13144-88-2

Usage

Uses

Used in Fragrance Industry:
1-(2,4,4,5,5-pentamethyl-1-cyclopenten-1-yl)ethan-1-one is used as a fragrance ingredient for its aromatic properties. It contributes to the overall scent profile of various perfumes, colognes, and other fragranced products, enhancing their appeal and longevity.
Used in Flavor Industry:
In addition to its use in fragrances, 1-(2,4,4,5,5-pentamethyl-1-cyclopenten-1-yl)ethan-1-one can also be used as a flavoring agent in the food and beverage industry. Its unique aroma can add depth and complexity to various flavors, creating a more enjoyable and memorable taste experience for consumers.

InChI:InChI=1/C12H20O/c1-8-7-11(3,4)12(5,6)10(8)9(2)13/h7H2,1-6H3

Upstream product

• 706-87-6 2,3,3,5-tetramethyl-2-(2-methyl-propenyl)-2,3-dihydro-furan 
• 64-19-7 acetic acid 
• 141-79-7 4-methyl-pent-3-en-2-one 

Relevant academic research and scientific papers

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.

Importance of Structure of α,β-Ethylenic Ketones during Their Reductive Coupling Promoted by the TiCl4-Mg Reagent

In most cases, the reductive coupling of α,β-ethylenic ketones by the TiCl4-Mg reagent leads to 1,3,5-trienes and bisallylic pinacols.Some α,β-enones of s-cis configuration, such as (+)-pulegone, show a particular reactivity: formation of dihydro ketones in the presence of tert-butyl alcohol and reductive alkylation with allylic halides or benzyl bromide.Results are accordance with a polymeric structure for the native low-valent titanium species, and in the case of some s-cis-enones, they can be explained by the intervention of a oxametallacyclopentene.

REDUCTIVE COUPLING OF α,β-ENONES PROMOTED BY Mg AND Mg-MgBr2

α,β-enones able to have a s-cis conformation can be reduced by Mg (turnings 99.8percent) or more efficiently by Mg(99.8percent)-MgBr2, 10 Et2O in dimers (resulting from the formation of a bond between the Cβ carbon atoms) and dihydroketones.

REDUCTIVE COUPLING OF α,β-ENONES I : REDUCTION OF METHYL-VINYL KETONE AND MESITYL OXIDE.

Reductive coupling of methyl-vinyl ketone with TiCl4-Mg gives pinacol 1 (25percent).According to the reducing agents, mesityl oxide yields 2,4,5,7-tetramethyl-octa-2,4,6-triene 3 (with 4TiCl3-LiAlH4), triene 3 or 2,4,5,7-tetramethyl-octa-2,6-dien-4,5-diol 5 (with TiCl4-Mg), pinacol 5 (with VCl3-Mg), and 2-acetyl-1,3,3,4,4-pentamethyl-cyclopentene 7 (with CrCl3-Mg or FeCl3-Mg or ZrCl4-Mg) as major products.