1 3-Acetyl-2,6,6-trimethyl-4-oxo-cyclohex-2-en-carbonsaeure-ethylester 
• 92730-20-6 3-Allyl-2,6,6-trimethyl-cyclohex-2-en-carbonsaeure-ethylester 
• 96849-99-9 ethyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate 
• 23115-91-5 4-Ethoxy-2,6,6-trimethyl-cyclohexa-1,3-dienecarboxylic acid ethyl ester 
• 126-29-4 Violaxanthin 
• 126-29-4 (15Z)-Violaxanthin 
• 28874-44-4 (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal 
• 23069-03-6 Triphenyl-(2,6,6-trimethyl-cyclohexa-1,3-dienylmethyl)-phosphonium; bromide 
• 85111-47-3 2-ethyl-3,5,5-trimethylcyclohex-2-en-1-one 
• 91968-28-4 2-Acetyl-3,5,5-trimethyl-cyclohex-2-en-1-on 

Relevant academic research and scientific papers

Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and γ-cyclogeraniol

A comprehensive study on the lipase PS-mediated resolution of different hydroxy-geraniol isomers is reported. A number of α-, β- and γ-isomers bearing a 2-, 3- or 4-hydroxy functional group were synthesised regioselectively and then submitted to the lipase-mediated kinetic acetylation. The latter experiments showed that the 2-hydroxy isomers 4, 5 and 14 (α, γ and β, respectively) as well as cis-3-hydroxy α-cyclogeraniol 7 and cis-4-hydroxy γ-cyclogeraniol 10 could be easily resolved by this procedure. The enantiomeric purity of the main part of these compounds was increased by recrystallisation and the enantiopure diols obtained were used as building blocks for the synthesis of the natural terpenoids karahana lactone, karahana ether and crocusatin C and for the preparation of the synthetic intermediate γ-cyclogeraniol. The absolute configurations of the enantiomers of the diols 7, 10, 14 and 19 were determined by chemical correlation with the known compounds 40, 41, 39 and 41, respectively.

Process for preparing seed germinating stimulants

Processes for preparing compounds which exhibit seed germinating activity are disclosed. An ester of acetoacetic acid is condensed with a ketone to produce a substituted cyclohexenone which is reacted with a thiol to get a dithioketal which is then desulfurized to produce an ester of a substituted cyclohex-2-ene-1-carboxylic acid which exhibits seed germinating activity. The same compound can be produced by a different process which reacts the substituted cyclohexenone with a reducing agent. An exemplary reducing agent would be an organosilane and a Lewis acid.

Syntheses of Enantiomerically Pure Violaxanthins and Related Compounds

The epoxides 16 and ent-16, prepared by Sharpless-Katsuki oxidation of 15 in excellent yield and very high enantiomeric purity, were used as synthons for the preparation of (+)-(S)-didehydrovomifoliol (45), (+)-(6S,7E,9E)-abscisic ester 46, (+)-(6S,7E,9Z)-abscisic ester 47, (-)-(3S,7E,9E)-xanthoxin (49), (-)-(3R,7E,9E)-xanthoxin (50), (3S,5R,6S,3'S,5'R,6'S,all-E)-violaxanthin (1), (3R,5R,6S,3'R,5'R,6'S,all-E)-violaxanthin (55) and their (9Z) (see 53, 57), (13Z) (see 54, 58), and (15Z) (see 60) isomers.The novel violadione (61) was prepared from 1 by oxidation with DMSO/Ac2O.By base treatment, 61 was converted into violadienedione (62), a potential precursor of carotenoids with phenolic end groups.

A New Synthetic Route to (+/-)-Strigol

A new more facile synthetic route to strigol, a potent weed seed germination stimulant, utilizes as starting material ethyl 4-oxo-2,6,6-trimethylcyclohex-2-ene-1-carboxylate (2), obtained by the condensation of mesityl oxide and ethyl acetoacetate.Compound 2 was converted in six steps in 38percent overall yield to the previously reported strigol intermediate, 1,4-dioxo-7,7-dimethyl-4,5,6,7-tetrahydro-2-indanacetic acid (11).The new approach is based upon inexpensive starting materials and reagents and is suitable for large-scale production.The key features of the synthesis include reduction of enone 2 to olefin 5 with triethylsilane and boron trifluoride etherate and a one-pot conversion of ethyl 2-(bromomethyl)-6,6-dimethyl-3-oxocyclohex-1-ene-1-carboxylate (10) to the diketo acid 11.

Cycloaliphatic unsaturated ketones as fragrance modifying agents

New cycloaliphatic unsaturated ketones and their use as perfuming and odor-modifying agents in the manufacture of perfumes and perfumed products, and as flavoring and taste-modifying agents in the preparation of foodstuffs in general and imitation flavors for foodstuffs, beverages, animal feeds, pharmaceutical preparations and tobacco products. Methods for preparing the said new compounds and certain of the starting materials used for their synthesis.

Trimethyl-1,4-dioxaspiro[4,5]dec-7-en-8-methanol

The compound 7,9,9-trimethyl-1,4-dioxoaspiro [4,5] dec-7-en-8-methanol an intermediate in the preparation of Zeaxanthin and Xanthophyll, known coloring agents for foodstuffs.