43052-87-5

Usage

Uses

Used in Flavor and Fragrance Industry:
1-(2,6,6-Trimethyl-cyclohex-2-enyl)-but-2-en-1-one is used as a flavoring agent for its sweet, fruity, and woody taste characteristics. It is also used as a fragrance ingredient for its pleasant fruity floral odor.
Used in Perfumery:
1-(2,6,6-Trimethyl-cyclohex-2-enyl)-but-2-en-1-one is used as a fixative in perfumery to enhance the longevity and intensity of fragrances. Its aroma threshold values are 100 ppb for the d-form and 1.5 ppb for the l-form, indicating its potency and effectiveness in small quantities.

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

Upstream product

• 59739-62-7 6,10-dimethyl-2,5,9-undectrien-4-one 
• 54095-64-6 (2Ξ,5E)-6,10-dimethyl-undeca-2,5,9-trien-4-one 
• 37079-64-4 1-[3-(2,6,6-trimethyl-cyclohex-2-enyl)-oxiranyl]-ethanone 
• 5146-66-7 geranonitrile 
• 564-24-9 (+/-)-α-cyclogeranic acid 
• 459-80-3 geranic acid 
• 61899-98-7 2,6,6-trimethylcyclohex-2-en-1-ylidene ketene 
• 107-05-1 3-chloroprop-1-ene 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 124572-59-4 α-ionone epoxyhydrazone 
• 28102-24-1 (Z)-2,6,6-Trimethyl-α-(1-propenyl)-2-cyclohexene-1-methanol 
• 25915-53-1 2,6,6-trimethyl-3-cyclohexenyl methyl ketone 
• 39900-15-7 (+/-)-3-hydroxy-1-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-1-one 
• 39900-11-3 1-(2,6,6-trimethyl-2-cyclohexenyl)-1,3-butanedione 

Downstream Products

• 23696-85-7 1-(2,6,6-trimethyl-1,3-cyclohexadiene-1-yl)-2-butene-1-one 

Relevant academic research and scientific papers

Synthetic method of alpha-damascone

The invention provides a synthetic method of alpha-damascone. According to the synthetic method, lemonile is used as a raw material, alpha-pseudoisodamascenone is generated through one-step reaction,oxidizing agents such as sodium dichromate or chromic ox

Method for synthesizing beta-damascenone

The invention discloses a method for synthesizing beta-damascenone. The method mainly comprises the following steps: oxidizing citral through sodium chlorite; carrying out catalytic cyclization through concentrated phosphoric acid to obtain alpha-cyclogeranic acid; eliminating the alkalinity of the alpha-cyclogeranic acid under the action of thionyl chloride to obtain cyclogeranenone; carrying outaddition on the cyclogeranenone and allylmagnesium chloride and carrying out acidic isomerization to obtain alpha-damascenone; carrying out epoxidation on the alpha-damascenon through peroxyacetic acid, and carrying out alkaline ring opening through potassium carbonate; catalytically heating and dehydrating through para-toluenesulfonic acid to obtain the beta-damascenone. The method disclosed bythe invention has the advantages that raw materials are cheap and easy to obtain, reaction conditions are moderate and the operation is simple and convenient; another useful spice alpha-damascenone can be synchronously synthesized and the method is a method which is suitable for industrial production of the beta-damascenone.

1 - (2, 6, 6 - trimethyl - cyclohexenyl) - 2 - butene - 1 - ketone

The invention provides a 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one preparation method, which comprises that 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione is subjected to isomerization to obtained an isomerized product; and the isomerized product reacts to obtain 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one, wherein the 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one comprises 1-(2,6,6-trimethyl-cyclohex-1-enyl)-2-buten-1-one and 1-(2,6,6-trimethyl-cyclohex-2-enyl)-2-buten-1-one. According to the present invention, the 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione is adopted as the raw material, such that the oxidation of the alcohol into the ketone is avoided compared with the prior art, and the environmental pollution is low; and the route is simple, and the scale production is easily achieved.

PROCESS FOR PREPARING ALPHA-DAMASCONE

The present invention relates to a process for preparing 1-(2,6,6-trimethylcyclohex-2- en-1-yl)but-2-en-1-one, which comprises a) providing 6,10-dimethylundeca-1,5,9-trien-4-ol, b) oxidizing 6,10-dimethylundeca-1,5,9-trien-4-ol provided in step a) with an oxidizing agent in the presence of at least one organic nitroxyl radical, at least one nitrate compound and an inorganic solid to yield 6,10-dimethylundeca-1,5,9- trien-4-one, c) reacting the 6,10-dimethylundeca-1,5,9-trien-4-one obtained in step b) with an acid to yield 1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one.

PROCESS FOR THE ISOMERISATION OF A CYCLOHEXENYL ALKYL OR ALKENYL KETONE

The present invention relates to a process for the carbon-carbon double bond isomerisation of a 2-alkyl-cyclohex-3-enyl alkyl or alkenyl ketone into a mixture comprising the corresponding 2-alkyl-cyclohex-2-enyl ketones and the corresponding 2-alkylene-cy

Precursors for fragrant ketones and fragrant aldehydes

The present invention refers to fragrance precursors of formula I for a fragrant ketone of formula II and one or more fragrant aldehydes or ketones of formula III and IV, These fragrance precursors are useful in perfumery, especially in the fine and functional perfumery.

Ketone precursors for organoleptic compounds

The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.

NEW DEVELOPMENTS OF THE WHARTON TRANSPOSITION

The synthetically useful Wharton transposition can be improved by using a more adequate procedure in the critical step of the intermediate α-epoxyhydrazone cleavage.Either for stable hydrazones or unstable ones, the yield of the transposed allylic alcohol is increased by treatment under anhydrous conditions with highly basic reagents (KDA in the former case, NEt3 in the latter).

CYCLIZATION OF ACYCLIC ISOPRENOIDS. III. MOLECULAR REARRANGEMENTS OF PSEUDODAMASCONES AND GERANATE ESTERS

Experimental evidence is offered for the first time to support the scheme of the cationoid molecular rearrangements of pseudodamascones and geranate esters with the detection of intermediate carbocations.Comparison of the behaviour of isomeric pseudodamascones and pseudoionones in superacids revealed the effect of structural modification on the mechanisms of the cationoid rearrangements of these conjugated ketones.In the case of geranate esters, the effect of the configuration of a conjugated double bond on the structure of the initial electrophilic cyclization products was shown.